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Cutchogue Vacation Rentals

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50 rentals in Cutchogue.
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Vintage Style Farmhouse  in the Heart of Wine Country, vacation rental in Cutchogue

Vintage Style Farmhouse in the Heart of Wine Country

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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North Fork Winter / Spring Getaway: Cozy Fireplaces, Farm Views,  Beach Sunsets, vacation rental in Cutchogue

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

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Perfect Cutchogue - North Fork Vacation Home.  Very Private yet close to all., vacation rental in Cutchogue

Perfect Cutchogue - North Fork Vacation Home. Very Private yet close to all.

3 bedrooms
2 bathrooms
Sleeps 6
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Cutchogue Beach Cottage, vacation rental in Cutchogue

Cutchogue Beach Cottage

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Perfect North Fork Getaway for All Seasons, vacation rental in Cutchogue

Perfect North Fork Getaway for All Seasons

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Spend the holidays overlooking the bay!, vacation rental in Cutchogue

Spend the holidays overlooking the bay!

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Sanctuary in the Vineyards Available  Labor Day week 2020, vacation rental in Cutchogue

Sanctuary in the Vineyards Available Labor Day week 2020

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Barn Life in Cutchogue, vacation rental in Cutchogue

Barn Life in Cutchogue

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Water Views, 2 minute walk to the beach, vacation rental in Cutchogue

Beautiful Water Views, 2 minute walk to the beach

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Fabulous Waterfront Property in the Heart of Wine Country, vacation rental in Cutchogue

Fabulous Waterfront Property in the Heart of Wine Country

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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MATTITUCK, The North Fork's #1 Beach & Winery Town!, vacation rental in Cutchogue

MATTITUCK, The North Fork's #1 Beach & Winery Town!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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***NEW HOT TUB AWAITS YOU***, vacation rental in Cutchogue

***NEW HOT TUB AWAITS YOU***

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bay Beach 3bd Cottage. Walk To Beach And Jitney!, vacation rental in Cutchogue

Bay Beach 3bd Cottage. Walk To Beach And Jitney!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Adorable Southold Cottage in the heart of LI's North Fork ~ Kayak & Paddle Board, vacation rental in Cutchogue

Adorable Southold Cottage in the heart of LI's North Fork ~ Kayak & Paddle Board

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful waterfront 2BR/2BA cottage, Great location in North Fork wine country, vacation rental in Cutchogue

Beautiful waterfront 2BR/2BA cottage, Great location in North Fork wine country

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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It's All About This Sandy Private Association Bay Beach....A North Fork Gem!, vacation rental in Cutchogue

It's All About This Sandy Private Association Bay Beach....A North Fork Gem!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beachfront home on the North Fork, vacation rental in Cutchogue

Beachfront home on the North Fork

3 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Summer 2021 calendar open! Long term rentals available., vacation rental in Cutchogue

Summer 2021 calendar open! Long term rentals available.

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Gorgeous Historical 7 bdrm House in the GREENPORT area for Bachelorettes., vacation rental in Cutchogue

Gorgeous Historical 7 bdrm House in the GREENPORT area for Bachelorettes.

7 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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North Fork Wine Country On The Bay, vacation rental in Cutchogue

North Fork Wine Country On The Bay

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Classic Arts and Crafts House on the North Fork, vacation rental in Cutchogue

Classic Arts and Crafts House on the North Fork

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mattituck Beach Gen. Spacious & Gorgeously Renovated Beach House Steps to Bay., vacation rental in Cutchogue

Mattituck Beach Gen. Spacious & Gorgeously Renovated Beach House Steps to Bay.

4 bedrooms
3 bathrooms
Sleeps 8
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Relaxing Home w/pool and private beach, vacation rental in Cutchogue

Relaxing Home w/pool and private beach

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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3 Br North Fork Getaway In Private Beach Community, vacation rental in Cutchogue

3 Br North Fork Getaway In Private Beach Community

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Gorgeous Beach House With Stunning 280 Degree Water Views, vacation rental in Cutchogue

Gorgeous Beach House With Stunning 280 Degree Water Views

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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3 Bedroom Waterfront House on Peconic Bay Sleeps 6, vacation rental in Cutchogue

3 Bedroom Waterfront House on Peconic Bay Sleeps 6

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Steps to Beach and Spectacular Sunsets, vacation rental in Cutchogue

Steps to Beach and Spectacular Sunsets

4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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North Fork cottage getaway with private beach, vacation rental in Cutchogue

North Fork cottage getaway with private beach

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Waterfront with dock on Goose Creek (just off Peconic Bay) and chef's kitchen, vacation rental in Cutchogue

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

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Architect-Renovated, Pristine Ranch, Modern Kitchen, Short Walk to Beach, vacation rental in Cutchogue

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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Southold Soundfront Private Beach, vacation rental in Cutchogue

Southold Soundfront Private Beach

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Wonderful sunsets overlooking LI Sound!, vacation rental in Cutchogue

Wonderful sunsets overlooking LI Sound!

4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Sea view beach house North Fork Vineyards Farm Stands Your own Private Beach!, vacation rental in Cutchogue

Sea view beach house North Fork Vineyards Farm Stands Your own Private Beach!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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piece of Heaven, vacation rental in Cutchogue

piece of Heaven

4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Home in Long Island Wine Country - Walk to Beach!, vacation rental in Cutchogue

Home in Long Island Wine Country - Walk to Beach!

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Beautiful Southold Home with a Water View - 3 Bedroom, 2.5 Bath, Sleeps 8, vacation rental in Cutchogue

Beautiful Southold Home with a Water View - 3 Bedroom, 2.5 Bath, Sleeps 8

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sand Dollar North Fork Beach House Vineyards, Farm Stands, Kayaks, vacation rental in Cutchogue

Sand Dollar North Fork Beach House Vineyards, Farm Stands, Kayaks

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Waterfront in Mattituck, vacation rental in Cutchogue

Waterfront in Mattituck

4 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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The Perfect Setting for a Magical Summer, vacation rental in Cutchogue

The Perfect Setting for a Magical Summer

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Brand New Construction - Beaches, Hiking, Wineries, Farms, Fine Dining, vacation rental in Cutchogue

Brand New Construction - Beaches, Hiking, Wineries, Farms, Fine Dining

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Charming farmhouse on creek, vacation rental in Cutchogue

Charming farmhouse on creek

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Modern Barn Loft in North Fork, ***. Wine Country in backyard Farm stands, vacation rental in Cutchogue

Modern Barn Loft in North Fork, ***. Wine Country in backyard Farm stands

3 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful cottage, large private yard, only two minutes walk from private beach, vacation rental in Cutchogue

Beautiful cottage, large private yard, only two minutes walk from private beach

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Long Island NY Luxury Getaway spa amenities Wineries INDOORPOOL   Gym hamptons, vacation rental in Cutchogue

Long Island NY Luxury Getaway spa amenities Wineries INDOORPOOL Gym hamptons

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Rustic North Fork Country Waterfront Home w/ Pool & Dock, vacation rental in Cutchogue

Rustic North Fork Country Waterfront Home w/ Pool & Dock

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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3BR Newly renovated Southold Beach Cottage steps to beach close to Greenport, vacation rental in Cutchogue

3BR Newly renovated Southold Beach Cottage steps to beach close to Greenport

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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2BR North Fork Southold Private Cottage Beach steps to beach 10minGreenport, vacation rental in Cutchogue

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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3 Bedroom newly renovated private waterfront Beachwood home!, vacation rental in Cutchogue

3 Bedroom newly renovated private waterfront Beachwood home!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Steve's Place Well Furnished 3 BR Southold Home Heated Pool, Town Near Beach, vacation rental in Cutchogue

Steve's Place Well Furnished 3 BR Southold Home Heated Pool, Town Near Beach

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Lovely Beachfront Cottage Steps to the Sound! Parks, Restaurants, Vineyards, vacation rental in Cutchogue

Lovely Beachfront Cottage Steps to the Sound! Parks, Restaurants, Vineyards

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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