Top 10 Vacation Rentals With Private Pool In Massachusetts, USA

vacation rentals with private pool in massachusetts
Nikki
Nikki 
Updated

Ever heard of Capeside, Massachusetts? If you did, then you must have been a fan or watched Dawson’s Creek. Unfortunately, Capeside doesn’t exist. But the show does give you an idea of what Massachusetts can offer. Enjoy a romantic walk at Cape Cod’s sandy beaches, then enjoy local seafood in the town’s beachside restaurants. Unleash your inner Pacey Witter and sail at the Charles River. Or, be like Joey and not only visit but study in Boston, Massachusetts. To truly immerse in the Massachusetts vibe, you must stay for a week at least. Here’s the lowdown on the top vacation rentals with private pool in Massachusetts, USA.

1. OB Pool House, Oak Bluffs (from USD 687)

Undoubtedly, the main feature of this home is its outdoor heated pool in the backyard. The blue water of the pool will instantly magnetize you the moment you lay eyes on it. The pool is closed from November 1st until Memorial Day though, so it’s better to book the accommodation outside these dates if you wish to use the pool. However, there’s more to OB Pool house than the pool. The inviting indoor living space offers warmth for every guest traveling in chilly seasons. The property also has a foosball table that can be enjoyed no matter what season it is. Its great location at the edge of Manuel F. Correllus State Forest also offers guests easy access to downtown Vineyard Haven, which is 4 mi (6.4 km) away from the house.

Luxury home w/pool & foosball-near 3 towns & many beaches
23 reviews
House 10 Guests 5 Bedrooms 5 Bathrooms

Accommodates: 10
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
a/c worked verify well as it was warm the week we stayed
very roomy nicely designed and the pool and hot tub are definitely a plus
beautiful home and the pool/spa is awes
the backyard pool and all around decor was lovely
Cleanliness:
the beds/couches were all so comfortable and the house spotless
overall we had a wonderful time we had a few issues with cleanliness and freezer problems
Read more reviews

2. Homey lodging near South Cape beach, Mashpee (from USD 350)

Located in the quiet neighborhood of New Seabury in Mashpee, this property offers an outdoor heated pool that guests of up to six people can enjoy. This two-bedroom home is perfect for a small family looking to have a vacation getaway for one week or more. There’s a living-cum-dining area and a family room with television to keep you entertained. The property is just a quick 5-minute drive to South Cape beach, and about 10-minute drive to shops and restaurants in Mashpee.

Patio home on the golf course with heated pool - private Listing ID 4548459
31 reviews  Wifi Available
House 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 6
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
the pool and yard was perfect for us we enjoyed our stay quite a bit
the yard is totally private and has a perfect sized pool for a family to enjoy
Cleanliness:
the house was clean and well-maintained
very clean and very nice accommodations
well maintained property and extremely clean
it was beautiful and very clean
clean spacious quiet and with a wonderful pool (with fun inflatables)
Host:
dina was pleasant and responsive to questions
the owner was great to work with
dina was very responsive before and during our stay
Location:
great location and property
the neighborhood and location were very nice
close to restaurants and great beaches
the location is perfect close to beach golfing shops and restaurants
Read more reviews

3. Katama Luxury, Edgartown (from USD 571)

This luxurious home located in Edgartown offers guests nicely landscaped walkways, carefully manicured lawns, and a relaxing outdoor pool. Relax at one of the pool’s chaises or share cocktails with friends while sitting on the comfortable outdoor couch. Inside, you’ll find a chef’s kitchen with a large kitchen island, great for family gatherings or hosting a celebration with friends. It might be too tempting to just stay and relax in this spacious home, but there are beaches nearby, which are worth checking out. South beach is 1.6 mi (2.6 km) away, while Katama beach is 3.6 mi (5.8 km) away from the property.

Katama Luxury - 5+ BR home w/ Heated Pool near The Field Club
22 reviews  Wifi Available
House 14 Guests 5 Bedrooms 6 Bathrooms

Accommodates: 14
Minimum Nights: 7
Refund Policy :

Top guest reviews
Amenities & Room:
the outside pool area is stunning great outdoor furniture with nice thick cushions to relax on
and the heated pool was the best
of course the real draw is the amazing pool and deck area
of course the real draw is the amazing pool and deck area
the kitchen was well stocked and made cooking easy
Cleanliness:
we’re rather picky but are always impressed with the cleanliness and décor
Host:
his caretaker craig is a sweetheart
you could host a cocktail party or swim party of 20 back there
you could host a cocktail party or swim party of 20 back there
the owner steve is very helpful as well as personable with any concerns or questions you may have
steve and his family are wonderful hosts
Location:
and the location is amazing
and the location is amazing
in summer it would be ideal positioned close to the bike path
inside outside and location were all perfect
it's also a short walk to the right fork diner one of our favorite breakfast and lunch spots
Read more reviews

4. Cozy, colonial-style home for 10, Edgartown (from USD 511)

This gorgeous home located in Edgartown offers spacious living areas and bedrooms for a group of up to 10 people. The property has a lot of recreational facilities, including a ping-pong table and a large flat-screen television in the family room. There is also an outdoor pool in the backyard, with heating open from Memorial Day through the end of September. For added security, the yard surrounding the pool is gated and the door entrance from the poolside has an alarm. This security feature enables guests to leave the house for a while and visit nearby attractions such as Katama beach, which is only 3.7 mi (5.95 km) from the property.

Gorgeous Edgartown Colonial with In- ground Pool, Central Air
41 reviews  Wifi Available
House 10 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 10
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
kitchen is very well equipped with most any tool/appliance you could need
the ping-pong room with big screen tv was a huge bonus for us
plenty of room for 7 of us adults and we so enjoyed the common areas to gather in
we loved the open kitchen/dining room/peninsula floor plan where we congregated the most
Cleanliness:
it is large clean and convenient to everything
so glad to have stayed in this spacious and clean home when we were in mv for ourfriends' wedding
the downstairs of the house is very spacious comfortable and well-laid out
Host:
sue was an incredible host answered all questions immediately offered great advice and provided a lovely home
the house was beautiful and the owners were very nice and helpful
Location:
we definitely needed a different location for thanksgiving
the house the grounds and the location all make for a terrific place to stay
Read more reviews

5. Spacious property for eight, West Barnstable (from USD 325)

This beautiful, colonial-style home offers an in-ground heated pool that is open from May until the end of September. The host of the property may allow extension of pool use even after September depending on the weather. If the pool is closed, worry not, because the property has a cozy porch that is great for sharing some drinks and stories with family and friends. The indoor living space has an open floor plan, with an updated kitchen that has modern appliances. The kitchen also has a window with a pool view.

PPP Peaceful, private with a pool! Available for off season rentals.
29 reviews  Wifi Available
House 8 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
pool and spacious deck can be enjoyed after a beach day
our favorite features of the house were the outdoor deck and the pool
Cleanliness:
we loved this house clean and nicely stocked
pool was warm and sparkling clean
the house was clean and in order upon arrival
it was very clean when we arrived and nelly (owner) was responsive prior during and after our stay
Host:
being pet friendly was a wonderful bonus
plenty of room to spread out inside and out nelly the owner is so sweet
Location:
good location in proximity to restaurants and beaches
it was the perfect place for 6 adults to get away and relax over the holidays
Read more reviews

6. General Williams Estate House, Lenox/Stockbridge, The Berkshires (from USD 850)

Live in luxury when you book this home situated close to the towns of Stockbridge and Lenox. This 6-bedroom home conveniently sleeps up to 16 people and each bedroom has its own bath. Relax in the estate’s private pool surrounded by luscious greenery. The spacious accommodation gives maximum privacy, with the property sitting on 4 acres (1.6 ha) of land. At the same time, it is situated in a convenient location, with Stockbridge Center just 2 mi (3.2 km) away from the estate.

General Williams Estate House Lenox/Stockbridge
87 reviews  Wifi Available
House 16 Guests 6 Bedrooms 6 Bathrooms

Accommodates: 16
Minimum Nights: 2
Refund Policy :

Top guest reviews
Amenities & Room:
the house is large and comfortable and there was plenty of space for our family
the kitchen is well stocked too with nice plates and everything you need
Cleanliness:
the house was clean and easy access to town and mountains
Host:
the owner was so helpful and responsive when i had any questions
andrea was very responsive to our inquiries beforehand and while we were staying
Location:
incredible house and great location
love the house and location
the proximity to shops and restaurants is perfect
the location was great next to lee and stockbridge
location is great house has plenty of room inside and out
Read more reviews

7. The Clearing, Cummington (from USD 128)

This cozy cottage located in Hampshire County, sits on top of a hill that changes hues every season. Visit in the winter and see a beautiful white landscape. Autumn brings warm colors from the surrounding trees, and in summer, the property is surrounded by greenery. Summer is the perfect time to use the property’s outdoor pool. It has one bedroom and can sleep up to three people. While you’re here, do explore the wonderful landscapes of Chesterfield Gorge, which is about 2.4 mi (3.9 km) away from the cottage.

Clearing - quiet - close to nature
Cummington, MA, US
1 Bedroom 1 Bathroom

8. Sweet Dreams Retreat, Sandisfield (from USD 235)

This lovely house in Sandisfield is perfect for a couple who wants to spend a romantic week together. With a minimum stay of three to six nights, get to enjoy the property’s beachy cottage feel that harkens to Massachusetts’s sandy shores. Located about 1.5 mi (2.4 km) from Sandisfield center, the property also offers easy access to Riska Apple Farm a few steps from the apartment. Apple picking is a great activity in the fall, while in summer (June until August), the property opens its outdoor pool. If you’re not visiting in the summer, you can still enjoy the property’s hot tub, and indoor and outdoor fireplace.

Sweet Dreams Retreat
27 reviews  Wifi Available
guest house 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
all great places for reading coffee and being cozy on crisp mornings and evenings
the apartment was clean comfortable and the amenities were great
the bed was the most comfortable bed i
bedroom is very pretty it’s nice linens and a king size bed which was especially nice
Cleanliness:
very clean with great touches
the place was clean and tastefully decorated
everything was very clean and fresh and clearly new and well thought out
Host:
the hosts were very kind and helpful
the hosts were so helpful and kind
host was very friendly and responsive
had the opportunity to chat with the owners a couple of times
the sweet dream retreat is lovingly built by the owner
Location:
beautiful location as well
the location is rural quiet and peaceful
it is close to the cute town of north barrington and surrounded by beautiful state forests
there were also many lovely places to visit for walks and hikes just a short drive away
this new listing popped up situated in a place know for its fall beauty
Read more reviews

9. Gorgeous apartment with pool access, Boston (from USD 412)

This modern apartment in Boston offers an open living space with floor-to-ceiling windows. The apartment is on the 11th floor, so you have a beautiful view of the city. Outside, you can view the street contrasted by the luscious greenery. The apartment also has a fully functional modern kitchen with an island, great for hosting a small get-together with family or friends. Staying in the property gives guests access to the building pool and other entertainment facilities. Boston University is just 1.5 mi (2.4 km) away from the property.

Amazing view 2br apt in Boston
6 reviews  Wifi Available
Apartment 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Host:
he was very quick to get back to me and so helpful and courteous
Location:
we loved it it was beautiful and walking distance to lots of stuff
Read more reviews

10. Luxurious estate with a private pool and beach, Ellisville

Live close to the water at this secluded property sitting on 10 acres (4 ha) of land. You don’t have to drive far to reach the beach. The property has a pathway leading you to a private beach. It also has a private pool and a hot tub open all year round. The property is surrounded by luscious greenery and a spacious lawn, great for family activities. The rooms are strategically built so you can have a view of the Atlantic Ocean from all the floors. In addition to this, the property also has access to a private pond, which is just a few steps away from the house, before you reach the beach.

10 Acres Ocean Estate, Private Deeded Beach, hot tub, Pool
Plymouth, MA, US
6 Bedrooms 7 Bathrooms

Cool off in a house with private pool

Whether you’re into history, modern culture, adventure or nature, Massachusetts has a place for you to explore. And to unwind after a long day of sightseeing, take a relaxing dip in the pool back at your vacation home. Dive into our above selection of vacation rentals with private pool in Massachusetts, USA.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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