Greenport West Rentals
From $522 per night (USD)VRBO
Lavender Field Retreat Nearby the Beach & Farms
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Situated on the North Fork of Long Island in the hamlet of East Marion, New York. This charming Lavender Fields ...
From $522 per night (USD)VRBO
From $914 per night (USD)VRBO
Beautiful Renovated Beachfront Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
High on a bluff overlooking the Sound, this amazing Sound front home has been completely renovated with a chef's gourmet ...
From $914 per night (USD)VRBO
From $2571 per night (USD)VRBO
Jewel of the North Fork -Bachelorette Paradise-Must Rent Full Weeks in Summer
- Bedrooms:
- 3
- Bathrooms:
- 3
- 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 $2571 per night (USD)VRBO
From $568 per night (USD)VRBO
Greenport Waterfront Cottage w/Private Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the historic and centuries-old town of Greenport Village with its quiet streets, serious dining options and ...
From $568 per night (USD)VRBO
From $1057 per night (USD)VRBO
Beach/Waterfront 7.2 ac Estate with Dockage -40 ft
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Same location I have two 2 cottages that sleep 4 each . See VRBO search bar [Where To] with the Listing ID 173361 and th ...
From $1057 per night (USD)VRBO
From $821 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 $821 per night (USD)VRBO
From $769 per night (USD)VRBO
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 $769 per night (USD)VRBO
From $785 per night (USD)VRBO
Lovely North Fork Sea Captain's Home
- Bedrooms:
- 2
- 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 $785 per night (USD)VRBO
From $316 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 $316 per night (USD)VRBO
From $1738 per night (USD)VRBO
Beautiful waterfront house in Southold
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Beautiful Waterfront Home With Stunning Views of Hashamomuck Pond. Escape from it all for a memorable family vacation in ...
From $1738 per night (USD)VRBO
From $705 per night (USD)VRBO
Brand new 2 bedroom, Greenport Village, walk to town Marina Views!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Luxury 2 bedroom, first floor apartment located across the street from Townsend Manor Marina in the heart of Greenport V ...
From $705 per night (USD)VRBO
From $1396 per night (USD)VRBO
Bohemian Old Life Saving Station with Beach & Pool
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 13
ONLY 1 WEEK RENTALS FROM MID JUNE TO MID SEPTEMBER RENTALS ARE FROM FRIDAY TO FRIDAY AVAILABILITY FOR JULY & AUGUST IS ...
From $1396 per night (USD)VRBO
From $534 per night (USD)VRBO
Private & Spacious Five Room Suite..Steps To Bay Beach and walk to Village.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
1896 Restored Victorian located within steps to a lovely Bay Beach. Village restaurants, shops, NYC Hampton Jitney Expre ...
From $534 per night (USD)VRBO
From $794 per night (USD)VRBO
Spacious Modern on wooded lot - 5 min from beach!
- Bedrooms:
- 3
- 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 $794 per night (USD)VRBO
From $775 per night (USD)VRBO
1820 Whaling Captain's Home - A walk to a coffee or cocktail!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Set in the historic section of Greenport village, the Captain’s House, built in 1820, is an elegant and charming 3 bedro ...
From $775 per night (USD)VRBO
From $908 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 $908 per night (USD)VRBO
From $720 per night (USD)VRBO
POOL + Beach 1 mi. to Greenport Village! July deal 7+ nights, just message
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Make yourself at home in this 5 bedroom / 3 full bathroom modern ranch featuring: * chef's eat-in kitchen w/ 2 ovens, lu ...
From $720 per night (USD)VRBO
From $1091 per night (USD)Expedia
🌟 Walk to the village ❤ of Greenport
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Stay in our Cozy Greenport home, in one of the most central and convenient locations in Greenport Village! *Amazing Wint ...
From $1091 per night (USD)Expedia
From $387 per night (USD)VRBO
Charming Northfork Getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Newly renovated and charming home in the NorthFork, a short walk to the village of Greenport, vineyards, and the breatht ...
From $387 per night (USD)VRBO
From $512 per night (USD)VRBO
Charming historic house on Sterling Harbor, water views, 5-min walk to village
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
REDUCED RATE FOR MONTH OF OCTOBER!! Tucked away in Sterling Harbor in the Historic District on Greenport's most desired ...
From $512 per night (USD)VRBO
From $338 per night (USD)VRBO
Architect Designed Home in Waterfront Village
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Designed and built in 2003, this cozy house has water views of Peconic Bay, enormous glass skylights, fully equipped kit ...
From $338 per night (USD)VRBO
From $297 per night (USD)VRBO
Waterfront Bungalow w/ Private Beach on Peconic Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Enjoy a variety of activities when staying at this charming bungalow with a private beach on the Peconic Bay. Enjoy the ...
From $297 per night (USD)VRBO
From $447 per night (USD)VRBO
Family and Friends in Historic Greenport
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Our house is an historic Dutch colonial, both cozy and spacious, with warm wood trim and wood floors throughout. The 20 ...
From $447 per night (USD)VRBO
From $280 per night (USD)Expedia
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located on a family-owned waterfront estate, The Gate House, a cozy 2-story, 2-bedroom cottage, is only steps away from ...
From $280 per night (USD)Expedia
From $567 per night (USD)VRBO
American Beech in Greenport - Two-Bedroom Apartment 8
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...
From $567 per night (USD)VRBO
From $410 per night (USD)Expedia
American Beech in Greenport - Deluxe King Suite 11
- 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 $410 per night (USD)Expedia
From $404 per night (USD)VRBO
American Beech - Deluxe King 5
- 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 $404 per night (USD)VRBO
From $358 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 $358 per night (USD)Expedia
From $410 per night (USD)VRBO
American Beech in Greenport - Deluxe King Suite 12
- 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 $410 per night (USD)VRBO
From $404 per night (USD)Expedia
American Beech in Greenport - Deluxe King 4
- 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 $404 per night (USD)Expedia
From $384 per night (USD)VRBO
American Beech in Greenport NY - King Suite 1
- 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 $384 per night (USD)VRBO
From $567 per night (USD)Expedia
American Beech - Luxury 2 Bedroom Apartment 10
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...
From $567 per night (USD)Expedia
From $456 per night (USD)VRBO
American Beech - Deluxe King Suite 14
- 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 $456 per night (USD)VRBO
From $384 per night (USD)Expedia
American Beech - King Suite 2
- 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 $384 per night (USD)Expedia
From $384 per night (USD)VRBO
American Beech in Greenport - Deluxe King 6
- 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 $384 per night (USD)VRBO
From $384 per night (USD)Expedia
American Beech in Greenport - King Suite 3
- 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 $384 per night (USD)Expedia
From $324 per night (USD)VRBO
Historic 1830s Greenport Home
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FALL 2025 AVAILABILITY! Looking to escape the city for a couple of weeks or even a month? The house is well set up fo ...
From $324 per night (USD)VRBO
From $755 per night (USD)Expedia
North Fork Waterfront + Private beaches + Spectacu
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Completely renovated in the last two years with new kitchen, two and a half new bathrooms, one with jetted tubs and both ...
From $755 per night (USD)Expedia
From $308 per night (USD)VRBO
Quaint DT Greenport Apt - 2 Mi to Shelter Island!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Surround yourself with seaside charm at this Greenport vacation rental. Perfect for couples and solo travelers, this 1-b ...
From $308 per night (USD)VRBO
From $356 per night (USD)Expedia
Bright Apartment - 1/2 Mi to Greenport Harbor!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Combine peace and quiet with bustling downtown action when you book this charming Greenport vacation rental! The 1-bedro ...
From $356 per night (USD)Expedia
From $800 per night (USD)VRBO
NEW VICTORIAN GEM IN GREENPORT
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Newly renovated Victorian house in Greenport. 5 queen bedrooms with private full baths, spacious, super clean and meticu ...
From $800 per night (USD)VRBO
From $1554 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 $1554 per night (USD)Expedia
From $467 per night (USD)VRBO
Gorgeous lakefront retreat
- Bedrooms:
- 2
- 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 $467 per night (USD)VRBO
From $789 per night (USD)Expedia
Renovated and Spacious Summer Home with Water View on Picturesque Island.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Steps from the beach, this beach house is the perfect destination to enjoy beautiful Shelter Island. Recently renovated ...
From $789 per night (USD)Expedia
From $332 per night (USD)VRBO
Cottage on Beach front Estate with Dockage .Walk to Village
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Charming 2-bedroom cottage located on a family-owned waterfront estate that was converted from a circa 1920s chicken coo ...
From $332 per night (USD)VRBO
From $842 per night (USD)VRBO
Renovated 4-Bedroom House with Heated Pool & Private Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Incredible beach house just minutes from Greenport! This freshly renovated home is a dream family vacation spot. It's ...
From $842 per night (USD)VRBO
From $573 per night (USD)VRBO
Seaside seclusion, salt water sanctuary!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Greenport is a charming seaside town with historic architecture with fantastic restaurants and plenty to see and do! Tr ...
From $573 per night (USD)VRBO
From $1411 per night (USD)VRBO
Dream Beach House on the North Fork: Waterfront, Private Beach + Stunning Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
One of the nicest spots on the North Fork (that's a quote from a knowledgeable local!), beautifully designer-renovated b ...
From $1411 per night (USD)VRBO
From $1148 per night (USD)VRBO
Elegant Victorian in the Heart of Greenport
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 13
Winter Harbor House is a stylish Victorian walking distance from the best restaurants, bars and beaches in Greenport Vil ...
From $1148 per night (USD)VRBO
From $925 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 $925 per night (USD)VRBO
From $585 per night (USD)VRBO
Waterfront, private beach, ready for adventure, light & bright!
- Bedrooms:
- 2
- 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 $585 per night (USD)VRBO
From $289 per night (USD)VRBO
Newly built ranch, beautifully landscaped with pool, large yard, patio,...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Please note that a reservation for this property needs to be approved before it is confirmed. Greenport Getaway Newly ...
From $289 per night (USD)VRBO
From $591 per night (USD)VRBO
Walk to private bay beach, close to Greenport, wineries, golf! Premier Host home
- Bedrooms:
- 2
- 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 $591 per night (USD)VRBO
From $448 per night (USD)VRBO
Lagoon Lodge North Fork, Charming 3Br, Waterfront
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Lagoon Lodge is a charming waterfront home with 3 bedrooms and 2 bathrooms, featuring central air and high-spee ...
From $448 per night (USD)VRBO
From $496 per night (USD)VRBO
Beautifully decorated water view resort condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Cliffside Resort is located on a bluff overlooking the Long Island sound with beautiful water vistas. The resort has an ...
From $496 per night (USD)VRBO
From $630 per night (USD)Expedia
Shelter Bay Cove Waterfront + Beach + spectacular
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Lovingly restored with new kitchen, refinished hardwood floors throughout, two full modern bathrooms, open fireplace, ce ...
From $630 per night (USD)Expedia
From $190 per night (USD)VRBO
Classic Waterview Victorian Summer Cottage in Park-Like-Setting
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 6
Charming turn-of-the century Victorian Summer cottage located on Rainbow Park with breathtaking views of Dering Harbor ...
From $190 per night (USD)VRBO
From $682 per night (USD)VRBO
Idyllic North Fork hideaway! Quiet 3 Bedroom cape in East Marion
- Bedrooms:
- 1
- 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 $682 per night (USD)VRBO
From $1943 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 $1943 per night (USD)VRBO
From $1167 per night (USD)Expedia
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 $1167 per night (USD)Expedia
From $594 per night (USD)VRBO
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 $594 per night (USD)VRBO
From $688 per night (USD)Expedia
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 $688 per night (USD)Expedia
From $605 per night (USD)VRBO
Relax in this light-filled home, steps from the beach and a short walk to town!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The perfect getaway. Within walking distance to beach, town, Jitney, LIRR and ferries to the South Fork. This quiet and ...
From $605 per night (USD)VRBO
From $857 per night (USD)VRBO
Antique house, Private & Peaceful Oasis
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Newly restored antique home, 3 bedrooms, 1.5 baths with outdoor shower surrounded by manicured lawn & bucolic grounds. ...
From $857 per night (USD)VRBO
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Perfect Getaway Apartment For Couples or Single Travelers
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Newly renovated apartment minutes away from the beach! This second floor space comes fully furnished with a full size be ...
Click For PricingVRBO
From $1088 per night (USD)VRBO
Scandinavian modern style meets the North Fork with gunite pool.
- 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 $1088 per night (USD)VRBO
From $826 per night (USD)VRBO
Newly Renovated Summer Retreat, Heated Pool, Walk to Beach, Designer Furnishings
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
*30 day minimum rental* Newly renovated modern farmhouse on a spacious property with a large heated saltwater pool and p ...
From $826 per night (USD)VRBO
From $677 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 $677 per night (USD)VRBO
From $411 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 $411 per night (USD)VRBO
From $487 per night (USD)Expedia
Cleves Point Estates Home, Private sandy beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful house is located in a private beach community. An 8 minute walk brings you to a private beach with view ...
From $487 per night (USD)Expedia
From $596 per night (USD)VRBO
Peaceful Retreat with 100 ft private deep water dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Comfortable waterfront home with private dock and large yard. Three bedrooms and two full baths. The house has Cable TV, ...
From $596 per night (USD)VRBO
From $1097 per night (USD)VRBO
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
NO EXTRA FEES FOR CLEANING, EXTRA GUESTS & AMENITIES! Relax in one of America's most beautiful seaside villages, histo ...
From $1097 per night (USD)VRBO
From $697 per night (USD)VRBO
Maritime Village House Walk or Bike to All
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful updated historic home in the village of Greenport. Central AC, newly renovated kitchens and bathrooms, large f ...
From $697 per night (USD)VRBO
From $684 per night (USD)Expedia
Shelter Island Serene Getaway. Amazing view, spacious & comfortable. Sleeps 6.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
When you turn the corner off the main road and see the house on the hill surrounded by over an acre of manicured lawn an ...
From $684 per night (USD)Expedia
From $1377 per night (USD)VRBO
Picturesque Views Of Gardiners Bay / Shelter Island With Heated Waterfront Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $1377 per night (USD)VRBO
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TRANQUIL RESORT STYLE RETREAT WITH LUXURY GUNITE POOL 2 MIN FROM SANDY BEACHES
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This newly renovated sun-drenched Shelter Island retreat with an exquisite 21'x42' Gunite, wifi-enabled luxury heated po ...
Click For PricingExpedia
From $994 per night (USD)VRBO
1905 North Fork restored farmhouse
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
This newly renovated 1905 North Fork farmhouse comes with lots of light, clean lines, and a brand new heated pool. More ...
From $994 per night (USD)VRBO
From $569 per night (USD)VRBO
Exquisite Waterfront Townhome in Greenport with Pool and Boat Slip. Walk to all!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautifully appointed townhouse in coveted Stirling Cove Condominiums. Enter a light filled room with magnificent views ...
From $569 per night (USD)VRBO
From $1285 per night (USD)VRBO
Gorgeous 5 bdrm home with beautiful bay views in the heart of Greenport Village
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Enchanted home with beautiful bay views. This house has it all. Modern updates with old-world charm. Gorgeous chefs ki ...
From $1285 per night (USD)VRBO
From $296 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 $296 per night (USD)VRBO
From $306 per night (USD)VRBO
Charming Greenport Gem 1, 1 Mile to Ferry!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Travel to the North Fork of Long Island for a much-needed getaway and experience both modern luxury and historic desire ...
From $306 per night (USD)VRBO
From $1624 per night (USD)Expedia
New Construction Greenport Pool House - 3 Blocks from Town
- Bedrooms:
- 4
- 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 $1624 per night (USD)Expedia
From $663 per night (USD)VRBO
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 $663 per night (USD)VRBO
From $637 per night (USD)VRBO
Unique waterfront home w/ stunning views, boat slip, walk to historic Greenport
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
North Fork living doesn’t get better than this. Enter to stunning waterfront views from every corner of this unique, lig ...
From $637 per night (USD)VRBO
From $1652 per night (USD)VRBO
5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views..
- Bedrooms:
- 3
- 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 $1652 per night (USD)VRBO
From $635 per night (USD)Expedia
Charming Northfork Townhouse- walk to all
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Fully Renovated Townhouse walking distance to town, beaches, parks, brewery and short bike to wineries. Brand new Kitche ...
From $635 per night (USD)Expedia
From $691 per night (USD)VRBO
Northfork Townhouse- walk to all/ newly renovated
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Fully Renovated Townhouse walking distance to town, beaches, parks, brewery and short bike to wineries. Brand new Kitche ...
From $691 per night (USD)VRBO
From $544 per night (USD)VRBO
4-bed 3.5-bath house with fenced heated pool and hot tub, fire pit, kids swings
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Family-friendly 2,200 square foot, 4-bedroom, 3.5-bathroom house for rent. The home has all the amenities you need for u ...
From $544 per night (USD)VRBO
From $1056 per night (USD)VRBO
Cozy Greenport village cottage
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Family friendly cottage, nestled in a quiet street in Greenport village. The private property has fully fenced backyard, ...
From $1056 per night (USD)VRBO
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Gorgeous Vintage Yacht in Wine Country NY
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
KINGFISHER is a stunning, 50 foot fully restored vintage motor yacht that offers timeless yachting experiences in Hampto ...
Click For PricingExpedia
From $801 per night (USD)VRBO
Cozy stylish home walking distance from private beach.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This home is in a quiet community walking distance from a private beach. Driveway parking on premises in a gated drivewa ...
From $801 per night (USD)VRBO
From $583 per night (USD)Expedia
Quiet street one block to shops, restaurants & waterfront. Barn with AC TV &WIFI
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Three bedrooms, 2 bathrooms completely renovated home. Sleeps 6. One full bath, one half bath. New outdoor shower. Fully ...
From $583 per night (USD)Expedia
Click For PricingVRBO
Cozy Farmhouse Secluded Community w/ Private Beach
- Bedrooms:
- 2
- 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 $596 per night (USD)VRBO
Sunrise Sunset! Beautiful waterfront property.
- Bedrooms:
- 2
- 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 $596 per night (USD)VRBO
From $1257 per night (USD)VRBO
Relax and Enjoy!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Stretch out and relax in this well-designed home high on a hill with truly spectacular water views from every room. Enjo ...
From $1257 per night (USD)VRBO
From $1010 per night (USD)Expedia
SUMMER RETREAT: Beach, Dock & Pool overlooking the Peconic Bay in Greenport!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Gull Harbor! New gunite pool, Summer 2025! See renderings, will provide photos upon completion. The house s ...
From $1010 per night (USD)Expedia
From $274 per night (USD)VRBO
Peaceful, clean cottage, 10 min walk to town. Monthly rates. Fenced backyard
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
We welcome you to our cottage away from it all but still close to all activities that make the North Fork a magical plac ...
From $274 per night (USD)VRBO
From $994 per night (USD)Expedia
Water front beach house w/ private beach with 3 bedrooms/2 bathrooms/Large Deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
In the picturesque seaside village of Greenport, this ocean-view three-bedroom retreat provides a peaceful and refreshin ...
From $994 per night (USD)Expedia
From $455 per night (USD)VRBO
WALK TO TOWN, BEACH, JITNEY, & FISHING---No Car Necessary!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Charming, in-town neighborhood. 10-minute walk to shops, beaches and fishing pier, the Hampton Jitney, LIRR and the Shel ...
From $455 per night (USD)VRBO
From $771 per night (USD)VRBO
Greenport renovated farmhouse
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Entirely renovated, spacious and quiet farmhouse two blocks from the marina, and a 5 minute bike ride to the beach or to ...
From $771 per night (USD)VRBO