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

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals with Pool
  3.  USA

  4.  New York

  5.  Riverhead

  6.  Sherwood House Vineyards - Jamesport Tasting House

Refine your search

Price per night

Amenity Filter

Rating

104 Best Vacation Rentals with Pool in Sherwood House Vineyards - Jamesport Tasting House (Starting from $224)

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
Check Availability
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
Check Availability
The Villa at Hampton Bays.Hampton's Summer Escape Nightlife Pool Spa.
The Villa at Hampton Bays.Hampton's Summer Escape Nightlife Pool Spa.
Villa
Sherwood House Vineyards - Jamesport Tasting House, Riverhead, New York, USA
8.3k from Sherwood House Vineyards - Jamesport Tasting House center

View, Parking, Air Conditioner, Kitchen, Ocean View, Pool, Balcony/Terrace

7 Bedrooms13 Guests
New to Booking
$1440
Average price / night
Check Availability
North Fork Beach House
North Fork Beach House
House
Laurel, NY, 11970, United States
1.6k from Sherwood House Vineyards - Jamesport Tasting House center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$1793
Average price / night
Check Availability
Tranquil Bays Estate
Tranquil Bays Estate
House
Hampton Bays, NY, USA
8.4k from Sherwood House Vineyards - Jamesport Tasting House center

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

4 Bedrooms10 Guests
New to Booking
$834
Average price / night
Check Availability
North Fork Oasis w/ Saltwater Pool & Steps 2 Beach
North Fork Oasis w/ Saltwater Pool & Steps 2 Beach
House
Jamesport, NY, 11742, United States
1.9k from Sherwood House Vineyards - Jamesport Tasting House center

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

3 Bedrooms6 Guests
New to Booking
$656
Average price / night
Check Availability
Hampton Bays 4bdr all Q size,IG Pool,Billiard, tennis
Hampton Bays 4bdr all Q size,IG Pool,Billiard, tennis
House
Hampton Bays, NY, USA
8.6k from Sherwood House Vineyards - Jamesport Tasting House center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1299
Average price / night
Check Availability
North Fork
North Fork
House
Riverhead, NY, 11901, United States
2.3k from Sherwood House Vineyards - Jamesport Tasting House center

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

5 Bedrooms10 Guests
New to Booking
$1870
Average price / night
Check Availability
Hamptons Vacation Rental with Seasonal Pool!
Hamptons Vacation Rental with Seasonal Pool!
House
Hampton Bays, NY, USA
8.6k from Sherwood House Vineyards - Jamesport Tasting House center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly

3 Bedrooms6 Guests
8.5

Very Good

4 reviews

$573
Average price / night
Check Availability
Sunny Breezy  Beach House With Huge Pool Overlooking  Fields
Sunny Breezy Beach House With Huge Pool Overlooking Fields
House
Aquebogue, NY, 11901, United States
2.9k from Sherwood House Vineyards - Jamesport Tasting House center

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

4 Bedrooms8 Guests
10.0

Exceptional

16 reviews

$1013
Average price / night
Check Availability
Respite Ranch: Private Pool, Hot Tub, Beach Access
Respite Ranch: Private Pool, Hot Tub, Beach Access
House
Mattituck, NY, USA
8.8k from Sherwood House Vineyards - Jamesport Tasting House center

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

3 Bedrooms6 Guests
New to Booking
$679
Average price / night
Check Availability
Stunning Farmhouse W/ Solar Heated Pool in North Fork, Farmstands, winery& beach
Stunning Farmhouse W/ Solar Heated Pool in North Fork, Farmstands, winery& beach
House
Riverhead, NY, 11901, United States
3.2k from Sherwood House Vineyards - Jamesport Tasting House center

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

4 Bedrooms8 Guests
10.0

Exceptional

13 reviews

$1200
Average price / night
Check Availability
Griffing Getaway
Griffing Getaway
House
East Quogue, NY, USA
9.3k from Sherwood House Vineyards - Jamesport Tasting House center

Parking, Pool, Wheelchair Accessible, Laundry, Internet, Child Friendly

4 Bedrooms10 Guests
New to Booking
$2223
Average price / night
Check Availability
Northfork Long Island House Rental-US Open-Shinnecock, Family Vacation, Wineries
Northfork Long Island House Rental-US Open-Shinnecock, Family Vacation, Wineries
House
Riverhead, NY, 11901, United States
3.5k from Sherwood House Vineyards - Jamesport Tasting House center

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

4 Bedrooms8 Guests
10.0

Exceptional

10 reviews

$763
Average price / night
Check Availability
North Fork Oasis: Heated Pool, Hot tub
North Fork Oasis: Heated Pool, Hot tub
House
Laurel, NY, 11948, United States
3.5k from Sherwood House Vineyards - Jamesport Tasting House center

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

4 Bedrooms8 Guests
8.0

Good

7 reviews

$1584
Average price / night
Check Availability
Family holiday Holiday house in wine country
Family holiday Holiday house in wine country
House
Riverhead, NY, 11901, United States
3.9k from Sherwood House Vineyards - Jamesport Tasting House center

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

5 Bedrooms9 Guests
10.0

Exceptional

1 reviews

$783
Average price / night
Check Availability
Pet-Friendly Apt w/ Hot Tub Near the Hamptons!
Pet-Friendly Apt w/ Hot Tub Near the Hamptons!
Apartment
Aquebogue, NY, 11931, United States
4.0k from Sherwood House Vineyards - Jamesport Tasting House center

AC, Barbecue, Free Parking, Heater, Hot Tub, Internet, Kitchen, Microwave, No Smoking

1 Bedroom3 Guests
9.2

Superb

5 reviews

$224
Average price / night
Check Availability
North Fork Family and Friends Getaway.  Great Location
North Fork Family and Friends Getaway. Great Location
House
Mattituck, NY, 11952, United States
4.2k from Sherwood House Vineyards - Jamesport Tasting House center

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

4 Bedrooms8 Guests
10.0

Exceptional

16 reviews

$1487
Average price / night
Check Availability
Bayfront Luxury Retreat with Heated Pool, Private Beach, and Sweeping Water...
Bayfront Luxury Retreat with Heated Pool, Private Beach, and Sweeping Water...
House
Hampton Bays, NY, 10014, United States
4.5k from Sherwood House Vineyards - Jamesport Tasting House center

AC, Balcony, Dryer, Free Parking, Heater, Hot Tub, Kitchen, Laundry, Microwave

4 Bedrooms6 Guests
New to Booking
$2061
Average price / night
Check Availability
Waterfront home, infinity pool, private beach, and amazing  sunsets!
Waterfront home, infinity pool, private beach, and amazing sunsets!
House
Hampton Bays, NY, 11946, United States
4.6k from Sherwood House Vineyards - Jamesport Tasting House center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$1566
Average price / night
Check Availability
“North Fork Winter Escape – Cozy Farmhouse by the Vineyards”
“North Fork Winter Escape – Cozy Farmhouse by the Vineyards”
House
Mattituck, NY, 11952, United States
4.6k from Sherwood House Vineyards - Jamesport Tasting House center

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

3 Bedrooms6 Guests
9.2

Superb

5 reviews

$909
Average price / night
Check Availability
Private home on a private road. Swimming pool, hot tub and complete gym.
Private home on a private road. Swimming pool, hot tub and complete gym.
House
Laurel, NY, 11948, United States
4.9k from Sherwood House Vineyards - Jamesport Tasting House center

AC, Barbecue, Dryer, Fitness Equipment, Heater, Hot Tub, Internet, Laundry, Microwave

3 Bedrooms6 Guests
New to Booking
$3472
Average price / night
Check Availability
Hamptons Waterview Custom Home with Designer Finishes
Hamptons Waterview Custom Home with Designer Finishes
House
Hampton Bays, NY, 11946, United States
5.3k 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

4 reviews

$889
Average price / night
Check Availability
Newly Renovated Modern Home With Beach Access and Pool!
Newly Renovated Modern Home With Beach Access and Pool!
House
Laurel, NY, 11948, United States
5.6k from Sherwood House Vineyards - Jamesport Tasting House center

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

3 Bedrooms7 Guests
10.0

Exceptional

24 reviews

$545
Average price / night
Check Availability
Contemporary Hampton Bays home on one acre of manicured lawn, private pool,...
Contemporary Hampton Bays home on one acre of manicured lawn, private pool,...
House
Hampton Bays, NY, 11946, United States
5.9k from Sherwood House Vineyards - Jamesport Tasting House center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$914
Average price / night
Check Availability
Chic North Fork Haven with Pool & Firepit - Minutes from Beaches, Wineries...
Chic North Fork Haven with Pool & Firepit - Minutes from Beaches, Wineries...
House
Mattituck, NY, 11952, United States
6.0k from Sherwood House Vineyards - Jamesport Tasting House center

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

5 Bedrooms9 Guests
8.0

Good

1 reviews

$1210
Average price / night
Check Availability
2 Bedroom Hamptons Waterfront Cottage Rental
2 Bedroom Hamptons Waterfront Cottage Rental
House
Hampton Bays, NY, 11946, United States
6.0k from Sherwood House Vineyards - Jamesport Tasting House center

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

2 Bedrooms4 Guests
10.0

Exceptional

17 reviews

$640
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 with Pool in Sherwood House Vineyards - Jamesport Tasting House.

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods

Sherwood House Vineyards - Jamesport Tasting House Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 104 verified vacation rentals with a pool in Sherwood House Vineyards - Jamesport Tasting House. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Sherwood House Vineyards - Jamesport Tasting House vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $224 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Sherwood House Vineyards - Jamesport Tasting House offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Sherwood House Vineyards - Jamesport Tasting House welcome pets. Currently, 27 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Sherwood House Vineyards - Jamesport Tasting House often include additional outdoor features such as Pool, Fireplace/Heating, and Laundry. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Sherwood House Vineyards - Jamesport Tasting House offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.