Cottage 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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28 Best Cottage Rentals in Pellegrini Vineyards (Starting from $122)

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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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
2.5k from Pellegrini Vineyards 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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Beautiful charming 1930s fully renovated cottage walking distance to the beach!
Beautiful charming 1930s fully renovated cottage walking distance to the beach!
Cottage
Cutchogue, NY, 11935, United States
2.9k from Pellegrini Vineyards center

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

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$640
Average price / night
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The Bay Breeze
The Bay Breeze
Cottage
Cutchogue, NY, 11935, United States
3.0k from Pellegrini Vineyards 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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Stunning, Waterfront, newly renovated cottage with deck on water.
Stunning, Waterfront, newly renovated cottage with deck on water.
Cottage
Cutchogue, NY, 11935, United States
3.2k from Pellegrini Vineyards 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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Modern Cottage with New Heated Pool
Modern Cottage with New Heated Pool
Cottage
Mattituck, NY, 11952, United States
3.3k from Pellegrini Vineyards center

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

2 Bedrooms4 Guests
10.0

Exceptional

22 reviews

$775
Average price / night
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The Melody Too
The Melody Too
Cottage
Cutchogue, NY, 11935, United States
3.3k from Pellegrini Vineyards 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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Waterfront Guest Cottage
Waterfront Guest Cottage
Cottage
Cutchogue, NY, 11935, United States
3.8k from Pellegrini Vineyards center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

2 Bedrooms4 Guests
10.0

Exceptional

5 reviews

$420
Average price / night
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Walk to Sandy Bay Beach~North Fork Wine Country Cottage SRP#0270
Walk to Sandy Bay Beach~North Fork Wine Country Cottage SRP#0270
Cottage
Mattituck, NY, 11952, United States
3.9k from Pellegrini Vineyards center

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

2 Bedrooms6 Guests
9.8

Exceptional

88 reviews

$377
Average price / night
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Walk to Love Lane! Immaculately renovated private cottage.
Walk to Love Lane! Immaculately renovated private cottage.
Cottage
Mattituck, NY, 11952, United States
3.9k from Pellegrini Vineyards center

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

1 Bedroom4 Guests
10.0

Exceptional

19 reviews

$519
Average price / night
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Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Cottage
Cutchogue, NY, 11935, United States
4.2k from Pellegrini Vineyards center

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

2 Bedrooms4 Guests
10.0

Exceptional

29 reviews

$451
Average price / night
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Walk to Breakwater Beach in Heart of Wine Country
Walk to Breakwater Beach in Heart of Wine Country
Cottage
Mattituck, NY, 11952, United States
4.6k from Pellegrini Vineyards center

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

2 Bedrooms6 Guests
9.8

Exceptional

14 reviews

$608
Average price / night
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Renovated 2 BR Cottage-Perfect for North Fork Beach,Vineyard,Wedding Vacations!
Renovated 2 BR Cottage-Perfect for North Fork Beach,Vineyard,Wedding Vacations!
Cottage
Mattituck, NY, 11952, United States
4.6k from Pellegrini Vineyards center

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

2 Bedrooms4 Guests
10.0

Exceptional

13 reviews

$433
Average price / night
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Incredible Beachfront Home w/ Private Beach!
Incredible Beachfront Home w/ Private Beach!
Cottage
Mattituck, NY, 11952, United States
5.9k from Pellegrini Vineyards center

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

3 Bedrooms5 Guests
10.0

Exceptional

27 reviews

$842
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
6.0k from Pellegrini Vineyards 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
6.0k from Pellegrini Vineyards 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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Lovely North Fork Beach Cottage (2 BR/2 bath)!
Lovely North Fork Beach Cottage (2 BR/2 bath)!
Cottage
Laurel, NY, 11948, United States
6.3k from Pellegrini Vineyards center

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

2 Bedrooms6 Guests
10.0

Exceptional

120 reviews

$751
Average price / night
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Southold Cottage w/ Patio & Grill - Walk to Beach!
Southold Cottage w/ Patio & Grill - Walk to Beach!
Cottage
Southold, NY, 11971, United States
6.7k from Pellegrini Vineyards center

Barbecue, Extra Bed, Fireplace, Free Parking, Internet, Kitchen, Microwave, No Smoking, Outdoor Grill

2 Bedrooms3 Guests
New to Booking
$161
Average price / night
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Bright light, water views, steps from the beach!
Bright light, water views, steps from the beach!
Cottage
Southold, NY, 11971, United States
7.2k from Pellegrini Vineyards center

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

3 Bedrooms6 Guests
New to Booking
$645
Average price / night
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Cute Cottage Apartment Near town, beaches and vineyards
Cute Cottage Apartment Near town, beaches and vineyards
Cottage
Southold, NY, 11971, United States
8.1k from Pellegrini Vineyards center

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

2 Bedrooms4 Guests
9.6

Exceptional

26 reviews

$457
Average price / night
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Lovely Cottage in the Heart of Long Island Wine country
Lovely Cottage in the Heart of Long Island Wine country
Cottage
Southold, NY, 11971, United States
8.2k from Pellegrini Vineyards center

AC, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

2 Bedrooms4 Guests
9.8

Exceptional

30 reviews

$297
Average price / night
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Secluded Lakefront Cottage Near Town Beaches and North Fork Wineries
Secluded Lakefront Cottage Near Town Beaches and North Fork Wineries
Cottage
Southold, NY, 11971, United States
8.3k from Pellegrini Vineyards center

AC, Free Parking, Internet, Kitchen, Microwave, Patio, TV

2 Bedrooms4 Guests
7.0

Good

9 reviews

$177
Average price / night
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Newly Renovated Beach Cottage in Jamesport, NY with a private beach.
Newly Renovated Beach Cottage in Jamesport, NY with a private beach.
Cottage
Jamesport, NY, 11947, United States
8.7k from Pellegrini Vineyards center

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

4 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$730
Average price / night
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Beachfront - endless sunsets, sandy beach,  cozy sunroom & open concept kitchen
Beachfront - endless sunsets, sandy beach, cozy sunroom & open concept kitchen
Cottage
Southold, NY, 11971, United States
8.8k from Pellegrini Vineyards center

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

3 Bedrooms8 Guests
10.0

Exceptional

30 reviews

$1085
Average price / night
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Wine Country Cozy Home Away in the Woods
Wine Country Cozy Home Away in the Woods
Cottage
Riverhead, NY, 11901, United States
9.4k from Pellegrini Vineyards center

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

1 Bedroom3 Guests
10.0

Exceptional

24 reviews

$122
Average price / night
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Charming Cottage
Charming Cottage
Cottage
Southold, NY, 11971, United States
9.4k from Pellegrini Vineyards center

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

2 Bedrooms4 Guests
10.0

Exceptional

34 reviews

$474
Average price / night
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Charming Beach Cottage, Steps to Beach, Enjoy Scenic Vineyards & Farm Stands
Charming Beach Cottage, Steps to Beach, Enjoy Scenic Vineyards & Farm Stands
Cottage
South Jamesport, NY, 11970, United States
9.7k from Pellegrini Vineyards center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$379
Average price / night
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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 Cottage Rentals in Pellegrini Vineyards.

Where to stay in Pellegrini Vineyards? Best neighborhoods & areas

Pellegrini Vineyards Cottage Rentals on the Map

Frequently Asked Questions

You can explore 28 verified cottage rentals in Pellegrini Vineyards. Our listings are sourced from a range of trusted booking providers, giving you access to charming coastal cottages, peaceful countryside escapes, and cozy stays—all in one place.

Cottage rental prices in Pellegrini Vineyards vary based on the season, location, and amenities offered. Rates typically start from around $122 per night, with higher prices during peak travel periods or in waterfront locations. Comparing different options can help you find a stay that fits both your preferences and budget.

Many cottages in Pellegrini Vineyards feature inviting outdoor areas such as private gardens, patios, or small yards. These spaces are ideal for relaxing, dining outdoors, or enjoying the surrounding scenery. You can use the available filters to quickly find cottages with outdoor features that match your preferences.

Yes, cottages are often a great choice for travelers with pets thanks to their cozy layouts and access to outdoor space. Currently, 13 listings in Pellegrini Vineyards welcome pets, making it easier to plan a comfortable stay with your companion.

For busy seasons such as summer holidays or long weekends, it’s a good idea to book your cottage 60 to 90 days in advance. Since cottages are typically smaller and more unique, the most desirable options tend to get reserved quickly during peak periods.

Cottages in Pellegrini Vineyards are known for their comfort and charm, often including amenities such as Kitchen, Bedding/Linens, and Balcony/Terrace. These features help create a relaxing and home-like atmosphere for guests.

Yes, many cottages in Pellegrini Vineyards are well-suited for longer stays. They often include essentials like full kitchens, laundry facilities, and comfortable living spaces, making them a practical option for extended vacations or remote work.