Vacation Rentals with Private Pool in Peconic Bay Winery, NY: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  New York

  5.  Cutchogue
  6.  Peconic Bay Winery

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80 Best Vacation Rentals with Private Pool in Peconic Bay Winery (Starting from $428)

Elevated North Fork Escape with Chic Interiors and Private Poolside Oasis -...
Elevated North Fork Escape with Chic Interiors and Private Poolside Oasis -...
House
Cutchogue, NY, 11935, United States
0.5k from Peconic Bay Winery center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms11 Guests
New to Booking
$1219
Average price / night
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Spacious  and Renovated Summer Home with w/ Pool & Hot tub
Spacious and Renovated Summer Home with w/ Pool & Hot tub
House
Cutchogue, NY, 11935, United States
0.8k from Peconic Bay Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$856
Average price / night
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Escape to serene 3BR Cutchogue haven with heated pool, near beaches & vineyards.
Escape to serene 3BR Cutchogue haven with heated pool, near beaches & vineyards.
House
Cutchogue, NY, 11935, United States
1.0k from Peconic Bay Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$744
Average price / night
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North Fork Wine Region—Walk to Beach
North Fork Wine Region—Walk to Beach
House
Cutchogue, NY, 11935, United States
1.4k from Peconic Bay Winery center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$770
Average price / night
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Spacious New 4 Bedroom Home With Pool on 2 Acre Property
Spacious New 4 Bedroom Home With Pool on 2 Acre Property
House
Cutchogue, NY, 11935, United States
1.7k from Peconic Bay Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
10.0

Exceptional

24 reviews

$1134
Average price / night
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New Suffolk Compound w/ Private Pool
New Suffolk Compound w/ Private Pool
House
New Suffolk, NY, 11956, United States
2.3k from Peconic Bay Winery center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater

5 Bedrooms12 Guests
New to Booking
$2285
Average price / night
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Relaxation Awaits-Fully renovated home heated pool, private manicured  grounds.
Relaxation Awaits-Fully renovated home heated pool, private manicured grounds.
House
Cutchogue, NY, 11935, United States
2.6k from Peconic Bay Winery center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$919
Average price / night
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The North Fork Summer House - Modern Farmhouse, Heated Pool & Wine Country
The North Fork Summer House - Modern Farmhouse, Heated Pool & Wine Country
House
Mattituck, NY, 11952, United States
3.0k from Peconic Bay Winery center

AC, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

5 Bedrooms10 Guests
New to Booking
$1062
Average price / night
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Beachfront New Suffolk Estate with Pool
Beachfront New Suffolk Estate with Pool
House
New Suffolk, NY, 11956, United States
3.0k from Peconic Bay Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1874
Average price / night
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North Fork Life: Pool, Beach, Wineries, Farmstands
North Fork Life: Pool, Beach, Wineries, Farmstands
House
Cutchogue, NY, 11935, United States
3.1k from Peconic Bay Winery center

AC, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet

4 Bedrooms8 Guests
10.0

Exceptional

17 reviews

$942
Average price / night
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Historic Luxury Seaside Getaway
Historic Luxury Seaside Getaway
House
New Suffolk, NY, 11956, United States
3.1k from Peconic Bay Winery center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater

6 Bedrooms16 Guests
10.0

Exceptional

35 reviews

$1386
Average price / night
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Exclusive Nassau Point House with Pool and Deeded Beach!
Exclusive Nassau Point House with Pool and Deeded Beach!
House
Cutchogue, NY, 11935, United States
3.3k from Peconic Bay Winery center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

5 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$841
Average price / night
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Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds,...
Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds,...
House
Peconic, NY, 11958, United States
3.6k from Peconic Bay Winery center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Kitchen, Laundry, Microwave

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$1506
Average price / night
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North Fork Family Villa- large family home with fenced in pool
North Fork Family Villa- large family home with fenced in pool
House
Peconic, NY, 11958, United States
3.6k from Peconic Bay Winery center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

5 Bedrooms10 Guests
8.0

Good

2 reviews

$1176
Average price / night
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Respite Ranch | Pool, Hot Tub & North Fork
Respite Ranch | Pool, Hot Tub & North Fork
House
Mattituck, NY, 11952, United States
3.6k from Peconic Bay Winery center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms6 Guests
10.0

Exceptional

11 reviews

$691
Average price / night
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North Fork Getaway: Cozy Fireplaces, Farm Views, Beach Sunsets
North Fork Getaway: Cozy Fireplaces, Farm Views, Beach Sunsets
House
Cutchogue, NY, 11935, United States
3.8k from Peconic Bay Winery center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking

4 Bedrooms8 Guests
10.0

Exceptional

41 reviews

$1158
Average price / night
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4BR+ Newly renovated home mins to top beaches and vineyards, new heated pool!
4BR+ Newly renovated home mins to top beaches and vineyards, new heated pool!
House
Southold, NY, 11971, United States
4.1k from Peconic Bay Winery center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$587
Average price / night
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Heated pool on Goose Creek, private dock, massive yard walk to beach, wineries
Heated pool on Goose Creek, private dock, massive yard walk to beach, wineries
House
Southold, NY, 11971, United States
4.9k from Peconic Bay Winery center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

3 Bedrooms7 Guests
9.6

Exceptional

24 reviews

$718
Average price / night
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Cozy North Fork Home with Direct Water Access, Private Dock, Close to Wineries
Cozy North Fork Home with Direct Water Access, Private Dock, Close to Wineries
House
Southold, NY, 11971, United States
5.3k from Peconic Bay Winery center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Kitchen, Laundry, Microwave

4 Bedrooms8 Guests
New to Booking
$1072
Average price / night
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Beach, Pool, Wine, Shopping!
Beach, Pool, Wine, Shopping!
House
Mattituck, NY, 11952, United States
5.4k from Peconic Bay Winery center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

78 reviews

$428
Average price / night
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Newly Constructed Modern Vacation Villa Minutes to some of the best...
Newly Constructed Modern Vacation Villa Minutes to some of the best...
House
Southold, NY, 11971, United States
5.5k from Peconic Bay Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$722
Average price / night
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Luxury north fork estate
Luxury north fork estate
House
Southold, NY, 11971, United States
5.5k from Peconic Bay Winery center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$2513
Average price / night
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Mattituck Beach Gem. Spacious & Gorgeously Renovated Beach House Steps to Bay.
Mattituck Beach Gem. Spacious & Gorgeously Renovated Beach House Steps to Bay.
House
Mattituck, NY, 11952, United States
5.5k from Peconic Bay Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

11 reviews

$1264
Average price / night
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HEATED POOL waterfront HOT TUB, GYM, Watersports, BOATER DELIGHT luxury modern
HEATED POOL waterfront HOT TUB, GYM, Watersports, BOATER DELIGHT luxury modern
House
Southold, NY, 11971, United States
5.5k from Peconic Bay Winery center

AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

6 Bedrooms14 Guests
10.0

Exceptional

12 reviews

$3783
Average price / night
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Steve’s Place | Heated Pool Southold Retreat
Steve’s Place | Heated Pool Southold Retreat
House
Southold, NY, 11971, United States
5.5k from Peconic Bay Winery center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$643
Average price / night
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NORTH FORK DREAM HOME, 4,000 Sq Ft, 1 Acre, Heated Pool!
NORTH FORK DREAM HOME, 4,000 Sq Ft, 1 Acre, Heated Pool!
House
Southold, NY, 11971, United States
5.6k from Peconic Bay Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms12 Guests
9.8

Exceptional

7 reviews

$1828
Average price / night
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NoFo Retreat  Mattituck - Across from Marina, near Vineyards, Beach & Love Lane
NoFo Retreat Mattituck - Across from Marina, near Vineyards, Beach & Love Lane
House
Mattituck, NY, 11952, United States
5.6k from Peconic Bay Winery center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
New to Booking
$654
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Private Pool in Peconic Bay Winery.

Where to stay in Peconic Bay Winery? Best neighborhoods & areas

Peconic Bay Winery Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 80 verified vacation rentals with a private pool in Peconic Bay Winery. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Peconic Bay Winery vary depending on the property size, location, and travel season. Rates typically start from around $428 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Peconic Bay Winery also welcome pets. Currently, 22 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Peconic Bay Winery often include additional features such as Bedding/Linens, Fireplace/Heating, and Kitchen. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Peconic Bay Winery include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.