Greenport West, New York Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Greenport West, New York on RentalSaver.com!

Greenport West Rentals

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VRBO
Beach Front House with Amazing Views on Private Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Freshly renovated beautiful beach front house on private beach. This quaint 2 bedrooms, 1 1/2 bathroom house has centra ...
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VRBO
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 $788 per night (USD)
VRBO
Greenport Village Getaway
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to the Greenport Getaway! Located in the center of the Greenport Village, this spacious residential home boasts ...
From $788 per night (USD)
VRBO
From $358 per night (USD)
VRBO
Sensational, newly remodeled waterfront Greenport condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A beautiful waterfront condo just a short walk from historic Greenport village, this newly remodeled unit provides stunn ...
From $358 per night (USD)
VRBO
$4BR Cape Home w Lg Screened Porch. 1m walk\/drive Greenport Shops + Dining.$
From $529 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 $529 per night (USD)
VRBO
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Expedia
Charming '30s cottage on water overlooking Shelter Island—5 mins from Greenport.
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Breezy Shores is like no other place on the North Fork. Our 1930s cottage is set on 80 acres of private, waterfront prop ...
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Expedia
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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! *** ...
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VRBO
From $286 per night (USD)
VRBO
Waterfront NoFo Cottage with public beach access
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Enjoy this waterfront cottage overlooking Marion Lake surrounded by lush landscape and wildlife. Experience the local Vi ...
From $286 per night (USD)
VRBO
From $308 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 $308 per night (USD)
VRBO
From $705 per night (USD)
Expedia
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 $705 per night (USD)
Expedia
From $740 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 $740 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
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VRBO
Paradise home in Greenport beach town
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
A traditional cedar shingle beach house, with comfortable contemporary interiors. Nestled on 1 acre of carefully landsca ...
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VRBO
From $1097 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 $1097 per night (USD)
Expedia
From $1041 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 2025 summer season. An impeccably res ...
From $1041 per night (USD)
VRBO
From $368 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 $368 per night (USD)
VRBO
From $465 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 $465 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 $287 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 $287 per night (USD)
VRBO
From $765 per night (USD)
VRBO
Overlook a Vineyard, Walk to the Beach, and only a Short Walk to Town - 5 Star!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Discounts available for stays >14 days. Please inquire prior to booking for details. Completely updated, modern and li ...
From $765 per night (USD)
VRBO
From $657 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 $657 per night (USD)
VRBO
From $1154 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 $1154 per night (USD)
VRBO
From $857 per night (USD)
VRBO
Beautiful condo on the Long Island Sound in a resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This condo is one of the nicest decorated in Cliffside. Gorgeous shiplap walls with navy accents. It has a beautiful f ...
From $857 per night (USD)
VRBO
From $864 per night (USD)
Expedia
Shorecrest Beach House + Beach Front + Ocean views
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
The Shorecrest beach house is located on a grassy bluff overlooking the waters of the Long Island Sound with its own pri ...
From $864 per night (USD)
Expedia
From $818 per night (USD)
VRBO
Greenport Waterfront Private Dock
Bedrooms:
3
Bathrooms:
6
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 $470 per night (USD)
Expedia
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
Bedrooms:
2
Bathrooms:
3
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 $470 per night (USD)
Expedia
From $2521 per night (USD)
VRBO
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 $2521 per night (USD)
VRBO
From $529 per night (USD)
VRBO
The Cottage at Sunset Bluff
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This newly renovated charming cottage is sure to spark your romantic side. Located just steps away from the Long Island ...
From $529 per night (USD)
VRBO
From $628 per night (USD)
VRBO
Beautiful Soundfront condominium
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful 2 bedroom 2 bathroom direct sound front condo in greenport at Cliffside resort direct view. heated pool, beac ...
From $628 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 $1617 per night (USD)
VRBO
Contemporary Colonial home with pristine Peconic bay views, steps to...
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Please note that a reservation for this property needs to be approved before it is confirmed. Vineyard Beach House Con ...
From $1617 per night (USD)
VRBO
From $707 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 $707 per night (USD)
Expedia
From $1089 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 $1089 per night (USD)
VRBO
$Updated and dog-friendly, close to seasonal activities with yard, & washer\/dryer$
From $465 per night (USD)
Expedia
Updated and dog-friendly, close to seasonal activities with yard, & washer\/dryer
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Modern on 9th Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $465 per night (USD)
Expedia
From $481 per night (USD)
VRBO
Cozy Beach Cottage with private shared beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Shabby-Chic Beach Cottage a short walk from a shared private beach. Bay beach is safe for young children to swim and has ...
From $481 per night (USD)
VRBO
From $308 per night (USD)
Expedia
Aqua Vista
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bar ...
From $308 per night (USD)
Expedia
From $262 per night (USD)
VRBO
The SandPiper
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 $262 per night (USD)
VRBO
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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 ...
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Expedia
From $680 per night (USD)
VRBO
Greenport 'Sunshine Home'
Bedrooms:
4
Bathrooms:
7
Sleeps:
10
This welcoming colonial is situated on three-fourths of an acre. Family friendly, the house is perfect for your time awa ...
From $680 per night (USD)
VRBO
From $749 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 $749 per night (USD)
VRBO
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VRBO
Your Summer Escape
Bedrooms:
4
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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VRBO
From $748 per night (USD)
Expedia
Greenport Walk to beach & vineyard from this brand new home
Bedrooms:
3
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 $748 per night (USD)
Expedia
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VRBO
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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VRBO
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Expedia
Waterfront + Complete Gym + Hot tub
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Renovated, waterfront property within close proximity to everything. Outstanding high speed internet, a perfect setup fo ...
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Expedia
From $2419 per night (USD)
VRBO
Modern Farmhouse Private Estate, 6.5 acres
Bedrooms:
6
Bathrooms:
4
Sleeps:
10
Welcome to your private 6.5 acre getaway. With 4 bedrooms and 6 bathrooms, this spacious and beautifully designed home i ...
From $2419 per night (USD)
VRBO
From $419 per night (USD)
VRBO
One bedroom Pied a Terre - a lovely new and clean Greenport place
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Rental Permit 1063 Live the perfect life with a new Pied a Terre on the North Fork in Greenport. This lovely one bedr ...
From $419 per night (USD)
VRBO
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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 ...
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VRBO
From $1002 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 $1002 per night (USD)
VRBO
From $442 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 $442 per night (USD)
VRBO
From $1249 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 $1249 per night (USD)
VRBO
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VRBO
Charming Historic Farmhouse in Greenport Village
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Beautiful Greenport Village Farmhouse situated on .37 Acres. Built in 1822 and restored with modern amenities. This is t ...
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VRBO
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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 ...
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Expedia
From $1050 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 $1050 per night (USD)
VRBO
From $1151 per night (USD)
Expedia
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 $1151 per night (USD)
Expedia
From $538 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 $538 per night (USD)
VRBO
From $393 per night (USD)
VRBO
Park-like setting, private lane, walk to beach, close to town. Boats welcome.
Bedrooms:
3
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 $393 per night (USD)
VRBO
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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 ...
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VRBO
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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 ...
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Expedia
From $1609 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 $1609 per night (USD)
VRBO
From $1747 per night (USD)
VRBO
Greenport Villa with a Pool
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Bring the whole family to this great place with lots of room for indoor and outdoor activities! Enjoy an entire Greenp ...
From $1747 per night (USD)
VRBO
$The Lucky Oyster Est 1886 3 Bd \/ 2 Ba Historic & Walk to Town$
From $1125 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 $1125 per night (USD)
VRBO
From $444 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 $444 per night (USD)
VRBO
From $411 per night (USD)
VRBO
Cozy Greenport Cottage | House in Greenport with a private pool & sauna
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Cozy Greenport Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $411 per night (USD)
VRBO
From $977 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 $977 per night (USD)
VRBO
From $354 per night (USD)
VRBO
Quiet Oasis Near Greenport and Safe Harbor Marina with Views of Lavendar Farm
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
LEGAL Rental on the North Fork located in near Greenport, NY in the heart of wine country, five minute drive from Greenp ...
From $354 per night (USD)
VRBO
From $1355 per night (USD)
Expedia
Pristine waterfront home with direct access to private bay and dock,...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Snug Harbor Stylish Pristine waterfront home with direct access to private bay and dock, primary bedroom balcony, spaci ...
From $1355 per night (USD)
Expedia
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VRBO
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 ...
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VRBO
$Blue Bay Dream w\/ Seasonal Outdoor Jacuzzi, Cabana + Office$
From $442 per night (USD)
Expedia
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 $442 per night (USD)
Expedia
From $996 per night (USD)
VRBO
Greenport Log Home in the woods. Pool&water access. GP Permit #0952
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
PLEASE READ FULL DESCRIPTION! Rental registry # 0952 Pool coming summer 2025!!!!Private modern 4 bedroom/2 bath cabin ne ...
From $996 per night (USD)
VRBO
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Expedia
Cozy Greenport Getaway
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
Family friendly cottage, nestled in a quiet street in Greenport village. The private property has fully fenced backyard, ...
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Expedia
From $686 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 $686 per night (USD)
VRBO
From $667 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 $667 per night (USD)
VRBO
$Modern Farmhouse Oasis in Greenport Village - 10 min walk to restaurants\/shops$
From $788 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 $788 per night (USD)
VRBO
From $1212 per night (USD)
VRBO
Luxurious living in Greenport's private Rock Cove Estates on the sound
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
2024 Rates: MD-June $28k, June $25k July $35k , Weekly rental $8,500/ week 2 week minimum. Luxurious living in Greenpor ...
From $1212 per night (USD)
VRBO
From $563 per night (USD)
VRBO
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 ...
From $563 per night (USD)
VRBO
From $326 per night (USD)
Expedia
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 $326 per night (USD)
Expedia
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VRBO
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 ...
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VRBO
From $514 per night (USD)
Expedia
Another rental season is coming up.
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 $514 per night (USD)
Expedia
From $960 per night (USD)
VRBO
New Four-bed Home with private Beach access for Rent
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Modern, brand new, house, with private beach, for rent. Experience North Fork summer living in this newly constructed ...
From $960 per night (USD)
VRBO
From $1543 per night (USD)
VRBO
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 $1543 per night (USD)
VRBO
From $732 per night (USD)
VRBO
Updated Historic shingle-style 1902 4-bedroom Beach House on Southold Bay!
Bedrooms:
4
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 $732 per night (USD)
VRBO
$Charming 3 Bed\/2.5 Bath Cottage In Historic Shelter Island Heights Walk to Ferry$
From $605 per night (USD)
Expedia
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)
Expedia
$Greenport Getaway w\/Pool & Fire Pit$
From $895 per night (USD)
VRBO
Greenport Getaway w\/Pool & Fire Pit
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to this stunning & newly renovated Greenport home. This magnificent home seamlessly blends comfort, style and lu ...
From $895 per night (USD)
VRBO
From $1369 per night (USD)
VRBO
Newly renovated ranch with large Pool in a quiet neighborhood, off main road
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Private home in quiet neighborhood Make yourself at home in this 3 bedroom, 2 full bathroom modern ranch featuring: ...
From $1369 per night (USD)
VRBO
From $514 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 $514 per night (USD)
VRBO
From $442 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 $442 per night (USD)
VRBO
From $901 per night (USD)
VRBO
Plan Your Perfect Summer Escape: Walk to Crescent Beach and to Pridwin!
Bedrooms:
3
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 $1142 per night (USD)
Expedia
Relax at a private beach! Three bedrooms await you near Shelter Island beaches!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Tranquil getaway in Shelter Island with private beach access. Modern, bright home newly decorated by top design firm is ...
From $1142 per night (USD)
Expedia
From $981 per night (USD)
VRBO
Historic Waterfront Home. Steps to North Ferry & Beach Club. Easy access to LIRR
Bedrooms:
3
Bathrooms:
5
Sleeps:
6
Our historic 5-bedroom Victorian home on Shelter Island Sound in the Heights has been in our family for 100 years. Buil ...
From $981 per night (USD)
VRBO
From $979 per night (USD)
VRBO
Stylish beach getaway: pool in prime location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our beautifully renovated, designer-decorated home in the heart of Southold, NY! Perfectly located within wal ...
From $979 per night (USD)
VRBO
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VRBO
Waterfront Southold Retreat < 3 Mi to Wineries!
Bedrooms:
3
Bathrooms:
6
Sleeps:
8
Escape to 'Kayak Point' and experience the beauty of Long Island's North Fork! This 4-bedroom, 2.5-bath home in Southold ...
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VRBO
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Expedia
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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Expedia
From $1457 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 $1457 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $617 per night (USD)
VRBO
Charming 3-bedroom cottage in fabulous Greenport
Bedrooms:
2
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 $617 per night (USD)
VRBO
From $854 per night (USD)
VRBO
Tranquil Splendor at The Pridwin - Waterfront Activities - Shelter Island
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Shelter Island's charm near Crescent Beach and Mashomack Preserve. Enjoy serene beaches, vibrant nature, and lo ...
From $854 per night (USD)
VRBO
From $743 per night (USD)
VRBO
Hillside Sanctuary with Private Terrace Dining and Complimentary Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Shelter Island's charm near Crescent Beach and Mashomack Preserve. Enjoy serene beaches, vibrant nature, and lo ...
From $743 per night (USD)
VRBO
From $648 per night (USD)
VRBO
Comfortable Coastal Hideaway with Game Room, Complimentary Bicycles & Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Shelter Island's charm near Crescent Beach and Mashomack Preserve. Enjoy serene beaches, vibrant nature, and lo ...
From $648 per night (USD)
VRBO
From $748 per night (USD)
VRBO
Hillside Room at The Pridwin - Watersports Hub & Elegant Dining - Shelter Island
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Shelter Island's charm near Crescent Beach and Mashomack Preserve. Enjoy serene beaches, vibrant nature, and lo ...
From $748 per night (USD)
VRBO
From $1220 per night (USD)
Expedia
Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Greenport Cove Contemporary Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families 4BR/3.5BA: privat ...
From $1220 per night (USD)
Expedia

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Results: 211 Rentals