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 October 27, 2025.
1. Spacious four-bedroom retreat in the Berkshires, Richmond
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.
Richmond, Massachusetts, United States
2. Expansive house with ample driveway parking, Bourne
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.
Bourne, Massachusetts, United States
3. Elegant manor with a fenced yard, Sandwich
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.
Sandwich, MA, US
4. Well-located retreat with a fenced backyard, Mashpee
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.
Mashpee, Massachusetts, United States
Top guest reviews
Host:
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 surpriseLocation:
beautiful property in a quiet neighborhood close to johns pondquite location makes for a good nights sleepexcellent location great cleanliness and reasonably pricedCleanliness:
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 wineRead more reviewsAmenities & Room:
loved all of the extra amenities including the patio heater fire pit and corn hole
5. Beautiful oasis with a hot tub and sauna, Provincetown
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.
Provincetown, Massachusetts, United States
Top guest reviews
Host:
the owner was very responsivethe owner is very responsiveour host was so welcoming and helpfulted was an excellent hostowner ted was very welcoming and friendlyLocation:
great location walk to town and beachhad amazing walks into the dunes with main trail entrances literally 5 minutes away from the houseCleanliness:
it is super clean and is stocked with all you will needRead more reviewsAmenities & Room:
the kids enjoyed floating in the pool and sitting out on the deck in the eveningsgreat amenities from pool to hot tub to sauna
6. Family-friendly abode with a seasonal pool, Nantucket
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.
Nantucket, MA, US
7. Peaceful hideaway with three bedrooms, Worcester
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.
Worcester, Massachusetts, United States
Top guest reviews
Host:
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 itLocation:
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 badCleanliness:
this is our 3rd stay at tania's beautiful house; it's clean modern and cozyRead more reviewsAmenities & 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 family
8. Spacious four-bedroom flat near the beach, Falmouth
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.
Falmouth, Massachusetts, United States
Top guest reviews
Host:
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 daughterLocation:
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 townCleanliness:
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 spaciousRead more reviewsAmenities & 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 trundle
9. OB Pool House, Oak Bluffs
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.
Oak Bluffs, Massachusetts, United States
Top guest reviews
Cleanliness:
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 problemsRead more reviewsAmenities & 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 lovely
10. Homey lodging near South Cape beach, Mashpee
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.
Mashpee, Massachusetts, United States
Top guest reviews
Host:
dina was pleasant and responsive to questionsthe owner was great to work withdina was very responsive before and during our stayLocation:
great location and propertythe neighborhood and location were very niceclose to restaurants and great beachesthe location is perfect close to beach golfing shops and restaurantsCleanliness:
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)Read more reviewsAmenities & 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 enjoy
11. Katama Luxury, Edgartown
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.
Edgartown, Massachusetts, United States
Top guest reviews
Host:
spotlessly clean and a friendly host/owner who checked in to make sure all was wellLocation:
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 locationsCleanliness:
the home has comfortable beds clean bathrooms and a nice sized side yard with heated poolRead more reviewsAmenities & Room:
the kitchen was well stocked and made cooking easy
12. Cozy, colonial-style home for 10, Edgartown
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.
Edgartown, Massachusetts, United States
Top guest reviews
Host:
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 helpfulLocation:
we definitely needed a different location for thanksgivingthe house the grounds and the location all make for a terrific place to stayCleanliness:
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 outRead more reviewsAmenities & 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 most
13. Spacious property for eight, West Barnstable
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.
Barnstable, Massachusetts, United States
Top guest reviews
Host:
being pet friendly was a wonderful bonusplenty of room to spread out inside and out nelly the owner is so sweetLocation:
good location in proximity to restaurants and beachesit was the perfect place for 6 adults to get away and relax over the holidaysCleanliness:
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 stayRead more reviewsAmenities & Room:
pool and spacious deck can be enjoyed after a beach dayour favorite features of the house were the outdoor deck and the pool
14. General Williams Estate House, Lenox/Stockbridge, The Berkshires
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.
Stockbridge, Massachusetts, United States
Top guest reviews
Host:
the owner was so helpful and responsive when i had any questionsandrea was very responsive to our inquiries beforehand and while we were stayingLocation:
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 outCleanliness:
the house was clean and easy access to town and mountainsRead more reviewsAmenities & 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 need
15. The Clearing, Cummington
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.
Cummington, Massachusetts, United States
16. Sweet Dreams Retreat, Sandisfield
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.
Sandisfield, Massachusetts, United States
Top guest reviews
Host:
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 ownerLocation:
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 beautyCleanliness:
very clean with great touchesthe place was clean and tastefully decoratedeverything was very clean and fresh and clearly new and well thought outRead more reviewsAmenities & 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 nice
17. Gorgeous apartment with pool access, Boston
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.
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 courteousRead more reviewsLocation:
we loved it it was beautiful and walking distance to lots of stuff
18. 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.
Plymouth, MA, US
19. Private pool house at New Seabury Resort, Mews Village
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.
Accommodates: 6
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 14 days before check-in.
Top guest reviews
Host:
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 helpfulLocation:
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)Cleanliness:
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 poolRead more reviewsAmenities & 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 pool
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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