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Cutchogue Holiday Apartments

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49 rentals in Cutchogue.
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Vintage Style Farmhouse  in the Heart of Wine Country, holiday rental in Cutchogue
Vintage Style Farmhouse  in the Heart of Wine Country, holiday rental in Cutchogue
Vintage Style Farmhouse  in the Heart of Wine Country, holiday rental in Cutchogue

Vintage Style Farmhouse in the Heart of Wine Country

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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HUGE house for an anytime  holiday . Family or friends gatherings, weddings!, holiday rental in Cutchogue
HUGE house for an anytime  holiday . Family or friends gatherings, weddings!, holiday rental in Cutchogue
HUGE house for an anytime  holiday . Family or friends gatherings, weddings!, holiday rental in Cutchogue

HUGE house for an anytime holiday . Family or friends gatherings, weddings!

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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North Fork Winter / Spring Getaway: Cozy Fireplaces, Farm Views,  Beach Sunsets, holiday rental in Cutchogue
North Fork Winter / Spring Getaway: Cozy Fireplaces, Farm Views,  Beach Sunsets, holiday rental in Cutchogue
North Fork Winter / Spring Getaway: Cozy Fireplaces, Farm Views,  Beach Sunsets, holiday rental in Cutchogue

North Fork Winter / Spring Getaway: Cozy Fireplaces, Farm Views, Beach Sunsets

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Perfect Cutchogue/Southold -North Fork Vacation Home. Very Private, close to all, holiday rental in Cutchogue
Perfect Cutchogue/Southold -North Fork Vacation Home. Very Private, close to all, holiday rental in Cutchogue
Perfect Cutchogue/Southold -North Fork Vacation Home. Very Private, close to all, holiday rental in Cutchogue

Perfect Cutchogue/Southold -North Fork Vacation Home. Very Private, close to all

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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North Fork Bayfront Home w Private Beach & Nearby the Finest Wineries & Eateries, holiday rental in Cutchogue
North Fork Bayfront Home w Private Beach & Nearby the Finest Wineries & Eateries, holiday rental in Cutchogue
North Fork Bayfront Home w Private Beach & Nearby the Finest Wineries & Eateries, holiday rental in Cutchogue

North Fork Bayfront Home w Private Beach & Nearby the Finest Wineries & Eateries

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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North Fork, New Construction with pool, walking distance to beach, holiday rental in Cutchogue
North Fork, New Construction with pool, walking distance to beach, holiday rental in Cutchogue
North Fork, New Construction with pool, walking distance to beach, holiday rental in Cutchogue

North Fork, New Construction with pool, walking distance to beach

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cutchogue Beach Cottage, holiday rental in Cutchogue
Cutchogue Beach Cottage, holiday rental in Cutchogue
Cutchogue Beach Cottage, holiday rental in Cutchogue

Cutchogue Beach Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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North Fork,Cutchogue-Nassau Point Home w Saltwater Pool, Private Beach Access, holiday rental in Cutchogue
North Fork,Cutchogue-Nassau Point Home w Saltwater Pool, Private Beach Access, holiday rental in Cutchogue
North Fork,Cutchogue-Nassau Point Home w Saltwater Pool, Private Beach Access, holiday rental in Cutchogue

North Fork,Cutchogue-Nassau Point Home w Saltwater Pool, Private Beach Access

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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North Fork Life: Pool, Beach, Wineries, Farmstands, holiday rental in Cutchogue
North Fork Life: Pool, Beach, Wineries, Farmstands, holiday rental in Cutchogue
North Fork Life: Pool, Beach, Wineries, Farmstands, holiday rental in Cutchogue

North Fork Life: Pool, Beach, Wineries, Farmstands

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Home Steps From Beach And Short Bike Ride To Vineyards, holiday rental in Cutchogue
Luxury Home Steps From Beach And Short Bike Ride To Vineyards, holiday rental in Cutchogue
Luxury Home Steps From Beach And Short Bike Ride To Vineyards, holiday rental in Cutchogue

Luxury Home Steps From Beach And Short Bike Ride To Vineyards

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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North Fork Beach House - walk to beach!, holiday rental in Cutchogue
North Fork Beach House - walk to beach!, holiday rental in Cutchogue
North Fork Beach House - walk to beach!, holiday rental in Cutchogue

North Fork Beach House - walk to beach!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy Cottage on the North Fork Close to Vineyards & Beaches, holiday rental in Cutchogue
Cozy Cottage on the North Fork Close to Vineyards & Beaches, holiday rental in Cutchogue
Cozy Cottage on the North Fork Close to Vineyards & Beaches, holiday rental in Cutchogue

Cozy Cottage on the North Fork Close to Vineyards & Beaches

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Perfect Family-Friendly North Fork Getaway for All Seasons, holiday rental in Cutchogue
Perfect Family-Friendly North Fork Getaway for All Seasons, holiday rental in Cutchogue
Perfect Family-Friendly North Fork Getaway for All Seasons, holiday rental in Cutchogue

Perfect Family-Friendly North Fork Getaway for All Seasons

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Beach House on the Bay, holiday rental in Cutchogue
Waterfront Beach House on the Bay, holiday rental in Cutchogue
Waterfront Beach House on the Bay, holiday rental in Cutchogue

Waterfront Beach House on the Bay

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Home in Long Island Wine Country - Walk to Beach!, holiday rental in Cutchogue
Home in Long Island Wine Country - Walk to Beach!, holiday rental in Cutchogue
Home in Long Island Wine Country - Walk to Beach!, holiday rental in Cutchogue

Home in Long Island Wine Country - Walk to Beach!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Barn Luxury Living in Town Center Near Public  Golf Course, holiday rental in Cutchogue
Barn Luxury Living in Town Center Near Public  Golf Course, holiday rental in Cutchogue
Barn Luxury Living in Town Center Near Public  Golf Course, holiday rental in Cutchogue

Barn Luxury Living in Town Center Near Public Golf Course

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Waterfront w/ Private Beach on Nassau Point, holiday rental in Cutchogue
Waterfront w/ Private Beach on Nassau Point, holiday rental in Cutchogue
Waterfront w/ Private Beach on Nassau Point, holiday rental in Cutchogue

Waterfront w/ Private Beach on Nassau Point

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Cozy Ranch in Broadwaters Cove: Beaches, Marinas and Wineries!, holiday rental in Cutchogue
Cozy Ranch in Broadwaters Cove: Beaches, Marinas and Wineries!, holiday rental in Cutchogue
Cozy Ranch in Broadwaters Cove: Beaches, Marinas and Wineries!, holiday rental in Cutchogue

Cozy Ranch in Broadwaters Cove: Beaches, Marinas and Wineries!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Barn Life in Cutchogue, holiday rental in Cutchogue
Barn Life in Cutchogue, holiday rental in Cutchogue
Barn Life in Cutchogue, holiday rental in Cutchogue

Barn Life in Cutchogue

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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North Fork Farms & Vineyards Near Beaches & 40 Minutes From The Hamptons, holiday rental in Cutchogue
North Fork Farms & Vineyards Near Beaches & 40 Minutes From The Hamptons, holiday rental in Cutchogue
North Fork Farms & Vineyards Near Beaches & 40 Minutes From The Hamptons, holiday rental in Cutchogue

North Fork Farms & Vineyards Near Beaches & 40 Minutes From The Hamptons

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spectacular Bay Front Sprawling Nassau Point Home, holiday rental in Cutchogue
Spectacular Bay Front Sprawling Nassau Point Home, holiday rental in Cutchogue
Spectacular Bay Front Sprawling Nassau Point Home, holiday rental in Cutchogue

Spectacular Bay Front Sprawling Nassau Point Home

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Exclusive Nassau Point House with Pool and Deeded Beach!, holiday rental in Cutchogue
Exclusive Nassau Point House with Pool and Deeded Beach!, holiday rental in Cutchogue
Exclusive Nassau Point House with Pool and Deeded Beach!, holiday rental in Cutchogue

Exclusive Nassau Point House with Pool and Deeded Beach!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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North Fork Waterfront Oasis, holiday rental in Cutchogue
North Fork Waterfront Oasis, holiday rental in Cutchogue
North Fork Waterfront Oasis, holiday rental in Cutchogue

North Fork Waterfront Oasis

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Private Family Beach Paradise, holiday rental in Cutchogue
Private Family Beach Paradise, holiday rental in Cutchogue
Private Family Beach Paradise, holiday rental in Cutchogue

Private Family Beach Paradise

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 9
Match: Sleeps
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Waterfront Home in the Heart of the North Fork, holiday rental in Cutchogue
Waterfront Home in the Heart of the North Fork, holiday rental in Cutchogue
Waterfront Home in the Heart of the North Fork, holiday rental in Cutchogue

Waterfront Home in the Heart of the North Fork

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Waterfront Beach Cottage on Peconic Bay, Cutchogue, NY, holiday rental in Cutchogue
Waterfront Beach Cottage on Peconic Bay, Cutchogue, NY, holiday rental in Cutchogue
Waterfront Beach Cottage on Peconic Bay, Cutchogue, NY, holiday rental in Cutchogue

Waterfront Beach Cottage on Peconic Bay, Cutchogue, NY

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Peconic Bay idyllic waterfront for perfect relaxation, holiday rental in Cutchogue
Peconic Bay idyllic waterfront for perfect relaxation, holiday rental in Cutchogue
Peconic Bay idyllic waterfront for perfect relaxation, holiday rental in Cutchogue

Peconic Bay idyllic waterfront for perfect relaxation

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Stylish and comfortable modern farmhouse Best Location! Short drive or even walk, holiday rental in Cutchogue
Stylish and comfortable modern farmhouse Best Location! Short drive or even walk, holiday rental in Cutchogue
Stylish and comfortable modern farmhouse Best Location! Short drive or even walk, holiday rental in Cutchogue

Stylish and comfortable modern farmhouse Best Location! Short drive or even walk

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Historic North Fork Farmhouse Near Wineries!, holiday rental in Cutchogue
NEW! Historic North Fork Farmhouse Near Wineries!, holiday rental in Cutchogue
NEW! Historic North Fork Farmhouse Near Wineries!, holiday rental in Cutchogue

NEW! Historic North Fork Farmhouse Near Wineries!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Cottage on the North Fork, holiday rental in Cutchogue
Waterfront Cottage on the North Fork, holiday rental in Cutchogue
Waterfront Cottage on the North Fork, holiday rental in Cutchogue

Waterfront Cottage on the North Fork

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful fall getaway in a newly renovated waterfront home, holiday rental in Cutchogue
Beautiful fall getaway in a newly renovated waterfront home, holiday rental in Cutchogue
Beautiful fall getaway in a newly renovated waterfront home, holiday rental in Cutchogue

Beautiful fall getaway in a newly renovated waterfront home

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Newly renovated North Fork beach house! 5 minutes from the beach!, holiday rental in Cutchogue
Newly renovated North Fork beach house! 5 minutes from the beach!, holiday rental in Cutchogue
Newly renovated North Fork beach house! 5 minutes from the beach!, holiday rental in Cutchogue

Newly renovated North Fork beach house! 5 minutes from the beach!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Wine Country Getaway on Private Street & Peconic Bay Neighborhood Beach Access, holiday rental in Cutchogue
Wine Country Getaway on Private Street & Peconic Bay Neighborhood Beach Access, holiday rental in Cutchogue
Wine Country Getaway on Private Street & Peconic Bay Neighborhood Beach Access, holiday rental in Cutchogue

Wine Country Getaway on Private Street & Peconic Bay Neighborhood Beach Access

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tranquil 5 Br North Fork Retreat With Pool And Huge Yard, Walk To Beach, holiday rental in Cutchogue
Tranquil 5 Br North Fork Retreat With Pool And Huge Yard, Walk To Beach, holiday rental in Cutchogue
Tranquil 5 Br North Fork Retreat With Pool And Huge Yard, Walk To Beach, holiday rental in Cutchogue

Tranquil 5 Br North Fork Retreat With Pool And Huge Yard, Walk To Beach

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Pace's Place Close to North Fork Vineyards, holiday rental in Cutchogue
Pace's Place Close to North Fork Vineyards, holiday rental in Cutchogue
Pace's Place Close to North Fork Vineyards, holiday rental in Cutchogue

Pace's Place Close to North Fork Vineyards

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Stunning Beach House - steps from Peconic Bay w/Heated Pool, holiday rental in Cutchogue
Stunning Beach House - steps from Peconic Bay w/Heated Pool, holiday rental in Cutchogue
Stunning Beach House - steps from Peconic Bay w/Heated Pool, holiday rental in Cutchogue

Stunning Beach House - steps from Peconic Bay w/Heated Pool

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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North Fork Wine Country, quiet tree lined street, walk to beach & bay, holiday rental in Cutchogue
North Fork Wine Country, quiet tree lined street, walk to beach & bay, holiday rental in Cutchogue
North Fork Wine Country, quiet tree lined street, walk to beach & bay, holiday rental in Cutchogue

North Fork Wine Country, quiet tree lined street, walk to beach & bay

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Bay Breeze, holiday rental in Cutchogue
The Bay Breeze, holiday rental in Cutchogue
The Bay Breeze, holiday rental in Cutchogue

The Bay Breeze

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Waterfront Serene Cottage, holiday rental in Cutchogue
Waterfront Serene Cottage, holiday rental in Cutchogue
Waterfront Serene Cottage, holiday rental in Cutchogue

Waterfront Serene Cottage

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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one of the best beaches on the North Fork; completely private, holiday rental in Cutchogue
one of the best beaches on the North Fork; completely private, holiday rental in Cutchogue
one of the best beaches on the North Fork; completely private, holiday rental in Cutchogue

one of the best beaches on the North Fork; completely private

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Tuscany in the North Fork - Spectacular Villa in the Midst of a Vineyard, holiday rental in Cutchogue
Tuscany in the North Fork - Spectacular Villa in the Midst of a Vineyard, holiday rental in Cutchogue
Tuscany in the North Fork - Spectacular Villa in the Midst of a Vineyard, holiday rental in Cutchogue

Tuscany in the North Fork - Spectacular Villa in the Midst of a Vineyard

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Airy Summer Retreat on Nassau Point – Short stroll to private beach, holiday rental in Cutchogue
Airy Summer Retreat on Nassau Point – Short stroll to private beach, holiday rental in Cutchogue
Airy Summer Retreat on Nassau Point – Short stroll to private beach, holiday rental in Cutchogue

Airy Summer Retreat on Nassau Point – Short stroll to private beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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North Fork Wine Region—Walk to Beach, holiday rental in Cutchogue
North Fork Wine Region—Walk to Beach, holiday rental in Cutchogue
North Fork Wine Region—Walk to Beach, holiday rental in Cutchogue

North Fork Wine Region—Walk to Beach

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Restored Farmhouse in The Heart of Wine and Farm Country, holiday rental in Cutchogue
Restored Farmhouse in The Heart of Wine and Farm Country, holiday rental in Cutchogue
Restored Farmhouse in The Heart of Wine and Farm Country, holiday rental in Cutchogue

Restored Farmhouse in The Heart of Wine and Farm Country

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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The Melody Too, holiday rental in Cutchogue
The Melody Too, holiday rental in Cutchogue
The Melody Too, holiday rental in Cutchogue

The Melody Too

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tastefully updated home closet vineyards and beaches, holiday rental in Cutchogue
Tastefully updated home closet vineyards and beaches, holiday rental in Cutchogue
Tastefully updated home closet vineyards and beaches, holiday rental in Cutchogue

Tastefully updated home closet vineyards and beaches

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Historic Renovated Farmhouse, 2min to Beach, Vineyards, Fireplace, Kid Friendly, holiday rental in Cutchogue
Historic Renovated Farmhouse, 2min to Beach, Vineyards, Fireplace, Kid Friendly, holiday rental in Cutchogue
Historic Renovated Farmhouse, 2min to Beach, Vineyards, Fireplace, Kid Friendly, holiday rental in Cutchogue

Historic Renovated Farmhouse, 2min to Beach, Vineyards, Fireplace, Kid Friendly

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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North Fork Vacation Home - Great location, Walk to Beach - with Hot Tub, holiday rental in Cutchogue
North Fork Vacation Home - Great location, Walk to Beach - with Hot Tub, holiday rental in Cutchogue
North Fork Vacation Home - Great location, Walk to Beach - with Hot Tub, holiday rental in Cutchogue

North Fork Vacation Home - Great location, Walk to Beach - with Hot Tub

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Incredible North Fork retreat.  Saltwater pool and minutes from the beach., holiday rental in Cutchogue
Incredible North Fork retreat.  Saltwater pool and minutes from the beach., holiday rental in Cutchogue
Incredible North Fork retreat.  Saltwater pool and minutes from the beach., holiday rental in Cutchogue

Incredible North Fork retreat. Saltwater pool and minutes from the beach.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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