Vacation Rentals in Southold, New York

35 Properties Available

Newly Renovated Open Layout 5bdrm in Peaceful Southold w/ Entertainers Pool/Yard Private vacation home
Newly Renovated Open Layout 5bdrm in Peaceful Southold w/ Entertainers Pool/Yard
$2484 / night
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Modern North Fork Haven: Beachfront,Private Pool Private vacation home
Modern North Fork Haven: Beachfront,Private Pool
$1929 / night
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5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views.. Private vacation home
5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views..
$1566 / night
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Panoramic Water Views, Plunge Pool, Hot Tub, Fire Pit & Walk to Beach Private vacation home
Panoramic Water Views, Plunge Pool, Hot Tub, Fire Pit & Walk to Beach
$1486 / night
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Truly special! Huge North Fork Villa Great for multiple families- Walk to beach Private vacation home
Truly special! Huge North Fork Villa Great for multiple families- Walk to beach
$1437 / night
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Steps from Surf and Sand in Southold! Private vacation home
Steps from Surf and Sand in Southold!
$1427 / night
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4 Bed \/ 2.5 Bath Stunning North Fork retreat with Heated Pool & Hot Tub Private vacation home
4 Bed \/ 2.5 Bath Stunning North Fork retreat with Heated Pool & Hot Tub
$1218 / night
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North Fork 7 Bedroom Farmhouse Escape Private vacation home
North Fork 7 Bedroom Farmhouse Escape
$1110 / night
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Waterfront Beach House Nestled Along the Wondrous North Fork Wine Trail,... Private vacation home
Waterfront Beach House Nestled Along the Wondrous North Fork Wine Trail,...
$959 / night
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Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining! Private vacation home
Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!
$921 / night
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Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches Private vacation home
Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
$900 / night
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Mint Condition Modern Farmhouse Gem Offers Best of North Fork Living! Private vacation home
Mint Condition Modern Farmhouse Gem Offers Best of North Fork Living!
$807 / night
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Enjoy Driftwood Landing - A Quiet Southold Escape Private vacation home
Enjoy Driftwood Landing - A Quiet Southold Escape
$805 / night
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Nautical Peconic Bayfront Home - Walk to Town Private vacation home
Nautical Peconic Bayfront Home - Walk to Town
$772 / night
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4BR+ Newly renovated home mins to top beaches and vineyards, new heated pool! Private vacation home
4BR+ Newly renovated home mins to top beaches and vineyards, new heated pool!
$680 / night
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Charming waterfront, 3-bedroom house on Goose Creek in welcoming Southold Private vacation home
Charming waterfront, 3-bedroom house on Goose Creek in welcoming Southold
$588 / night
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Expansive North Fork Estate on almost 3 Acres, Close to Vineyards and... Private vacation home
Expansive North Fork Estate on almost 3 Acres, Close to Vineyards and...
$560 / night
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NorthFork Serenity, next to beach and wineries Private vacation home
NorthFork Serenity, next to beach and wineries
$553 / night
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Between the Vineyard and Sea on the North Fork. Permit #: 0378 Private vacation home
Between the Vineyard and Sea on the North Fork. Permit #: 0378
$494 / night
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Cottage by Cedar Beach Cottage
Cottage by Cedar Beach
$488 / night
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Cedar Point Cove - Waterfront Escape with Private Dock and Peconic Bay Views Private vacation home
Cedar Point Cove - Waterfront Escape with Private Dock and Peconic Bay Views
$473 / night
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Lovely, Serene and Stylish Country Home Private vacation home
Lovely, Serene and Stylish Country Home
$459 / night
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Southold McCabe's Beach Retreat - Walk to the beach; Relax & enjoy all seasons! Private vacation home
Southold McCabe's Beach Retreat - Walk to the beach; Relax & enjoy all seasons!
$445 / night
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Eat, Love, Stay, Swim Southold North Fork\nCentrally Located and Walkable Agritourism
Eat, Love, Stay, Swim Southold North Fork\nCentrally Located and Walkable
$428 / night
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Dog-friendly, comfortable home with private pool, large yard, WiFi, & fire pit Private vacation home
Dog-friendly, comfortable home with private pool, large yard, WiFi, & fire pit
$424 / night
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Beautiful North Fork 3-Bedroom Home Steps Away from a Private Sandy Bay Private vacation home
Beautiful North Fork 3-Bedroom Home Steps Away from a Private Sandy Bay
$409 / night
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2 Bedroom Apartment in Historic Home with private yard (WBH) Apartment
2 Bedroom Apartment in Historic Home with private yard (WBH)
$402 / night
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House central to North Fork wineries restaurants + beaches. Walk to town. Cottage
House central to North Fork wineries restaurants + beaches. Walk to town.
$290 / night
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Goose Creek Getaway: Modern Home with Beach Access Private vacation home
Goose Creek Getaway: Modern Home with Beach Access
$0 / night
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Historic cottage near the NoFo beach Cottage
Historic cottage near the NoFo beach
$0 / night
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Private Guest Room-heart of Long Island's North Fork wine country-steps to beach Apartment
Private Guest Room-heart of Long Island's North Fork wine country-steps to beach
$0 / night
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Southold near vineyard & beach Private vacation home
Southold near vineyard & beach
$0 / night
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Stunning Home & Private Beach on the North Fork Private vacation home
Stunning Home & Private Beach on the North Fork
$0 / night
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The Stucco House Private vacation home
The Stucco House
$0 / night
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White Blossom House Inn Hotel
White Blossom House Inn
$0 / night
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