Vacation Rentals with Pool in Cutchogue, NY: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  New York

  5.  Cutchogue

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76 Best Vacation Rentals with Pool in Cutchogue (Starting from $304)

Respite Ranch: Private Pool, Hot Tub, Beach Access
Respite Ranch: Private Pool, Hot Tub, Beach Access
House
Mattituck, NY, USA
3.0k from Cutchogue center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$679
Average price / night
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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
1.3k from Cutchogue center

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

4 Bedrooms11 Guests
New to Booking
$1219
Average price / night
Check Availability
Steve's Place: Heated Pool, 3BR Southold Home, Beach
Steve's Place: Heated Pool, 3BR Southold Home, Beach
House
Southold, NY, USA
6.2k from Cutchogue center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$304
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
1.5k from Cutchogue 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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North Fork House for Rent
North Fork House for Rent
House
Mattituck, NY, USA
7.8k from Cutchogue center

Wellness Facilities, Air Conditioner, Smoking, View, Laundry, Parking, Guest Services

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1600
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
1.6k from Cutchogue 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
1.9k from Cutchogue 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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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
1.9k from Cutchogue 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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North Fork, New Construction with heated pool, walking distance to beach
North Fork, New Construction with heated pool, walking distance to beach
House
Cutchogue, NY, 11935, United States
2.1k from Cutchogue center

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

4 Bedrooms8 Guests
9.8

Exceptional

32 reviews

$1371
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 Cutchogue 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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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
2.4k from Cutchogue 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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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
2.4k from Cutchogue 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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Serene North Fork Oasis
Serene North Fork Oasis
House
Mattituck, NY, 11952, United States
2.7k from Cutchogue center

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

3 Bedrooms8 Guests
10.0

Exceptional

18 reviews

$685
Average price / night
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Exclusive Vineyard Retreat
Exclusive Vineyard Retreat
House
Cutchogue, NY, 11935, United States
2.8k from Cutchogue center

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

6 Bedrooms12 Guests
New to Booking
$2746
Average price / night
Check Availability
Respite Ranch | Pool, Hot Tub & North Fork
Respite Ranch | Pool, Hot Tub & North Fork
House
Mattituck, NY, 11952, United States
3.0k from Cutchogue 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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Your North Fork Happy Place—New Reno Built for Families w/Pool, Private Beach
Your North Fork Happy Place—New Reno Built for Families w/Pool, Private Beach
House
Cutchogue, NY, 11935, United States
3.1k from Cutchogue center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Laundry, Microwave

3 Bedrooms10 Guests
New to Booking
$658
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
3.1k from Cutchogue 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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Historic Luxury Seaside Getaway
Historic Luxury Seaside Getaway
House
New Suffolk, NY, 11956, United States
3.2k from Cutchogue 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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North Fork Getaway: Cozy Fireplaces, Farm Views, Beach Sunsets
North Fork Getaway: Cozy Fireplaces, Farm Views, Beach Sunsets
House
Cutchogue, NY, 11935, United States
3.2k from Cutchogue 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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Historic House Getaway
Historic House Getaway
House
Peconic, NY, 11958, United States
3.6k from Cutchogue center

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

6 Bedrooms9 Guests
9.6

Exceptional

139 reviews

$1076
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
3.7k from Cutchogue 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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Exclusive Nassau Point House with Pool and Deeded Beach!
Exclusive Nassau Point House with Pool and Deeded Beach!
House
Cutchogue, NY, 11935, United States
3.9k from Cutchogue center

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

5 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$841
Average price / night
Check Availability
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
4.0k from Cutchogue center

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

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$1506
Average price / night
Check Availability
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
4.0k from Cutchogue center

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

5 Bedrooms10 Guests
8.0

Good

2 reviews

$1176
Average price / night
Check Availability
Family friendly house with pool & walk to the beach in the heart of NOFO
Family friendly house with pool & walk to the beach in the heart of NOFO
House
Mattituck, NY, 11952, United States
4.8k from Cutchogue center

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

3 Bedrooms6 Guests
10.0

Exceptional

8 reviews

$515
Average price / night
Check Availability
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
4.8k from Cutchogue center

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

4 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$587
Average price / night
Check Availability
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
4.9k from Cutchogue 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 Pool in Cutchogue.

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Cutchogue Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 76 verified vacation rentals with a pool in Cutchogue. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Cutchogue vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $304 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Cutchogue offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Cutchogue welcome pets. Currently, 23 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Cutchogue often include additional outdoor features such as Pool, Fireplace/Heating, and Laundry. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Cutchogue offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.