Greenport West Rentals
From $1097 per night (USD)VRBO
🌟 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 $1097 per night (USD)VRBO
From $287 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 $287 per night (USD)VRBO
From $487 per night (USD)VRBO
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)VRBO
From $1047 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 $1047 per night (USD)Expedia
From $627 per night (USD)VRBO
Beautiful home minutes away from village, restaurants, beach, and wineries!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Come to our beautiful village of Greenport! Open concept home with pool. Three bedrooms four baths and large basement, ...
From $627 per night (USD)VRBO
From $910 per night (USD)Expedia
Greenport Getaway the perfect blend of relaxation, nature, and North Fork charm.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
🏡 Charming Family Getaway with Heated Pool, Private Beach Access & Kayaks in Greenport 5 Bedrooms • 4 Bathrooms • Slee ...
From $910 per night (USD)Expedia
From $687 per night (USD)VRBO
Charming 3-bedroom cottage in fabulous Greenport
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
This charming 1870’s schoolhouse has been converted into a cozy, modern home with comfortable furniture and a rustic-yet ...
From $687 per night (USD)VRBO
From $513 per night (USD)Expedia
Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Greenport Cove Contemporary Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families 4BR/3.5BA: privat ...
From $513 per night (USD)Expedia
From $425 per night (USD)VRBO
Waterfront Greenport Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This two-bedroom, two-bathroom condo at Cliffside Resort offers a serene escape with breathtaking views of the Long Isla ...
From $425 per night (USD)VRBO
From $793 per night (USD)VRBO
Delightful 4-bedroom Cape with heated saltwater pool in the heart of Greenport!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This delightful little Cape is an optical illusion, beguiling all who enter as they exclaim, “how does this house fit wi ...
From $793 per night (USD)VRBO
From $746 per night (USD)VRBO
NOFO ESCAPE relax-swim-enjoy. Bachelorettes-Weddings-Family vacation
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Bachelorette, weddings and big party escape. Go fishing, boating, hiking, golfing, antique shopping etc walk to town, wa ...
From $746 per night (USD)VRBO
From $818 per night (USD)VRBO
Greenport Waterfront Private Dock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
GREENPORT CONKLING PT CREEKFRONT MINT 3BR COTTAGE W/PRIME VIEWS - This cottage on a half-acre lot fronts on the pristine ...
From $818 per night (USD)VRBO
From $485 per night (USD)VRBO
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Waterfront Water's Edge luxury suite, Suite C-204 accommodates up to 6 guests (see below) with two bedrooms and two bath ...
From $485 per night (USD)VRBO
From $905 per night (USD)Expedia
Greenport Village walking distance to all
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
3 bedroom 2 floor cape with large great room and enclosed patio perfect for families and small groups. Relax in the hot ...
From $905 per night (USD)Expedia
From $482 per night (USD)VRBO
North Beach Fork Beach House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy our tranquil home in a private beach community.Located on a half acre of private land, this home has all the ameni ...
From $482 per night (USD)VRBO
From $631 per night (USD)VRBO
Walk to Beach and Greenport Village, Two King Beds
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
A quiet Cape home within walking distance to all Greenport Village has to offer - dining, shopping, the beach and transp ...
From $631 per night (USD)VRBO
From $656 per night (USD)VRBO
Overlook a Vineyard, Walk to the Beach, and only a Short Walk to Town - 5 Star!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discounts available for stays >14 days. Please inquire prior to booking for details. Completely updated, modern and li ...
From $656 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 $586 per night (USD)VRBO
POOL + Beach 1 mi. to Greenport Village! Winter deals for 4+ nights...
- 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 $586 per night (USD)VRBO
From $565 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 $565 per night (USD)VRBO
From $868 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 $868 per night (USD)VRBO
From $272 per night (USD)Expedia
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 $272 per night (USD)Expedia
From $563 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 $563 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 $460 per night (USD)VRBO
'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 $460 per night (USD)VRBO
From $357 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 $357 per night (USD)VRBO
From $1276 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 $1276 per night (USD)VRBO
From $843 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 $843 per night (USD)VRBO
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Your Summer Escape
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
This is a fully equipped home with an open floor plan kitchen and living room, a dining room, screened-in sunroom, a la ...
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From $322 per night (USD)Expedia
Modern home in Greenport, close to beaches, outdoor dining, perfect for families
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Greenport Coastal Retreat Modern home in Greenport, close to beaches, outdoor dining, perfect for families 2BR/1.5BA: ...
From $322 per night (USD)Expedia
From $535 per night (USD)VRBO
Old meets new in this fully renovated 19th century farm house.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This 2-bedroom house in Greenport with modern amenities for stylish uncluttered living. Perfect for a small family or c ...
From $535 per night (USD)VRBO
From $1628 per night (USD)VRBO
North Fork Escape: Spacious, Stylish, Serene Yard
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Escape to the charm of East Marion and settle into this bright, beautifully maintained home nestled in the hear ...
From $1628 per night (USD)VRBO
From $876 per night (USD)VRBO
Family friendly 4 BR Greenport retreat w/ Pool and Private Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to The Cove North Fork, a light-filled, family friendly escape in Greenport just steps to your private beach. Th ...
From $876 per night (USD)VRBO
From $733 per night (USD)VRBO
Charming 2-bedroom house in Greenport. Walk to a vineyard and 67 Steps Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to this enchanting house in Greenport. This beautiful property features 2 cozy bedrooms with a mix of sleeping a ...
From $733 per night (USD)VRBO
From $491 per night (USD)VRBO
The Saltbox Greenport-19th Century meets 21st Century
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This unique home has a style all its own. Stylish and chic, an impeccably restored historic Salt Box. It boasts an updat ...
From $491 per night (USD)VRBO
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Exquisite dog-friendly home with large yard, furnished porch, & firepit
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Serene Bay Breezes - Private Bay Beach Community Our calendar is updated in real-time & our nightly rates are accuratel ...
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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 $440 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 $440 per night (USD)VRBO
From $524 per night (USD)VRBO
4BR Cape Home w Lg Screened Porch. 1m walk/drive Greenport Shops + Dining.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Renovated cape-style home with central AC - Living room w55" Smart TV + sound system - Sunny, large den with w65" Smart ...
From $524 per night (USD)VRBO
From $1056 per night (USD)Expedia
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)Expedia
From $837 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 $837 per night (USD)VRBO
From $701 per night (USD)VRBO
Greenport Getaway w/Heated Saltwater Pool- Close to Greenport Village & Wineries
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this stunning & newly renovated Greenport home. This magnificent home seamlessly blends comfort, style and lu ...
From $701 per night (USD)VRBO
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Perfect Greenport Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Walk and/or bike everywhere you want from this gem. Rarely rented out, my personal summer rental. Be one of the first t ...
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Waterfront + Complete Gym + Hot tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Renovated, waterfront property within close proximity to everything. Outstanding high speed internet, a perfect setup fo ...
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From $391 per night (USD)VRBO
Park-like setting, private lane, walk to beach, close to town. Boats welcome.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Enjoy this spacious one level home with all the amenities located on a quiet private lane, yet so close to the beach! S ...
From $391 per night (USD)VRBO
From $551 per night (USD)VRBO
Bright and Modern North Fork Living
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 5
Enjoy all the best the North Fork has to offer. Newly renovated Cape Cod style home walkable to beaches, marinas, resta ...
From $551 per night (USD)VRBO
From $3120 per night (USD)VRBO
The Whitehouse North Fork
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 14
Step back in time without sacrificing modern luxury in this beautifully restored 19th-century Victorian farmhouse locate ...
From $3120 per night (USD)VRBO
From $747 per night (USD)Expedia
Shelter Island Spacious Getaway with Cozy Fireplace
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to Shelter Island’s Hidden Gem! Walking distance to multiple beaches this charming 3-bedroom, 2-bath home is your ...
From $747 per night (USD)Expedia
From $1165 per night (USD)VRBO
Relax at a private beach! Three bedrooms await you near Shelter Island beaches!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Tranquil getaway in Shelter Island with private beach access. Modern, bright home newly decorated by top design firm is ...
From $1165 per night (USD)VRBO
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Thanksgiving - Group Holidays rental with staff!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Luxury, warm, contemporary art. En suite guest rooms. Walk to Sunset Beach and TOP restaurant: Leon 1909. Cotton lin ...
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From $2828 per night (USD)VRBO
Shore House - A Luxury Beach Retreat
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This extraordinary modern home offers an abundance of amenities with easy access to the white sands of Sunset Beach. Per ...
From $2828 per night (USD)VRBO
From $543 per night (USD)Expedia
Updated Historic shingle-style 1902 4-bedroom Beach House on Southold Bay!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
You are invited to have a wonderful time in this Southold, Long Island beach house. You will have a fabulous time of sun ...
From $543 per night (USD)Expedia
From $655 per night (USD)VRBO
Greenport Walk to beach & vineyard from this brand new home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Take it easy at this brand new unique retreat. Walking to distance to the beach and winery. Less than a 2 minute drive ...
From $655 per night (USD)VRBO
From $301 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 $301 per night (USD)VRBO
From $781 per night (USD)VRBO
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 $781 per night (USD)VRBO
From $758 per night (USD)Expedia
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 $758 per night (USD)Expedia
From $252 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 $252 per night (USD)VRBO
From $488 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 $488 per night (USD)VRBO
From $695 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 $695 per night (USD)VRBO
From $638 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 $638 per night (USD)Expedia
From $946 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 $946 per night (USD)VRBO
From $1285 per night (USD)Expedia
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)Expedia
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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 ...
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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 $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 $701 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 $701 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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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 ...
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From $1346 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 $1346 per night (USD)VRBO
From $834 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 $834 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 $1652 per night (USD)Expedia
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)Expedia
From $646 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 $646 per night (USD)VRBO
From $2344 per night (USD)VRBO
Spacious house next to the beach, Ferry and Eateries.
- Bedrooms:
- 4
- 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 $2344 per night (USD)VRBO
From $1381 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 $1381 per night (USD)VRBO
From $505 per night (USD)Expedia
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 $505 per night (USD)Expedia
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 $473 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 $473 per night (USD)VRBO
From $315 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 $315 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 $613 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 $613 per night (USD)VRBO
From $684 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 $684 per night (USD)VRBO
From $638 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 $638 per night (USD)VRBO
From $327 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 $327 per night (USD)VRBO
From $783 per night (USD)VRBO
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 $783 per night (USD)VRBO
From $874 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 $874 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 $638 per night (USD)Expedia
Greenport Gem: Private Saltwater Pool, Awesome Basement, Walk to Everything!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to our charming Greenport Village oasis! Nestled in a quiet neighborhood just a short stroll from the vibrant hea ...
From $638 per night (USD)Expedia
From $706 per night (USD)VRBO
Rose Cottage by the Bay.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Seaside Greenport Village Historic District, on Long Island’s North Fork, New York. “Rose Cottage” is within the Greenp ...
From $706 per night (USD)VRBO
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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 $399 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 $399 per night (USD)VRBO
From $901 per night (USD)VRBO
Plan Your Perfect Summer Escape: Walk to Crescent Beach and to Pridwin!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Get ahead of summer and book your stay at our stunning, newly built (2024) beach retreat on Shelter Island! Just a 5-min ...
From $901 per night (USD)VRBO
From $374 per night (USD)VRBO
Cozy North Fork Home Close to Beaches, Wineries, and Town, Perfect for Families
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Please note that a reservation for this property needs to be approved before it is confirmed. Island's End Retreat Coz ...
From $374 per night (USD)VRBO
From $1019 per night (USD)VRBO
Newly Renovated 4BR Charming Home on best block in Greenport
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Newly renovated 4 bedroom 3.5 bathroom home on the best block in historic Greenport Village. The house has two master su ...
From $1019 per night (USD)VRBO
From $363 per night (USD)VRBO
Beautiful home short walk to the beach, w/ outdoor shower, grill & central AC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Briar Patch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $363 per night (USD)VRBO
From $424 per night (USD)Expedia
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to <b>The Greenport Beach Cottage</b> — your coastal retreat on the North Fork. The 750 sq ft completely renov ...
From $424 per night (USD)Expedia
From $497 per night (USD)VRBO
Come stay at The Whitman House a magical gem in the heart of Historic Greenport
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Stay in the Historic Whitman House nestled in the quaint village of Greenport Step back in time while enjoying modern c ...
From $497 per night (USD)VRBO
From $1481 per night (USD)VRBO
Casa Greenport
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 11
Come enjoy all Casa Greenport has to offer! Just one block from main street walk to several restaurants, shops, and the ...
From $1481 per night (USD)VRBO