Greenport West Rentals
- From $612 per night (USD)
VRBO
90 feet of private waterfront w beach, new renovation, panoramic views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Spacious and Luxurious 3 bedroom; brand new construction with 120 feet of waterfront and spectacular sunset views • 2 l ...
From $612 per night (USD)VRBO
- From $384 per night (USD)
VRBO
Storybook Beautiful 3-Bedroom Cape
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Rental Permit # 0573 This is a newly renovated 3 bedroom ( one bedroom is in the loft) cottage in the beautiful histori ...
From $384 per night (USD)VRBO
- From $968 per night (USD)
VRBO
Beautiful Secluded Family Home on Shelter Island.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This is a magical house. It is surrounded by woods and a pond. The only sounds you hear are the birds and other animals, ...
From $968 per night (USD)VRBO
- From $389 per night (USD)
VRBO
Charming historic house on Sterling Harbor, water views, 5-min walk to village
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Tucked away in Sterling Harbor in the Historic District on Greenport's most desired street sits this lovely, 3-bedroom 1 ...
From $389 per night (USD)VRBO
- From $273 per night (USD)
VRBO
Architect Designed Home in Waterfront Village
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Designed and built in 2003, this cozy house has water views of Peconic Bay, enormous glass skylights, fully equipped kit ...
From $273 per night (USD)VRBO
- From $646 per night (USD)
VRBO
Unique Southold waterfront luxury home with heated pool on Long Creek
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
We bought our wonderful house five years ago and have made many important renovations. The newest is a hybird bocce cour ...
From $646 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Unspoiled North Fork Charm, walk to bay & sound beaches, minutes to Greenport
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Vintage North Fork cottage tucked away under the trees. Enjoy cool breezes through the many spacious windows. An easy ca ...
From $250 per night (USD)VRBO
- From $1198 per night (USD)
VRBO
Bohemian Old Life Saving Station with Beach & Pool
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 13
ONLY 1 WEEK RENTALS FROM MID JUNE TO MID SEPTEMBER RENTALS ARE FROM FRIDAY TO FRIDAY AVAILABILITY FOR JULY & AUGUST IS ...
From $1198 per night (USD)VRBO
- From $460 per night (USD)
VRBO
Private & Spacious Five Room Suite..Steps To Bay Beach and walk to Village.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
1896 Restored Victorian located within steps to a lovely Bay Beach. Village restaurants, shops, NYC Hampton Jitney Expre ...
From $460 per night (USD)VRBO
- From $730 per night (USD)
VRBO
Spacious Modern on wooded lot - 5 min from beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Newly renovated, spacious, 4 bedroom, 3.5 bath house on 1.25 acres in the Hay Beach neighborhood of Shelter Island overl ...
From $730 per night (USD)VRBO
- From $418 per night (USD)
VRBO
First Floor 1905 Victorian home in the heart of Greenport Village
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Home has a full kitchen and a washer/dryer. There are two bedrooms with queen size beds plus a Murphy double bed. One ba ...
From $418 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Tranquil, Beachfront Getaway with Dock, Fabulous Sunset Views!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This Shelter Island beach house has all the necessary ingredients for a fabulous year-round getaway. Located on a shy ac ...
From $450 per night (USD)VRBO
- From $707 per night (USD)
VRBO
Renovated Waterfront Cottage With Spectacular Views And Private Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This home sits on the edge of a bluff with unobstructed views of the water and a secluded cove with direct access to a b ...
From $707 per night (USD)VRBO
- From $1236 per night (USD)
Expedia
Greenport Magical Gem - Beautiful Backyard And Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The uniqueness of this wonderful home is the backyard which is lavishly landscaped with both beautiful flowers and lush ...
From $1236 per night (USD)Expedia
- From $418 per night (USD)
VRBO
Gorgeous lakefront retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning 3 bedroom ranch style home on the lake in East Marion. Sleeps 6 in comfort. Come and watch the Ospreys fish fro ...
From $418 per night (USD)VRBO
- From $765 per night (USD)
VRBO
Newly renovated! Shelter Island Gem, 3 blocks from Sunset Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beat the heat in this fabulous summer retreat on laid back Shelter Island. This newly gut renovated charmer is nestle ...
From $765 per night (USD)VRBO
- From $540 per night (USD)
VRBO
Waterfront, private beach, ready for adventure, light & bright!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Set on a magical one-acre promontory, jutting into beautiful Long Creek with spectacular water views from every room, th ...
From $540 per night (USD)VRBO
- From $552 per night (USD)
VRBO
Shelter Bay Cove Waterfront, North Fork , Hamptons ,Long Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
World class views of water and sunsets are the signature features of this charming, 3 bedroom house with 90 feet of wate ...
From $552 per night (USD)VRBO
- From $780 per night (USD)
VRBO
Classic Waterview Victorian Summer Cottage in Park-Like-Setting
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 6
Beautiful turn-of-the century Victorian Summer Beautiful turn of the century home located on Rainbow Park with breatht ...
From $780 per night (USD)VRBO
- From $1540 per night (USD)
VRBO
One Of A Kind, Resort- Like Waterfront Cottage In Wine Country
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
LI Sound Waterfront Cottage with 2 Bedrooms and 1 Bathroom. Completely Renovated and Modern Living Space with Open Layou ...
From $1540 per night (USD)VRBO
- From $603 per night (USD)
VRBO
House by the Bay with Large In-ground Pool, Steps from Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Have a perfect vacation in our pristine two-story farmhouse style house. There are three bedrooms and two full baths. On ...
From $603 per night (USD)VRBO
- From $338 per night (USD)
VRBO
Beachy Cottage by the Bay
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Our family cottage has provided joy and memories for decades, and after fixing it up over the past year we are excited t ...
From $338 per night (USD)VRBO
- From $479 per night (USD)
VRBO
Scandinavian modern style meets the North Fork. NEW 18 x 40 gunite pool June 1.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Newly remodeled, clean and peaceful North Fork beach house. Minutes from Greenport and Orient. 18 x 40 gunite heated po ...
From $479 per night (USD)VRBO
- From $929 per night (USD)
VRBO
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
NO EXTRA FEES FOR CLEANING, EXTRA GUESTS & AMENITIES! Relax in one of America's most beautiful seaside villages, histo ...
From $929 per night (USD)VRBO
- From $629 per night (USD)
VRBO
Maritime Village House Walk or Bike to All
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful updated historic home in the village of Greenport. Central AC, newly renovated kitchens and bathrooms, large f ...
From $629 per night (USD)VRBO
- From $565 per night (USD)
VRBO
Shelter Island Beauty by the bay! Quiet neighborhood with day dock, bay access.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful home has spectacular views from all windows. It is spotless, upscale with attention to details. Such as ...
From $565 per night (USD)VRBO
- From $1207 per night (USD)
VRBO
Picturesque Views Of Gardiners Bay \/ Shelter Island With Heated Waterfront Pool
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The charming 3 bedroom, 2 bath house is located in East Marion; a (literal) stone's throw from a private sand beach, a f ...
From $1207 per night (USD)VRBO
- From $2051 per night (USD)
VRBO
Spacious house next to the beach, Ferry and Eateries.
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 11
Located on one acre in the highest part of Shelter island Heights, this home offers 6 bedrooms, 4.5 baths, a fireplace a ...
From $2051 per night (USD)VRBO
- From $525 per night (USD)
VRBO
Sunrise Sunset! Beautiful waterfront property.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Imagine beautiful views of both sunrise and sunset from one of 3 beautiful decks. Amazing views of Bug Light House and M ...
From $525 per night (USD)VRBO
- From $267 per night (USD)
VRBO
Private Pebble Beach Community with Tennis next to Island End Public Golf Course
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tucked away between farmland and Long Island Sound in Pebble Beach Farms, East Marion, this very clean, single story ran ...
From $267 per night (USD)VRBO
- From $457 per night (USD)
VRBO
Peaceful Shelter Island sanctuary with heated gunite saltwater pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This property is extremely quiet and peaceful sitting on almost an acre of beautifully landscaped gardens and backing on ...
From $457 per night (USD)VRBO
- From $576 per night (USD)
VRBO
Family friendly home near beach with wonderful deck!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
You can walk to the beach from this attractive home that comfortably sleeps 7. Enjoy cocktails and outdoor dining on th ...
From $576 per night (USD)VRBO
- From $402 per night (USD)
VRBO
Spacious apartment, 3 blocks to downtown and steps to fishing pier.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Property Charming and newly updated second floor apartment, less than a 5 minute walk to downtown. Enjoy our incredi ...
From $402 per night (USD)VRBO
- From $1392 per night (USD)
Expedia
5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views..
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Guests are sure to enjoy a memorable vacation in this fully furnished, 5 bedroom/3.5 bath newly renovated expansive mode ...
From $1392 per night (USD)Expedia
- From $849 per night (USD)
VRBO
Greenport Gem: Private Saltwater Pool, Awesome Basement, Walk to Everything!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to our charming Greenport Village oasis! Nestled in a quiet neighborhood just a short stroll from the vibrant hea ...
From $849 per night (USD)VRBO
- From $1062 per night (USD)
VRBO
Impeccably Restored & Charming Victorian Summer Cottage-5 Bed, 4 Bath, Sleeps 10
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Please contact us if you are interested in booking a month or longer stay for the 2024 summer season. An impeccably res ...
From $1062 per night (USD)VRBO
- From $858 per night (USD)
VRBO
Beach Front in Southold; newly renovated\/baths\/kitchen\/2nd floor family room!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Newly renovated with two full bathrooms, kitchen and second floor entertainment/family/ bedroom with glorious views over ...
From $858 per night (USD)VRBO
- From $441 per night (USD)
VRBO
Rose Cottage by the Bay.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Seaside Greenport Village Historic District, on Long Island’s North Fork, New York. “Rose Cottage” is within the Greenp ...
From $441 per night (USD)VRBO
- From $1101 per night (USD)
VRBO
Waterfront house on steerling harbor, views from every room.
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Fully furnished monthly, summer or year round rental on Sterling Harbor with spectacular views out to Bay. A five minute ...
From $1101 per night (USD)VRBO
- From $293 per night (USD)
VRBO
NEWLY Renovated Family Home Great Area - Beach - Greenport - Ferry - Restaurants
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
PLEASE READ Please park in the street when arriving as many spots along the streets are available. Laundry + Dryer is ...
From $293 per night (USD)VRBO
- From $422 per night (USD)
VRBO
Newly Renovated - Walk to Town and Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Brand new gut renovation - 3br, 3 full bath unit in the heart of Greenport Village! Have it all - walk to the train and ...
From $422 per night (USD)VRBO
- From $2263 per night (USD)
Expedia
Stunning Shelter Island Estate
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 14
Stunning Shelter Island traditional over 3 floors with pool and separate contemporary guest house in luxury settings. Sh ...
From $2263 per night (USD)Expedia
- From $309 per night (USD)
VRBO
Charming 2 bedroom apartment in the heart of Greenport.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Your family will be close to everything Greenport has to offer when you stay at this centrally-located 2 bedroom apartme ...
From $309 per night (USD)VRBO
- From $734 per night (USD)
VRBO
Fall Getaway: Walk to the Beach and Fine Dining!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Unwind and reconnect this Fall at our stunning, newly built (2024) beach getaway on Shelter Island! Perfect for families ...
From $734 per night (USD)VRBO
- From $1800 per night (USD)
VRBO
Spacious Home with Pool in Southold
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Discover this sun-filled 4-bedroom Southold home, perfect for a relaxing escape. Enjoy a luxurious saltwater pool, cozy ...
From $1800 per night (USD)VRBO
- From $550 per night (USD)
VRBO
On Shelter Heights, Huge Outdoor Decks, Separate Guest House
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
Please note that a reservation for this property needs to be approved before it is confirmed. Set on one acre in the hi ...
From $550 per night (USD)VRBO
- From $440 per night (USD)
VRBO
Relaxing water front newly renovated condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Tennis, swimming, walk to town, sailboats, birds of all kinds in this private community with spectacular views of Sterli ...
From $440 per night (USD)VRBO
- From $339 per night (USD)
Expedia
North Fork seaside retreat for design lovers
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A thoughtfully renovated, direct waterfront home on Long Island's North Fork. Situated on the coveted bay side, where th ...
From $339 per night (USD)Expedia
- Click For Pricing
VRBO
Southold near vineyard & beach
- Bedrooms:
- 0
- Bathrooms:
- 0
- Sleeps:
- 0
Enjoy a stylish experience at this centrally-located historic charmer. Have cocktails on the balcony, cook in the fully ...
Click For PricingVRBO
- Click For Pricing
Expedia
Intimate Island Getaway with Stunning 180˚ Waterfront Views
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Savor a romantic and secluded summer getaway. Enjoy a front row seat to breathtaking and dramatic views of the Shelter ...
Click For PricingExpedia
- From $908 per night (USD)
VRBO
Very Large, Comfortable, Victorian 4 Bedroom House + Beach Club
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Shelter Island Heights 1875 Large Historic Victorian Home For Rent, Sunny 4 bedrooms, 2 baths, Central AC, full dining ...
From $908 per night (USD)VRBO
- From $818 per night (USD)
VRBO
Coastal Getaway, water views, walk to beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Coastal Vibes: Home with waterviews, short distance from a secluded beach on Pipes Cove overlooking Shelter Island. Bea ...
From $818 per night (USD)VRBO
- From $553 per night (USD)
VRBO
Restored Artist's House in Heart of Village
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Eclectic, recently renovated house circa 1880 located in the charming Greenport Village. Equipped with modern amenities, ...
From $553 per night (USD)VRBO
- From $1183 per night (USD)
VRBO
Sandy Bay Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Stunning waterfront location with amazing sugar sand beach! Well proportioned home with beautiful symmetry. The centra ...
From $1183 per night (USD)VRBO
- From $605 per night (USD)
VRBO
Charming 3 Bed\/2.5 Bath Cottage In Historic Shelter Island Heights Walk to Ferry
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your perfect getaway within the coveted Shelter Island Heights Historic District. This fully renovated, charm ...
From $605 per night (USD)VRBO
- From $1079 per night (USD)
Expedia
Greenport Village Home with Heated Salt Water Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Discount for taking all of June - August! One of a kind Greenport Village rental! This 1926 renovated 4 bedroom 2.5 bath ...
From $1079 per night (USD)Expedia
- From $1051 per night (USD)
VRBO
Newly renovated farmhouse - steps to Greenport Village
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Luxury home on a quiet street in the Village of Greenport. This brand new Farmhouse has been fully renovated with all m ...
From $1051 per night (USD)VRBO
- From $1050 per night (USD)
VRBO
Resort Style Home- Family Friendly
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 6
Located in beautiful Hay Beach, this home has four bedrooms and three full bathrooms. The main bedroom has a king bed an ...
From $1050 per night (USD)VRBO
- From $646 per night (USD)
VRBO
Contemporary Colonial home with pristine Peconic bay views, steps to...
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Vineyard Beach House Contemporary Colonial home with pristine Peconic bay views, steps to private beach, Weber grill, f ...
From $646 per night (USD)VRBO
- From $492 per night (USD)
Expedia
Relaxation in Greenport
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Renovated house located in the heart of Greenport is perfect for family getaways. Blocks away from Main Street. With ama ...
From $492 per night (USD)Expedia
- Click For Pricing
VRBO
2-bedroom in Heart of Greenport Historic District
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Centrally located in the Greenport historic district and just a 5-7 min walk from all the stores, cafes, and restaurants ...
Click For PricingVRBO
- From $201 per night (USD)
VRBO
Waterfront NoFo Cottage with public beach access
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Modern and chic waterfront cottage overlooking Marion Lake. 2 bedroom, 1 bath home with an open plan living room/kitchen ...
From $201 per night (USD)VRBO
- From $242 per night (USD)
VRBO
5 minute walk to beaches and beautiful downtown Greenport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Lovely Victorian home with private entrance, porch, and brick patio. Floor to ceiling windows in light filled large bed ...
From $242 per night (USD)VRBO
- From $439 per night (USD)
Expedia
Charming Northfork Townhouse- walk to all
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Fully Renovated Townhouse walking distance to town, beaches, parks, brewery and short bike to wineries. Brand new Kitche ...
From $439 per night (USD)Expedia
- Click For Pricing
VRBO
Cozy Farmhouse Secluded Community w\/ Private Beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Beautiful farmhouse nestled amongst the private community in East Marion minutes from the beach. This home is great for ...
Click For PricingVRBO
- From $262 per night (USD)
Expedia
Charming Greenport Gem 1, 1 Mile to Ferry!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Travel to the North Fork of Long Island for a much-needed getaway and experience both modern luxury and historic desire ...
From $262 per night (USD)Expedia
- From $1045 per night (USD)
VRBO
New Construction Greenport Pool House - 3 Blocks from Town
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 16
This brand new construction house is perfect for large groups. Gather with friends and family in the double height ceili ...
From $1045 per night (USD)VRBO
- From $518 per night (USD)
Expedia
Entire, new, roomy, village beach house close to beach, park, and town center
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our most lovely Greenport Beach Home.....800 feet to sixth street beach and playground. A true beach getaway, ...
From $518 per night (USD)Expedia
- Click For Pricing
VRBO
Vintage Cottage in Greenport Village
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
*** As we’re brand-new to VRBO, we’re happy to offer our cottage at a reduced rate to our first couple of renters! *** ...
Click For PricingVRBO
- From $346 per night (USD)
Expedia
Lagoon Lodge: North Fork,Charming 3Br, Waterfront, near Greenport, WIFI
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lagoon Lodge is a charming waterfront home with 3 bedrooms, and 2 bathrooms, and has central air and high-speed internet ...
From $346 per night (USD)Expedia
- From $1021 per night (USD)
VRBO
Picture Perfect Greenport Cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Well appointed cottage for all seasons. Picture perfect privet lined outdoor living space with sofas, dining area, fire ...
From $1021 per night (USD)VRBO
- From $370 per night (USD)
Expedia
Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy this beautifully renovated first floor “Captains House” apartment in the heart of Greenport Village. Harbor Views ...
From $370 per night (USD)Expedia
- From $583 per night (USD)
VRBO
Idyllic North Fork hideaway! Quiet 3 Bedroom cape in East Marion
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Relax, rejuvenate and recharge in this updated North Fork gem with new kitchen, outdoor deck, screened in porch and larg ...
From $583 per night (USD)VRBO
- From $209 per night (USD)
Expedia
American Beech in Greenport - Petite King Room 7
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...
From $209 per night (USD)Expedia
- From $191 per night (USD)
VRBO
Harbor Heights
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Discover this marvelous 2-bedroom gem in Greenport. This cool apartment boasts a cozy living room with a phenomenal sofa ...
From $191 per night (USD)VRBO
- Click For Pricing
Expedia
Charming Home in the heart of Greenport Village!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy all that Greenport has to offer by staying in the center of it all. Relax in the large fenced yard or screened in ...
Click For PricingExpedia
- From $450 per night (USD)
VRBO
Enjoy Autumn with us.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Hi everyone: I hope you'll look at the photos of our property and our guest reviews. But please allow me to say we do ha ...
From $450 per night (USD)VRBO
- From $1060 per night (USD)
Expedia
Brand New! 6BR, 4.5 Bath, Pool, Hot Tub, Walk to Beach
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
2 week minimum stay only. This newly constructed spacious 6-bedroom, 5-bathroom home offers the perfect escape for your ...
From $1060 per night (USD)Expedia
- Click For Pricing
VRBO
Charming and cozy home in the heart of Greenport Village.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 1
Three room suite available in a historic home. Large bedroom with a view of the sunrise, bathroom with a clawfoot tub an ...
Click For PricingVRBO
- From $900 per night (USD)
VRBO
North Fork Waterfront Spectacular Views Cottage circa 1930
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 10
North Fork Waterfront Spectacular Views Cottage circa 1930' On Golden Pond' Private road, amazing waterfront vie ...
From $900 per night (USD)VRBO
- From $764 per night (USD)
VRBO
Gorgeous Greenport Beach House right on the Sound! Breathtaking views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Villa Sonore. A gorgeous beachfront home in Greenport located right on the LI Sound. Walk to restaurants and ...
From $764 per night (USD)VRBO
- From $575 per night (USD)
VRBO
The Lucky Oyster Est 1886 3 Bd \/ 2 Ba Historic & Walk to Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located steps from town, this historic gem is perfect for a weekend getaway. With a spacious kitchen, living and dining ...
From $575 per night (USD)VRBO
- Click For Pricing
VRBO
Breathtaking Waterfront Greenport Village Condo, private beach, pool, tennis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Unending water views. Luxury beachfront condo, overlooking Greenport Harbor and Shelter Island. Private beach, pool, ten ...
Click For PricingVRBO
- From $489 per night (USD)
VRBO
Sea Pine Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in the woods just behind the Pridwin Hotel, walk to Crescent Beach, Perlman Music and Sunset Beach. 1930''s Shel ...
From $489 per night (USD)VRBO
- From $386 per night (USD)
VRBO
Dog-friendly modern charmer with wood-burning fireplace, grill, W\/D, and AC
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
North Fork Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $386 per night (USD)VRBO
- From $685 per night (USD)
VRBO
Restored Seaport Village Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Please Note : Guests must add a message with their reservation request, and kindly indicate who is traveling. Welcome! ...
From $685 per night (USD)VRBO
- From $828 per night (USD)
VRBO
Beautiful Ranch Style Shelter Island Home with Private Pool, Close to Golf...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Please note that a reservation for this property needs to be approved before it is confirmed. Shelter Island Modern Ran ...
From $828 per night (USD)VRBO
- Click For Pricing
Expedia
Greenport Loft Apartment
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy this newly renovated 2 bedroom 2 bath loft apartment centrally located in the village of Greenport. Conveinient 5 ...
Click For PricingExpedia
- From $260 per night (USD)
VRBO
Blue Bay Dream w\/ Seasonal Outdoor Jacuzzi, Cabana + Office
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bar ...
From $260 per night (USD)VRBO
- From $857 per night (USD)
VRBO
North Fork Waterfront Gem!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Live the waterfront life! Kayak, paddle board, boat from your front door! Enjoy gathering your own oysters and clams fro ...
From $857 per night (USD)VRBO
- From $334 per night (USD)
VRBO
Quiet Oasis in the Heart of North Fork with Magnificent Views of Lavendar Farm
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
LEGAL Rental on the North Fork located in East Marion, NY in the heart of wine country, five minute drive from Greenport ...
From $334 per night (USD)VRBO
- From $408 per night (USD)
VRBO
Greenport Village On The Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Waterfront condo in the heart of wine country. 2 blocks walk to town and train. 2 bedrooms 2 baths, pool, tennis court, ...
From $408 per night (USD)VRBO
- From $702 per night (USD)
VRBO
Tennis Court, Open and Spacious Living and Dining Areas, Close Proximity to...
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 10
Please note that a reservation for this property needs to be approved before it is confirmed. Great Circle Serenity Te ...
From $702 per night (USD)VRBO
- Click For Pricing
Expedia
Historic Stunner in Heart of Village
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy this centrally-located historic home restored w/ modern conveniences. 1st FL includes sunny living room w/ comfort ...
Click For PricingExpedia
- From $724 per night (USD)
VRBO
Modern Farmhouse Oasis in Greenport Village - 10 min walk to restaurants\/shops
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Newly renovated modern farmhouse with the perfect blend of style & comfort. Bask in the serenity of our fully equipped 6 ...
From $724 per night (USD)VRBO
- From $340 per night (USD)
VRBO
Heavenly Craftsman Just minutes to beaches, vineyards, ferries and Greenport!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Rental Permit 1048 Perfect and original Craftsman Arts and Crafts style house. This is the loveliest historic house l ...
From $340 per night (USD)VRBO
- From $694 per night (USD)
VRBO
Lovely North Fork Sea Captain's Home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Town of Southold Rental Permit 0605 The Sea Captain's Home is a sprawling, well-preserved, 4-bedroom-plus Italianate V ...
From $694 per night (USD)VRBO
- From $2250 per night (USD)
VRBO
Jewel of the North Fork -Bachelorette Paradise-Must Rent Full Weeks in Summer
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
This extraordinarily beautiful, one-of-a-kind beach house is located on 4+ acres with a private beach spanning 1,100' on ...
From $2250 per night (USD)VRBO
- From $1525 per night (USD)
VRBO
Beautiful waterfront house in Southold
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Beautiful Waterfront Home With Stunning Views of Hashamomuck Pond. Escape from it all for a memorable family vacation in ...
From $1525 per night (USD)VRBO
- From $503 per night (USD)
Expedia
Walk to private bay beach, close to Greenport, wineries, golf! Premier Host home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Our home has been a family retreat for over 20 years, and has been completely refreshed in 2022. Interior painted, new f ...
From $503 per night (USD)Expedia