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

Southold Rentals

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VRBO
Historic cottage near the NoFo beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
We are renting our warm, wonderful and rustic 3 bedroom cottage in Southold for parts of July and August. We are steps f ...
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VRBO
From $464 per night (USD)
VRBO
Kenney's Beach House, Short Walk to Best Swimming and Sunset Sound Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Beautifully appointed and ultra-comfortable home with sunny, sky-lit, open floor plan. 2+ Bed/2 Bath Southold getaway w ...
From $464 per night (USD)
VRBO
From $290 per night (USD)
VRBO
House central to North Fork wineries restaurants + beaches. Walk to town.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Comfortable House on a quiet private road 0.5 mile to Southold town center. Would work well for a small family or two co ...
From $290 per night (USD)
VRBO
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Expedia
Beautiful private home with beach access down the block
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
1/2 acre fenced property. open floor plan. Master with en suite bathroom. additional bedrooms and bathrooms for your use ...
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Expedia
From $1328 per night (USD)
VRBO
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
Bedrooms:
7
Bathrooms:
8
Sleeps:
12
Town of Southold Rental Permit Number 0816 A beautiful brand new estate home with a heated pool, situated in t ...
From $1328 per night (USD)
VRBO
From $1042 per night (USD)
VRBO
Perfect Waterfront Family Vacation Home next to the best vineyards in NY!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Completely renovated 3 bedroom, 2 bath Beachfront Cottage. Step outside and enjoy outdoor dining, playing games on th ...
From $1042 per night (USD)
VRBO
$Charming home with fireplace, kayaks, patio, fast WiFi, & washer\/dryer-dogs ok$
From $236 per night (USD)
VRBO
Charming home with fireplace, kayaks, patio, fast WiFi, & washer\/dryer-dogs ok
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Minnehaha Marvel Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $236 per night (USD)
VRBO
From $467 per night (USD)
Expedia
Dog-friendly, comfortable home with private pool, large yard, WiFi, & fire pit
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Southold Serenity Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $467 per night (USD)
Expedia
From $419 per night (USD)
VRBO
NF Wine Country Retreat with Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy this idyllic family friendly home in the heart of North Fork, Long Island. It's a newly renovated and spacious 4 b ...
From $419 per night (USD)
VRBO
From $646 per night (USD)
Expedia
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)
Expedia
From $644 per night (USD)
VRBO
Cozy Long Island Escape
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Enjoy all the beauty of Long Island’s North Fork with this conveniently located farmhouse. Close to wineries, farms and ...
From $644 per night (USD)
VRBO
From $818 per night (USD)
VRBO
Host your holidays here! Hot tub, sauna, fire pit, beach - minutes to vineyards!
Bedrooms:
3
Bathrooms:
6
Sleeps:
10
Welcome to our modern beach house, boasting all the amenities you could ask for including 6 Bedrooms and 3 Full Baths, a ...
From $818 per night (USD)
VRBO
From $751 per night (USD)
VRBO
Amazing Beach House in the North Fork Wineries
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Heart of wine country, steps from the beach, minutes to Greenport. Spacious 3 bedroom/ 2.5 bath boasts vaulted ceilings ...
From $751 per night (USD)
VRBO
$LI Sound view, walk to beaches,lake access\/kayaking, fishing$
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Expedia
LI Sound view, walk to beaches,lake access\/kayaking, fishing
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Water views from every room of LI Sound and Great Pond. Walk to beautiful sound beaches and watch the sunset from the de ...
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Expedia
From $511 per night (USD)
VRBO
Newly Renovated Gem on the Cedar Beach Peninsula!
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Come and experience the peaceful tranquility of the North Fork with this newly renovated gem in the heart of Southold. I ...
From $511 per night (USD)
VRBO
From $409 per night (USD)
Expedia
Beautiful North Fork 3-Bedroom Home Steps Away from a Private Sandy Bay
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Beautiful vacation home in the Bay Haven community of Southold. The house is on a fully landscaped property of over a th ...
From $409 per night (USD)
Expedia
From $1007 per night (USD)
VRBO
Waterfront property with own dock and stunning views, overlooking Southold Bay.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to our home, a one of a kind Bayfront property with a private dock, a large, expansive deck, overlooking Southol ...
From $1007 per night (USD)
VRBO
From $764 per night (USD)
Expedia
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)
Expedia
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
$Serene bay front home with a private beach, deck, board games, & washer\/dryer$
From $660 per night (USD)
Expedia
Serene bay front home with a private beach, deck, board games, & washer\/dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Watersedge Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $660 per night (USD)
Expedia
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VRBO
Enjoy Wine Country and Walk The Beautiful Beach At Sunset
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
* 10 min walk to neighborhood sandy beach! * 5 min walk to vineyard with tasting room. Spacious Contemporary home. ...
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VRBO
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Expedia
Enjoy Wine Country and Take Walks On Beautiful, Solitary beaches At Sunset
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
* 10 min walk to neighborhood sandy beach * 5 min walk to vineyard with tasting room. Spacious Contemporary home. Ma ...
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Expedia
From $471 per night (USD)
VRBO
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Steps from Peconic Bay and Cedar beach. Stay in our Southold home in the heart of North Fork and enjoy the best the No ...
From $471 per night (USD)
VRBO
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Expedia
Stunning Home & Private Beach on the North Fork
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Welcome to a slice of Heaven on the pastoral North Fork. Jaw dropping views, visible from almost every room in the house ...
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Expedia
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VRBO
The Stucco House
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Very unique style house in the area. Updated with newly Gut renovated bathroom and new appliances. Large enclosed porch ...
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VRBO
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Expedia
Cozy Cottage on North Fork
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cozy Cottage. Great Location and nice yard with BBQ and rear deck. Fully furnished Site says I have to have 96 more le ...
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Expedia
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VRBO
Palm Springs Vibes on the North Fork
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Feel the happy vibes of Palm Springs with a fully guy renovated ranch home on an acre of land. Brand new appliances. Clo ...
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VRBO
From $473 per night (USD)
VRBO
Secluded charmer with gunnite, saltwater pool and fireplace, steps to beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Built in 1928, this gorgeous shingled home is fully equipped to host your getaway. You're within easy walking distance o ...
From $473 per night (USD)
VRBO
From $1229 per night (USD)
VRBO
Well-appointed coastal home with large yard, pool, basketball, & outdoor kitchen
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Secret Garden Estate Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $1229 per night (USD)
VRBO
From $322 per night (USD)
VRBO
Horton House
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Horton House, located in the historic district of Southold, NY, is one of the oldest English houses in the state. Loving ...
From $322 per night (USD)
VRBO
From $290 per night (USD)
VRBO
Waterfront Beach House Nestled Along the Wondrous North Fork Wine Trail,...
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Wine Trail Waterfront Waterfront Beach House Nestled Along the Wondrous North Fork Wine Trail, Perfect for Families 4B ...
From $290 per night (USD)
VRBO
From $442 per night (USD)
VRBO
STATELY, PEACEFUL & TASTEFUL WITH SPARKLING POOL AND FIREPLACES
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
Beautiful home on gorgeous tree-lined street in Southold on the North Fork, Long Island. Near Greenport, Orient, Shelter ...
From $442 per night (USD)
VRBO
From $1107 per night (USD)
VRBO
A cozy and family-friendly haven with heated pool, minutes from the beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
13
A family-friendly home that covers all the bases. Everything your family needs (toys, cribs, bouncers, tub, playmats, hi ...
From $1107 per night (USD)
VRBO
From $450 per night (USD)
Expedia
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)
Expedia
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VRBO
North Fork Waterfront Home - Lots of Room - Luxurious Comfort
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
Waterfront private dock-Luxury comfort on North Fork -perfect for family fun-Lots of room Amenities include newly renova ...
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VRBO
From $331 per night (USD)
VRBO
Lovely 4 Bedroom Southold Home Walking Distance to Peconic Bay
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Beautiful and quiet corner home in a lovely neighborhood in Southold. 100 year old farmhouse but with modern convenienc ...
From $331 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 $387 per night (USD)
VRBO
Charming, Historic Farmhouse close to restaurants, vineyards and beach.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
New to the Market this season! Charming historic 1909 farmhouse with 3 bedrooms and 1 1/2 baths and modern amenities. ...
From $387 per night (USD)
VRBO
From $418 per night (USD)
VRBO
Heated pool on Goose Creek, private dock, massive yard walk to beach, wineries
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
Southold Permit # 0361. Pool opens Mid April! One season off of a full renovation - reviews before 2022 are from befo ...
From $418 per night (USD)
VRBO
From $515 per night (USD)
VRBO
Cottage by Cedar Beach
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
Cute as a button cottage with 2 bedrooms and 1.5 bath. Oversized outside patio with large teak dining table and huge con ...
From $515 per night (USD)
VRBO
From $469 per night (USD)
VRBO
Water View Beach House just steps to Private Sandy Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Just steps from a private sandy beach with a beautiful view across the Peconic Bay to Sag Harbor and perfect sunsets. Ho ...
From $469 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 $209 per night (USD)
VRBO
Cottage on private road and 5-min walk to beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Perfect all-season cottage with easy access to beaches, wineries, restaurants, and all the great things the North Fork h ...
From $209 per night (USD)
VRBO
From $667 per night (USD)
VRBO
North Fork Sound Front Beach House
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Designed by renowned architects Abercrombie & Vieyra for their private use, this 4 bedroom, sound front home with a priv ...
From $667 per night (USD)
VRBO
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VRBO
Private Guest Room-heart of Long Island's North Fork wine country-steps to beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Small clean guestroom with private entrance and private bath located on private road with minimal traffic. Free onsite p ...
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VRBO
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Expedia
Southold by the bay
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Beautiful ranch style home within walking distance of the beach. Has a large backyard and deck for entertaining. Featur ...
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Expedia
From $400 per night (USD)
VRBO
Charming Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Charming cozy cottage located in the heart of the Northfork, East End of Long Island. Come explore the beautiful vineyar ...
From $400 per night (USD)
VRBO
From $357 per night (USD)
VRBO
House in North Fork Beach Access minutes walk to private beach⛱️
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This house is beautifully decorated and comfortable, light and spacious with it's wooden floors throughout with every a ...
From $357 per night (USD)
VRBO
From $813 per night (USD)
VRBO
Mint Condition Modern Farmhouse Gem Offers Best of North Fork Living!
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
"Haven on Birch" is your perfect North Fork escape! Our beautifully appointed, immaculately maintained, three-story home ...
From $813 per night (USD)
VRBO
From $422 per night (USD)
Expedia
Southold, NY- Heart of North Fork Wine Country
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This is a Spacious & Meticulous Cape On Great Hogs Neck Peninsula ~ This Charming 4-Plus Bedroom 3.5 Bath Expanded Cape ...
From $422 per night (USD)
Expedia
$Water front beach house w\/ private beach$
From $1247 per night (USD)
VRBO
Water front beach house w\/ private beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Beach front with a private beach. Ideal for sunbathing, swimming, fishing & kayaking. Enjoy daily gorgeous sunset views ...
From $1247 per night (USD)
VRBO
From $450 per night (USD)
VRBO
Southold Escape with Large Saltwater Pool on Wine Trail
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
3 bedroom, 2.5 bathroom home on a 0.55 acre property with large pool and outdoor deck in enclosed private backyard. Bran ...
From $450 per night (USD)
VRBO
From $435 per night (USD)
VRBO
Peconic Sound Beach Home: Backyard & Vineyards
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Peconic Sound Beach Home in Peconoc Southold is a quaint beach cottage that has a charming allure. Enjoy your access to ...
From $435 per night (USD)
VRBO
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Expedia
Cozy Retreat surrounded by Wine Country and Beach Sunsets
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
This retreat is the ultimate country escape. The house has a spacious living space perfect for entertaining or kids. T ...
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Expedia
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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
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Expedia
Cute and simple summer cottage
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Tucked in a shady private road in the heart of the North Fork wine district with access to the white sandy beach of the ...
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Expedia
From $913 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 $913 per night (USD)
VRBO
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Expedia
Experience the North Fork!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This beautifully renovated farmhouse is centrally located next to multiple award-winning wineries which is why we named ...
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Expedia
From $917 per night (USD)
VRBO
Modern North Fork Retreat with massive pool and Private Beach Access
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Newly built farmhouse-style retreat with in-ground pool and private beach access in the heart of the North Fork. This lo ...
From $917 per night (USD)
VRBO
From $639 per night (USD)
Expedia
LUXURIOUS 2-HOME ESTATE COMPLETELY SECLUDED ON 8 ACRES; PROFESSIONALLY...
Bedrooms:
7
Bathrooms:
5
Sleeps:
10
Shelter Island Manor LUXURIOUS 2-HOME ESTATE COMPLETELY SECLUDED ON 8 ACRES; PROFESSIONALLY MANICURED GARDENS & HEATED ...
From $639 per night (USD)
Expedia
From $607 per night (USD)
VRBO
The North Fork Loft
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Spectacular Waterfront Loft in the heart of The North Forks' Wine Country. Enjoy the tranquil setting at this waterfront ...
From $607 per night (USD)
VRBO
From $409 per night (USD)
Expedia
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
CHECK OUT OUR REDUCED SEASONAL RATES 6 WINERIES IN UNDER A MILE NO CLEANING FEES NO EXTRA PERSON FEES FREE BIKES FREE B ...
From $409 per night (USD)
Expedia
From $485 per night (USD)
VRBO
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 $485 per night (USD)
VRBO
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Expedia
Private beach house and Long Island sound views, North Fork
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
This two bedroom home sits on a lush bluff overlooking the Long Island sound in the North Fork. The guest house with a l ...
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Expedia
From $434 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 $434 per night (USD)
VRBO
$Relax and walk to Croteaux Vineyard and South Harbor Beach\n$
From $434 per night (USD)
VRBO
Relax and walk to Croteaux Vineyard and South Harbor Beach\n
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Escape to our charming 3-bedroom vacation home in the heart of Southold, where you can immerse yourself in the beauty of ...
From $434 per night (USD)
VRBO
From $654 per night (USD)
VRBO
Wineries, Apple Picking, Pumpkin Picking, Outdoor Restaurants and Beaches!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Spacious home great layout for work or school from home. Featured 3-4 bedrooms, 3.5 baths, CAC, hardwood floors, gourmet ...
From $654 per night (USD)
VRBO
From $307 per night (USD)
VRBO
Classic North Fork Beach Home
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Amazing comfort and privacy on this acre plus setting. Home is crisp, clean and ready for you to enjoy. South Harbors ex ...
From $307 per night (USD)
VRBO
From $787 per night (USD)
VRBO
Shelter Island Waterfront Home!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
A water front home with magnificent Shelter Island Sound views from the entire main area, including living room, porch, ...
From $787 per night (USD)
VRBO
From $1345 per night (USD)
VRBO
Dream Beach House on the North Fork: Waterfront, Private Beach + Stunning Views
Bedrooms:
3
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 $1345 per night (USD)
VRBO
From $1020 per night (USD)
VRBO
Sun-Filled 4-BR Home, North Fork - amid Dunes, Beach & Spectacular Sunsets. 3-BA
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
We fell in love with this inlet, this neighborhood, this beach, these dunes, and this home the first time we visited in ...
From $1020 per night (USD)
VRBO
From $1156 per night (USD)
VRBO
North Fork Family Villa- large family home with fenced in pool
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Grand Beach Home, Room For Family and guests. 5 BR, 3.5 BA, Radiant Heat, Gourmet Kitchen With gas Wolf Stove. 10 Foot ...
From $1156 per night (USD)
VRBO
From $1013 per night (USD)
VRBO
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 $1013 per night (USD)
VRBO
From $424 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 $424 per night (USD)
Expedia
From $299 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 $299 per night (USD)
VRBO
From $742 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 $742 per night (USD)
VRBO
From $349 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 $349 per night (USD)
VRBO
From $663 per night (USD)
Expedia
Warm Peconic home…short walk to a private beach.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Minimum 14 day rental required (as per Town of Southold) Quaint cozy quiet private road short walk to sandy private bea ...
From $663 per night (USD)
Expedia
$Southold Cottage w\/ Patio & Grill - Walk to Beach!$
From $185 per night (USD)
VRBO
Southold Cottage w\/ Patio & Grill - Walk to Beach!
Bedrooms:
1
Bathrooms:
3
Sleeps:
3
If you’re a nature lover, a beach lover, a wine lover, or just in need of an escape, plan your dates for a stay at this ...
From $185 per night (USD)
VRBO
From $476 per night (USD)
Expedia
Waterfront home with private beach on property!
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
"Baydreams" is an amazing bayfront home ready for rent to create memories! Walk out onto the large deck which extends to ...
From $476 per night (USD)
Expedia
From $1091 per night (USD)
VRBO
Historic North Fork retreat, large pool, deck, overlooks preserved land,...
Bedrooms:
4
Bathrooms:
7
Sleeps:
10
North Fork Gem Historic North Fork retreat, large pool, deck, overlooks preserved land, lovely sunsets, and minutes to ...
From $1091 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
$NorthFork \nPeaceful Peconic Getaway- center of Wine Country$
From $515 per night (USD)
VRBO
NorthFork \nPeaceful Peconic Getaway- center of Wine Country
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Newly refurbished ranch style home in the heart of the North Fork wine country and close to all the best beaches , farms ...
From $515 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 $830 per night (USD)
VRBO
Beach House near Greenport Village
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
3 bedroom with deeded beach rights and partial water view. 5 minute walk to the beach and short drive to the heart of th ...
From $830 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
Two minuet walk to the beach. On a quiet private road
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Located in the north forks famous wine district. Can sleep up to five. Eat in glassed/screened front porch faces the sou ...
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VRBO
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Expedia
Water views Beach and pool!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Spacious entertainment, relax by the fireplace or relax in the closed porch , Private Beach on the corner of property. E ...
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Expedia
$Hidden Estate with Guest Cottage and Pool\n\n$
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VRBO
Hidden Estate with Guest Cottage and Pool\n\n
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
A short walk to Bootleggers Beach, and 4 minute drive to Crescent Beach, this luxurious, secluded estate sits on six spr ...
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VRBO
$Sandpoint by Rove Travel | Modern 5BR w\/ Pool$
From $599 per night (USD)
VRBO
Sandpoint by Rove Travel | Modern 5BR w\/ Pool
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Summary: Welcome to Sandpoint, a Rove Travel Home! Rove is a brand of luxury property rentals designed for the modern ...
From $599 per night (USD)
VRBO
From $780 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 $780 per night (USD)
VRBO
From $857 per night (USD)
VRBO
Waterfront Beach House Gem with Bay Views Steps to Pipes Cove!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Our Greenport beach house is steps from Pipes Cove Beach with beach access, water views from the house, a big yard, and ...
From $857 per night (USD)
VRBO

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