Find Your Ideal Apartment in Greenport, NY

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"

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"

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"

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."

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.

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

This rental is a first floor apartment in a legal two family home. The second floor apartment is owner occupied. 1880's Victorian with lovely antique wood floors and wrap around porch. Just a 3 minute walk to public transportation (Hampton Jitney, Long Island Railroad, Shelter Island Ferry) & the heart of Greenport Village. Two bedroom (One Queen Bedroom, One Bedroom with two twin beds), One Full Bath w/ walk in shower, One Half Bath off Master Bedroom, Eat in Kitchen with large Island and seating for 6+, Dishwasher, electric stove/oven, Keurig coffee maker & K-cups, cookware/bakeware, place setting for 6, washer/dryer. Smart TVs and free Wireless Internet. Large back deck with gas fire pit, gas grill and patio table covered by an awning & seating for 6, side screen porch, on-site parking for two cars. Additional free parking is available on the side streets. Ceiling fans through out, window A/C in bedrooms, oil fired baseboard heat. Sleeps 4 very comfortably. A 5th guest is accommodated with a comfy cot including pillows and linens. Total occupancy is limited to 5. One Night Stay available but will incur a surcharge as follows: $100/Night on Fri or Sat. in July & August

FEES & TAXES:
SERVICE FEE is paid directly to Home-away.
ONE NIGHT STAY FEE: *One Night Stay available but will incur a surcharge as follows:$100/Night on Fri or Sat. in July & August
TAXES are collected as follows:
3% Suffolk County hotel motel tax
4% New York State sales tax
4.625% Suffolk County sales tax

- "Fabulous location and gracious hosts. Beautiful home. They've thought of everything. We would definitely stay there again!" - "We loved our stay here! The walk into Greenport is easy, and the hosts are super welcoming but definitely give you your own space (and supply you with everything you need). We'll be back - and we'll be recommending this property to others!" - "Porch on Front is the perfect place for we five sailing buddies to stay. Mindy and Jim Ryan are wonderful innkeepers who made sure we had everything we needed. The ferry over to Shelter Island and the Shelter Island Yacht Club is only a ten minute walk, as are some of the best restaurants in Greenport [highly recommend Agave!]. The back deck provided a delightful place to bbq steaks and just relax around the fire pit after a very hot, no wind, "Lets get this boat MOVING for heaven's sake before we all roast to death!!!" day of sailing. Thank you Porch on Front..... We'll be coming back! JC"

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.

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

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!"

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."

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."

Home has a full kitchen and a washer/dryer. There are two bedrooms with queen size beds plus a Murphy double bed. One bathroom is en suite with a shower. The other has a tub and shower. Outdoor patio with table/chairs plus covered porch

- "Great location and cute house and garden" - "Joyce and Hector were amazing hosts! They were very responsive and provided us with some great recommendations in the area. Their beautiful unit is very close to all you could want to see and visit in the North Fork." - "A trip to Greenport never disappoints! The house was in a great location and easy walk to town. Joyce was welcoming and gracious!" - "Charming, comfortable, convenient. A lovely, interesting house in a delightful neighborhood full of fascinating, unique homes, close to downtown. Our hosts, Joyce and Hector, have thought of everything and made our stay an effortless delight. We intend to come back here soon."

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!"

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."

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."

This unique place is close to town giving you everything you need for your vacation, making it easy to plan your visit. Close proximity to the water, Second story Balcony looking over the heart of Greenport, surrounded by shops and amazing restaurants.

There is a electric awning for shade- If would like to use the shade there will be a $500 deposit that will be returned after inspection. please ask host for me details.

- "So clean, spacious, and very centrally located!! There were restaurants and shops all within walking distance! We sat out on the second story deck at night and had complete privacy yet we could hear the nightlife and we actually got to see fireworks!! It was such a wonderful place and a great experience!! Jimmy, we’ll be back!!" - "Great weekend on the East End with staying at this convenient Greenport location. It was clean, and suitable for all our needs. There's more conveniences than the listing shows such as a Keurig, toaster and other useful items. Location is in town which makes the visit walkable to anywhere you might want to go. Communication with Jimmy was quick and easy, check-in smooth, information clear."

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!"

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 !!!"

Welcome to CASA GREENPORT, Apt 2, your North Fork oasis! This family-friendly apartment features 3 bedrooms, 2 baths, kitchen, laundry room, kid's play nook, and oversized terrace with BBQ, overlooking your own private backyard with heated swimming pool.

Located in the heart of Greenport Village, this home is the perfect destination for those looking for a relaxing retreat yet want to be within walking distance to downtown Greenport.

[This is a two-family home. The downstairs apartment is not available to rent, but will be unoccupied during your stay to ensure your privacy.]

- 2024 Pool dates: May 1st to Sept 30th
- Must be 27+ YOA to book [ID required]
- 6 adults max allowed
- Crib set up available upon request

Apt #2 features 3 bedrooms, 2 full baths, laundry room with brand new Samsung washer and dryer, luxury hotel linens and bedding, living room with smart tv, record player, spacious kitchen with dining for six, an oversized terrace with Weber gas grill, and a brand new swimming pool.

BEDROOM ONE: King Bed + Ensuite (with sliding door leading to oversized terrace)
BEDROOM TWO: Queen Bed + desk
BEDROOM THREE: Two Twin Bed + Children's play nook
SPECIAL FEATURES: Oversized terrace, gas grill, patio furniture and private pool access [seasonal]
FAMILY-FRIENDLY FEATURES: Kid's play nook with toys and books, games, Joovy high chair, Babyletto crib, crib sheets, changing mat, kid's dinnerware, pool toys, children's beach toys and chairs, and pool fence for peace of mind.
EXTRA AMENITIES PROVIDED: Hair dryer, steamer, iron, complimentary Native bath products, coffee maker with complimentary coffee, complimentary welcome wine from Bedell, wireless internet, air conditioning, white noise machines, laundry detergent, basic paper product necessities, first aid kit, beach chairs and oversized beach towels, and a fully stocked kitchen.

Other things to note:
-Pool hours are from 9am to 8pm.
-Outside music must be off by 8pm.
-Small BBQs ok but please no parties or large gatherings.
This is to keep noise levels down and respect this lovely and tranquil neighborhood. Thank you for your understanding!

- "You cannot beat this place. The home has been gut renovated and is spotless. You can tell it was designed with children in mind - my littles loved the playroom, it came equipped with cribs, sound machines, safety furnishings, and tons of toys etc. I appreciated that the host thought of all the small things…we stay in rentals a ton throughout the year and are not picky at all, but the small luxuries of this place were such a perk. The coffee machine came with pods, sweetener and creamer (again, small luxury but so appreciated). The bathrooms had amazing Native products, they actually had spare TP, garbage bags, paper towels (can’t count the amount of homes I’ve stayed at where we have had to go out and purchase garbage bags etc). You are also greeted with a bottle of wine and tote bags (both equally as needed with kids!) The location is amazing - easily walkable into town, even with a 6 yr old who complains about everything. The pool can’t be beat - it’s heated and spotless. We had an amazing time. Claudia is incredibly responsive and accommodating. She was on top of everything and a pleasure to work with. Again, my husband and I rent at least 8-10 times a year and this place is definitely one of the best we’ve stayed at. We’ll be back!!"

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!

- "The condo was just as pictured. Very clean with necessary supplies. We have been spoiled at other places with bottled water and cable that actually works but this was a good spot for the weekend. The setting was wonderful and we truly enjoyed the small private beach with the amazing sunsets. "

Adorable fantastic getaway with outdoor deck overlooking preserve! New and super comfortable with air conditioning. A historical renovated one-bedroom Greenport getaway with elegant decor and high-end furnishings, everything you need for an extended stay or quick getaway. The natural grounds, is sure to provide a relaxing and luxurious experience. The close proximity to the beach, 67 Steps is just a 5-minute walk away, offers easy access to the waterfront.

Being close to Greenport Village means you'll have access to charming shops, restaurants, and local attractions. Exploring the village and enjoying the local dining options will enhance your overall experience. Additionally, the nearby vineyards and wineries are perfect for wine enthusiasts or those looking to experience the region's renowned wine culture.

Convenience is also a plus, as the Jitney bus service being close allows for easy transportation to and from the area. Overall, this fully furnished, renovated one-bedroom getaway in Greenport offers a combination of comfort, style, and proximity to various attractions, making it an ideal retreat for anyone seeking a peaceful and enjoyable vacation.

Air Conditioner • Laundry • Bedding/Linens • Child Friendly

Apartment in beautiful Victorian home in the Village of Greenport. There are two bedrooms with one double bed, one full bed and a daybed in living room. There is a full bathroom, full kitchen with new appliances , dining room and outside deck.

Kitchen • Bedding/Linens • Balcony/Terrace • Tv • Air Conditioner

Close to sailing, surfing, and more, this pet-friendly apartment brings it all within reach. There's convenient onsite parking, so you can leave your vehicle behind and let your feet make short work of the 12-minute walk to Greenport Carousel or the 15-minute walk to East End Seaport Maritime Museum.

Once you get back, you can enjoy your surroundings with the garden and BBQ grill. For a change of scenery, come inside and enjoy the WiFi and TV.

As you settle into the place, you'll find a living room, a safe, air conditioning, and limo/town car service. Bathroom amenities include a hair dryer, towels, and toilet paper. And you won't have to pack extra clothes, because you'll have a washer and dryer, too.

Child Friendly • Spa • Balcony/Terrace • Air Conditioner • Other • Laundry • Internet • Oceanfront • Wellness Facilities • Security/Safety • View • Parking

bright & airy farmhouse apt with a loft-like feel. Recently renovated 2nd floor apt has a separate entrance, open kitchen and roof deck. Conveniently located in the heart of Greenport village; close to shops, restaurants, and the historic waterfront. A quick walk to the LIRR train, Hampton Jitney bus & Shelter Island ferry

Laundry • Security/Safety • Air Conditioner • Internet • Bedding/Linens • Child Friendly • Other • Wellness Facilities

This phenomenal rental in Greenport offers a cozy retreat for guests. Walk to the best the village has to offer right from the rental. With 2 bedrooms, heating, WiFi, and a washing machine, this cool space has everything you need for a comfortable stay. Relax in the inviting atmosphere and soak in the charm of Greenport during your visit. Enjoy the backyard patio and grill on a summer night. Come and experience the magic of Greenport at our rental.

Internet • Bedding/Linens • Fireplace/Heating • Wellness Facilities • Balcony/Terrace • Laundry • Air Conditioner • Child Friendly • Security/Safety

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.

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

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.

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.

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

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!

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

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

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

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

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

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!

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

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.

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

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!

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

One bedroom hideaway in the heart of Historic Maritime Village of Greenport, NY. 2nd floor apartment with full galley kitchen, dining area, living room and cozy bedroom. Close to all of Greenport's amenities... beaches, dining, shopping, art galleries, wineries, boating, fishing, golfing and more. Quiet location just 2 blocks from downtown Greenport Village.

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

Charming and cozy basement apartment located just steps away from downtown Greenport. This 1BR/1BA space comes with its own entrance and sleeps up to four guest. Do not have a car? No problem! An 8-10 minute walk is all it takes to get to the local bus, train, jitney, Shelter Island Ferry, downtown & a beautiful beach located at the end of 6th street.

The space
You will have the basement "in-law apartment" entirely to yourselves. The space receives a ton of natural light through the large standard sized windows. It is very clean and has recently been updated with a fresh coat of paint and all new furnishings. You are locked off from the rest of the house so you can enjoy your privacy. You will also have your own private entrance and parking spot in the driveway.

Hot water • Dove body soap • Essentials • Bed linens • Extra pillows and blankets • Cleaning products • Iron • Hangers • Bathtub • Hair dryer

Our quaint apartment is located in the heart of Greenport, it is walking distance to anything you'll need (2 blocks to be exact). The eat-in kitchen has everything you'll need to have a nice home meal. The balcony has comfortable furniture to enjoy a cup of coffee in the morning. We use a August Smart lock for entry.

The space
Our apartment is tiny but comfortable! The house was built in the late 1800's and after our renovations we tried to keep a lot of the original aspects intact. The hard wood floors were refurbished, the ceilings are low and the windows are old. Since we've done the whole remodel ourselves, while still working full time, there are still projects we would like to complete. Like the windows and siding on the house! The bedrooms are spacious and comfortable. There is a large closet with hangers for clothing and other items and another large closet consisting of cleaning supplies, extra liens, pillows and blankets. The single beds in the front room have storage drawers under the beds as well. There are window blinds throughout, so you have plenty of privacy or sunlight. The kitchen and living room area are one big area so you're always together. The kitchen has beautiful quartz countertops and new stainless steel appliances. The kitchen also comes equipped with an island and 3 stools. The island can be moved to wherever in the kitchen that suits you best during your stay. The island can also be used as a desk, as it has a built-in outlet source. Our apartment is listed for a 4 person rental, how ever we can sleep 6. The apartment is tiny and we feel our guests would be more comfortable and less crowed. Reserving anything over 4 people we charge $100 per person per night.

Guest access
Since we, the homeowners, live on the first floor of the house guests are allowed to use the entire second floor. Guests have their own private entrance with a balcony. If you don't see the upstairs balcony, you're on the wrong side of the house. We use August Smart lock to have entry to the apartment. The August Smart lock is an automatic locking system using a key pad. I will reach out to you prior to your arrival with a code that will only allow you access to the apartment during your requested time. There is an emergency exit door that leads to the first floor and front door. We ask you only use this door in the case of an emergency since we live on the first floor and would like our privacy as well.

Other things to note
We’re a family of three, we welcomed our boy in January of 2023. We also have a 20lb 5 year old Mini Goldendoodle named Lacy, she's friendly but skittish. We ask you always close the gates to the yard.

Restored apartment in a Victorian home, centrally located in the Village of Greenport. Short, few minutes walk to restaurants, shops, cafes in town. Also, conveniently located (10 minute walk) to the Hampton Jitney bus stop, LI Railroad and Shelter Island Ferry as well as local beaches. Enjoy the charm of a historic home, with all the convenience of modern amenities!

The space
The apartment has been thoughtfully curated for a perfect vacation getaway. The main bedroom with queen bed is a sunny, breezy oasis with French doors and a Juliet balcony. The second small bedroom is cozy and comfy, with a plush twin XL bed. Perfect for snoozing or it can be used as a separate work/office room.

The bathroom includes the original clawfoot tub, newly refinished. Ideal for a bubble bath or long soak. For those who prefer the feel of falling water, there is also a separate shower with decadent rain shower head (adjusts for high pressure too!). In the cold season, the tiled floor is warmed by radiant heat to keep your feet toasty!

The kitchen has all Bosch appliances, including dishwasher, and induction cooktop/oven. Compact washer and dryer is tucked away in a closet nearby.

A high-efficiency, split AC system is installed so you can stay cool after a hot day at the beach. There are individual remote controls for the main space (living room and kitchen) and also main bedroom. There are ceiling fans in the living room and main bedroom too. The small bedroom is cooled with a window AC unit during the warm season. (The split AC system provides heat in the fall/winter season to keep you warm and cozy.)

There is also dock nearby, just a 2 minute walk away! So you can take a quick dip into the bay to cool off during the day. Or it's perfect for watching the sunrise, sunset or star gazing at night. Take your pick!

Guest access
Access to the private apartment is through the front door of the house, which opens to a stair vestibule. Once inside the vestibule, you will go up the stairs to enter your private apartment. Electronic keypads are on both on the front entry door and separate apartment door. (Photos of entrance are shown in listing.)

The stairs leading up to the apartment are on the steep side and may not be ideal for all guests.

Other things to note
Families with children are welcome, but please note that childproof devices (cabinet locks, window guards, etc.) have not been installed.

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

The space
Its a newly renovated, spacious two bedroom apartment located in the heart of downtown Greenport. The first floor is currently rented out as a retail boutique.

Guest access
The entire upstairs apartment is for your use.

Welcome to our centrally located & recently renovated top floor apt. in the historic Sterling Harbor neighborhood. Enjoy views of the local marina from our kitchen. A public dock is at the end of our street. The center of town is just a few short blocks away. Both bedrooms are nicely separated. One has a king bed, the other a queen. Both the living room & the kitchen are spacious & light filled. The kitchen is well equipped for those who prefer to stay in. Enjoy morning coffee on the front porch

The space
We chose our building because all of the rooms are large and light filled. Both the kitchen and living room are spacious. The main bedroom easily fits a king bed. The second bedroom has a queen bed.

Guest access
Guests will have use of the top floor and the front porch.

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

We are centrally located in a quiet neighborhood within blocks from the heart of Greenport Village, Peconic Bay Beach, LIRR/Jitney, restaurants, shopping, Mitchell Park, and more! Explore local farms, wineries, breweries and all the North Fork has to offer.
Beautifully furnished, ground floor apt with private entrance & patio area comfortably sleeps four, features a queen Tempur-Pedic mattress & convertible couch. Friendly, housetrained pets are welcome for an additional charge.

The space
Please see list of full amenities.

Guest access
Everything is within walking distance or a short bike ride. We are steps away from the beach and the LIRR/Jitney.

Other things to note
We will welcome you with coffee, bottled water, beer, wine and treats for the pets.

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

Upscale 2- story building offers 3 bedrooms, 2 baths spacious apartment in the heart of Greenport. A vaulted ceiling in the great room (kitchen, dining & living room) with large windows and hardwood floors with plenty of natural light. Utilities included. CAC, Laundry. Less than a mile to a public beach, public transportation, restaurants, shops and Mitchell park. Off street parking for 2-3 cars.

Bathtub • Hot water • Bed linens • Hangers • Washer • Iron • Extra pillows and blankets • Hair dryer • Essentials • Dryer

Beautiful junior one bedroom in the heart of Greenport Village. Located in the historical district, our basement apartment is walking distance (2-Blocks) to downtown Greenport. Perfect for a couples weekend, girls trip, or for a small family.
Our apartment includes one queen bed and a twin day bed with trundle underneath. (Sleeps 4 total) TV with streaming service and WiFi are included. W/D are available upon request.

The space
Two blocks from downtown Greenport, our apartment has everything you’re looking for when it comes to a getaway. We offer a queen bed and a daybed with trundle, sleeping up to 4 persons. The apartment would be a great stay for a girls trip, couples week/weekend away, or a family vacation.

Guest access
Access is available down our driveway towards the backyard. There are steps going down to the apartment. There is a shared door between the apartment and our house for guest emergency use only.

Other things to note
The “resort fee” is actually a Suffolk County Short Term Rental Tax (unfortunately Airbnb does not have an option to name it otherwise). To read more, please visit the Suffolk County Comptrollers Hotel & Motel
Tax Page

Essentials • Extra pillows and blankets • Room-darkening shades • Hair dryer • Bed linens • Hot water • Free dryer – In unit • Free washer – In unit • Hangers • Cleaning products

Have fun with the whole family at this stylish place.

Come enjoy all Casa Greenport 1st floor has to offer! Just one block from main street walk to several restaurants, shops, and the waterfront. 15 min walk from the Greenport train and Jitney Stop.

Not enough space for your group check out our listing for both floors. https://www.airbnb.com/
If you'd like to book the upstairs instead feel free to check out airbnb.com/h/casagreenportfullhome
Want to rent something else entirely, we have other homes in the area just let me know.

The space
Bedroom 1: King Bed
Bedroom 2: Two Twin Beds
Bedroom 3: One Twin Bed and Desk
1 Full Bathroom
Office
Kitchen
Livingroom
Washer, Dryer, Dishwasher
Outdoor Dining Area
Pool Access shared with upstairs apartment

Guest access
Apt 1 Front Entrance
Everything on the first floor
Pool(shared access with upstairs)
Outdoor Dining Area

Upstairs deck for 2nd floor apartment only
Driveway for upstairs unit only

Other things to note
Pool is shared between the upstairs and downstairs apartments. Pool is open May - September. Pool can be heated for a $100 fee for bookings 1 week or less in length. For bookings longer than 1 week we will bill you after your stay when we get the bill.

Driveway is for the downstairs apartment. Street parking in front of the house is for the upstairs unit.

Garage and basement are not spaced open to the guests.

Essentials • Dryer • Bathtub • Bed linens • Hair dryer • Outdoor shower • Iron • Hangers • Hot water • Washer

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 space
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: Stairs required to access
PARKING: Street parking
ADDT'L ACCOMMODATIONS: An additional 1-bedroom property for 2 guests (Listing #346802) 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

Guest access
Guests will have access to the entire property

Other things to note
- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Must be at least 25 years old to book
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: This property is not suitable for young children
- 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

Outdoor playground • Bed linens • Central heating • Hot water • Hair dryer • Ethernet connection • Central air conditioning • Essentials • TV • Shampoo

This updated 2-bedroom, 2-bathroom condo offers the perfect blend of comfort, style, and breathtaking views. Relax on your private balcony overlooking the serene Long Island Sound, where you can sip your morning coffee or unwind with a glass of wine as you watch the sunsets in the evening.

Whether you're looking for a midweek escape or a weekend getaway, this condo is the ideal setting.

Make this waterfront condo your peaceful sanctuary and experience everything the North Fork has to offer.

The space
Breathtaking Waterfront 2 bedroom 2 bath 2nd floor condo. This unit offers a queen bed in one room and two doubles in another. A kitchenette is set up with a cook top, mini fridge, coffee maker, and other kitchen amenities like kitchen utensils.

Guest access
Guess will be sent access information prior to check in via Airbnb

The space
Two bedroom two full bathroom corner condo, this condo offers an extended balcony size, with great views of the sunset and ideally located between the pool and beach and surrounded by the great lawn with easy access the bbq grills, picnic tables and adirondack chairs.

Guest access
seasonal outdoor pool limited hours.

Other things to note
Check in time is 5PM. Check out time is 10AM

Enjoy this newly renovated 2 bedroom 2 bath loft apartment centrally located in the village of Greenport. Conveinient 5 minute walk to Front street, Main street shops, restaurants, bars and across from park/playground. Private rear deck for outdoor dining and a covered front porch for a glass of wine or morning coffee. Parking for 2 midsize cars in driveway. Power outlet available for EVs. Private yard with BBQ, firepit, adirondack chairs grassy area and lounges for sunning, reading or napping.

Guest access
Guests can access the loft apartment through the front entry door locted on the large front covered porch. Guests can unlock the front door by using the electronic keypad lock. There are no keys necessary and the access code ro the electronic lock will be provided the day of check-in.

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 space
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
PARKING: Driveway (1 vehicle), safe street parking in front of house
ADDT'L ACCOMMODATIONS: An additional 1-bedroom property for 2 guests (Listing #346800) 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

Guest access
Guests will have access to the entire property

Other things to note
- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Must be at least 25 years old to book
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: This property is not suitable for young children
- 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

TV • Central air conditioning • Essentials • Iron • Ethernet connection • Shampoo • Bed linens • Hot water • Hair dryer • Outdoor playground

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 space
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, 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

Guest access
Guests will have access to the entire property via keyless entry

Other things to note
- No smoking
- No pets allowed
- No events, parties or large gatherings
- Must be at least 25 years old to book
- 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

Hot water • Central air conditioning • Pack ’n play/Travel crib • TV • Hair dryer • Hangers • Essentials • Bed linens • Board games • Books and reading material