Explore Diverse Accommodations in Greenport, NY

ZEY HOTEL offers accommodations in Greenport, 26 miles from Splish Splash. The bed and breakfast also offers free Wifi, free private parking, and facilities for disabled guests. The bed and breakfast offers a flat-screen TV and a private bathroom with bathrobes, slippers, and shower. The units have air conditioning, and some units at the bed and breakfast have a terrace. The rooms are equipped with heating facilities. The area is popular for cycling and fishing, and free use of bicycles is available at ZEY HOTEL. An indoor play area is also available at the accommodation, while guests can also relax in the garden. Long Island MacArthur Airport is 48 miles from the property.

- "Unbeatable location right in the heart of Greenport! Mia was an excellent host and very attentive." - "Beautiful space to stay.and enjoy Greenport" - "Excellent stay will definitely be back" - "ZEY Stay" - "Perfect" - "Awesome!" - "Recommended 100%" - "Loved the place! The staff is super hospitable. Mia is fantastic" - "A charming and affordable gem in Greenport" - "Great comfy community living spaces to place board games or just relax. Nice bright Sunny room to have free coffee juic"

Beach aparthotel in Greenport with free parking
Guests at this beach aparthotel will appreciate convenient onsite amenities such as barbecue grills and a picnic area.
Each apartment provides a kitchenette with a refrigerator, a stovetop, a microwave, and a dishwasher. Guests can appreciate conveniences like 2 bathrooms and a sitting area, and other amenities include free WiFi and a furnished balcony. Change of towels is available on request.
Cliffside Resort Condominiums offers 68 accommodations with coffee/tea makers and hair dryers. Rooms open to furnished balconies. Accommodations offer separate sitting areas. Accommodations at this 3-star aparthotel have kitchenettes with refrigerators, stovetops, microwaves, and cookware/dishes/utensils. Bathrooms include bathtubs or showers.

This Greenport aparthotel provides complimentary wireless Internet access. Flat-screen televisions are featured in guestrooms.

- "Wonderful stay and super clean! Can’t wait to come back. " - "quiet" - "Spacious and they allowed an early check in. " - "Excellent location with access to private beach" - "Clean, beautiful place on the shore of the ocean, very comfortable apartment for a family, the bedrooms are located far from each other, each bedroom has its own separate toilet and bathroom, there is a shower and a bath, the apartment is very clean, cozy. The staff is very nice and helpful. There are many good restaurants and cafes in Greenport, tasty and not expensive. I give this rezoot 5 stars"

Providing a garden, The Stirling House Waterfront Inn Greenport features accommodations in Greenport. This 4-star bed and breakfast offers luggage storage space and a concierge service. The bed and breakfast provides sea views, a sun terrace, and free Wifi is available throughout the property. The bed and breakfast will provide guests with air-conditioned units with an oven, a coffee machine, a shower, bathrobes, a flat-screen TV with cable channels, and a DVD player. Every room has a private bathroom with a hair dryer and free toiletries. Additional in-room amenities include wine or champagne, fruit, and chocolates or cookies. There is a snack bar, bar, and lounge. Sightseeing tours are available nearby. A bicycle rental service is available at the bed and breakfast. Splish Splash is 26 miles from The Stirling House Waterfront Inn Greenport. Long Island MacArthur Airport is 48 miles away.

- "The Best B&B" - "Very nice place and host. Would recommend." - "Clay and Frank were very nice and accommodating." - "Wonderful weekend getaway spot!!" - "We have a wonderful stay and would love to go back and spend more time. Highly recommend" - "Overall my visit was very pleasant."

Bayside bed & breakfast with a nearby private beach and free breakfast
This smoke-free bed & breakfast features a bar/lounge, a snack bar/deli, and concierge services. Free full breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, express check-in, express check-out, and free newspapers are onsite.
Stirling House Bed & Breakfast offers 3 accommodations with fireplaces and iPod docking stations. Beds feature premium bedding. Flat-screen televisions come with premium cable channels and DVD players.

Bathrooms include bathrobes, designer toiletries, complimentary toiletries, and hair dryers. Guests can surf the web using the complimentary wireless Internet access. Additionally, rooms include minibars and complimentary newspapers. Housekeeping is provided daily.

- "Very comfortable king size bed. Excellent gourmet breakfast, discreet host. Older house, but all the comforts. Absolutely every need provided for. " - "This was a great place to stay with old word charm. If you are looking for a quiet getaway with a beautiful view of the ocean this is it. The breakfast that we had were much better that what you could get in town. My wife and I can't wait to go back." - "We booked this property to celebrate our 17th anniversary for an 1 night night getaway. Upon check in we were greeted with the most delicious homemade cupcakes with our name on it and warmly welcomed by Clay, the property host. We parked right in front, and walked to various bars and restaurants so it was so convenient and vibrant and didn’t have to worry about driving. On the way back we saw the most amazing moonset on the water (the property is basically on the water separated by a street), there’s a dock you can walk out to. Clay cooked us the best farm to table breakfast, it was so delicious, he really takes the time and effort to make everything perfect. We will definitely stay here again!"

Modern on 9th offers accommodations in Greenport, 25 miles from Splish Splash. The vacation home has access to a restaurant. Opening onto a patio, the vacation home consists of 3 bedrooms. The air-conditioned vacation home also provides a TV, a fully equipped kitchen with a dishwasher, a seating area, washing machine, and 3 bathrooms with a walk-in shower. The property has an outdoor dining area. Long Island MacArthur Airport is 47 miles away.

Security/Safety • Balcony/Terrace • Child Friendly • Pet Friendly • Air Conditioner • Fireplace/Heating • Restaurant • Guest Services • Laundry

Beachfront, with seasonal outdoor pool
This smoke-free bed & breakfast features a bar/lounge, a seasonal outdoor pool, and a meeting room. Free WiFi in public areas and free self parking are also provided. Additionally, a library, a garden, and a picnic area are onsite.
Harbor Knoll Bed & Breakfast offers 3 accommodations with private pools and complimentary newspapers. Rooms open to balconies or patios. Each accommodation is individually furnished and decorated. Select Comfort beds feature Egyptian cotton sheets and premium bedding. Guests can surf the web using the complimentary wireless Internet access. Bathrooms include showers with hydromassage showerheads, bathrobes, slippers, and hair dryers. Additionally, rooms include complimentary bottled water and irons/ironing boards. Housekeeping is provided daily.
Recreational amenities at the bed & breakfast include a seasonal outdoor pool.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "Charming bed and breakfast in a great location right on the water…perfect for a romantic getaway!" - "We stayed here for our mini moon and couldn't have asked for a better weekend! We loved hanging out at the inn and getting to know Leueen and the other guests. The inn is walking distance to the main streets and the train. Will definitely visit again!" - "Beautiful bed and breakfast with gorgeous views. Close to shops and restaurants but far enough to be private and quiet. Will definitely be coming back"

Cozy Greenport Cottage offers accommodations in Greenport, 26 miles from Splish Splash. Guests can benefit from a patio and an outdoor fireplace. The vacation home has an outdoor pool and a sauna. The spacious vacation home is composed of 3 bedrooms, 2 living rooms with dining area, a fully equipped kitchen, and 3 bathrooms. Towels and bed linen are provided in the vacation home. The property has an outdoor dining area. The vacation home has a picnic area where you can spend the day outdoors. Long Island MacArthur Airport is 47 miles away.

Security/Safety • Wellness Facilities • Pool • Barbecue/Outdoor Cooking • Balcony/Terrace • Guest Services • Laundry • Child Friendly • Fireplace/Heating • Sports/Activities

Your family will be close to everything Greenport has to offer when you stay at this centrally-located 2 bedroom apartment. Close to scenic beaches, local vineyards and brewery. Walking distance to Long Island Railroad, Hampton Jitney, Shelter Island Ferry and downtown boutiques. Enjoy fine dinning at our neighborhood restaurants. There are many opportunities for boating, fishing and water sports.

- "We loved our stay in Greenport. The location is perfect to explore the town and the area. Very comfortable apartment and the owners were friendly and helpful. We would definitely stay again. " - "Lovely newly renovated modern apartment right in the heart of Greenport. Walk to everything - restaurants, docks, stores, groceries, …. We parked our car and didn’t use it again for the four days of our stay. Host was responsive but had we no issues. Will definitely return."

With beautiful views of the sunsets over Long Island Sound, this Greenport resort features spacious grounds and a private beach. Free Wi-Fi is available in all areas. A private balcony provides a relaxing viewing point from each apartment of Cliffside Resort Condominiums – Greenport. A flat-screen TV, wine refrigerator and kitchenette are included. Guests of Cliffside Resort can enjoy the seasonal outdoor pool or relax in chairs nestled on the bluffs. A club house and barbeque grills are also provided. Downtown Greenport is less than 2.5 miles from the resort. The Hortons Point Lighthouse is 7 minutes away.

- "Best trip" - "Amazing experience!" - "Went out east for a party. This was a very comfortable overnight stay that had everything we needed at a reasonable off" - "We like The Cliffside Resort so much, we are already looking to book our next stay." - "Clean, great value!" - "Great base to explore the North Fork!" - "We would, definitely, return. The resort was close to everything." - "Very good for family vacation"

1896 Restored Victorian located within steps to a lovely Bay Beach. Village restaurants, shops, NYC Hampton Jitney Express Bus and Shelter Island Ferry are all within a short stroll. Fresh produce farms, vineyards, hills and fields surround this very special place to rejuvenate your spirit and have fun. Fishing off the pier, sun bathing, swimming and people watching are all available within a two minute walk. Orient State Park is within a few miles and also offers nature lovers breath taking views of birds and marshes as well as the Long Island Sound. Also in Orient is a Sea Jet Ferry available to those who may want to enjoy the Mohegan Sun Casino in Connecticut across the Long Island Sound or travel north.

Private and spacious accomodations for four adults include two bedrooms each with a separate living space and a fully equipped kitchen and bath decorated in a casual antique pine style. Our charming second floor apartment is peaceful, perfect for two couples or a family.

2021 HVAC upgrade includes UV /HEPA airflow filtration. Exterior security cameras offer added measure of safety during your stay.

Typical Day : Easy to rise in the morning and have a cup of coffee in the garden ..take a stroll down to the beach and people watch.. come back..get ready for the day..

Leave the 'House'.. walk left toward the village and turn right on Clark Street ..now take a three block walk to the village along fourth street and the bay..enjoy the many restored village homes and the simple life..
So... are you ready to explore the village? The antique Carousel on Front Street..antique shops..maybe a cup of stronger coffee at Aldo's...
Stroll up and down Main Street..and Front Street and find your favorite shops/spots...Book, Toy, Cooking, Clothing......Art Galleries..Restaurants...Antiques...something for everyone.

- "We spent a wonderful 5 days in this beautiful home. John and Maritza are the most gracious hosts, offering recommendations and good cheer. The house is 1/2 block from the beach, or 1 block to the lagoon, which we also enjoyed. It is approximately a 15 minute walk or quick drive into town. The home is ideally situated. The kitchen was well-stocked with utensils, cookware and dishware; each bedroom has a sitting room/living room so there is plenty of privacy. Would love to return to this lovely home!"

Harbor Knoll Bed and Breakfast in Greenport provides accommodations with a seasonal outdoor swimming pool, a garden, and a bar. This beachfront property offers access to free Wifi and free private parking. Guests can make use of the sun terrace or the outdoor fireplace, or enjoy views of the sea and garden. Featuring a patio, the units offer air conditioning and have a flat-screen TV and a private bathroom with walk-in shower and bathrobes. Every room includes a coffee machine, while selected rooms are equipped with a fully equipped kitchen with an oven, a microwave, and a toaster. At the bed and breakfast, every unit includes bed linen and towels. A private beach area is available on-site and cycling can be enjoyed close to the bed and breakfast. Splish Splash is 26 miles from Harbor Knoll Bed and Breakfast. Long Island MacArthur Airport is 48 miles away.

- "Will be back to stay longer next time!" - "An ideal location to experience all that the North Fork has to offer" - "Very nicely luween who is the owner very nice room and pool can be improved and not a place for chil" - "Lovely stay in a beautiful home very close to the town centre"

Combine peace and quiet with bustling downtown action when you book this charming Greenport vacation rental! The 1-bedroom, 1-bath apartment sits on a peaceful side street right off of Main Rd allowing you easy access to unique shops, restaurants, and the Shelter Island ferry. With inviting decor, large windows, a Smart TV, and a fully equipped kitchen, this home is perfect for solo travelers and couples looking to explore all that Greenport has to offer. Plan your vacay your way - book now!

-- THE PROPERTY --

Greenport STR Permit 22-082 | Walkable Location | Free WiFi | 3 Blocks to Front St.

Ride the famous Antique Carousel, take a wine tour, or simply enjoy some R&R - the choice is yours when you book this delightful Greenport getaway!

Bedroom: King Bed

OUTDOOR LIVING: Front porch, lounge & rocking chairs
INDOOR LIVING: Smart TV w/ streaming capabilities, dining table
KITCHEN: Fully equipped, drip coffee maker, toaster, ice maker, microwave, stainless steel appliances, spices, dishware & flatware
GENERAL: Internet connection, A/C, central heat, complimentary toiletries, towels/linens, hair dryer
FAQ: Stairs required for entry, steep staircase, not childproofed
PARKING: Driveway (1 vehicle), safe street parking in front of house
ADDT'L ACCOMMODATIONS: An additional property is available on-site with separate nightly rates. If you would like to reserve both rentals, please inquire for more information prior to booking

-- THE LOCATION --

WINERIES: Long Island North Fork Wine Tours (0.5 miles), Kontokosta Winery (1.4 miles), The Old Field Vineyards (3.9 miles), One Woman Wines & Vineyards (4.5 miles), Sparkling Pointe (6.4 miles)
THINGS TO DO: Stirling Historical Society of Greenport (0.3 miles), Antique Carousel (0.4 miles), North Ferry to Shelter Island (0.8 miles), East End Seaport Museum and Marine Foundation (0.8 miles)
FOOD & BEVS (~0.5 miles): Greenport Harbor Brewing Company, Stirling Sake, SpecialTea House, 1943 Pizza Bar, Crazy Beans, Claudio's and Fortino Tavern, The Frisky Oyster
AIRPORT: LaGuardia Airport (91.7 miles)

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: This property may not be suitable for young children due to the steep staircase and lack of childproofing
- NOTE: The property requires stairs and may be difficult for guests with limited mobility
- NOTE: There is another bookable vacation rental on-site; other travelers may be present during your stay

- "Great place. Have stayed there before. Wonderful location and owner. Highly recommend!!!" - "Very good location, minutes away from all businesses but a quiet street. Clean, airy and roomy apartment. Great communication with the host" - "Great stay in Greenport. The hosts, accommodations are location are wonderful. Look forward to another visit." - "The hosts, accommodations and location were all wonderful. The house was clean, well decorated, comfortable and had all the amenities you would need. We really enjoyed our stay and would definitely recommend this place to anyone considering staying in Greenpoint."

17 miles from Long Island Railroad in Greenport, Bright Apartment - half Mi to Greenport Harbor! provides accommodations with access to a spa center. Guests staying at this apartment have access to a patio. Free Wifi is available throughout the property and Splish Splash is 26 miles away. The air-conditioned apartment is composed of 1 separate bedroom, a fully equipped kitchen with a dishwasher and an oven, and 1 bathroom. Towels and bed linen are provided in the apartment. For added privacy, the accommodation features a private entrance. Long Island MacArthur Airport is 48 miles away.

- "It was perfect" - "100% satisfied" - "Beautiful appartment close walk to everything" - "Lovely apartment, clean and updated, close to town, very easy to park and walk." - "Cozy and comfortable apartment" - "Excellent location.Easy to walk to town. Parking was on street and lots of it! HIGHLY recommend this great place! Great" - "Wonderful place to stay!" - "Beautiful, convenient apartment!" - "Loved Greenport & the surrounding area more fun than staying in a hotel"

The Property
Charming and newly updated second floor apartment, less than a 5 minute walk to downtown. Enjoy our incredible restaurants, shopping and more. Large living room with bay window, ample seating and flat screen TV, nicely equipped kitchen, large dining area for 6, and newly remolded bathroom.
Private entrance and laundry room included. Relax on the front porch, grill in private side yard reserved for our guests, enjoy the outdoor shower after your day at the beach.
This second floor apartment in our historic home has been updated while
maintaining the original wide pine floors and historic details. Windows are plentiful providing a bright and cheerful feel.

Location
The sparkling village of Greenport is a 5 minute walk away.
Restaurants and Shopping are steps away....
Greenport offers dining experiences from casual to upscale. You can enjoy fresh seafood, wood-fired pizza, delicious Latin American, new American, pub-style, sushi, mediterranean and more within walking distance. There are also tasting rooms for beer, wine and tea, as well as coffee shops and restaurants specializing in breakfast and lunch. Stop in at the galleries, boutiques and antique stores as you stroll to and from your dining destination
And be sure to make time for....

Other attractions within walking distance.
Enjoy Greenport's seaport by taking in the picturesque sites along the docks or in the historic neighborhoods. Be sure to visit the Seaport Museum, the Railroad Museum, vintage Greenport Movie Theater, the antique carousel, the fire fighter boat, and our beautiful century old public library.
If you'd like to explore beyond the village, you are also within walking distance to the ferry to Shelter Island (a beautiful10 minute cruise), the Long Island Railroad which allows you to take make a day trip to New York City or the Hampton Jitney also enables jaunts to the city or airports.

Other Local Amenities
Beaches, wineries, fishing, golf, charter boats, and hikes are all an easy walk, bike or car ride away.
Closest winery: 1.3 miles. There are 40 vineyards on the North Fork.
Closest golf course: 1.5 miles.
Closest State Park: Orient State Park (10 miles)
Beautiful maintained hiking trails: The North Fork offers many trails between Orient and Riverhead.
Charters: Both fishing and sailing charters are available within the village.
We are happy to provide information on these and other happenings in the area.

- "I highly recommend Eileen’s place! The location is fantastic, the apartment is very spacious and comfortable, and Eileen is a responsive and helpful host. A perfect stay" - "This spacious second floor rental was a perfect location for walking to downtown and a central starting point for exploring the North Fork. Having been our first visit to the North Fork, we felt lucky that we picked Greenport and the accommodations we chose. I was the liveliest of the area villages (making it a good home base) and we had the best, most attentive hosts we could hope for. The space was fresh and clean; the hosts provided special touches (wine, snacks, a folder that included information on all things to do in the area, kind notices, etc.), offered to supply whatever else we might need and to quickly take care of any incidents that may occur. We would definitely request to re-book the same address on future visits."

Charming Greenport Gem 1, 1 Mile to Ferry! offers accommodations in Greenport, 17 miles from Long Island Railroad. Free Wifi is available throughout the property and Splish Splash is 26 miles away. The air-conditioned apartment consists of 2 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 1 bathroom with a shower and a hair dryer. Towels and bed linen are available in the apartment. For added privacy, the accommodation features a private entrance. Long Island MacArthur Airport is 48 miles from the property.

Other • Child Friendly • Guest Services • Parking • Security/Safety • Fireplace/Heating • Sports/Activities • Accessibility • Internet

Surround yourself with seaside charm at this Greenport vacation rental. Perfect for couples and solo travelers, this 1-bedroom, 1-bath apartment has everything you need for a memorable New York retreat. Enjoy your morning coffee on your own little private porch before heading out to explore the bustling downtown area. Visit Front St. for scrumptious eateries and shopping, then take the ferry to Shelter Island where you'll find quiet beaches, nature preserves, and a laidback atmosphere. Book now!

-- THE PROPERTY --

Greenport STR Permit 24-068 | Free WiFi | Walkable Location | 1 Block to Greenport Harbor

Discover Greenport's rich maritime history, take a tour of regional wineries, and create a truly unique vacation experience from this delightful, no-frills coastal getaway!

Bedroom: Queen Bed

OUTDOOR LIVING: Porch, 2 chairs
INDOOR LIVING: 28" Smart TV w/ streaming capabilities, walk-in shower
KITCHEN: Well-equipped, drip coffee maker, toaster oven, microwave, spices, dishware & flatware, breakfast bar
GENERAL: A/C, central heat, complimentary toiletries, towels/linens, hair dryer
FAQ: Steep stairs, lead paint & not childproof
ACCESSIBILITY: Stairs required to access
PARKING: Street parking
ADDT’L ACCOMMODATIONS: An additional property is available on-site with separate nightly rates. If you would like to reserve both rentals, please inquire for more information prior to booking

-- THE LOCATION --

WINERIES: Long Island North Fork Wine Tours (0.5 miles), Kontokosta Winery (1.4 miles), The Old Field Vineyards (3.9 miles), One Woman Wines & Vineyards (4.5 miles), Sparkling Pointe (6.4 miles)
THINGS TO DO: Stirling Historical Society of Greenport (0.3 miles), Antique Carousel (0.4 miles), North Ferry to Shelter Island (0.8 miles), East End Seaport Museum and Marine Foundation (0.8 miles), Bike to Orient or Shelter Island (0.8 miles)
FOOD & BEVS (~0.5 miles): Greenport Harbor Brewing Company, Stirling Sake, SpecialTea House, 1943 Pizza Bar, Crazy Beans, Claudio's Restaurant, Fortino Tavern, The Frisky Oyster
AIRPORT: LaGuardia Airport (91.7 miles)

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: This property may not be suitable for children due to steep stairs, potential lead paint, and it is not childproofed
- NOTE: The property requires stairs and may be difficult for guests with limited mobility
- NOTE: There are 2 other bookable vacation rentals on-site; there may be other travelers present during your stay
- NOTE: Vrbo's 'Explore the area' section is auto-generated by Vrbo and does not best represent nearby attractions and restaurants. We recommend reviewing the content under 'About this property' and using the map for the most accurate area information

- "Very clean, quiet street with super local close to town. Host very welcoming!" - "Very nice spot for a couple to stay. Fully equipped and thoughtfully laid out. Comfortable bed. Updated in all ways. Exceptionally clean and well stocked. Very convenient to downtown and extremely walkable." - "Very nice, clean and convienent place to stay. Very comfortable." - "This is our fourth stay here! Wonderful efficient mini one bedroom With full kitchen and nice large bathroom. The apartment is in excellent shape and super super clean.Plus the host lives on site and is wonderful. Best part is how easy it is to walk straight into the heart of Greenport from the house, Just two blocks away.And he has 2 units here, so you can travel with friends, and both get your own unit in the same house.Highly recommend!"

Featuring a spa and wellness center, Quaint DT Greenport Apt - 2 Mi to Shelter Island! features accommodations in Greenport. Guests staying at this apartment have access to a patio. Free Wifi is available throughout the property and Splish Splash is 26 miles away. The air-conditioned apartment is composed of 1 separate bedroom, a fully equipped kitchen with an oven and a toaster, and 1 bathroom. Towels and bed linen are offered in the apartment. For added privacy, the accommodation features a private entrance. Long Island MacArthur Airport is 48 miles from the property.

Spa • Accessibility • Parking • Other • View • Security/Safety • Internet • Fireplace/Heating

PLEASE READ

Please park in the street when arriving as many spots along the streets are available.

Laundry + Dryer is only available for reservations over 7 days (1 week).

Newly Renovated 2BR Apartment House - 1st Floor
Private Entrance - Full Apartment House

No pets
No shared space
Separate entrance
Close to wineries and transportation S92 bus, Hampton Jitney, Long Island/North Fork/Connecticut Ferries, restaurant and beaches!

Check-in is anytime after 3PM
Check-out at 11AM

Single Apartment Includes 2 Bedrooms, Living Room, Kitchen and 1 Bathroom - WiFi and Cable is also Included as well as a 42"+ TV - Fully Renovated at Jun 2016 - Walk-able to Restaurants, Bars, Beaches, and more - Close-by to Ferries - Duplex - Apartments are very family-friendly and fully furnished - Owners are very friendly - Beaches are nice - Weddings, Couples, Family Vacations packages are available

- "Went with my adult daughter. Nicer to have 2 bedrooms as opposed to one hotel room. Very clean, plenty of toiletries, excellent shower, comfortable beds. Extremely convenient location, able to walk to center of Greenport in a few blocks. Would recommend" - "Great location, clean, well stocked. Thank you for a great stay." - "Great location- a short walk to the restaurants, shops, and activities of Greenport, NY, a lovely seaport community. This first floor unit of a two family house was efficient and clean. We heard nothing from the upstairs occupants.The owner supplied us with everything we needed. Even though the houses on the street are somewhat close together, the neighborhood was quiet and the surrounding properties were well maintained. After a small communication snafu when we first arrived, our stay went flawlessly. I would rent this unit again."

North Fork Cottages & RV Resort in Greenport provides accommodations with a seasonal outdoor swimming pool and a garden. With free private parking, the property is 25 miles from Splish Splash and 16 miles from Long Island Railroad. Outdoor seating is also available at the campground. Some units are air conditioned and include a seating and/or dining area and a flat-screen TV. At the campground, the units include a private bathroom. Westerly State Airport is 45 miles from the property.

Parking • Pool • Security/Safety • View • Other • Child Friendly • Air Conditioner

FALL 2025 AVAILABILITY!

Looking to escape the city for a couple of weeks or even a month? The house is well set up for working remotely and we are pet friendly!

We value inclusion and respect and happily welcome guests of all backgrounds.

A cozy getaway in the heart of the Village of Greenport. 2 Bedrooms and 3 baths, sleeps 6 adults. On a quiet street with very little through traffic.

Living Room with flatscreen TV and cozy seating (includes full sofa bed). Spacious dining room perfect for enjoying leisurely meals. Well stocked kitchen with large island for cooking or hanging out.

Bedroom 1 (also has a small room attached): Queen bed
Bedroom 2: Queen bed
(There is also a full sofa bed sleeping 2 in the living room.)

Bathroom 1: Tub & Shower
Bathroom 2: Shower
Bathroom 3: Tub

Wi-Fi available. Apple TV. DVD player.

Large backyard with a swingset for the kids. BBQ grill for your use. The home has a lovely side porch perfect for morning coffee or evening cocktails.

Two week minimum stay.

- "Great house for a small family. We had a great time. There was an issue with the hot water heater one morning, but Jen was easy to get ahold of and the problem was fixed in no time!" - "Great location in great destination. Perfect host. Very well equipped kitchen. Only negative is a lack of a guest bath on second floor." - "Just got home from a two night stay at this property. I almost don’t want to give it 5 stars, because I want it to be my secret. The house is absolutely adorable, but unlike a real estate listing, that doesn’t mean small. Located on a quiet residential street just two short walkable blocks from town, the house is equipped with everything you could possibly need for a stay of any length. The house is beautifully decorated, clean, comfortable, with a deep, private yard, and a porch swing you will not want to get out of. After one night, you will wish it were YOUR house. Couldn’t recommend it any more enthusiastically. I will be back."

Beachfront Greenport Villa offers accommodations in Greenport, 23 miles from Splish Splash and 14 miles from Long Island Railroad. The vacation home features both Wifi and private parking free of charge. The air-conditioned vacation home is composed of 3 separate bedrooms, a living room, a fully equipped kitchen, and 3 bathrooms. A flat-screen TV is featured. The accommodation is non-smoking. Long Island MacArthur Airport is 45 miles away.

Child Friendly • Internet • Security/Safety • Parking • Air Conditioner • Barbecue/Outdoor Cooking

Designed and built in 2003, this cozy house has water views of Peconic Bay, enormous glass skylights, fully equipped kitchen, two bedroom, two bath, washer, dryer, Wifi, flat screen tv, private rose garden, outdoor studio/bedroom, private parking, a kayak, bicycles, public swimming dock at end of block, and is one block from the charming seaside village of Greenport, NY. We are located 95 miles east of New York City on Long Island's North Fork with 5 minute walking access to NY city bus and train. Great small restaurants & a terrific micro brewery are 1/2 block away.

- "House was compact, modern house filled with art & light. Lots of windows & sliding doors with screens leading to front & back patios. Small private backyard with table, chairs & umbrella. Open concept living, dining, kitchen, bedrm & bathrm on ground floor. High ceilings in living & dining areas. House clean & well stocked. Property on lovely street about 11/2 blocks to town & shops. Great vac rental." - "I put a lot of stock in guest reviews, and they were on point for this listing! The house is even better than it appears in the photos. It is incredibly bright and cheerful, and it is so charming to stay in a place with such a sense of personality and history. You can tell that it is a much beloved home. It is full of wonderful art; my personal favorite was the huge, medieval city (?) sketch (watercolor?) in the darling studio. The location truly can’t be beat: on a gorgeous, tree-lined, friendly, PEACEFUL street, with a beautiful view at the bay dock - and yet just steps away from multiple good restaurants, and just around the corner from the main drag, with many more restaurants and shops. The host was very easy to communicate with, as was access to the house. One thing I really loved that isn’t mentioned or obvious from the pictures is that the backyard has really good visual privacy. I always feel weird when I’m sitting on a patio and can be seen by neighbors. Not here! FYI to future guests: the second bedroom (with the full-size bed and the futon) - along with the second bathroom with shower stall - is up the stairs in a beautiful, airy, bright loft with no door or walls fully separating it from downstairs. As such, most of the space has decent visual privacy, but not sound privacy, with the downstairs open common area (kitchen, dining, living, foyer, hallway to downstairs primary bedroom). Didn’t bother us but mentioning for those who may need to know."

Newly renovated and charming home in the NorthFork, a short walk to the village of Greenport, vineyards, and the breathtaking 67 Steps beach, among other local attractions. Spend an afternoon or evening entertaining your friends at the home's outdoor oasis complete with a year-round hot tub.

The home features two bedrooms with queen beds. There is also an air mattress / rollaway twin bed if needed.

This is a perfect stay for a small family, two couples or a small group of friends.

Backyard party deck complete with year-round hot tub, enclosed outdoor shower (seasonal), built-in grill, outdoor bar, giant table plus lounge area.

The interior features a beautiful dining/sun room plus state-of-the-art kitchen with stainless steel appliances, washer & dryer, A/C, music sound-system, TV and more.

This home has all the North Fork has to offer for a summer, autumnal or winter getaway.

Inquire within for monthly rental rates.

- "We loved our stay here. Such a nice house and it was so close to Greenport’d downtown, beaches, and the Shelter Island Ferry. The back yard was such a great place for the kids too!" - "We loved our stay in Greenport for a long weekend! The back yard is undersold in the photos. It’s a gorgeous oasis and great place to relax, the hot tub was amazing. Adam was very responsive and made sure we got in okay and didn’t have any issues. We are already planning our next trip back!"

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney.

My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

This property has two apartments. The Sandpiper Apt. 1 and Aqua Vista Apt.2 (see listing on VRBO website that can accommodate 12 people when available at the same time for larger families and wedding parties. (PLEASE NOTE - that outdoor BBQ and is only available from April to November.)

- "Fun and relaxing " - "My husband & I have spent every year in the greenport / shelter island area for our anniversary. Unfortunately, my husband suffers from a rare diagnosis which recently left him homebound. Twice now, we have stayed at the Sandpiper and hope to stay there for many years to come! This is our 1x / year excursion that we both look forward to knowing that our stay will be perfect here. It's the perfect location, beautiful home, always clean and the host is always so communicative and flexible to your needs. We truly appreciate all the thought they have put into their property and your experience there. We can't say better things about this spot - def choose the Sandpiper if you want a seamless experience, great location & positive experience. Looking fwd to staying again next summer!"

Travel to the North Fork of Long Island for a much-needed getaway and experience both modern luxury and historic desire at this 2-bedroom, 1-bathroom vacation rental! Situated in the heart of Greenport, this apartment provides an updated interior, historic feel, a fully equipped kitchen, and a walkable location near town attractions. Take the ferry to Shelter Island and enjoy a day on Shell Beach. Explore Orient Beach State Park and grab a glass of wine at a vineyard on the way back.

-- THE PROPERTY --

2nd-Floor Apartment in Historic Home | Walk to Downtown Boutiques & Restaurants | Near Beaches

Bedroom 1: Queen Bed | Bedroom 2: Full Bed | Living Room: Queen Sleeper Sofa | Additional Sleeping: Pack ‘n Play

APARTMENT FEATURES: 3 flat-screen TVs w/ cable, dining table, laptop-friendly workspace, garden
KITCHEN: Stainless steel appliances, dishwasher, cooking basics & spices, Keurig coffee maker, blender, toaster, tea kettle knife set, dishware & flatware
GENERAL: Free WiFi, central A/C, linens & towels, central heating, complimentary toiletries, trash bags & paper towels, hair dryer, hangers, self check-in
FAQ: Ring Doorbell device (facing front door entry), quiet hours (11:00 PM-8:00 AM), no porch access, addt'l rental on-site (separate unit & entrance)
ACCESSIBILITY: Stairs required for access, entire 2nd-floor unit
PARKING: Street parking (first-come, first-served), no driveway parking
ADDT’L ACCOMMODATIONS: An additional 1-bedroom property for 4 guests is available on-site with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to booking

-- THE LOCATION --

THINGS TO SEE + DO: Antique Carousel (0.4 miles), East End Seaport Museum & Marine Foundation (0.7 miles), The Fire Fighter (0.7 miles), Ferry to Shelter Island (0.7 miles), Railroad Museum of Long Island (0.7 miles), Horton Point Lighthouse Nautical Museum (5.5 miles)
OUTDOOR RECREATION: 67 Steps Beach (1.1 miles), Norman E. Klipp Marine Park (1.8 miles), Crescent Beach (2.7 miles, accessible by ferry), Truman’s Beach (4.0 miles), Mashomack Preserve (6.4 miles, accessible by ferry), Shell Beach (6.4 miles, accessible by ferry), Orient Beach State Park (10.4 miles)
WINERIES + BREWERIES: Greenport Harbor Brewing Company (0.3 miles), One Woman Winery Greenport (0.4 miles), Kontokosta Winery (1.2 miles), The Old Field Vineyards (4.0 miles)
AIRPORTS: Long Island Islip MacArthur Airport (44.0 miles), Laguardia Airport (90.9 miles), John F. Kennedy International Airport (91.9 miles)

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: This apartment is an entire 2nd-floor unit of the building and requires stairs to access
- NOTE: There is an additional rental unit on-site with a completely separate entrance
- NOTE: Your safety matters. This property features a Ring Doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device (including devices linked to the camera such as the alarm system’s motion detector) or when the video doorbell button is pressed
- NOTE: Please observe quiet hours between 11:00 PM to 8:00 AM
- NOTE: The porch is not available for guest use

- "This home was gorgeous inside and out. Every time we walked through the garden, we were so happy. The unit was extremely clean and nicely appointed. It was a beautiful and quick walk into town; within a block, you’re hitting restaurants and stores. The kitchen had everything we needed and there were extras of everything (paper goods, towels, blankets, etc!). Nice to have smart TVs in each room too. Toni and Frank were kind, responsive, and generous hosts."

Enjoy this beautifully renovated first floor “Captains House” apartment in the heart of Greenport Village. Harbor Views! Walk to town.

This 2 bedroom, 2 full bathroom home is bright with sunshine, has soaring ceilings and hard wood floors, easy to maintain for beachside living.

Gourmet kitchen - top of line appliances

- "This historic house is completely renovated inside. We easy and comfortably fit 2 adults and 4 children. The beds and bedding were fresh and cosy. z the house was clean. A quick walk to all Greenport has to offer." - "Pristine beautiful property. Loved the bedding and decor. Walked into GreenPort. It was lovely." - "Clean, large, modern, great shower pressure. The owner was quick to respond throughout. Thank you!!" - "Cute little apartment. Great location and very helpful and accommodating host. Thank you for having us."

Luxury 2 bedroom, first floor apartment located across the street from Townsend Manor Marina in the heart of Greenport Village . Walk to town and enjoy the amazing restaurants and shopping that Greenport has offer. This custom Victorian Farmhouse has been fully renovated with all modern amenities.

The custom gourmet kitchen has a sub zero refrigerator, Wolf stove, farmhouse sink. Gas grill located outside where you can enjoy evening dinner under the stars.

You will find 2 Flat screen SMART TVs. There is Wifi throughout the house.

The large wrap around deck is the perfect spot to have your coffee or glass of wine with marina views and great people watching.

The first floor apartment is bright with sunshine and hard wood floors. Easy to maintain for beachside living.

The airy master bedroom has a Samsung smart flat screen TV. Enjoy a great nights sleep on the temperdic King Size bed.

The guest bedroom has a queen size bed as well as a gorgeous wood barn door.

There is a full bathroom, laundry in the apartment and an outdoor shower in the private backyard.

The driveway can fit 3 cars and the home has plenty of public parking in front and behind.

This apartment has it all. Under 1 mile from the fifth street public beach. 1/2 mile to the Commuter station - train, bus, ferry is located walking distance to restaurants, shopping and bars. Close to wineries

- "The house was beautiful, spacious and very comfortable! The beds also were super comfortable, which is so important for a few nights away from the kids when sleeping in is one of the luxuries! :) The house was well stocked, clean and in a convenient location! Very close to town and also not far from a lot of the wineries. It made for a very memorable 40th birthday getaway with friends. I would definitely return!" - "I stayed in the house with my family for a long weekend. The house was a quick walk to town and short drive to the beach. The house looked as pictured. The host answered all our questions with quick and helpful replies! The house is newly renovated but still has the charm and noises of an old house."

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney.
Aqua Vista is the second floor apartment with a separate entrance.
My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).
This property has two apartments. The Aqua Vista Apt.2 and The Sandpiper Apt. 1 (see listing on VRBO website that can accommodate 12 people when available at the same time for larger families and wedding parties

- "Great spot for all things North-Fork" - "I was looking for a quiet, enjoyable place near the water and got just what I was looking for. My visit was during the off season early in the week so there wasn’t much to do in town but that was exactly what I was looking for. Really enjoyed it and look forward to returning in the future." - "What a great little spot in a great little town. The location couldn’t be easier and convenient. The train is literally across the street and Main Street a 5 min walk to the water and shops! The Apt is clean, well appointed, and so comfortable. This was a real find!!"

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney.

My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).
The space
The house has been completely renovated and everything is brand-new.
Everything is walking distance to the house and the location is unbeatable.

This property has two apartments. The Blue Bay Dream Apt.1 and Harbor Heights Apt. 2 (see listing on VRBO website that can accommodate 12 people when available at the same time for larger families and wedding parties

We have recently added new amenities to the VRBO rental Apartment 1 that you would occupying. In the backyard, the blue garage has been converted to a cabana, which includes two televisions, lounge area with a wet bar, refrigerator, game area for the kids and a home office work station with a full size convertible bed in the cabana section and a queen size futon in the home office work room. Wifi is available in the cabana and office. As a bonus, there is a 5 person jacuzzi outside with complete privacy. (PLEASE NOTE - that outdoor BBQ and jacuzzi are only available from April to November)

- "As described, Nice little rental very close to GPV. Clean, Well maintained place. Had the good fortune of meeting the owners, very good people. Would stay here again." - "Thanks Christopher! Great location! Only a few minutes walk from Greenport’s Main Street and the Fifth Street beach The house was nicely furnished and clean Felt like a hone away from home" - "Great communication from the owner. Comfortable apartment. Walking distance to town. Apartment is well-appointed with comfortable beds, plenty of towels, soap/shampoo, pretty much all you need for a stay. Street parking was easy."

This condo is one of the nicest decorated in Cliffside. Gorgeous shiplap walls with navy accents. It has a beautiful fireplace, new deck and much more. This unit has the capabilities to be handicap accessible. The master bathroom has a queen size bed and private bath. The second bedroom has 2 twins and also a private bath. The sectional in the living room opens up to a full sleeper making this condo able to sleep 6 people. All rooms have flat screen tv's.
Being on the property of the Cliffside Resort makes this an excellent choice for a getaway. There is a heated pool and clubhouse on property. They have Bar-B-Q's for your use. This resort is located on the Long Island Sound and equipped with lounge chairs for your use. The Cliffside Resort has many activities morning yoga on the lawn, movies under the stars and much more.

The town of Greenport is less than a 5 minute drive. Greenport has many restaurants, shops and activities. Being on Long Islands north folk you only minutes away from the wineries.

- "Great location and value for being in Greenport" - "Great place for a long weekend getaway. Nice views. Perfect location for Greenport and wineries. Will definitely want to come back. Good communication with host. " - "Beautiful place with water views, casual outdoor seating, and minutes to restaurants/wineries/breweries. Google maps had the address a little off but be sure to follow directions/location on the listing you will be all set "

Discover this marvelous 2-bedroom gem in Greenport. This cool apartment boasts a cozy living room with a phenomenal sofa bed, perfect for extra guests. The bedrooms offer a comfortable queen bed and a full bed, ensuring a restful night's sleep for all. With amenities like a washing machine, hair dryer, AC, heating, iron, and WiFi, you'll have everything you need for a delightful stay. The bathroom is equipped with a hair dryer for your convenience. This newly renovated 2 family home is in walking distance to all the restaurants, bars, shopping, coffee shops, Shelter Island Ferry, Log Island railroad and Hampton Jitney.
Guests are 4 blocks from the local beach which provides parking at no cost. Beach chairs and umbrellas are provided in the backyard. Washing Machine and Dryer are located in basement. Enjoy your time in Greenport at our apartment.

This property has two apartments. The Blue Bay Dream Apt. 1 and Harbor Heights Apt. 12 (see listing on VRBO website that can accommodate 12 people when available at the same time for larger families and wedding parties

Harbor Heights is the second floor stair walk up apartment.

- "We had an absolutely wonderful stay in this apartment - it is cozily decorated, spotlessly clean, the kitchen is extremely well stocked (Keurig machine with K cups - for all the coffee fiends like us 😁 - plus anything else we needed), the hosts thoughtfully left lists of recommendations and sightseeing and food along with all the local papers, and the location is unbeatable - a short walk to Greenport town, the marina, and the beach. We were four adults and two kids and we slept comfortably between the two bedrooms + sofa bed in the living room. Highly recommend this stay and looking forward to visiting again! THANK YOU to our hosts!"

This 2-bedroom house in Greenport with modern amenities for stylish uncluttered living. Perfect for a small family or couples and conveniently located in a quiet neighborhood near town, park and beach.

- "The house was spotlessly clean and well-maintained, making me feel comfortable right from the start. The location was perfect—local attractions and great restaurants, which made exploring the town very convenient. Walter was incredibly responsive and accommodating, always quick to reply to any questions or requests. Overall, I highly recommend this home for a friendly and hassle-free stay!" - "Our family were completely overjoyed by our week in this beautifully decorated and updated farmhouse. Sitting on the porch, grilling in the backyard, strolling to the beach and walking into Greenport were all this gem offers and much more. Couldn’t be happier with the communicative host. Highly recommended. "

Lovely Victorian home with private entrance, porch, and brick patio. Floor to ceiling windows in light filled large bedroom with en suite bathroom. Cozy den has a beautiful bay window and a queen size pull out sofa bed for additional guests. Sunny sitting room just off of the kitchen for reading or games. Full kitchen, washer dryer, high speed internet, brand new flat screen TV can be found in the unit. The West Elm king size bed, mattress and sofa bed are all new.
No car needed as the train station, fantastic restaurants, bars, shops and Shelter Island ferry are less than half a mile walk from the house.
Enjoy all that Greenport and the North Fork have to offer from this amazing location!

- "Great spot! Great location! Lots of room - especially loved the little porch with swing! Highly recommend!" - "huge flat, very bright and clean. plenty of kitchen and bathroom supplies. easy check in and check out, plenty of parking space on the street in front of the house. very pretty, quiet and safe neighborhoods (i’m travelling solo). lovely town of Greenport within walking distance as well as 2 beaches and a big park. i loved it! thank you Kevin and Laura"

Rental Permit 1063 Live the perfect life with a new Pied a Terre on the North Fork in Greenport. This lovely one bedroom apartment has everything you need for a getaway of any length. Well appointed furnishings, walking distance to the beach and village too. Your home has its own washer and dryer too!
Explore the Village of Greenport and the harbor and all of the North Fork wine country.
Minimum stays required as per Southold Town Code
Rental Permit 1063

- "Has all you need for a comfortable stay in a good location. Walk 10 minutes to the beach or 15 minutes downtown. 10 minutes to a wonderful winery." - "Nice clean comfortable place to stay. Convenient to Greenport and area attractions." - "Very clean and close to Greenport." - "Great place very clean ! They left lots of options to eat in the area as well! I would only wish there was a full length mirror and a tv in bedroom, other then that I would def stay here again !!!"

The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scenery, and return to a memorable and comfortable room at the end of your day. The boutique hotel features eleven suites, including two, double-bedroom apartments.

Our guests pay a resort fee of $30 per night, including additional taxes at check in.
For those looking for a cozy stay at our hotel, we have just the room for you! Room 7 is our only Petite King Room, making it our smallest king room available. This room is perfect for those who pack lightly and would prefer to spend their stay exploring the Village of Greenport and its surrounding diversions. Don’t underestimate the luxuries of this room though! After a day of wine tours, shopping and enjoying local cuisine, return to Room 7 and relax on your king sized bed wrapped in our Frette robes, pour yourself a cup of espresso from your in-room espresso machine and enjoy your favorite television shows. All of our rooms come with a fully stocked mini-bar and mini-fridge, Smart TV, glass shower door, iron, ironing board, hairdryer and Maison Margiela amenities. Each room has robes, Frette beach towels, and heated floors to make your stay as comfortable as possible. We also provide a Nespresso machine with complimentary coffee. If there is anything else you need, please let us know!

Please note: In order to access this room, you are required to climb one flight of stairs — But don’t worry! We only have a maximum of 2 floors at this hotel. Free public parking is on the streets surrounding our hotel. We highly recommend parking on Bay Avenue, which is perpendicular to Main Street and has direct access to Sterling Square. Guests can shop, eat, drink, and spend the night—all within arms’ reach! Stirling Square can be quite lively at night; please consider this before booking.

- "We thoroughly enjoyed our stay!" - "Great room - super clean- and in a perfect spot for exploring. Hosts were excellent and the stay was more than comfortable." - "An Event was being hosted by the hotel, limited the access to food and bar area. Virtually no parking available at night, got out early to move from bank parking lot. Breakfast not available til 9am, had to request earlier, 8:30 Best they could do. Bath towels , only 1 facecloth, fixed upon request. No microwave Overall disappointed for the price. Great town and location for what we needed. This walls, sound traveled from adjoining room "

Please note that a reservation for this property needs to be approved before it is confirmed.

Greenport Coastal Retreat

Modern home in Greenport, close to beaches, outdoor dining, perfect for families

2BR/1.5BA: modern kitchen, outdoor deck, outdoor dining, gas BBQ, walkable to beaches, fenced in yard

Nestled in the charming village of Greenport, this modern and updated home offers a luxurious escape for sophisticated travelers seeking relaxation, adventure, and the ultimate North Fork experience. Ideally situated on a private block, this stunning two-bedroom, one-and-a-half-bathroom retreat comfortably accommodates up to five guests. Its prime location is just moments from the towns renowned beaches, parks, and wineries, making it the perfect haven for couples, families, or small groups looking to unwind in style.

Upon arrival, guests are welcomed by a beautifully landscaped property that offers total privacy. A fully fenced-in backyard provides a serene oasis, complete with multiple seating areas designed for both quiet morning coffees and lively evening cocktails. The expansive deck features an elegant outdoor dining setup, where guests can savor farm-to-table meals or enjoy a glass of local wine under the stars. A gas BBQ invites effortless al fresco dining, while the lush greenery and peaceful ambiance create the perfect backdrop for memorable gatherings. For those arriving by car, the home boasts ample free parking, ensuring a stress-free stay.

Step inside to discover an inviting open-concept living space bathed in natural light. The airy and thoughtfully designed floor plan allows guests to flow effortlessly from one area to the next. The spacious living room features a plush, oversized sectionalideal for cozy movie nights or afternoon reading sessions. Adjacent to the living area, a charming breakfast nook provides a delightful spot to sip morning espresso. The sleek, fully equipped kitchen is outfitted with modern appliances, a coffee maker, and all essential cookware. Whether preparing a gourmet meal or a simple snack, every culinary need is met. The stylish island and adjacent dining space are perfectly suited for hosting intimate dinners or casual brunches with friends and family. High-speed Wi-Fi, central air conditioning, and the convenience of a washer and dryer ensure a seamless and comfortable stay.

Guests will find two beautifully appointed bedrooms designed for rest and rejuvenation. The primary bedroom exudes elegance with its plush queen size bed, fresh linens, and thoughtfully curated decor. The second bedroom features full size bunk beds, making it ideal for families or close friends. Each room is equipped with ample storage and soft lighting to create a warm, restful ambiance. The renovated full bathroom boasts modern fixtures, fluffy towels, and all the essentials needed for a refreshing start to the day. A convenient half-bath adds an extra touch of practicality to this well-appointed home. For some extra sleeping space, there is a foldable murphy style bed available in the den.

Beyond the comfort of the home, guests will find themselves in the heart of Greenports vibrant coastal scene. Just a short walk away, an array of charming boutiques, art galleries, and award-winning restaurants await. Stroll along the historic streets and discover local favorites like Noahs, The Frisky Oyster, and Little Creek Oyster Farm & Marketeach offering an unforgettable dining experience. For those eager to explore the area's natural beauty, the pristine beaches of 67 Steps and Inlet Point Park are mere moments away, perfect for sunbathing, paddleboarding, or simply taking in the breathtaking waterfront views. Wine enthusiasts will delight in the proximity to North Forks acclaimed vineyards, including Kontokosta Winery, where they can indulge in tastings while admiring sweeping Long Island Sound vistas. Whether its biking through the scenic countryside, embarking on a sailing excursion, or perusing the bustling farmers' markets, this exceptional retreat offers something for every traveler.

This property has a max occupancy of 5

Bedrooms

Bedroom 1 - Primary: One Queen Bed, 2nd Floor, Air Conditioning, Streaming TV, Standard Closet

Bedroom 2 - Bunk Beds: One Bunk Bed, 2nd Floor, Air Conditioning, Streaming TV, Standard Closet

Den - Foldable Bed: One Murphy Bed, First Floor/Main Floor, Air Conditioning, Streaming TV, Privacy

Bathrooms

Bathroom 1 - Half: Half Bath, First Floor/Main Floor

Bathroom 2 - Full: Full Bath, 2nd Floor, Shower/Tub Combo

TVs

Bedroom 1 - Primary: Streaming

Bedroom 2 - Bunk Beds: Streaming

Den - Foldable Bed: Streaming

Outdoors
Deck/Patio (Uncovered), Grill (Gas), Patio Furniture (Table, Chairs, Umbrella), Fence Around The Yard

Amenities
Bed Linens, Air Conditioning (Central Air), Dryer, Heating, Internet (Wifi), Washer, Living Room, Parking, Bath Towels, Microwave, Coffee (Pot), Dishes and Silverware, Pots and Pans, Toaster, Television (Main Living Room), Private Entrance, Kitchen, Carbon Monoxide Detector, Smoke Detector, Hot Water, Refrigerator, Oven, Stove, Dishwasher, Smart TV, Ice Maker, Laptop-Friendly Workspace, Essentials

Location

Nearby Beaches:
67 Steps Beach
Sandy Beach

Nearby Grocery Stores:
IGA Greenport

Nearby Restaurants and Bars:
Claudio's Waterfront
Lucharitos
Greenport Harbor Brewing Company
Kontokosta Winery

Other Location Information:
Inlet Pond County Park

Suitability: Primary renter must be at least 21 years old.

Pet Policy: One dog of 50 lbs or less is permitted for an additional $250.00 per booking. Dogs over 50 lbs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire).

Utility Disclaimer: Utility fees are included in the total rental amount. Guest shall be responsible for the costs associated with excessive usage of utilities during the term of the Reservation.

Cleaning Disclaimer: One light cleaning per every seven (7) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense.

Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed.

Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking.

Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Marquis will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners'). Should Marquis be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Marquis is notified in writing 72 hours or more prior to the start of the reservation.

Note: All payments must be made prior to check-in.

VRBO charges the guest directly for their service fee and applicable taxes, while StayMarquis charges separately for the rental rate. As a result, you will see two separate charges at the time of booking-one from VRBO and one from StayMarquis.

If there is a second installment, it will be collected directly by StayMarquis shortly after the first installment.

Payment Method: Balance payments made with credit card are capped at $3,500. Payments over $3,500 shall be made by check, ACH or wire.

Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $5,000 of damage protection. Coverage details are provided in the booking agreement.

The guest experience for this property is managed by StayMarquis, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property.

Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

- "Great place"

Beautifully appointed townhouse in coveted Stirling Cove Condominiums. Enter a light filled room with magnificent views of the cove and bay. Featuring newly renovated, spacious kitchen, dining room, elegant living room with wood burning fireplace, water view deck, and powder room. Second floor has master bedroom suite with expanded, renovated bath and private water view balcony. A guest room with private bath and laundry complete the floor plan. Unit comes with a private boat slip in the protected basin with easy access to the cove and bay. Complex offers heated in-ground pool, tennis courts, private beach - all just a short walk to Greenport Village restaurants, shopping, and grocery. Near Islands End golf course and access to all that the North Fork has to offer. Full-time on-site management. Inquire with host for reduced rates or one month stay or longer summer specials.

- "Perfect location, very easy communication with Anita, clean and comfortable condo - loved every minute of our stay!"

North Fork living doesn’t get better than this. Enter to stunning waterfront views from every corner of this unique, light-filled, freestanding corner unit, just a short walk from historic Greenport’s shops, restaurants, and waterfront.

Experience spectacular sunrises from the upstairs bedrooms, watch an endless parade of boats on the upstairs or downstairs deck overlooking Peconic Bay. Prepare fresh, farmers market cuisine in the fully remodeled kitchen. And bask in the amenities of our private community, including an award-winning, waterfront pool, two tennis courts, and a designated boat slip.

The home includes a pull-out queen-sized couch, a king-sized guest bed, and a queen-sized bed in the master bedroom, where a vaulted ceiling and a wall of glass deliver an airy, relaxed vibe.

One of just two corner units in all of Stirling Cove, this home offers some of the best views you'll find in the area. It’s your perfect home base for days exploring Shelter Island, Orient, and all the wineries and farm stands the North Fork has to offer.

We are not allowing pets; however, if you have a small pet (under 10 lbs.) there will be an additional fee of $35 p/night.

Also, if A/C is used, there will be a fee of $100 for the entire stay.

Additional guests (more than two adults) will be charged an additional fee of $100 p/guest p/night.

- "I had a wonderful stay at Carole’s property. The home has everything you need and the views of the water, boats and beach are absolutely amazing. Carole was very pleasant, responsive and answered all questions almost immediately. The pool and grounds are impeccably kept. There is also a fireplace which would be lovely in the winter. You can walk right to downtown Greenport for shopping, food and sightseeing. It was an amazing stay and I will be back."

Ranked #1 AirBNB. Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney.

My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

The space
The house has been completely renovated and everything is brand-new.
Everything is walking distance to the house and the location is unbeatable.

We have recently added new amenities to the Airbnb rental that you are occupying. In the backyard, the blue garage has been converted to a cabana, which includes two televisions, lounge area with a wet bar, refrigerator, game area for the kids and a home office work station with a full size convertible bed in the cabana section and a queen size futon in the home office work room. Wifi is available in the cabana and office. As a bonus, there is a 5 person jacuzzi outside with complete privacy. (PLEASE NOTE - That the jacuzzi and outdoor BBQ are only accessible from April to November.)

Guest access
We have recently added new amenities to the Airbnb rental that you are occupying. In the backyard, the blue garage has been converted to a cabana, which includes two televisions, lounge area with a wet bar, refrigerator, game area for the kids and a home office work station with a full size convertible bed in the cabana section and a queen size futon in the home office work room. Wifi is available in the cabana and office. As a bonus, there is a 5 person jacuzzi outside with complete privacy. (Please Note That Jacuzzi and Cabana are only accessible from April to November.)

Other things to note
This property has two apartments. The Blue Bay Dream Apt.1 and Harbor Heights Apt. 2 (see listing on AIRBNB website that can accommodate 12 people when available at the same time for larger families and wedding parties

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney.

My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Other things to note
This property has two apartments. The Aqua Vista Apt.2 and The Sandpiper Apt. 1 (see listing on AIRBNB website that can accommodate 12 people when available at the same time for larger families and wedding parties

Cleaning products • Body soap • Bathtub • Outdoor shower • Shampoo • Hot water • Conditioner • Shower gel • Hair dryer • Washer

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney.

My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Other things to note
This property has two apartments. Harbor Heights Apt. 2 andThe Blue Bay Dream Apt.1 (see listing on AIRBNB website that can accommodate 12 people when available at the same time for larger families and wedding parties

Cleaning products • Washer • Dryer • Conditioner • Shampoo • Bathtub • Body soap • Shower gel • Hair dryer • Hot water

Welcome to The Greenport Suite! With its separate entrance, secluded outdoor patio space and ideal location, this newly-redesigned private suite in our contemporary Village home is perfect for enjoying a North Fork getaway. We are located just a few short blocks from bay beaches, the harbor, and public transport, while the area's celebrated wineries are a short drive or bike ride away. Come see why Forbes named Greenport one of the 11 prettiest villages in the United States!

The space
Your private suite with its own entrance is part of our contemporary home in the heart of Greenport Village. Your personal area of the house is separate from ours and completely your own. It includes a comfortable bedroom, a brand new bathroom with a gorgeous shower and Jolie shower head, a spacious entryway, plus a separate coded entrance to come and go as you please, as well as a private outdoor patio space. The guest suite also features a Keurig coffee machine for that first cup of the day, a kettle if you're a tea-drinker, filtered water, plus a built-in mini fridge to keep your rosé suitably chilled. Freshly-laundered towels, clean linens, high-quality toiletries and toilet paper are also provided. You will also have use of wifi, an iron and a hairdryer.

Guest access
Once you key into your suite using the coded lock, you will have access to a delightfully furnished queen-sized bedroom looking out to a private patio, a brand new bathroom with a gorgeous shower, and a spacious entryway area. Your suite is closed off from the rest of the house, affording you a space that is completely your own.

Other things to note
Our neighborhood is close to all the action, yet tranquil and friendly. We value our neighbors, and hope you do too. Please respect their peace and privacy (i.e., no parties, etc.).

In these uncertain times of Covid-19, please rest assured that the suite, in addition to being completely private, allows you to remain six feet away from us. Additionally, we have equipped our home with hospital grade HVAC filters and are taking extra care to disinfect anything a guest might touch, such as light switches and doorknobs.

Shower gel • Hot water • Bed linens • Body soap • Hair dryer • Shampoo • Conditioner • Cleaning products • Essentials • Hangers

Fully Renovated Townhouse walking distance to town, beaches, parks, brewery and short bike to wineries. Brand new Kitchen, bathrooms & bedrooms. Enjoy all the North Fork has to offer: wineries, breweries, amazing restaurants, shops and beaches! 3 Bedrooms 1.5 bathrooms. We welcome you to come stay in our beautiful home and take in all the beauty of the North Fork. You can park your car and not have to drive again till you leave!

The space
Close to town and beaches. Guests have use of the entire townhouse and outdoor space. The home is two side by side townhouses. Original Home is over 100 years old with all its charm that has been newly renovated. Master is very spacious with a king sized bed, off the master is a small room with bunk beds, and the third bedroom has two twin beds (one being a Murphy bed). Full bathroom is spacious with a tub and shower. There is a pullout queen bed in the den. Open floor plan with kitchen that opens to dining room and den with direct access to the back patio area. There is also a half bath off the kitchen.

Guest access
Backyard with rocked patio. Outdoor grill. Outdoor seating.

Other things to note
Everything is brand new. This home was just renovated. Central AC. All brand new appliances.

Puracy body soap • Cleaning products • Puracy shampoo • Garden view • Puracy conditioner • Washer • Hair dryer • Bathtub • Shower gel • Hot water

Fully Renovated Townhouse walking distance to town, beaches, parks, restaurants, brewery and short bike to wineries. Brand new Kitchen, bathrooms & bedrooms. Enjoy all the North Fork has to offer: wineries, breweries, amazing restaurants, shops and beaches! We welcome you to come stay in our beautiful home and take in all the beauty of the North Fork. You can park your car and not have to drive again till you leave!

The space
Close to town and beaches. Guests have use of the entire townhouse and fenced in outdoor space with seating and outdoor grill. The home is two side by side townhouses, backyard serrated by fence. Home is over 100 years old with all its charm that has been newly renovated. Master is very spacious with a king sized bed, off the master is a small room with a twin bed which is part of the master, and the other bedroom has a full bed. Full bathroom is spacious with a tub and shower. There is a pullout queen bed in the den. Open floor plan with kitchen that opens to dining room and den with direct access to the back patio area. There is also a half bath off the kitchen.

Guest access
Backyard with rocked patio and outdoor grill.

Other things to note
Everything is brand new. This home was just renovated. Central AC. All brand new appliances.

Shampoo • Cleaning products • Conditioner • Hot water • Hair dryer • Bathtub • Bathroom • Bedroom and laundry • Shower gel • Body soap

Cozy Village artist's home!Private bedroom w/adjacent private bath. Very comfortable living room, sun room and large backyard. Just a few blocks from "Downtown" Greenport &bay beach at end of street. Location is perfect...just a few short blocks from the Jitney stop +LIRR. In addition, Suffolk County Comptroller's Office requires I collect a 5.5% per night Occupancy Tax from my guests.

The space
Very welcoming, warm and comfortably chic in its own artistic way. Love people and love hosting! NO PETS Allowed

Guest access
Guests can access living room, sunroom and large backyard with table and chairs - It's truly a little piece of paradise here in Greenport!

During your stay
Happy to help you navigating the area

Other things to note
It's pretty simple - my friends and family love to be here and I believe you would also find it a peaceful, comfortable place to be

Extra pillows and blankets • Conditioner • Hot water • Body soap • Bed linens • Shampoo • Cleaning products • Hangers • Essentials • Hair dryer

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney.

My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

The space
The house has been completely renovated and everything is brand-new.
Everything is walking distance to the house and the location is unbeatable. Please note that BBQ is only available from April to November.

Other things to note
This property has two apartments. The Sandpiper Apt. 1 and Aqua Vista Apt.2 (see listing on AIRBNB website that can accommodate 12 people when available at the same time for larger families and wedding parties

Hot water • Hair dryer • Conditioner • Cleaning products • Shower gel • Washer • Shampoo • Bathtub • Body soap • Outdoor shower

Enjoy the sounds of nature when you stay in this unique place. Close to beaches, wineries & Greenport Village. A perfect spot in the North Fork that is peaceful and beautiful.

Walking distance to Greenport Village, Sound and Bay Beaches! 1200 sq ft Victorian cottage perfect for a retreat from the heat. Large patio, new kitchen and bath!

The space
1840s historic poet's house, perfect for couples, small family or single seeking reprieve from Manhattan. Original hardwood floors, 2 story house, large sunny entertaining deck, cool breezes on the front porch. Please note, the upstairs bedrooms are connected railroad style—so you have to walk through one to get to the stairs. Also, the bathroom is on the first floor.

Guest access
Access is to the entire house and property including on site laundry and nearby beaches.

Beautifully appointed 1bdrm apt. Farm meets beach chic. Small living room, bedroom, full kitchen & bath. Perfect little getaway space.
If you do bring along your pup, please let us know. We cover certain furniture & provide some different amenities. :)

The space
Full apartment is yours for the stay. No restrictions on access to any amenity.

Other things to note
We are located directly in the village with 2-5 minutes walks anywhere you would want to visit; brewery, local supermarket, shops, carousel, marina, museum, art galleries and farmers market.

Hangers • Bathtub • Iron • Room-darkening shades • Extra pillows and blankets • Bed linens • Cleaning products • Hot water • Hair dryer • Essentials

Our peaceful, centrally-located apartment in Greenport Village is walking distance to town, rail station & Jitney. Enjoy short walk to shops, restaurants, park, piers and bay beach, or drive & park free. The spacious 2nd fl apt accommodates 4 adults comfortably in 2 bedrooms, 1 full bath, lg living rm & lg kitchen with small work station. Amenities: central A/C, large TV, Wifi, cable, equipped kitchen, towels, sheets, beach supplies. Front porch, BBQ, grape vine covered dinning area & seating.

A sunny & cheerful 2-bedroom space with a private bathroom on the 2nd floor of a charming house centrally located in Greenport. Walking distance to all of the main shops & restaurants, and a quick drive or enjoyable walk to two lovely beaches. Each bedroom has a queen-size bed that comfortably sleeps two adults, but we can also provide a cot & air mattress to help accommodate one additional guest per room.

The space
A charming, two-floor cape located in the heart of Greenport. Our backyard garden is regularly visited by a variety of birds, squirrels, and rabbits. Across the street is a historical cemetery with a family of deer that you can often see grazing throughout the day.

Guest access
You'll have the entire 2nd floor to yourselves, with a private entrance through the front door, which uses a keypad lock for your convenience. You will also have a mini-fridge that you can use to store leftovers, drinks, and snacks.

During your stay
My wife & I will be available throughout your stay, but we have a privacy wall that separates the upstairs and downstairs portions of the house. You'll also be the only ones using the front door during your stay.

Conditioner • Hot water • Cleaning products • Shampoo • Shower gel • Hangers • Essentials • Body soap • Hair dryer • Bathtub

Enjoy all that Greenport has to offer by staying in the center of Greenport, less than 2 blocks from the carousel. Relax in the large fenced yard or screened in porch. Effortless walk to shops, great restaurants, coffee spots, night life, the LIRR Station, Jitney, Shelter Island Ferry.
Super easy check in and out.
Dogs allowed but breed restrictions apply. All pets must be pre approved by the host.
I am in the neighborhood and always available by phone or email.

Free washer – In unit • Body soap • Shampoo • Hot water • Conditioner • Hair dryer • Bathtub • Shower gel • Free dryer • Cleaning products

This stylish place to stay is perfect for group trips. Short walking distance to town and restaurants. Approximately a half mile to the Shelter Island Ferry and other attractions.

Cleaning products • Generic body soap • Dryer • Hot water • Generic conditioner • Free washer – In unit • Shampoo • Courtyard view • Bidet • Hair dryer

Upstairs bedroom with queen bed and private bath. Walk to Village everything. No car needed! Historic district. Water and garden views. Just renovated with modern amenities.

The space
Out of the tourist loop yet within walking distance to shops, restaurants, and all waterfronts. Comfortable, restful accommodations summer or winter.

Guest access
Rental is a second floor private bedroom and private bath. Licensed massage therapist and private yacht charters can be arranged with ease.

During your stay
Owner is a native East Ender and can be available to help provide info on both forks and the waters in between :-)

Other things to note
Guests need to be OK with house cats. Sorry, we cannot allow guests' dogs because our cats are very territorial.

Iron • Extra pillows and blankets • Hangers • Essentials • Air conditioning • Hair dryer • Hot water • Bed linens • Shampoo • Heating

Lovely Victorian home with private entrance, porch, & patio.
Floor to ceiling windows in light filled large bedroom with king sized bed & ensuite bathroom. Cozy den has a beautiful bay window and a queen-size pull-out sofa bed for additional guests. Sunny sitting room just off of the kitchen for reading or games. Full kitchen, washer dryer, high speed internet, and new flat screen TV can be found in the unit. Restaurants, wineries, beaches are nearby.
Enjoy all the North Fork as to offer!

Essentials • Hair dryer • Hangers • Body soap • Bay view • Hot water • Free dryer – In unit • Cleaning products • Bathtub • Free washer – In unit

Charming, quirky, historic 1 bed/1 bathroom apartment in the heart of Greenport Village. Walking distance to business district and public transportation to NYC
half a mile to the nearest beach. 3 blocks to the nearest dock 🧜🏻‍♀️
Private, airy, excellent light and salty ocean breeze.
Owned/ occupied by a local (and fun) family- separate from the rental unit.
All walks of life welcome, pets accepted on a limited basis
good living & good times encouraged, but respect/decency required.
🌱 friendly

The space
Private & Furnished 1 bed/1 bath apartment

-Bedroom
-Living Room
-Eat in kitchen
-private bathroom with shower
-Basic essentials supplied

-light, airy, breezy, lots of plants

Guest access
Front door entry, private quarters.

Other things to note
We adore pets, and have a few that live on the property.
Pets are permitted on a selective basis and subject to a minor surcharge- but will not be permitted in the backyard. After booking- please send a note about your pet for approval: breed/temperament, pics are welcome! 🐾
We ask this to ensure the comfort of all; fur-guests included. The host reserves the right to decline any pet, for any reason.

Note: the village is super dog/pet friendly and very walkable

Hangers • Cleaning products • Extra pillows and blankets • Iron • Bed linens • Hot water • Free dryer – In unit • Body soap • Hair dryer • Essentials

Welcome to our home away from home! You'll find everything you need to relax 'out east'. Fully stocked kitchen, beach chairs, high speed internet, comfortable Queen bed with high-end bedding. Fenced in backyard with high end furniture to enjoy the meals you grill. 10-15 minute walk to downtown Greenport village, shops, restaurants and beaches and to train station as well as Jitney from the city.. Inquire about long term rental rates!

The space
Our cottage in on a property in a residential area of Greenport which was once a fisherman's village. Note that all houses are close to one another as its the village, but the tradeoff is the convenience of being within walking distance to everything Greenport has to offer. You have your own private large fenced in back yard and parking spot. Away from the traffic of the village but still close enough.

Guest access
The whole space is yours to use!

Other things to note
1 Queen sized bed in the 1 BR and a trundle sofa in the living room. Front porch is a 3 season which we use as a home office, in addition to a small office space we created on the back porch. This is a home for those looking for central location for access to all that Greenport has to offer. Sorry - no parties permitted on the property out of respect for our neighbors in this residential street.

TV • Room-darkening shades • Bed linens • Conditioner • Essentials • Hot water • Free dryer • Shampoo • Shower gel • Washer

PLEASE READ

Weekend nights require a 3 night minimum for the month of July and August

Please park in the street when arriving as many spots along the streets are available.

Laundry + Dryer only for monthly rsvp.

Newly renovated 2BR Duplex Apartment House

No pets
No shared space
Separate entrance
Close to wineries and transportation S92 bus, Hampton Jitney, Long Island/North Fork/Connecticut Ferries, restaurant and beaches!

Check-in is anytime after 3PM
Check-out at 11AM

Washer • TV with standard cable • Smoke alarm • Dryer • Hangers • Hot water • Air conditioning • Carbon monoxide alarm • Essentials • Heating

The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scenery, and return to a memorable and comfortable room at the end of your day. The boutique hotel features eleven suites, including two, double-bedroom apartments.

Our guests pay a resort fee of $35 per night, with additional taxes at check in.

The space
Each of our rooms come with a fully stocked mini-bar, Nespresso machine, Smart TV, glass shower door, iron, ironing board, hairdryer and Maison Margiela amenities. We've also included robes, Frette beach towels, the resort fee includes breakfast, coffee pods, Rose hour and bike rental to make your stay all the more memorable!

Guest access
Our hotel reception can be found in Stirling Square, inside of Alex Vinash's vibrant clothing boutique. The square is active with lots of seating areas. Our restaurant and bar are just adjacent, with delicious 1943 Pizza in between. Room keys are required for entry to each hotel room, as well as for street-facing doors. If guests need further information, don't hesitate to call 631-477-5939—we're always happy to help!

Other things to note
American Beech is located in Stirling Square, Greenport's hub for nightlife. During our high season, the square is the perfect spot for a great time, equipped with music, dancing, delicious food and elevated cocktails!

We can always be reached at frontdesk@americanbeech. com, as well as our off-hours emergency line provided to guests at check-in.

We are a pet-friendly hotel with an $ 85+ tax pet fee. Please keep in mind that not all of our rooms are pet-friendly. If you are booked in a room that is not pet-friendly, you may be subject to a room move without notice as well as a fine of $250. Please feel free to reach out to us with any questions!

Shampoo • Hair dryer • Hot water • Iron • Pack ’n play/Travel crib • Extra pillows and blankets • Bed linens • Air conditioning • TV • Hangers

The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scenery, and return to a memorable and comfortable room at the end of your day. The boutique hotel features eleven suites, including two, double-bedroom apartments.

Our guests pay a resort fee of $35 per night, including additional taxes at check in.

The space
Each of our rooms come with a fully stocked mini-bar, Nespresso machine, Smart TV, glass shower door, iron, ironing board, hairdryer and Maison Margiela amenities. We've also included robes, Frette beach towels, the resort fee includes breakfast, coffee pods and Rose hour to make your stay all the more memorable!

Guest access
Our hotel reception can be found in Stirling Square, inside of Alex Vinash's vibrant clothing boutique. The square is active with lots of seating areas. Our restaurant and bar are just adjacent, with delicious 1943 Pizza in between. Room keys are required for entry to each hotel room, as well as for street-facing doors. If guests need further information, don't hesitate to call 631-477-5939—we're always happy to help!

Other things to note
American Beech is located in Stirling Square, Greenport's hub for nightlife. During our high season, the square is the perfect spot for a great time, equipped with music, dancing, delicious food and elevated cocktails!

We can always be reached at frontdesk@americanbeech. com, as well as our off-hours emergency line provided to guests at check-in.

We are a pet-friendly hotel with an $ 85+ tax pet fee. Please keep in mind that not all of our rooms are pet-friendly. If you are booked in a room that is not pet-friendly, you may be subject to a room move without notice as well as a fine of $250. Please feel free to reach out to us with any questions!

Air conditioning • Shampoo • Pack ’n play/Travel crib • Extra pillows and blankets • Hot water • TV • Iron • Hair dryer • Hangers • Bed linens

The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scenery, and return to a memorable and comfortable room at the end of your day. The boutique hotel features eleven suites, including two, double-bedroom apartments.

Our guests pay a resort fee of $35 per night, including additional taxes at check in.

The space
Each of our rooms come with a fully stocked mini-bar, Nespresso machine, Smart TV, glass shower door, iron, ironing board, hairdryer and Maison Margiela amenities. We've also included robes, Frette beach towels, the resort fee includes breakfast, coffee pods and Rose hour to make your stay all the more memorable!

Guest access
Our hotel reception can be found in Stirling Square, inside of Alex Vinash's vibrant clothing boutique. The square is active with lots of seating areas. Our restaurant and bar are just adjacent, with delicious 1943 Pizza in between. Room keys are required for entry to each hotel room, as well as for street-facing doors. If guests need further information, don't hesitate to call 631-477-5939—we're always happy to help!

Other things to note
American Beech is located in Stirling Square, Greenport's hub for nightlife. During our high season, the square is the perfect spot for a great time, equipped with music, dancing, delicious food and elevated cocktails!

We can always be reached at frontdesk@americanbeech. com, as well as our off-hours emergency line provided to guests at check-in.

We are a pet-friendly hotel with an $ 85+ tax pet fee. Please keep in mind that not all of our rooms are pet-friendly. If you are booked in a room that is not pet-friendly, you may be subject to a room move without notice as well as a fine of $250. Please feel free to reach out to us with any questions!

Iron • TV with standard cable • Hangers • Shampoo • Air conditioning • Pack ’n play/Travel crib • Hot water • Bed linens • Extra pillows and blankets • Hair dryer

The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scenery, and return to a memorable and comfortable room at the end of your day. The boutique hotel features eleven suites, including two, double-bedroom apartments.

Our guests pay a resort fee of $35 per night, including additional taxes at check in.

The space
Each of our rooms come with a fully stocked mini-bar, Nespresso machine, Smart TV, glass shower door, iron, ironing board, hairdryer and Maison Margiela amenities. We've also included robes, Frette beach towels, the resort fee includes breakfast, coffee pods and Rose hour to make your stay all the more memorable!

Guest access
Our hotel reception can be found in Stirling Square, inside of our boutique. The square is active with lots of seating areas. Our restaurant and bar are just adjacent, with delicious 1943 Pizza in between. Room keys are required for entry to each hotel room, as well as for street-facing doors. If guests need further information, don't hesitate to contact us—we're always happy to help!

Other things to note
American Beech is located in Stirling Square, Greenport's hub for nightlife. During our high season, the square is the perfect spot for a great time, equipped with music, dancing, delicious food and elevated cocktails!

We can always be reached at frontdesk@americanbeech. com, as well as our off-hours emergency line provided to guests at check-in.

We are a pet-friendly hotel with an $ 85+ tax pet fee. Please keep in mind that not all of our rooms are pet-friendly. If you are booked in a room that is not pet-friendly, you may be subject to a room move without notice as well as a fine of $250. Please feel free to reach out to us with any questions!

This historic Captain's house is located in the heart of beautiful Greenport Village. It dates back to 1830 and has been beautifully renovated preserving its historic detail. It has a huge garden with mature trees, plants and a wonderful gazebo. Once you step outside, you can walk to all the restaurants, bars, shops, the water as well as the Hampton Jitney and the LIRR. It's an ideal yet very quaint location.

The space
This is the garden wing of a beautifully renovated historic Greenport house dating back to 1830. It's one of the oldest in the Village of Greenport. The garden wing offers 2 bedrooms both with queen beds. One is next to the cozy living room on the ground floor. The second one is on the second floor off the big eat in kitchen with its vaulted ceiling.

The garden wing is abundant with historic details, most notably the impressed tin ceilings and walls in the living room and first floor bedroom as well as original doors and windows. Everything has been carefully restored giving the house its wonderful old charm combined with modern amenities.

There's a very big, private and fully fenced in garden complete with gazebo and deck. The garden wing has its entrance through the garden.

I stay in the front part of the house. It is completely separate from the garden wing (it's a very long house) and both parts have their own entrances and even different addresses.
The garden is for your private use only - I don’t use it when the garden wing is rented.

Guest access
The garden wing with exclusive use of the garden.

Other things to note
There's wireless Internet throughout the house and garden, a washer/dryer and easy parking on the street.

Essentials • Shower gel • Hot water • Hangers • Dryer • Hair dryer • Bed linens • Garden view • Washer • Shampoo

Sunny and relaxing two bedroom Bungalow perfect for exploring all the North Fork has to offer! Our place is located within walking distance to Kontokosta Winery, beach, restaurants, bars, shopping, coffee shops, Shelter Island Ferry, Long Island Railroad (LIRR), and the Hampton Jitney.

The space
The house contains a beautiful open-concept space with tons of natural light making this bungalow feel open and airy. Our home features two bedrooms, each with a queen sized bed. A full sized daybed is situated in the sun room (please let me know if this will be used). Newly rennovated full bath with stand up shower and modern finishes as well as a recently added half bath!

Other amenities include: cable with smart TV, wireless internet, washer/dryer (with approval and on longer stays). Kitchen is stocked with essentials (please let me know before your stay if you have questions on what we have!) Linens and towels provided. Parking provided in front of the house.

Although there are so many places to see and things to eat throughout the North Fork, this house puts you in a position to enjoy all Greenport has to offer without the need of a car. Amazing restaurants like American Beech, Alpina, Lucharitos, Frisky Oyster and Noah's to name a few and local craft beer at Little Creek Oysters and Greenport Brewery. Please look through my Guidebook to see my recommendations and if you have any questions please feel free to message me!

Guest access
Guests will have full access of the house as well as basement if doing laundry is needed (will need prior approval and depends on length of stay).

Hair dryer • Conditioner • Garden view • Shampoo • Shower gel • Hangers • Cleaning products • Hot water • Bed linens • Essentials

Beautiful and spacious Airstream situated within a block of a private beach. This cozy oasis experience is walking or biking distance to Kontokosta Winery, Island's End Golf & Country Club, Lavender By the Bay and a five minute drive to the Village of Greenport.
Experience the perfect blend of nature and modern comfort at this luxury Airstream retreat. Netflix/Hulu included. Please note, 2 Bikes/1 Paddle Board/1 Kayak & Life Jackets provided May-Sept. Dock usage is also available upon request.

The space
Dock Access available upon request.

Other things to note
This home is located in a residential neighborhood so please acknowledge and abide 8PM quiet hours.

We ask that your pet companions are designated to the den area of the home during your stay.

Check-in - anytime after 4PM (If you would like to check-in or drop off bags earlier please message to confirm)

Check-out - 10AM (If you would like to check-out later please message to confirm)

We look forward to hosting your stay in Greenport.
-HTB

Body soap • Hangers • Free dryer – In unit • Shampoo • Essentials • Shower gel • Hot water • Conditioner • Washer • Cleaning products

Walk the 5 min into town with restaurants and bars, shops and cafes or enjoy the quiet neighbourhood and take a stroll down the block to watch the sailboats cruise into Sterling Harbor. This sunny apartment is situated on the second floor of a 1860's house on one of Greenport's prettiest streets. Its the true couples getaway!

Bed linens • Shampoo • Dryer • Hot water • Essentials • Hangers • Hair dryer • Washer • Iron • Air conditioning

Located in the heart of Greenport Village with easy walking access to restaurants, shops, Greenport Brewery, Kontakasta Winery, and much much more!

Originally from Greenport, we look forward to hosting you and sharing our local favorites to make your stay memorable.

The space
Our sunny second floor private apartment in the heart of Greenport features two bedrooms, each with a queen sized bed. Great walkable rental if looking to explore all the Village of Greenport has to offer. The rental was recently renovated. The original pine floors were refinished dating back to the early 1900’s. The new custom built kitchen with beautiful granite countertops is fully equipped for your stay. A full sized sleeper sofa is situated in the living room. Full bath with shower and tub. Private entrance to rental.

Other amenities include: smart TV, wireless internet, front loader washer/dryer. Linens and towels provided. Parking provided in front of the house. We have beach chairs for your use. This is a non-smoking rental.

Our rental has obtained an approved Town of Southold Permit necessary for short term rentals.

Iron • Hot water • Washer – In unit • Hangers • Dryer – In unit • TV • Pack ’n play/Travel crib • Booster seat high chair • Hair dryer • Essentials

Renovated farm house apt with a loft like feel and lots of sunlight. the second floor apt has a separate entrance and foyer on first floor. Located in the heart of Greenport village close to shops, restaurants, and the historic waterfront. Walking distance to LIRR train, Hampton jitney bus and shelter island ferry service.

The space
Apt is a sun filled space to relax with a terrace overlooking the garden for your morning coffee or an afternoon read. Full of vintage touches and character you will feel at home in the seaside village

Guest access
Private foyer entrance on the first floor leading up to the 2 nd full floor apt with private deck

Cleaning products • Bathtub • Dryer • Washer • Hangers • Hot water • Bed linens • Iron • Essentials • Hair dryer

Our heated pool is open until the beginning of October in 2025. A brand-new two-bedroom chalet that opens onto a heated, saltwater pool directly outside your patio doors. This is your ideal year-around gateway to experience Greenport. This private oasis is walking distance to Greenport Village, 4th & 5th Street beaches, as well as the train station and Jitney stop.

The space
The heated pool is open until the first week of October.

Please note that the chalet has a spiral staircase for access to the second floor where the bedrooms are. The staircase may not be suitable for families with small children or groups with guests who may be less mobile or has disability.

Downstairs of the chalet has an open concept living room with a kitchen (pic) and a bathroom. The living room area doors open directly onto the patio that surrounds the swimming pool.

A spiral staircase goes up to the second floor for access to the two bedrooms. Each of the bedrooms contain a queen bed, with a closet and a dresser.

The newly installed, fully equipped kitchen includes a fridge freezer, cooktop and an air fryer which has an oven function (no full-size oven or dishwasher).

The large private patio outside with the pool includes separate dining and seating areas, BBQ, as well as sun loungers to make the most of the warm, North Fork sunshine.

This house is located in a double lot and separated by a fence from the other half of the lot. This listing does not have access to the other lot.

The property is monitored (externally) by Ring Cams for security purposes.

Guest access
Guests have full and sole access to this lot (house and swimming pool which is open from Memorial Day in May to Aug). Access is through private metal gates and up to three cars can be securely parked inside the gravel driveway, in front of the house.

Other things to note
Number of guests to be confirmed during booking request. No extra people are allowed; no “local friend stopping by” to use the pool or hosting others. Any additional guests (without prior agreement during booking) will be reported as breaking rules and reported to Airbnb.

Air conditioning • Hot water • Hair dryer • Essentials • TV with standard cable • Hangers • Iron • Room-darkening shades • Bed linens • Outdoor shower

This two-bedroom, two-bathroom condo at Cliffside Resort offers a serene escape with breathtaking views of the Long Island Sound.

Your stay includes access to Cliffside Resort’s fantastic amenities. Enjoy a heated swimming pool for relaxing swims, private beach access with lounge chairs for soaking up the sun, and a great lawn ideal for picnics, outdoor games, or a barbecue.

Book your stay today and explore the vibrant attractions of Greenport and the North Fork!

Essentials • Paid crib - available upon request • Air conditioning • Clothing storage • Bed linens • TV • Extra pillows and blankets • Heating • Hangers • Hot water