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Southold Vacation Rentals

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121 rentals in Southold.
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Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub & Beaches, vacation rental in Southold
Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub & Beaches, vacation rental in Southold
Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub & Beaches, vacation rental in Southold

Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub & Beaches

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 10
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Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board, vacation rental in Southold
Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board, vacation rental in Southold
Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board, vacation rental in Southold

Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
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Spectacular waterfront property, with magnificent views from all sides., vacation rental in Southold
Spectacular waterfront property, with magnificent views from all sides., vacation rental in Southold
Spectacular waterfront property, with magnificent views from all sides., vacation rental in Southold

Spectacular waterfront property, with magnificent views from all sides.

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
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Family-friendly, dog-friendly modern getaway near wineries and beaches!, vacation rental in Southold
Family-friendly, dog-friendly modern getaway near wineries and beaches!, vacation rental in Southold
Family-friendly, dog-friendly modern getaway near wineries and beaches!, vacation rental in Southold

Family-friendly, dog-friendly modern getaway near wineries and beaches!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Quaint and Quiet cottage. Newly renovated, heated built in pool!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Beachfront home on the North Fork, vacation rental in Southold
Beachfront home on the North Fork, vacation rental in Southold
Beachfront home on the North Fork, vacation rental in Southold

Beachfront home on the North Fork

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
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Entertainers Delight Just Steps From The Beach, vacation rental in Southold
Entertainers Delight Just Steps From The Beach, vacation rental in Southold
Entertainers Delight Just Steps From The Beach, vacation rental in Southold

Entertainers Delight Just Steps From The Beach

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Great Location!!  Walk to Town & Train!!, vacation rental in Southold
Great Location!!  Walk to Town & Train!!, vacation rental in Southold
Great Location!!  Walk to Town & Train!!, vacation rental in Southold

Great Location!! Walk to Town & Train!!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 3
Match: Sleeps
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North Fork Beach House, vacation rental in Southold
North Fork Beach House, vacation rental in Southold
North Fork Beach House, vacation rental in Southold

North Fork Beach House

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Located in the heart of wine country/BEACHES/shops., vacation rental in Southold
Located in the heart of wine country/BEACHES/shops., vacation rental in Southold
Located in the heart of wine country/BEACHES/shops., vacation rental in Southold

Located in the heart of wine country/BEACHES/shops.

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
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Curated Country Living In A Historic Farmhouse, vacation rental in Southold
Curated Country Living In A Historic Farmhouse, vacation rental in Southold
Curated Country Living In A Historic Farmhouse, vacation rental in Southold

Curated Country Living In A Historic Farmhouse

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
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Waterfront, private beach, ready for adventure, flexcation!, vacation rental in Southold
Waterfront, private beach, ready for adventure, flexcation!, vacation rental in Southold
Waterfront, private beach, ready for adventure, flexcation!, vacation rental in Southold

Waterfront, private beach, ready for adventure, flexcation!

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront, New Construction North Fork Beach House, vacation rental in Southold
Waterfront, New Construction North Fork Beach House, vacation rental in Southold
Waterfront, New Construction North Fork Beach House, vacation rental in Southold

Waterfront, New Construction North Fork Beach House

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
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Southold Soundfront Private Beach, vacation rental in Southold
Southold Soundfront Private Beach, vacation rental in Southold
Southold Soundfront Private Beach, vacation rental in Southold

Southold Soundfront Private Beach

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
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Kenneys Beach retreat by the Wineries, vacation rental in Southold
Kenneys Beach retreat by the Wineries, vacation rental in Southold
Kenneys Beach retreat by the Wineries, vacation rental in Southold

Kenneys Beach retreat by the Wineries

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
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Renovated American Farmhouse in the heart of Southold with heated saltwater pool, vacation rental in Southold
Renovated American Farmhouse in the heart of Southold with heated saltwater pool, vacation rental in Southold
Renovated American Farmhouse in the heart of Southold with heated saltwater pool, vacation rental in Southold

Renovated American Farmhouse in the heart of Southold with heated saltwater pool

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Three Bed, Three Bath Home Close to Beaches, Vineyards and Breweries, vacation rental in Southold
Three Bed, Three Bath Home Close to Beaches, Vineyards and Breweries, vacation rental in Southold
Three Bed, Three Bath Home Close to Beaches, Vineyards and Breweries, vacation rental in Southold

Three Bed, Three Bath Home Close to Beaches, Vineyards and Breweries

Condo/Apartment
0 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Southold McCabe's Beach Retreat - Walk to the beach; Relax & enjoy all seasons!, vacation rental in Southold
Southold McCabe's Beach Retreat - Walk to the beach; Relax & enjoy all seasons!, vacation rental in Southold
Southold McCabe's Beach Retreat - Walk to the beach; Relax & enjoy all seasons!, vacation rental in Southold

Southold McCabe's Beach Retreat - Walk to the beach; Relax & enjoy all seasons!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Cute Cottage Apartment Near town, beaches and vineyards (WBH), vacation rental in Southold
Cute Cottage Apartment Near town, beaches and vineyards (WBH), vacation rental in Southold
Cute Cottage Apartment Near town, beaches and vineyards (WBH), vacation rental in Southold

Cute Cottage Apartment Near town, beaches and vineyards (WBH)

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Truly special! Huge North Fork Villa Great for multiple families- Walk to beach, vacation rental in Southold
Truly special! Huge North Fork Villa Great for multiple families- Walk to beach, vacation rental in Southold
Truly special! Huge North Fork Villa Great for multiple families- Walk to beach, vacation rental in Southold

Truly special! Huge North Fork Villa Great for multiple families- Walk to beach

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Unique Southold waterfront luxury home with heated pool on Long Creek, vacation rental in Southold
Unique Southold waterfront luxury home with heated pool on Long Creek, vacation rental in Southold
Unique Southold waterfront luxury home with heated pool on Long Creek, vacation rental in Southold

Unique Southold waterfront luxury home with heated pool on Long Creek

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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FOR SALE — Stroll to Beaches & Town! Beautifully Renovated 1890s Farmhouse, vacation rental in Southold
FOR SALE — Stroll to Beaches & Town! Beautifully Renovated 1890s Farmhouse, vacation rental in Southold
FOR SALE — Stroll to Beaches & Town! Beautifully Renovated 1890s Farmhouse, vacation rental in Southold

FOR SALE — Stroll to Beaches & Town! Beautifully Renovated 1890s Farmhouse

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Northfork home., vacation rental in Southold
Charming Northfork home., vacation rental in Southold
Charming Northfork home., vacation rental in Southold

Charming Northfork home.

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Waterfront Home with Outstanding Waterviews!, vacation rental in Southold
Spacious Waterfront Home with Outstanding Waterviews!, vacation rental in Southold
Spacious Waterfront Home with Outstanding Waterviews!, vacation rental in Southold

Spacious Waterfront Home with Outstanding Waterviews!

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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Classic Arts and Crafts House on the North Fork, vacation rental in Southold
Classic Arts and Crafts House on the North Fork, vacation rental in Southold
Classic Arts and Crafts House on the North Fork, vacation rental in Southold

Classic Arts and Crafts House on the North Fork

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Midcentury North Fork Beach House walking distance to beach, vacation rental in Southold
Midcentury North Fork Beach House walking distance to beach, vacation rental in Southold
Midcentury North Fork Beach House walking distance to beach, vacation rental in Southold

Midcentury North Fork Beach House walking distance to beach

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Shorecrest Beach House, 4 bedroom private beach front, new renovation, vacation rental in Southold
Shorecrest Beach House, 4 bedroom private beach front, new renovation, vacation rental in Southold
Shorecrest Beach House, 4 bedroom private beach front, new renovation, vacation rental in Southold

Shorecrest Beach House, 4 bedroom private beach front, new renovation

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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3 Br North Fork Getaway In Private Beach Community, vacation rental in Southold
3 Br North Fork Getaway In Private Beach Community, vacation rental in Southold
3 Br North Fork Getaway In Private Beach Community, vacation rental in Southold

3 Br North Fork Getaway In Private Beach Community

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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2 Bedroom Apartment in Historic Home with private yard (WBH), vacation rental in Southold
2 Bedroom Apartment in Historic Home with private yard (WBH), vacation rental in Southold
2 Bedroom Apartment in Historic Home with private yard (WBH), vacation rental in Southold

2 Bedroom Apartment in Historic Home with private yard (WBH)

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Sea Breeze & Sunsets, Beach house steps to Beach & Vineyards, vacation rental in Southold
Sea Breeze & Sunsets, Beach house steps to Beach & Vineyards, vacation rental in Southold
Sea Breeze & Sunsets, Beach house steps to Beach & Vineyards, vacation rental in Southold

Sea Breeze & Sunsets, Beach house steps to Beach & Vineyards

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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AUGUST WEEKS STILL AVAILABLE - Cottage in Private North Fork Beach Community, vacation rental in Southold
AUGUST WEEKS STILL AVAILABLE - Cottage in Private North Fork Beach Community, vacation rental in Southold
AUGUST WEEKS STILL AVAILABLE - Cottage in Private North Fork Beach Community, vacation rental in Southold

AUGUST WEEKS STILL AVAILABLE - Cottage in Private North Fork Beach Community

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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WATERFRONT Southold Retreat! Steps to Beaches!, vacation rental in Southold
WATERFRONT Southold Retreat! Steps to Beaches!, vacation rental in Southold
WATERFRONT Southold Retreat! Steps to Beaches!, vacation rental in Southold

WATERFRONT Southold Retreat! Steps to Beaches!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES, vacation rental in Southold
PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES, vacation rental in Southold
PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES, vacation rental in Southold

PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Updated farmhouse in the heart of wine country.  10 minute drive to Greenport., vacation rental in Southold
Updated farmhouse in the heart of wine country.  10 minute drive to Greenport., vacation rental in Southold
Updated farmhouse in the heart of wine country.  10 minute drive to Greenport., vacation rental in Southold

Updated farmhouse in the heart of wine country. 10 minute drive to Greenport.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beach Community home nestled in the heart of Long Island's North Fork, vacation rental in Southold
Beach Community home nestled in the heart of Long Island's North Fork, vacation rental in Southold
Beach Community home nestled in the heart of Long Island's North Fork, vacation rental in Southold

Beach Community home nestled in the heart of Long Island's North Fork

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Nature Lover's Paradise on North Fork, vacation rental in Southold
Nature Lover's Paradise on North Fork, vacation rental in Southold
Nature Lover's Paradise on North Fork, vacation rental in Southold

Nature Lover's Paradise on North Fork

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 2
Match: Sleeps
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Southold, NY- Heart of North Fork Wine Country, vacation rental in Southold
Southold, NY- Heart of North Fork Wine Country, vacation rental in Southold
Southold, NY- Heart of North Fork Wine Country, vacation rental in Southold

Southold, NY- Heart of North Fork Wine Country

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Pristine Oveanview Getaway Sanctuary, vacation rental in Southold
Pristine Oveanview Getaway Sanctuary, vacation rental in Southold
Pristine Oveanview Getaway Sanctuary, vacation rental in Southold

Pristine Oveanview Getaway Sanctuary

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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4 Bed / 2.5 Bath Stunning North Fork retreat with Heated Pool & Hot Tub, vacation rental in Southold
4 Bed / 2.5 Bath Stunning North Fork retreat with Heated Pool & Hot Tub, vacation rental in Southold
4 Bed / 2.5 Bath Stunning North Fork retreat with Heated Pool & Hot Tub, vacation rental in Southold

4 Bed / 2.5 Bath Stunning North Fork retreat with Heated Pool & Hot Tub

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Kayak in Peconic Bay! Tranquil Northfork Retreat in the Heart of Wine Country, vacation rental in Southold
Kayak in Peconic Bay! Tranquil Northfork Retreat in the Heart of Wine Country, vacation rental in Southold
Kayak in Peconic Bay! Tranquil Northfork Retreat in the Heart of Wine Country, vacation rental in Southold

Kayak in Peconic Bay! Tranquil Northfork Retreat in the Heart of Wine Country

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront with dock on Goose Creek (just off Peconic Bay) and chef's kitchen, vacation rental in Southold
Waterfront with dock on Goose Creek (just off Peconic Bay) and chef's kitchen, vacation rental in Southold
Waterfront with dock on Goose Creek (just off Peconic Bay) and chef's kitchen, vacation rental in Southold

Waterfront with dock on Goose Creek (just off Peconic Bay) and chef's kitchen

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views.., vacation rental in Southold
5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views.., vacation rental in Southold
5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views.., vacation rental in Southold

5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views..

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Lovely, Serene and Stylish Country Home, vacation rental in Southold
Lovely, Serene and Stylish Country Home, vacation rental in Southold
Lovely, Serene and Stylish Country Home, vacation rental in Southold

Lovely, Serene and Stylish Country Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Private waterfront home w Dock Kayaks town of Southold, near Greenport,, vacation rental in Southold
Private waterfront home w Dock Kayaks town of Southold, near Greenport,, vacation rental in Southold
Private waterfront home w Dock Kayaks town of Southold, near Greenport,, vacation rental in Southold

Private waterfront home w Dock Kayaks town of Southold, near Greenport,

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2BR North Fork Southold Private Cottage Beach steps to beach 10min Greenport, vacation rental in Southold
2BR North Fork Southold Private Cottage Beach steps to beach 10min Greenport, vacation rental in Southold
2BR North Fork Southold Private Cottage Beach steps to beach 10min Greenport, vacation rental in Southold

2BR North Fork Southold Private Cottage Beach steps to beach 10min Greenport

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Great Relaxing Summer Family  House, vacation rental in Southold
Great Relaxing Summer Family  House, vacation rental in Southold
Great Relaxing Summer Family  House, vacation rental in Southold

Great Relaxing Summer Family House

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Charming North Fork Farmhouse in Southold minutes from beaches and vineyards, vacation rental in Southold
Charming North Fork Farmhouse in Southold minutes from beaches and vineyards, vacation rental in Southold
Charming North Fork Farmhouse in Southold minutes from beaches and vineyards, vacation rental in Southold

Charming North Fork Farmhouse in Southold minutes from beaches and vineyards

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Gorgeous Estate with Pool by Beach, Lighthouse, Wineries & Farmers Market, vacation rental in Southold
Gorgeous Estate with Pool by Beach, Lighthouse, Wineries & Farmers Market, vacation rental in Southold
Gorgeous Estate with Pool by Beach, Lighthouse, Wineries & Farmers Market, vacation rental in Southold

Gorgeous Estate with Pool by Beach, Lighthouse, Wineries & Farmers Market

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 11
Match: Sleeps
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Waterfront Oasis on the North Fork, vacation rental in Southold
Waterfront Oasis on the North Fork, vacation rental in Southold
Waterfront Oasis on the North Fork, vacation rental in Southold

Waterfront Oasis on the North Fork

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Architect-Renovated, Pristine Ranch, Modern Kitchen, Short Walk to Beach, vacation rental in Southold
Architect-Renovated, Pristine Ranch, Modern Kitchen, Short Walk to Beach, vacation rental in Southold
Architect-Renovated, Pristine Ranch, Modern Kitchen, Short Walk to Beach, vacation rental in Southold

Architect-Renovated, Pristine Ranch, Modern Kitchen, Short Walk to Beach

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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