Vacation Rentals in Pellegrini Vineyards, NY: Compare 10+ Sites & Save

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  3.  USA

  4.  New York

  5.  Cutchogue
  6.  Pellegrini Vineyards

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248 Best Vacation Rentals in Pellegrini Vineyards (Starting from $164)

Respite Ranch: Private Pool, Hot Tub, Beach Access
Respite Ranch: Private Pool, Hot Tub, Beach Access
House
Mattituck, NY, USA
1.1k from Pellegrini Vineyards 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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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
0.9k from Pellegrini Vineyards 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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Mattituck Home with Fireplaces - Near Wineries
Mattituck Home with Fireplaces - Near Wineries
House
Mattituck, NY, USA
1.3k from Pellegrini Vineyards 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 Updated Wine Country Charmer!!!
Newly Updated Wine Country Charmer!!!
House
Mattituck, NY, 11952, United States
1.1k from Pellegrini Vineyards center

Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

3 Bedrooms6 Guests
New to Booking
$532
Average price / night
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The Endless Summer Cottage
The Endless Summer Cottage
House
Cutchogue, NY, USA
3.9k from Pellegrini Vineyards 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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Respite Ranch | Pool, Hot Tub & North Fork
Respite Ranch | Pool, Hot Tub & North Fork
House
Mattituck, NY, 11952, United States
1.1k from Pellegrini Vineyards 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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Nature's Paradise: Private Dock & Water Views
Nature's Paradise: Private Dock & Water Views
House
Mattituck, NY, USA
4.4k from Pellegrini Vineyards 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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Mattituck Home w/ Fireplaces - Near Wineries
Mattituck Home w/ Fireplaces - Near Wineries
House
Mattituck, NY, 11952-1936, United States
1.3k from Pellegrini Vineyards center

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

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$533
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
4.4k from Pellegrini Vineyards 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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Serene North Fork Oasis
Serene North Fork Oasis
House
Mattituck, NY, 11952, United States
1.4k from Pellegrini Vineyards 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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Peconic Sound Beach Home: Backyard & Vineyards
Peconic Sound Beach Home: Backyard & Vineyards
House
Peconic, NY, USA
6.1k from Pellegrini Vineyards 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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Enjoy the Serenity of Wine Country on Long Island's North Fork!!!
Enjoy the Serenity of Wine Country on Long Island's North Fork!!!
House
Mattituck, NY, 11952, United States
1.5k from Pellegrini Vineyards center

AC, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry, Living Area, No Smoking

3 Bedrooms6 Guests
New to Booking
$464
Average price / night
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North Fork House for Rent
North Fork House for Rent
House
Mattituck, NY, USA
6.2k from Pellegrini Vineyards 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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New Suffolk Compound w/ Private Pool
New Suffolk Compound w/ Private Pool
House
New Suffolk, NY, 11956, United States
1.6k from Pellegrini Vineyards 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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Southold Cottage with Patio and Grill - Walk to Beach!
Southold Cottage with Patio and Grill - Walk to Beach!
House
Pellegrini Vineyards, Cutchogue, New York, USA
6.7k from Pellegrini Vineyards 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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North Fork Wine Country On The Bay
North Fork Wine Country On The Bay
House
Mattituck, NY, 11952, United States
1.7k from Pellegrini Vineyards center

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

4 Bedrooms8 Guests
10.0

Exceptional

9 reviews

$919
Average price / night
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Bahia Mar: Beach House, North Fork
Bahia Mar: Beach House, North Fork
House
Laurel, NY, USA
6.9k from Pellegrini Vineyards center

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

3 Bedrooms9 Guests
New to Booking
$1922
Average price / night
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Brand New Waterfront Home with Boat Dock & Hot Tub
Brand New Waterfront Home with Boat Dock & Hot Tub
House
Mattituck, NY, 11952, United States
1.7k from Pellegrini Vineyards center

AC, Balcony, Barbecue, Dryer, Hot Tub, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
New to Booking
$1371
Average price / night
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Minnehaha Marvel
Minnehaha Marvel
House
Southold, NY, USA
7.2k from Pellegrini Vineyards 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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North Fork Waterfront Oasis in Mattituck
North Fork Waterfront Oasis in Mattituck
House
Mattituck, NY, 11952, United States
2.0k from Pellegrini Vineyards center

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

3 Bedrooms6 Guests
New to Booking
$1126
Average price / night
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Newly Renovated Home On The North Fork
Newly Renovated Home On The North Fork
House
Mattituck, NY, 11952, United States
2.1k from Pellegrini Vineyards center

AC, Barbecue, Dryer, Heater, Kitchen, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
New to Booking
$571
Average price / night
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Charming New Suffolk Home In Heart Of Wine Country - Close to Beach & Town
Charming New Suffolk Home In Heart Of Wine Country - Close to Beach & Town
House
New Suffolk, NY, 11956, United States
2.1k from Pellegrini Vineyards center

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

3 Bedrooms6 Guests
9.6

Exceptional

14 reviews

$458
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
2.1k from Pellegrini Vineyards 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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Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach
Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach
House
New Suffolk, NY, 11956, United States
2.2k from Pellegrini Vineyards center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

2 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$441
Average price / night
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Wake up on the Beach
Wake up on the Beach
Cottage
New Suffolk, NY, 11956, United States
2.2k from Pellegrini Vineyards center

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

3 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$1034
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
2.4k from Pellegrini Vineyards 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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Northfork Contemporary Cottage
Northfork Contemporary Cottage
House
Cutchogue, NY, 11935, United States
2.5k from Pellegrini Vineyards center

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

3 Bedrooms5 Guests
10.0

Exceptional

2 reviews

$349
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 Pellegrini Vineyards.

Where to stay in Pellegrini Vineyards? Best neighborhoods & areas

Pellegrini Vineyards Vacation Rentals on the Map

Frequently Asked Questions

You can explore 248 verified vacation rentals in Pellegrini Vineyards. 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 Pellegrini Vineyards 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 Pellegrini Vineyards 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 Pellegrini Vineyards welcome pets. Currently, 25 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 Pellegrini Vineyards often include amenities such as Fireplace/Heating, Laundry, and View. 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.