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Cutchogue Vacation Rentals

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Bedrooms

Bathrooms

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5 mi
54 rentals in Cutchogue.
Newly renovated North Fork beach house! 5 mins from the beach w/ new game room, vacation rental in Cutchogue
Newly renovated North Fork beach house! 5 mins from the beach w/ new game room, vacation rental in Cutchogue
Newly renovated North Fork beach house! 5 mins from the beach w/ new game room, vacation rental in Cutchogue

Newly renovated North Fork beach house! 5 mins from the beach w/ new game room

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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North Fork Spring Getaway: Cozy Fireplaces, Farm Views, Beach Sunsets, vacation rental in Cutchogue
North Fork Spring Getaway: Cozy Fireplaces, Farm Views, Beach Sunsets, vacation rental in Cutchogue
North Fork Spring Getaway: Cozy Fireplaces, Farm Views, Beach Sunsets, vacation rental in Cutchogue

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

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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North Fork, New Construction with heated pool, walking distance to beach, vacation rental in Cutchogue
North Fork, New Construction with heated pool, walking distance to beach, vacation rental in Cutchogue
North Fork, New Construction with heated pool, walking distance to beach, vacation rental in Cutchogue

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Pace's Place Close to North Fork Vineyards, vacation rental in Cutchogue
Pace's Place Close to North Fork Vineyards, vacation rental in Cutchogue
Pace's Place Close to North Fork Vineyards, vacation rental in Cutchogue

Pace's Place Close to North Fork Vineyards

Rental Home
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Cozy Cottage on the North Fork Close to Vineyards & Beaches, vacation rental in Cutchogue
Cozy Cottage on the North Fork Close to Vineyards & Beaches, vacation rental in Cutchogue
Cozy Cottage on the North Fork Close to Vineyards & Beaches, vacation rental in Cutchogue

Cozy Cottage on the North Fork Close to Vineyards & Beaches

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful fall getaway in a newly renovated waterfront home, vacation rental in Cutchogue
Beautiful fall getaway in a newly renovated waterfront home, vacation rental in Cutchogue
Beautiful fall getaway in a newly renovated waterfront home, vacation rental in Cutchogue

Beautiful fall getaway in a newly renovated waterfront home

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Barn Luxury Living in Town Center Near Public  Golf Course, vacation rental in Cutchogue
Barn Luxury Living in Town Center Near Public  Golf Course, vacation rental in Cutchogue
Barn Luxury Living in Town Center Near Public  Golf Course, vacation rental in Cutchogue

Barn Luxury Living in Town Center Near Public Golf Course

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Totally Renovated Cottage on the North Fork 7 min. walk to the Beach, vacation rental in Cutchogue
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach, vacation rental in Cutchogue
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach, vacation rental in Cutchogue

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Barn Life in Cutchogue, vacation rental in Cutchogue
Barn Life in Cutchogue, vacation rental in Cutchogue
Barn Life in Cutchogue, vacation rental in Cutchogue

Barn Life in Cutchogue

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Melody Too, vacation rental in Cutchogue
The Melody Too, vacation rental in Cutchogue
The Melody Too, vacation rental in Cutchogue

The Melody Too

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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North Fork Wine Country, quiet tree lined street, 4 min walk to beach & bay, vacation rental in Cutchogue
North Fork Wine Country, quiet tree lined street, 4 min walk to beach & bay, vacation rental in Cutchogue
North Fork Wine Country, quiet tree lined street, 4 min walk to beach & bay, vacation rental in Cutchogue

North Fork Wine Country, quiet tree lined street, 4 min walk to beach & bay

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Bay Breeze, vacation rental in Cutchogue
The Bay Breeze, vacation rental in Cutchogue
The Bay Breeze, vacation rental in Cutchogue

The Bay Breeze

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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North Fork Beach House - short walk to Peconic Bay, vacation rental in Cutchogue
North Fork Beach House - short walk to Peconic Bay, vacation rental in Cutchogue
North Fork Beach House - short walk to Peconic Bay, vacation rental in Cutchogue

North Fork Beach House - short walk to Peconic Bay

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Historic North Fork Farmhouse Near Wineries!, vacation rental in Cutchogue
Historic North Fork Farmhouse Near Wineries!, vacation rental in Cutchogue
Historic North Fork Farmhouse Near Wineries!, vacation rental in Cutchogue

Historic North Fork Farmhouse Near Wineries!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Waterfront Cottage - minutes from the North Fork beaches and wineries!, vacation rental in Cutchogue
Waterfront Cottage - minutes from the North Fork beaches and wineries!, vacation rental in Cutchogue
Waterfront Cottage - minutes from the North Fork beaches and wineries!, vacation rental in Cutchogue

Waterfront Cottage - minutes from the North Fork beaches and wineries!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Airy Summer Retreat on Nassau Point – Short stroll to private beach, vacation rental in Cutchogue
Airy Summer Retreat on Nassau Point – Short stroll to private beach, vacation rental in Cutchogue
Airy Summer Retreat on Nassau Point – Short stroll to private beach, vacation rental in Cutchogue

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming home with a fire pit, grill, W/D, & AC - North Fork Wine Country, vacation rental in Cutchogue
Charming home with a fire pit, grill, W/D, & AC - North Fork Wine Country, vacation rental in Cutchogue
Charming home with a fire pit, grill, W/D, & AC - North Fork Wine Country, vacation rental in Cutchogue

Charming home with a fire pit, grill, W/D, & AC - North Fork Wine Country

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Just Discounted for July!  Book now! Cozy Ranch in Broadwaters Cove, vacation rental in Cutchogue
Just Discounted for July!  Book now! Cozy Ranch in Broadwaters Cove, vacation rental in Cutchogue
Just Discounted for July!  Book now! Cozy Ranch in Broadwaters Cove, vacation rental in Cutchogue

Just Discounted for July! Book now! Cozy Ranch in Broadwaters Cove

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Country Home, Minutes to Sandy beaches, in the Heart of Wine Country, vacation rental in Cutchogue
Charming Country Home, Minutes to Sandy beaches, in the Heart of Wine Country, vacation rental in Cutchogue
Charming Country Home, Minutes to Sandy beaches, in the Heart of Wine Country, vacation rental in Cutchogue

Charming Country Home, Minutes to Sandy beaches, in the Heart of Wine Country

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Perfect Cutchogue/Southold -North Fork Vacation Home. Very Private, close to all, vacation rental in Cutchogue
Perfect Cutchogue/Southold -North Fork Vacation Home. Very Private, close to all, vacation rental in Cutchogue
Perfect Cutchogue/Southold -North Fork Vacation Home. Very Private, close to all, vacation rental in Cutchogue

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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North Fork Beach Cottage in Fleets Neck - walk to Beach and close to Vineyards!, vacation rental in Cutchogue
North Fork Beach Cottage in Fleets Neck - walk to Beach and close to Vineyards!, vacation rental in Cutchogue
North Fork Beach Cottage in Fleets Neck - walk to Beach and close to Vineyards!, vacation rental in Cutchogue

North Fork Beach Cottage in Fleets Neck - walk to Beach and close to Vineyards!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Peconic Bay idyllic waterfront for perfect relaxation, vacation rental in Cutchogue
Peconic Bay idyllic waterfront for perfect relaxation, vacation rental in Cutchogue
Peconic Bay idyllic waterfront for perfect relaxation, vacation rental in Cutchogue

Peconic Bay idyllic waterfront for perfect relaxation

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Great Getaway! Exceptional Cottage in Best Location, vacation rental in Cutchogue
Great Getaway! Exceptional Cottage in Best Location, vacation rental in Cutchogue
Great Getaway! Exceptional Cottage in Best Location, vacation rental in Cutchogue

Great Getaway! Exceptional Cottage in Best Location

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Nassau Point Home in Long Island Wine Country, vacation rental in Cutchogue
NEW! Nassau Point Home in Long Island Wine Country, vacation rental in Cutchogue
NEW! Nassau Point Home in Long Island Wine Country, vacation rental in Cutchogue

NEW! Nassau Point Home in Long Island Wine Country

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Wine Country Getaway on Private Street & Peconic Bay Neighborhood Beach Access, vacation rental in Cutchogue
Wine Country Getaway on Private Street & Peconic Bay Neighborhood Beach Access, vacation rental in Cutchogue
Wine Country Getaway on Private Street & Peconic Bay Neighborhood Beach Access, vacation rental in Cutchogue

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Family-friendly getaway walk to beach in private community, w/ park, playground, vacation rental in Cutchogue
Family-friendly getaway walk to beach in private community, w/ park, playground, vacation rental in Cutchogue
Family-friendly getaway walk to beach in private community, w/ park, playground, vacation rental in Cutchogue

Family-friendly getaway walk to beach in private community, w/ park, playground

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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North Fork Farms & Vineyards Near Beaches & 40 Minutes From The Hamptons, vacation rental in Cutchogue
North Fork Farms & Vineyards Near Beaches & 40 Minutes From The Hamptons, vacation rental in Cutchogue
North Fork Farms & Vineyards Near Beaches & 40 Minutes From The Hamptons, vacation rental in Cutchogue

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Fully renovated home with pool and private manicured  grounds., vacation rental in Cutchogue
Fully renovated home with pool and private manicured  grounds., vacation rental in Cutchogue
Fully renovated home with pool and private manicured  grounds., vacation rental in Cutchogue

Fully renovated home with pool and private manicured grounds.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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one of the best beaches on the North Fork; completely private, vacation rental in Cutchogue
one of the best beaches on the North Fork; completely private, vacation rental in Cutchogue
one of the best beaches on the North Fork; completely private, vacation rental in Cutchogue

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

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Beach Cottage on Peconic Bay, Cutchogue, NY, vacation rental in Cutchogue
Waterfront Beach Cottage on Peconic Bay, Cutchogue, NY, vacation rental in Cutchogue
Waterfront Beach Cottage on Peconic Bay, Cutchogue, NY, vacation rental in Cutchogue

Waterfront Beach Cottage on Peconic Bay, Cutchogue, NY

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Tastefully Renovated Cutchogue Home w/ Waterviews & Sunsets in Fleet’s Neck, vacation rental in Cutchogue
Tastefully Renovated Cutchogue Home w/ Waterviews & Sunsets in Fleet’s Neck, vacation rental in Cutchogue
Tastefully Renovated Cutchogue Home w/ Waterviews & Sunsets in Fleet’s Neck, vacation rental in Cutchogue

Tastefully Renovated Cutchogue Home w/ Waterviews & Sunsets in Fleet’s Neck

Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Perfect Family-Friendly Home on the North Fork With Pool + Steps to the Beach, vacation rental in Cutchogue
Perfect Family-Friendly Home on the North Fork With Pool + Steps to the Beach, vacation rental in Cutchogue
Perfect Family-Friendly Home on the North Fork With Pool + Steps to the Beach, vacation rental in Cutchogue

Perfect Family-Friendly Home on the North Fork With Pool + Steps to the Beach

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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North Fork Vacation Home - Great location, Walk to Beach - with Hot Tub, vacation rental in Cutchogue
North Fork Vacation Home - Great location, Walk to Beach - with Hot Tub, vacation rental in Cutchogue
North Fork Vacation Home - Great location, Walk to Beach - with Hot Tub, vacation rental in Cutchogue

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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North Fork Life: Pool, Beach, Wineries, Farmstands, vacation rental in Cutchogue
North Fork Life: Pool, Beach, Wineries, Farmstands, vacation rental in Cutchogue
North Fork Life: Pool, Beach, Wineries, Farmstands, vacation rental in Cutchogue

North Fork Life: Pool, Beach, Wineries, Farmstands

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Recently Updated Waterfront Home, vacation rental in Cutchogue
Charming Recently Updated Waterfront Home, vacation rental in Cutchogue
Charming Recently Updated Waterfront Home, vacation rental in Cutchogue

Charming Recently Updated Waterfront Home

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Incredible North Fork retreat.  Saltwater pool and minutes from the beach., vacation rental in Cutchogue
Incredible North Fork retreat.  Saltwater pool and minutes from the beach., vacation rental in Cutchogue
Incredible North Fork retreat.  Saltwater pool and minutes from the beach., vacation rental in Cutchogue

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Gorgeous, Creek-front vacation rental, vacation rental in Cutchogue
Gorgeous, Creek-front vacation rental, vacation rental in Cutchogue
Gorgeous, Creek-front vacation rental, vacation rental in Cutchogue

Gorgeous, Creek-front vacation rental

Rental Home
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Stunning, Waterfront, newly renovated cottage with deck on water., vacation rental in Cutchogue
Stunning, Waterfront, newly renovated cottage with deck on water., vacation rental in Cutchogue
Stunning, Waterfront, newly renovated cottage with deck on water., vacation rental in Cutchogue

Stunning, Waterfront, newly renovated cottage with deck on water.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cutchogue Home with Pool and Access to Association only Beach!, vacation rental in Cutchogue
Cutchogue Home with Pool and Access to Association only Beach!, vacation rental in Cutchogue
Cutchogue Home with Pool and Access to Association only Beach!, vacation rental in Cutchogue

Cutchogue Home with Pool and Access to Association only Beach!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Perfect Getaway. Pool. Beach walks. Vineyards. Apple & Pumpkin picking., vacation rental in Cutchogue
Perfect Getaway. Pool. Beach walks. Vineyards. Apple & Pumpkin picking., vacation rental in Cutchogue
Perfect Getaway. Pool. Beach walks. Vineyards. Apple & Pumpkin picking., vacation rental in Cutchogue

Perfect Getaway. Pool. Beach walks. Vineyards. Apple & Pumpkin picking.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Historic Renovated Farmhouse, 2min to Beach, Vineyards, Fireplace, Kid Friendly, vacation rental in Cutchogue
Historic Renovated Farmhouse, 2min to Beach, Vineyards, Fireplace, Kid Friendly, vacation rental in Cutchogue
Historic Renovated Farmhouse, 2min to Beach, Vineyards, Fireplace, Kid Friendly, vacation rental in Cutchogue

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Beach House on the Bay, vacation rental in Cutchogue
Waterfront Beach House on the Bay, vacation rental in Cutchogue
Waterfront Beach House on the Bay, vacation rental in Cutchogue

Waterfront Beach House on the Bay

Rental Home
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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North Fork Waterfront Oasis, vacation rental in Cutchogue
North Fork Waterfront Oasis, vacation rental in Cutchogue
North Fork Waterfront Oasis, vacation rental in Cutchogue

North Fork Waterfront Oasis

Rental Home
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Spacious New 4 Bedroom Home With Pool on 2 Acre Property, vacation rental in Cutchogue
Spacious New 4 Bedroom Home With Pool on 2 Acre Property, vacation rental in Cutchogue
Spacious New 4 Bedroom Home With Pool on 2 Acre Property, vacation rental in Cutchogue

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Exclusive Nassau Point House with Pool and Deeded Beach!, vacation rental in Cutchogue
Exclusive Nassau Point House with Pool and Deeded Beach!, vacation rental in Cutchogue
Exclusive Nassau Point House with Pool and Deeded Beach!, vacation rental in Cutchogue

Exclusive Nassau Point House with Pool and Deeded Beach!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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North Fork Wine Region—Walk to Beach, vacation rental in Cutchogue
North Fork Wine Region—Walk to Beach, vacation rental in Cutchogue
North Fork Wine Region—Walk to Beach, vacation rental in Cutchogue

North Fork Wine Region—Walk to Beach

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Restored Farmhouse in The Heart of Wine and Farm Country, vacation rental in Cutchogue
Restored Farmhouse in The Heart of Wine and Farm Country, vacation rental in Cutchogue
Restored Farmhouse in The Heart of Wine and Farm Country, vacation rental in Cutchogue

Restored Farmhouse in The Heart of Wine and Farm Country

Rental Home
3 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
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Tranquil 5 Br North Fork Retreat With Pool And Huge Yard, Walk To Beach, vacation rental in Cutchogue
Tranquil 5 Br North Fork Retreat With Pool And Huge Yard, Walk To Beach, vacation rental in Cutchogue
Tranquil 5 Br North Fork Retreat With Pool And Huge Yard, Walk To Beach, vacation rental in Cutchogue

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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront w/ Private Beach on Nassau Point, vacation rental in Cutchogue
Waterfront w/ Private Beach on Nassau Point, vacation rental in Cutchogue
Waterfront w/ Private Beach on Nassau Point, vacation rental in Cutchogue

Waterfront w/ Private Beach on Nassau Point

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Cutchogue Farmhouse Estate with hot tub and gardens, walk to beach & vineyards, vacation rental in Cutchogue
Cutchogue Farmhouse Estate with hot tub and gardens, walk to beach & vineyards, vacation rental in Cutchogue
Cutchogue Farmhouse Estate with hot tub and gardens, walk to beach & vineyards, vacation rental in Cutchogue

Cutchogue Farmhouse Estate with hot tub and gardens, walk to beach & vineyards

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Showing results 1-50 of 54
Frequently Asked Questions about Cutchogue