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, whether in luxury cabins or Airbnb tiny houses. For the best accommodation options, continue reading to learn about the top vacation rentals with private pool in Massachusetts, USA.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 11, 2024.
1. Spacious four-bedroom retreat in the Berkshires, Richmond (from USD 409)
This spacious rental, nestled on 2 acres (0.81 hectares) amid the gorgeous Berkshires, is a 3-minute ride from downtown West Stockbridge and Great Barrington is a 20-minute drive away.
Lounge in the family room and watch a show on the 60-inch (152.40-centimeter) TV or hang out in the sunroom. Remote workers can work in the office and use Wi-Fi to attend Zoom meetings.
Enjoy a refreshing swim later in the outdoor heated pool, available from Memorial Day through Labor Day. If you are visiting with young children, you are advised to watch out during their time in the pool. Signing a pool waiver is mandatory and while a designated amount of propane is supplied for heating the pool, should you exceed it, you can purchase some more at the market rate. The patios are where you can relish your morning coffee or have dinner in an alfresco setting.
2. Expansive house with ample driveway parking, Bourne (from USD 428)
This cozy three-bedroom rental features an in-ground pool in the fenced-in backyard, open from Memorial Day to October, depending on the weather. You can bask in the sunshine after your swim in the seasonal heated pool while resting on the loungers or relax with a drink while watching your kid splash about and play with pool noodles and floats.
Thanks to the outdoor dining, you can enjoy alfresco meals admiring the azure pool and plan a cookout under the sky with the barbecue grill.
The home is strategically located close to shops, lakes, and beaches. Cape Cod Canal is a short walk away where you can go fishing or stroll with your companions. Don’t wish to dine outside? Prepare a scrumptious meal in the fully equipped kitchen and enjoy your food at the sunroom dining table. Other amenities include ample parking, high-speed Wi-Fi, and Xbox One for indoor entertainment.
3. Elegant manor with a fenced yard, Sandwich (from USD 299)
Moon Compass Manor is a tastefully appointed rental near several beaches on both the bay and the Atlantic. If the salty waves and white sands are not your thing, however, you can swim in the private pool of the rental instead. This amenity is open to guests from Memorial Day to Labor Day. It is also placed out in the fenced yard, surrounded by sitting areas and greenery.
Indoor features of the manor include cooking basics in the kitchen, a flat-screen TV in the living room, and complimentary Wifi throughout the whole place.
4. Private pool house at New Seabury Resort, Mews Village (from USD 275)
This lovely pool house is nestled in the luxurious New Seabury Resort. When you’re not playing golf on the putting green or taking a stroll on the beach less than a mile away, you can enjoy refreshing swims in this rental’s pool, which is surrounded by a fence for privacy. The pool deck also comes with lounge chairs for relaxation and dining furniture for alfresco meals.
Inside the house are modern conveniences, including air conditioning, Wifi, and a Smart TV. With a parking space available on the property, guests can bring their cars so they can easily reach nearby points of interest such as concert venues and shops.
Top guest reviews
Amenities & Room:
) our only suggestion is we could have used one more comfortable chair in the living roomthe home is quite spacious with all the amenities to make a very comfortable staythis was a very well kept house with a pleasant outdoor area and a very nice poolCleanliness:
not only was it exceptionally clean there was an attention to details (ethe house and pool were clean and a perfect size for our family of fourlovely clean comfortable well-equipped patio home with poolHost:
dealing with the owner is also very easy and problem freenice condo with everything you could need provided by ownerlarry the owner was extremely communicative and helpful making our stay a memorable onethe extra condiments in the kitchen are very helpful salt container was emptylarry was very responsive and helpfulRead more reviewsLocation:
the location was ideal for location to beachessuper close to the beachclose to beaches golf mashpee commons and the bike trail for a nice ride to woods holethe house is close to shopping and fun cape things to doperfectly located near shopping/outlets short drive to beaches and falmouth (with nice shops and restaurants)
5. Well-located retreat with a fenced backyard, Mashpee (from USD 196)
This vacation rental offers guests a wonderful getaway filled with fun activities – from biking through the trails of Mashpee to enjoying live music at the nearby New Seabury Resort. Just steps away from the property is the beautiful John’s Pond, great for swimming, fishing, and boating. Guests will have no shortage of things to do during their stay.
After a long, adventurous day, guests can soak in the private pool in the fully fenced backyard. This above-ground amenity is placed beside the fire pit area and hammock. Other conveniences that come with the rental include air conditioning, Wifi, a Smart TV, and an attached garage. Water sports items such as boogie boards and skim boards are also provided.
Top guest reviews
Amenities & Room:
loved all of the extra amenities including the patio heater fire pit and corn holeCleanliness:
clean and had everything we neededplace was so clean and invitingthe house was exceptionally cleanthe house was clean and very well stockedthe home was spotless and we were welcomed with cape cod chips and a bottle of wineHost:
we enjoyed all the owner was terrific & responded to all questions very fasteli was easy to communicate with and responsivethe property is exactly as pictured and communication with the owners was excellentcommunication with the owners was great and we appreciated the sweet welcome surpriseRead more reviewsLocation:
beautiful property in a quiet neighborhood close to johns pondquite location makes for a good nights sleepexcellent location great cleanliness and reasonably priced
6. Beautiful oasis with a hot tub and sauna, Provincetown (from USD 851)
Perched on a bluff, Oasis House is an ideal getaway spot, especially for those who prefer long-term stays. Its unique location rewards guests with incredible views of Provincetown Harbor, the Province Lands’ dunes, and downtown Provincetown. It also comes with modern conveniences, including Wifi, air conditioning, cable TVs, and a hot tub – not to mention a redwood sauna for guests who want a good sweat session! To top it all off is the large heated pool on the deck. It is built on the ground and surrounded by greenery.
Guests who want to explore the area can easily get to public beaches and other attractions.
Top guest reviews
Amenities & Room:
the kids enjoyed floating in the pool and sitting out on the deck in the eveningsgreat amenities from pool to hot tub to saunaCleanliness:
it is super clean and is stocked with all you will needHost:
the owner was very responsivethe owner is very responsiveour host was so welcoming and helpfulted was an excellent hostowner ted was very welcoming and friendlyRead more reviewsLocation:
great location walk to town and beachhad amazing walks into the dunes with main trail entrances literally 5 minutes away from the house
7. Family-friendly abode with a seasonal pool, Nantucket (from USD 650)
Featuring a strategic location and a well-appointed living space, this four-bedroom home is a perfect getaway spot for you and your loved ones. It is conveniently located near beaches, bike paths, restaurants, and gourmet supermarkets. The rental also offers a heated saltwater pool that is open from Memorial Weekend until the first week of October. The pool area does not come with shared access so you can enjoy total privacy during your stay.
Inside the rental are Wifi, board games, and a Smart TV for indoor entertainment. You can also book a Thai massage with the host to complete your relaxing getaway.
8. Peaceful hideaway with three bedrooms, Worcester (from USD 240)
Enjoy a peaceful getaway when you stay in this three-bedroom resort. It boasts a beautiful outdoor pool where family and friends can have fun swimming and sunbathing. Show your cooking skills in the fully equipped kitchen and have delightful meals in the dining room.
There is also a table on the pool deck where you can eat or have evening drinks. You will find a projector in the living room, perfect for late-night movies. Each bedroom is furnished with cozy beds and can sleep a total of six people comfortably.
Top guest reviews
Amenities & Room:
our family enjoyed the spaciousness of the home large kitchen comfortable beds and soothing outdoor water featurewe appreciated the well-equipped kitchen the very comfortable beds and the projection tvthe yard was beautiful with waterfall budda outdoor fire pit hammock gazebo and of course the poolthe backyard and the pool provided hours of fun for the familyCleanliness:
this is our 3rd stay at tania's beautiful house; it's clean modern and cozyHost:
the vrbo site was user friendly and detailedtania the owner is wonderfultania was extremely helpful and hospitable and responded to texts within minutestania was always friendly and super responsive to any issues that we hadand she was very helpful in getting our roku unit working with itRead more reviewsLocation:
the location is very safe and quietyou can get around from this location very wellwell appointed and in a lovely peaceful locationand oh yes the neighborhood is wonderfully quiet at nighti also realized it was an ideal location for negotiating worcester where the traffic is pretty bad
9. Spacious four-bedroom flat near the beach, Falmouth (from USD 694)
This spacious home is only seven minutes away from the sunny and sandy beach. If you just want the smell of sea breeze but don’t want to come out of your beautiful rental, you can also just enjoy swimming in the saltwater pool.
This flat features a large kitchen, fully equipped with stainless steel appliances and a six-seater dining set. It has a living room with a flat-screen TV and a family room with comfy sofas. There are four bedrooms, two of which include a private bath and TV.
Top guest reviews
Amenities & Room:
gorgeous the decor the natural light the warm pool large table for family dinners the amazing grillthe pool is lovely and totally secluded from the neighbor’s viewthe other 2 rooms were perfect for the kids with one having a bunk bed with trundleCleanliness:
extremely clean which is very important to methe house was beautiful very clean comfortable and privateplenty of space very clean and well furnished with well outfitted kitchenthe beds are very comfortable and both primary suites are spaciousHost:
they were lovely hostsowner is very positive and communicativethe host family kate and frank are very thoughtful and responsivekate and frank are incredibly friendly kind and prompt in responsesthey also left the most kind welcome basket with items for us and our daughterRead more reviewsLocation:
location is great - private but close to everything definitely a great vacation spotit’s in a great location a short walk to wood neck beach and a quick drive into townwarm pool spacious rooms comfy linens … and a great secluded spot close to town
10. OB Pool House, Oak Bluffs (from USD 890)
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.
Top guest reviews
Amenities & Room:
a/c worked verify well as it was warm the week we stayedvery roomy nicely designed and the pool and hot tub are definitely a plusbeautiful home and the pool/spa is awesthe backyard pool and all around decor was lovelyRead more reviewsCleanliness:
the beds/couches were all so comfortable and the house spotlessoverall we had a wonderful time we had a few issues with cleanliness and freezer problems
11. Homey lodging near South Cape beach, Mashpee (from USD 400)
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.
Top guest reviews
Amenities & Room:
the pool and yard was perfect for us we enjoyed our stay quite a bitthe yard is totally private and has a perfect sized pool for a family to enjoyCleanliness:
the house was clean and well-maintainedvery clean and very nice accommodationswell maintained property and extremely cleanit was beautiful and very cleanclean spacious quiet and with a wonderful pool (with fun inflatables)Host:
dina was pleasant and responsive to questionsthe owner was great to work withdina was very responsive before and during our stayRead more reviewsLocation:
great location and propertythe neighborhood and location were very niceclose to restaurants and great beachesthe location is perfect close to beach golfing shops and restaurants
12. Katama Luxury, Edgartown (from USD 764)
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.
Top guest reviews
Amenities & Room:
the kitchen was well stocked and made cooking easyCleanliness:
the home has comfortable beds clean bathrooms and a nice sized side yard with heated poolHost:
spotlessly clean and a friendly host/owner who checked in to make sure all was wellRead more reviewsLocation:
in summer it would be ideal positioned close to the bike pathwhat a joy perfect location to the beach and to downtown we rode bikes everywherean easy 10 min cycle to both locations
13. Cozy, colonial-style home for 10, Edgartown (from USD 862)
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.
Top guest reviews
Amenities & Room:
kitchen is very well equipped with most any tool/appliance you could needthe ping-pong room with big screen tv was a huge bonus for usplenty of room for 7 of us adults and we so enjoyed the common areas to gather inwe loved the open kitchen/dining room/peninsula floor plan where we congregated the mostCleanliness:
it is large clean and convenient to everythingso glad to have stayed in this spacious and clean home when we were in mv for ourfriends' weddingthe downstairs of the house is very spacious comfortable and well-laid outHost:
sue was an incredible host answered all questions immediately offered great advice and provided a lovely homethe house was beautiful and the owners were very nice and helpfulRead more reviewsLocation:
we definitely needed a different location for thanksgivingthe house the grounds and the location all make for a terrific place to stay
14. Spacious property for eight, West Barnstable (from USD 429)
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.
Top guest reviews
Amenities & Room:
pool and spacious deck can be enjoyed after a beach dayour favorite features of the house were the outdoor deck and the poolCleanliness:
we loved this house clean and nicely stockedpool was warm and sparkling cleanthe house was clean and in order upon arrivalit was very clean when we arrived and nelly (owner) was responsive prior during and after our stayHost:
being pet friendly was a wonderful bonusplenty of room to spread out inside and out nelly the owner is so sweetRead more reviewsLocation:
good location in proximity to restaurants and beachesit was the perfect place for 6 adults to get away and relax over the holidays
15. 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.
Top guest reviews
Amenities & Room:
the house is large and comfortable and there was plenty of space for our familythe kitchen is well stocked too with nice plates and everything you needCleanliness:
the house was clean and easy access to town and mountainsHost:
the owner was so helpful and responsive when i had any questionsandrea was very responsive to our inquiries beforehand and while we were stayingRead more reviewsLocation:
incredible house and great locationlove the house and locationthe proximity to shops and restaurants is perfectthe location was great next to lee and stockbridgelocation is great house has plenty of room inside and out
16. The Clearing, Cummington (from USD 150)
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.
17. Sweet Dreams Retreat, Sandisfield (from USD 332)
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.
Top guest reviews
Amenities & Room:
all great places for reading coffee and being cozy on crisp mornings and eveningsthe apartment was clean comfortable and the amenities were greatthe bed was the most comfortable bed ibedroom is very pretty it’s nice linens and a king size bed which was especially niceCleanliness:
very clean with great touchesthe place was clean and tastefully decoratedeverything was very clean and fresh and clearly new and well thought outHost:
the hosts were very kind and helpfulthe hosts were so helpful and kindhost was very friendly and responsivehad the opportunity to chat with the owners a couple of timesthe sweet dream retreat is lovingly built by the ownerRead more reviewsLocation:
beautiful location as wellthe location is rural quiet and peacefulit is close to the cute town of north barrington and surrounded by beautiful state foreststhere were also many lovely places to visit for walks and hikes just a short drive awaythis new listing popped up situated in a place know for its fall beauty
18. Gorgeous apartment with pool access, Boston (from USD 474)
This house rental with an indoor pool in Massachusetts offers an open living space with floor-to-ceiling windows. This 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 on the property gives guests access to many entertainment facilities. Boston University is just 1.5 mi (2.4 km) away from the property.
Top guest reviews
Host:
he was very quick to get back to me and so helpful and courteousRead more reviewsLocation:
we loved it it was beautiful and walking distance to lots of stuff
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.
Frequently asked questions about vacation rentals with a private pool in Massachusetts
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