Vacation Rentals in Sherwood House Vineyards - Jamesport Tasting House, NY: Compare 10+ Sites & Save

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244 Best Vacation Rentals in Sherwood House Vineyards - Jamesport Tasting House (Starting from $112)

Charming Cottage in The Heart of the North Fork
Charming Cottage in The Heart of the North Fork
House
Jamesport, NY, USA
1.5k from Sherwood House Vineyards - Jamesport Tasting House center

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

3 Bedrooms8 Guests
New to Booking
$482
Average price / night
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Stylish and Rustic Decor, Vineyard Tours, Tasting Room
Stylish and Rustic Decor, Vineyard Tours, Tasting Room
House
Jamesport, NY, 11947, United States
0.3k from Sherwood House Vineyards - Jamesport Tasting House center

AC, Barbecue, Free Parking, Heater, Kitchen, No Smoking, TV

3 Bedrooms6 Guests
9.8

Exceptional

24 reviews

$664
Average price / night
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Classy Getaway with Deck and Yard Less Than 1 Mi to Beach
Classy Getaway with Deck and Yard Less Than 1 Mi to Beach
House
Riverhead, NY, USA
1.5k from Sherwood House Vineyards - Jamesport Tasting House center

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

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$564
Average price / night
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North Fork Charmer
North Fork Charmer
Apartment
Aquebogue, NY, 11948, United States
0.8k from Sherwood House Vineyards - Jamesport Tasting House center

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

1 Bedroom4 Guests
New to Booking
$532
Average price / night
Check Availability
Premier Waterfront Cottage 1
Premier Waterfront Cottage 1
House
Riverhead, NY, USA
1.9k from Sherwood House Vineyards - Jamesport Tasting House center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$633
Average price / night
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Cozy North Fork Home Among the Best Wineries in the Northeast, Minutes to...
Cozy North Fork Home Among the Best Wineries in the Northeast, Minutes to...
House
Aquebogue, NY, 11931, United States
0.9k from Sherwood House Vineyards - Jamesport Tasting House center

AC, Dryer, Free Parking, Heater, Kitchen, Laundry, Microwave, No Smoking, Patio

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$278
Average price / night
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Premier Waterfront Cottage 3
Premier Waterfront Cottage 3
House
Riverhead, NY, USA
1.9k from Sherwood House Vineyards - Jamesport Tasting House center

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

2 Bedrooms5 Guests
New to Booking
$250
Average price / night
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Center of Jamesport, New Pool!
Center of Jamesport, New Pool!
House
Jamesport, NY, 11947, United States
1.1k from Sherwood House Vineyards - Jamesport Tasting House center

AC, Internet, Laundry, No Smoking, Washer

4 Bedrooms8 Guests
New to Booking
$770
Average price / night
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Premier Waterfront Cottage 2
Premier Waterfront Cottage 2
House
Riverhead, NY, USA
1.9k from Sherwood House Vineyards - Jamesport Tasting House center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

2 Bedrooms5 Guests
9.3

Superb

3 reviews

$250
Average price / night
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Elegant and spacious North Fork home; near beaches, vineyards, farms and dining.
Elegant and spacious North Fork home; near beaches, vineyards, farms and dining.
House
Jamesport, NY, 11901, United States
1.1k from Sherwood House Vineyards - Jamesport Tasting House center

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

5 Bedrooms12 Guests
10.0

Exceptional

99 reviews

$1060
Average price / night
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Waterfront Cottage 4
Waterfront Cottage 4
House
Riverhead, NY, USA
1.9k from Sherwood House Vineyards - Jamesport Tasting House center

View, Internet, Parking, Balcony/Terrace, Air Conditioner, Pet Friendly, Barbecue/Outdoor Cooking

2 Bedrooms5 Guests
10.0

Exceptional

2 reviews

$519
Average price / night
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Manor Cottage: Beach Hopping | Outdoor Shower
Manor Cottage: Beach Hopping | Outdoor Shower
House
Jamesport, NY, 11947, United States
1.2k from Sherwood House Vineyards - Jamesport Tasting House center

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

3 Bedrooms6 Guests
New to Booking
$665
Average price / night
Check Availability
Bahia Mar: Beach House, North Fork
Bahia Mar: Beach House, North Fork
House
Laurel, NY, USA
3.6k from Sherwood House Vineyards - Jamesport Tasting House 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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3-bedroom house in peaceful Jamesport- near water, Riverhead, and Shinnecock.
3-bedroom house in peaceful Jamesport- near water, Riverhead, and Shinnecock.
House
Jamesport, NY, 11947, United States
1.2k from Sherwood House Vineyards - Jamesport Tasting House center

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

3 Bedrooms7 Guests
New to Booking
$636
Average price / night
Check Availability
Pet-Friendly Apt with Hot Tub Near the Hamptons!
Pet-Friendly Apt with Hot Tub Near the Hamptons!
Apartment
Aquebogue, NY, USA
4.0k from Sherwood House Vineyards - Jamesport Tasting House center

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

1 Bedroom3 Guests
New to Booking
$112
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
1.2k from Sherwood House Vineyards - Jamesport Tasting House 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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North Fork House for Rent
North Fork House for Rent
House
Mattituck, NY, USA
4.6k from Sherwood House Vineyards - Jamesport Tasting House 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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Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!
Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!
House
Jamesport, NY, 11947, United States
1.3k from Sherwood House Vineyards - Jamesport Tasting House center

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

3 Bedrooms8 Guests
10.0

Exceptional

11 reviews

$603
Average price / night
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Vacation home
Vacation home
House
Riverhead, NY, USA
6.4k from Sherwood House Vineyards - Jamesport Tasting House center

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

5 Bedrooms10 Guests
9.5

Superb

2 reviews

$409
Average price / night
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NorthFork Getaway with Beach Access 4br 3bath
NorthFork Getaway with Beach Access 4br 3bath
House
Jamesport, NY, 11947, United States
1.4k from Sherwood House Vineyards - Jamesport Tasting House center

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

4 Bedrooms12 Guests
10.0

Exceptional

6 reviews

$1452
Average price / night
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Hamptons Escape: Near Beaches, Restaurants, Wineries.
Hamptons Escape: Near Beaches, Restaurants, Wineries.
House
Hampton Bays, NY, USA
6.8k from Sherwood House Vineyards - Jamesport Tasting House center

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

5 Bedrooms12 Guests
New to Booking
$926
Average price / night
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Coastal Haven: Private Pool, Bay Access
Coastal Haven: Private Pool, Bay Access
House
North Fork, NY, 11970, United States
1.4k from Sherwood House Vineyards - Jamesport Tasting House center

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

4 Bedrooms8 Guests
9.6

Exceptional

5 reviews

$320
Average price / night
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Cozy beach house surrounded by nature, vineyards, farms, stables and much more
Cozy beach house surrounded by nature, vineyards, farms, stables and much more
House
Riverhead, NY, 11901, United States
1.5k from Sherwood House Vineyards - Jamesport Tasting House center

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

3 Bedrooms7 Guests
New to Booking
$389
Average price / night
Check Availability
Jamesport Cottage | Walk to Peconic Bay, Fire Pit
Jamesport Cottage | Walk to Peconic Bay, Fire Pit
House
Jamesport, NY, 11947, United States
1.5k from Sherwood House Vineyards - Jamesport Tasting House center

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

3 Bedrooms8 Guests
10.0

Exceptional

42 reviews

$212
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
1.5k from Sherwood House Vineyards - Jamesport Tasting House 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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Stunning Waterfront Jamesport Home, Private Dock, Great for Groups
Stunning Waterfront Jamesport Home, Private Dock, Great for Groups
House
Jamesport, NY, 11947, United States
1.5k from Sherwood House Vineyards - Jamesport Tasting House center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Kitchen, Microwave, No Smoking

6 Bedrooms12 Guests
New to Booking
$8631
Average price / night
Check Availability
'OUR NANTUCKET - PRIVATE NORTH FORK LOCAL
'OUR NANTUCKET - PRIVATE NORTH FORK LOCAL
House
Aquebogue, NY, 11931, United States
1.5k from Sherwood House Vineyards - Jamesport Tasting House center

AC, Balcony, Dryer, Fireplace, Free Parking, Heater, Kitchen, Laundry, Living Area

4 Bedrooms10 Guests
9.6

Exceptional

7 reviews

$1529
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 Sherwood House Vineyards - Jamesport Tasting House.

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Frequently Asked Questions

You can explore 244 verified vacation rentals in Sherwood House Vineyards - Jamesport Tasting House. 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 Sherwood House Vineyards - Jamesport Tasting House vary depending on the season, property size, and location. Rates typically start from around $112 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 Sherwood House Vineyards - Jamesport Tasting House 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 Sherwood House Vineyards - Jamesport Tasting House welcome pets. Currently, 29 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 Sherwood House Vineyards - Jamesport Tasting House often include amenities such as Fireplace/Heating, Internet, and Balcony/Terrace. 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.