Vacation Rentals with Pool in West Chop, MA: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Massachusetts

  5.  Vineyard Haven
  6.  West Chop

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54 Best Vacation Rentals with Pool in West Chop (Starting from $151)

#OB Pool House
#OB Pool House
House
Oak Bluffs, MA, USA
7.3k from West Chop center

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

5 Bedrooms10 Guests
1.0

Review score

1 reviews

$1516
Average price / night
Check Availability
Stunning Tisbury Retreat with Pool
Stunning Tisbury Retreat with Pool
House
Tisbury, MA, 02568, United States
1.2k from West Chop center

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

5 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$2752
Average price / night
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InnSeason Resorts Captain's Quarters
InnSeason Resorts Captain's Quarters
Apartment
Falmouth, MA, USA
7.5k from West Chop center

Apartments, Accommodations, Pools, Parking, 3-star, Lodgings, Vacation rentals, Beach, Places to stay

33 Bedrooms14 Guests
9.5

Superb

187 reviews

$151
Average price / night
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Mink Meadows Luxury Getaway With Pool
Mink Meadows Luxury Getaway With Pool
House
Vineyard Haven, MA, 02568, United States
1.2k from West Chop center

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

5 Bedrooms10 Guests
10.0

Exceptional

5 reviews

$2627
Average price / night
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InnSeason Resorts Surfside
InnSeason Resorts Surfside
Apartment
West Chop, Vineyard Haven, Massachusetts, USA
7.6k from West Chop center

Apartments, Cheap, Accommodations, Pools, Parking, Serviced apartments, 3-star, Lodgings, Vacation rentals

57 Bedrooms8 Guests
9.1

Superb

199 reviews

$258
Average price / night
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PRIVACY & RELAXATION ON MARTHA'S VINEYARD
PRIVACY & RELAXATION ON MARTHA'S VINEYARD
House
Tisbury, MA, 02568, United States
1.2k from West Chop center

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

6 Bedrooms12 Guests
10.0

Exceptional

8 reviews

$1785
Average price / night
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Near Parks and Dining Expansive Falmouth Retreat!
Near Parks and Dining Expansive Falmouth Retreat!
House
Falmouth, MA, USA
9.3k from West Chop center

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

3 Bedrooms10 Guests
New to Booking
$648
Average price / night
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West Chop Tashmoo Beach Townhouse w/Pool Pickleball & Tennis borders Golf Course
West Chop Tashmoo Beach Townhouse w/Pool Pickleball & Tennis borders Golf Course
House
Tisbury, MA, 02568, United States
1.5k from West Chop center

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

3 Bedrooms5 Guests
New to Booking
$422
Average price / night
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Serene 6-bedroom Vineyard Haven Retreat
Serene 6-bedroom Vineyard Haven Retreat
House
Tisbury, MA, 02568, United States
1.9k from West Chop center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

6 Bedrooms12 Guests
New to Booking
$3877
Average price / night
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Spacious 6-bedroom house sleeps 12+ with pool, close to Tashmoo and pet friendly
Spacious 6-bedroom house sleeps 12+ with pool, close to Tashmoo and pet friendly
House
Tisbury, MA, 02568, United States
2.4k from West Chop center

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

6 Bedrooms14 Guests
New to Booking
$3956
Average price / night
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Luxe 4 Bed/4 Ensuite Bath, A/C In-Town Vineyard Haven, Gunite Pool and Spa
Luxe 4 Bed/4 Ensuite Bath, A/C In-Town Vineyard Haven, Gunite Pool and Spa
House
Vineyard Haven, MA, 02568, United States
2.8k from West Chop center

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

4 Bedrooms9 Guests
10.0

Exceptional

24 reviews

$1664
Average price / night
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Beautiful home with pool in great location- close to everything!
Beautiful home with pool in great location- close to everything!
House
Oak Bluffs, MA, 02568, United States
2.8k from West Chop center

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

2 Bedrooms6 Guests
10.0

Exceptional

22 reviews

$709
Average price / night
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Bright condo w Pool, walking distance to town!
Bright condo w Pool, walking distance to town!
Condo
Tisbury, MA, 02568, United States
3.0k from West Chop center

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

1 Bedroom2 Guests
9.4

Superb

3 reviews

$223
Average price / night
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East Chop Beach House w/Pool
East Chop Beach House w/Pool
House
Oak Bluffs, MA, 02568, United States
3.1k from West Chop center

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

5 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$2479
Average price / night
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Tisbury - Airy 4-bedroom with Peaceful Pool
Tisbury - Airy 4-bedroom with Peaceful Pool
House
Tisbury, MA, 02568, United States
3.4k from West Chop center

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

4 Bedrooms8 Guests
New to Booking
$1024
Average price / night
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Modern 4 bed/3.5 bath Farmhouse, private HEATED POOL and AC on bike path
Modern 4 bed/3.5 bath Farmhouse, private HEATED POOL and AC on bike path
House
Oak Bluffs, MA, 02568, United States
3.5k from West Chop center

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

6 Bedrooms10 Guests
10.0

Exceptional

71 reviews

$1206
Average price / night
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Retreat to Martha's Vineyard with a Private Pool & Outdoor Living in Oak Bluffs\n
Retreat to Martha's Vineyard with a Private Pool & Outdoor Living in Oak Bluffs\n
House
Oak Bluffs, MA, 02557, United States
5.0k from West Chop center

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

4 Bedrooms9 Guests
10.0

Exceptional

7 reviews

$1326
Average price / night
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 Relax & Renew at Luxury Villa with Heated Pool & Hot Tub,Tennis,Bikes,Firepit!
Relax & Renew at Luxury Villa with Heated Pool & Hot Tub,Tennis,Bikes,Firepit!
House
Oak Bluffs, MA, 02557, United States
5.1k from West Chop center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

5 Bedrooms10 Guests
9.4

Superb

13 reviews

$1592
Average price / night
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4-BR, Hot tub, Wifi, AC, Fire pit. No Pets.
4-BR, Hot tub, Wifi, AC, Fire pit. No Pets.
House
Oak Bluffs, MA, 02557, United States
5.5k from West Chop center

AC, Arcade, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms12 Guests
New to Booking
$1508
Average price / night
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Grand Coastal-Style Estate In The Preserve
Grand Coastal-Style Estate In The Preserve
House
Oak Bluffs, MA, 02557, United States
5.7k from West Chop center

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

5 Bedrooms12 Guests
10.0

Exceptional

4 reviews

$2315
Average price / night
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Luxury 4-Bedroom Property with Private Beach on Seaview Ave in Oak Bluffs
Luxury 4-Bedroom Property with Private Beach on Seaview Ave in Oak Bluffs
House
Oak Bluffs, MA, 02557, United States
6.2k from West Chop center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, No Smoking

4 Bedrooms9 Guests
New to Booking
$2585
Average price / night
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THE PARK ESTATE! Your Martha's Vineyard Getaway!
THE PARK ESTATE! Your Martha's Vineyard Getaway!
House
Oak Bluffs, MA, 02557, United States
6.4k from West Chop center

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

6 Bedrooms16 Guests
9.8

Exceptional

17 reviews

$7810
Average price / night
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Carriage House, Swimming, Boating, Kayaking, just steps from your door...
Carriage House, Swimming, Boating, Kayaking, just steps from your door...
House
Oak Bluffs, MA, 02557, United States
6.6k from West Chop center

AC, Barbecue, Breakfast Available, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
9.8

Exceptional

63 reviews

$921
Average price / night
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Oak Bluffs Retreat. NEW PRIVATE POOL
Oak Bluffs Retreat. NEW PRIVATE POOL
House
Oak Bluffs, MA, 02568, United States
6.7k from West Chop center

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

3 Bedrooms6 Guests
10.0

Exceptional

14 reviews

$3725
Average price / night
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Beautiful Estate with salt water pool  & pond with kayaks
Beautiful Estate with salt water pool & pond with kayaks
House
Oak Bluffs, MA, 02557, United States
6.8k from West Chop center

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

5 Bedrooms12 Guests
New to Booking
$4877
Average price / night
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Oak Bluffs Renovated Retreat With Pool, Tennis, and Sengekontacket Pond Access!
Oak Bluffs Renovated Retreat With Pool, Tennis, and Sengekontacket Pond Access!
House
Edgartown, MA, 02539, United States
6.9k from West Chop center

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

3 Bedrooms8 Guests
New to Booking
$1669
Average price / night
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Lovely spacious MV 3-bdr, 3 bath island home, sleeps 12,  air and comm. pool.
Lovely spacious MV 3-bdr, 3 bath island home, sleeps 12, air and comm. pool.
House
West Tisbury, MA, 02575, United States
7.0k from West Chop center

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

3 Bedrooms12 Guests
New to Booking
$879
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 West Chop.

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West Chop Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 54 verified vacation rentals with a pool in West Chop. 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 West Chop vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $151 per night, with private pool homes and peak travel periods often costing more.

Many rentals in West Chop 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 West Chop welcome pets. Currently, 11 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 West Chop often include additional outdoor features such as Pool, Laundry, and Fireplace/Heating. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in West Chop 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.