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

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243 Best 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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The Endless Summer Cottage
The Endless Summer Cottage
House
Cutchogue, NY, USA
3.8k from Waters Crest Winery center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$252
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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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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Charming Country Home, Minutes to Sandy beaches, in the Heart of Wine Country
Charming Country Home, Minutes to Sandy beaches, in the Heart of Wine Country
House
Cutchogue, NY, 11935, United States
1.8k from Waters Crest Winery center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

4 Bedrooms8 Guests
9.8

Exceptional

58 reviews

$557
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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Northfork Contemporary Cottage
Northfork Contemporary Cottage
House
Cutchogue, NY, 11935, United States
1.8k from Waters Crest Winery center

AC, Dryer, Fireplace, Free Parking, Heater, Laundry, Microwave, No Smoking, TV

3 Bedrooms5 Guests
10.0

Exceptional

2 reviews

$349
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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Spacious and Modern North Fork Home Close to Multiple Wineries, Perfect for...
Spacious and Modern North Fork Home Close to Multiple Wineries, Perfect for...
House
Cutchogue, NY, 11935, United States
1.9k from Waters Crest Winery center

AC, Arcade, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$1038
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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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
1.9k from Waters Crest Winery 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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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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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
2.1k from Waters Crest 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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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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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
2.2k from Waters Crest 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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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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North Fork Getaway: Cozy Fireplaces, Farm Views, Beach Sunsets
North Fork Getaway: Cozy Fireplaces, Farm Views, Beach Sunsets
House
Cutchogue, NY, 11935, United States
2.2k from Waters Crest 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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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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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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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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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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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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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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3-bedroom house in charming Cutchogue with AC, WiFi. Enjoy your stay
3-bedroom house in charming Cutchogue with AC, WiFi. Enjoy your stay
House
Cutchogue, NY, 11935, United States
2.6k from Waters Crest Winery center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
New to Booking
$2300
Average price / night
Check Availability
The Melody Too
The Melody Too
Cottage
Cutchogue, NY, 11935, United States
2.6k from Waters Crest Winery center

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

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$576
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
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 in Waters Crest Winery.

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Frequently Asked Questions

You can explore 243 verified vacation rentals in Waters Crest Winery. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Waters Crest Winery vary depending on the season, property size, and location. Rates typically start from around $164 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Waters Crest Winery include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Waters Crest Winery welcome pets. Currently, 27 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Waters Crest Winery often include amenities such as Fireplace/Heating, View, and Laundry. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.