Best Apartments in Greenport

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.

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

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.

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

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.

Child Friendly • Bedding/Linens • Laundry • Air Conditioner