Family-Friendly Vacation Rentals in Waters Crest Winery, NY: Compare 10+ Sites & Save

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103 Best Family Vacation Rentals in Waters Crest Winery (Starting from $164)

Peconic Sound Beach Home: Backyard & Vineyards
Peconic Sound Beach Home: Backyard & Vineyards
House
Peconic, NY, USA
3.1k from Waters Crest Winery center

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

3 Bedrooms7 Guests
New to Booking
$984
Average price / night
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Exclusive Vineyard Retreat
Exclusive Vineyard Retreat
House
Cutchogue, NY, 11935, United States
1.4k from Waters Crest Winery center

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

6 Bedrooms12 Guests
New to Booking
$2746
Average price / night
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Respite Ranch: Private Pool, Hot Tub, Beach Access
Respite Ranch: Private Pool, Hot Tub, Beach Access
House
Mattituck, NY, USA
3.9k from Waters Crest Winery 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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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
1.5k from Waters Crest 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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Mattituck Home with Fireplaces - Near Wineries
Mattituck Home with Fireplaces - Near Wineries
House
Mattituck, NY, USA
4.2k from Waters Crest Winery center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
New to Booking
$471
Average price / night
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Newly renovated North Fork beach house! 5 mins from the beach w/ new game room
Newly renovated North Fork beach house! 5 mins from the beach w/ new game room
House
Cutchogue, NY, 11935, United States
2.2k from Waters Crest Winery center

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

2 Bedrooms5 Guests
9.6

Exceptional

25 reviews

$565
Average price / night
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Walk to Beach Long Island Wine Country Home!
Walk to Beach Long Island Wine Country Home!
House
Cutchogue, NY, USA
4.8k from Waters Crest Winery center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Beach

3 Bedrooms7 Guests
New to Booking
$271
Average price / night
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Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Cottage
Cutchogue, NY, 11935, United States
2.2k from Waters Crest Winery center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms6 Guests
9.8

Exceptional

18 reviews

$646
Average price / night
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Southold Cottage with Patio and Grill - Walk to Beach!
Southold Cottage with Patio and Grill - Walk to Beach!
House
Waters Crest Winery, Cutchogue, New York, USA
4.9k from Waters Crest Winery center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms3 Guests
New to Booking
$164
Average price / night
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Best Waterfront VIEW ON THE NORTH FORK MATURE GARDENS QUIET STREET PRIVATE BEACH
Best Waterfront VIEW ON THE NORTH FORK MATURE GARDENS QUIET STREET PRIVATE BEACH
House
Cutchogue, NY, 11935, United States
2.3k from Waters Crest Winery center

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

3 Bedrooms5 Guests
10.0

Exceptional

11 reviews

$782
Average price / night
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Nature's Paradise: Private Dock & Water Views
Nature's Paradise: Private Dock & Water Views
House
Mattituck, NY, USA
5.0k from Waters Crest Winery center

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

4 Bedrooms9 Guests
New to Booking
$1046
Average price / night
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Stunning, Waterfront, newly renovated cottage with deck on water.
Stunning, Waterfront, newly renovated cottage with deck on water.
Cottage
Cutchogue, NY, 11935, United States
2.5k from Waters Crest Winery center

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

4 Bedrooms8 Guests
10.0

Exceptional

9 reviews

$854
Average price / night
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Bright Oasis in Beautiful North Fork Wine Country
Bright Oasis in Beautiful North Fork Wine Country
House
Southold, NY, USA
5.4k from Waters Crest Winery center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$391
Average price / night
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The Bay Breeze
The Bay Breeze
Cottage
Cutchogue, NY, 11935, United States
2.5k from Waters Crest Winery center

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

2 Bedrooms4 Guests
9.0

Fabulous

2 reviews

$598
Average price / night
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NF Wine Country Retreat with Dock
NF Wine Country Retreat with Dock
House
Southold, NY, USA
5.4k from Waters Crest Winery center

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

1 Bedroom8 Guests
New to Booking
$499
Average price / night
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Charming Recently Updated Waterfront Home
Charming Recently Updated Waterfront Home
House
Cutchogue, NY, 11935, United States
2.7k from Waters Crest Winery center

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

3 Bedrooms6 Guests
10.0

Exceptional

17 reviews

$430
Average price / night
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Minnehaha Marvel
Minnehaha Marvel
House
Southold, NY, USA
5.7k from Waters Crest Winery center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Beach, Places to stay

1 Bedroom4 Guests
New to Booking
$296
Average price / night
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Family-friendly getaway walk to beach in private community, w/ park, playground
Family-friendly getaway walk to beach in private community, w/ park, playground
House
Cutchogue, NY, 11935, United States
2.8k from Waters Crest Winery center

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

3 Bedrooms6 Guests
New to Booking
$444
Average price / night
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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 Waters Crest Winery 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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Historic House Getaway
Historic House Getaway
House
Peconic, NY, 11958, United States
2.9k from Waters Crest Winery 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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Classic Southold Country Charmer
Classic Southold Country Charmer
House
Southold, NY, USA
6.5k from Waters Crest Winery center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Accessible hotels

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$233
Average price / night
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Fabulous Waterfront Property in the Heart of Wine Country
Fabulous Waterfront Property in the Heart of Wine Country
Cottage
Peconic, NY, 11958, United States
3.1k from Waters Crest Winery center

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

3 Bedrooms5 Guests
10.0

Exceptional

184 reviews

$525
Average price / night
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Private Coastal Two Bedroom Cottage on the Water
Private Coastal Two Bedroom Cottage on the Water
Cottage
Peconic, NY, 11958, United States
3.1k from Waters Crest Winery center

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

3 Bedrooms6 Guests
10.0

Exceptional

82 reviews

$490
Average price / night
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Sun-Filled 4-BR Home, North Fork - amid Dunes, Beach & Spectacular Sunsets. 3-BA
Sun-Filled 4-BR Home, North Fork - amid Dunes, Beach & Spectacular Sunsets. 3-BA
House
Peconic, NY, 11958, United States
3.2k from Waters Crest Winery center

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

4 Bedrooms10 Guests
10.0

Exceptional

37 reviews

$1131
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
3.2k from Waters Crest Winery 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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Serene North Fork Oasis
Serene North Fork Oasis
House
Mattituck, NY, 11952, United States
3.2k from Waters Crest Winery 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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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
3.3k from Waters Crest 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
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 Family Vacation Rentals in Waters Crest Winery.

Where to stay in Waters Crest Winery? Best neighborhoods & areas

Waters Crest Winery Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 103 verified family-friendly vacation rentals in Waters Crest Winery. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Waters Crest Winery vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $164 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Waters Crest Winery offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Waters Crest Winery are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Waters Crest Winery often include amenities such as Child Friendly, Fireplace/Heating, and View. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.