Home to the famous Harvard University and the country’s first subway, Massachusetts features plenty of interesting places for tourists to visit. It also offers a lot of mouthwatering homegrown dishes that will leave visitors wanting more. If you are traveling with your family, visit the Boston Children’s Museum, one of the US’ oldest museums for kids. In addition, Cape Cod is a famous summer destination that you should not miss, boasting pristine beaches and quaint villages. Signature dishes in the state include clam chowder, Boston cream pie, and lobster rolls. With plenty of things to do and see here, it is important to book accommodations where you can relax and have fun. For options, scroll down to see the best Airbnbs with pool in Massachusetts, USA.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 12, 2024.
1. Spacious five-bedroom home, East Sandwich (from USD 523)
Cape Home features spacious accommodations and modern conveniences such as a washer and dryer, air conditioning, and a dishwasher. The property can host up to 12 guests, offering 5 bedrooms to ensure that there is plenty of space for your whole crew to move around.
If you want to go outdoors, there is a nearby private beach that you can visit. There is a private heated pool with lights on the premises for those who do not want to go out, and this is available from the weekend before Memorial Day to early October. A TV in the living room and a complimentary WiFi connection are also available for entertainment.
Top guest reviews
Amenities & Room:
the wifi was great and the space is lovelypool is heated and great patiocouch was so comfortable that i'm going to buy onethe house is as described and we really enjoyed the swimming poolthe heated pool is always amazing tooCleanliness:
everything was very clean and had an abundance of nice towels which i lovedthe house is very comfortable and cleanHost:
weiguo was a nice hostweiguo is a great host he is quick to answer any questions and fix any issuesweiguo is a fantastic hostweiguo was a great host very quick to respond to any questionsweiguo was a fantastic hostRead more reviewsLocation:
great location short walk to a private beach great back yard with fantastic pool with 100%privacyamazing house 3 minute walk to the beach and plenty of room for two familiesamazing home with a great pool and perfect location near a private beachand with the beach so close to the house it was easy to setup the perfect family photoshootbeautiful for taking a walk or sitting for a while and taking pictures
2. Spacious family-friendly home with sunroom, Dalton (from USD 449)
This 9-acre (3.6-hectare) property with four bedrooms features clean, stylish, and spacious interiors, ideal for groups of eight. It has a sunroom with plenty of seating and beautiful views, a great spot for just sitting back and relaxing. For guests who need to get some work done, there is a library where you can enjoy some quiet time to focus on your tasks.
If you are visiting during summer and would love to take advantage of the weather, there is an on-site pool where you can do laps. For families who are traveling with their kids, there is a tipi tent and a kitchen for young ones.
Top guest reviews
Amenities & Room:
the house is beautifully decorated lots of cosy furniture really well equipped kitchenthis house is perfect for groups - very spacious with plenty of living rooms (plural ) to spread out inthe kitchen is really well stocked with plates cups utensils etcCleanliness:
the house is clean roomy and well appointedwe loved our stay very clean and lots of nice touchesthe pool was clean and lots of pool toys to play withvery clean and welcoming homevery clean comfortable and stylish we had a great timeRead more reviewsLocation:
the house is great cozy and spacious and a great location for cute berkshire dining/shopping and outdoor funvery peaceful setting well stocked close to townthe house felt secluded but within close proximity to lenox jimmy peak and other berkshire attractions
3. Craigsville, Barnstable (from USD 450)
This massive 4-bedroom house offers 4,500 sq. ft. (418 sqm) of space to accommodate 10 guests. It features amenities that are perfect for those looking for a fun vacation with their loved ones. For a memorable get-together with the whole family, there is an indoor pool on the property that you can use. You can request pool toys for free and water heating for an extra fee.
This rental also features a game room with air hockey and Xbox to keep everyone entertained. Family holidays will not be complete without deliciously cooked meals. Don’t worry as there is a fully equipped kitchen here as well. After a busy day, have a relaxing soak in the hot tub in the main bathroom.
Top guest reviews
Amenities & Room:
there are a lot of amenities and the pool/outdoor space was fantasticget the pool heated the extra 6 degrees is well worth it especially in the winter monthswifi and multiple tv's were also appreciatedair hockey table in the room adjacent to the pool is a nice touchfor an extra fee kirill will heat it to 84 degrees which was quite comfortableCleanliness:
the house was very clean and spacious- house is very cleanthe whole house was very cleanbeds were so comfortable and entire house was very cleankirill's place is nice and clean and spaciousHost:
kirill was a great hostgreat host and super responsivehost was available and very responsivethe host was extremely responsive and friendly in his communicationsgreat host everything you need is thereRead more reviewsLocation:
the location was fantasticgreat location we would definitely consider staying here againgreat location for delicious food and activitieskids loved the indoor pool and the location was perfectit's also easy to get to martha's vineyard or nantucket from this location
4. Private suite near North Shore beaches, Beverly (from USD 85)
Nature lovers and history buffs will have a great time at this private suite near North Shore beaches and historical sites. The suite is complete with a separate entrance and a private bathroom. It also features a bedroom with a king-sized bed and a living area with a sofa bed for extra sleeping space.
A coffee station is also available, great for those who like to start their day with caffeine. There is a mini-refrigerator to ensure that you have cold drinks throughout the day. For a refreshing stay, you can go for a relaxing swim at the rental’s pool deck that’s open from June through September. The host provides pool towels, too. Note that guests under 18 years old must be supervised by an adult if using the pool.
Top guest reviews
Amenities & Room:
coffee was great bed was huge and comfortablethe bed is incredibly comfortable and the whole space is big buy cozywonderful comfortable and fantastic location stayed here with my sister and niece for a weekend whale watching tripthis is a nice little space with it's own living roomCleanliness:
very clean interior great communication and kind hoststhe suite was clean and cozythe place was spotless and the bed was very comfortableveronica's place was quaint clean and affordablethe rental was very clean and had a great bedHost:
veronica was very helpful and kindthe host communicated very wellveronica was easy to communicate with and was a great hostveronica is incredibly friendly and very helpful with quick responses every timehost was very friendly and quick to respondRead more reviewsLocation:
wow great location near gordon collegealso very close to a beautiful walking park along the coastgood location to the highwaygreat location with quiet surroundingsthe house was great and location was ideal
5. Country Cottage in the City, Dedham (from USD 129)
This one-bedroom cottage is a great choice for couples on a romantic getaway in Dedham. Nestled in the woods, Country Cottage in the City provides plenty of privacy, ideal for those who want a quiet retreat amidst nature. Spend some quality time with your loved one at the on-site swimming pool located beside two ponds with decorative fish.
For a memorable dining experience at the rental, you can prepare a savory meal for your partner using the gas grill. A bus stop is nearby if you want to visit the city’s top attractions. The area is also accessible to ride-hailing applications such as Uber.
Top guest reviews
Amenities & Room:
cozy space in a lovely wooded setting comfortable bed and furniture pleasant decor friendly and helpful hosts nearbypool and patio seating for good weather beautiful gardenwonderful charming rustic cottage with a pool fishpond and waterfallthe setting overlooking the pool is lovely and the garden meticulously maintaineda small fridge coffeemaker toaster and misc kitchen utensils were helpful to have on handCleanliness:
the cottage was clean and cozyclean quiet and conveniently locatedit is clean inside with everything you could want for your staya quiet space that is clean comfortable and feels like homeit was clean comfortable and mark was a wonderful hostHost:
exceptionally nice and helpful hostshighly recommend great hostshe was a super friendly host without being overbearing and made sure we had everything we neededthe hosts were very friendly overall a great experiencemark is great hostRead more reviewsLocation:
great location nestled away in the woodland but a short drive to everything you could needthis was in a great locationnot walking distance from town thus very peaceful and quieti would recommend anyone visiting to consider this locationmark's place is so cute and such a great value
6. Suite for five guests in a farm, Rutland (from USD 135)
It is always exciting when you are traveling with a group. What’s makes it even better is finding accommodations that suit everyone’s needs. In this suite on a small farm, you will find a sofa bed, a bunk bed, an air mattress, and a floor mattress, perfect for five guests. The rental has a kitchen with a microwave and a small refrigerator for convenience.
There is a playground and a trampoline at the property for kids who want to have fun outdoors. A swimming pool is also available, and you can request floaties from the host. There is complimentary WiFi on the premises to ensure you stay updated.
Top guest reviews
Amenities & Room:
the small apartment is comfortable for a weekend staythe property is great with lots of activities for kids like trampolines swings pool etcCleanliness:
apartment is clean and well furnishedthe room was updated and cleanthe space is clean and has everything you'll needclean spacious and a lot of fun highly recommendedthe apartment was clean and just right for usHost:
the hosts are wonderfulthe farm is delightful and roger was a consummate hostexcellent and helpful hostsme and my family had a great time everyone is so friendly and welcomingwe enjoyed feeding animals beautiful and friendly atmosphere vegetables roger let us pick for cookingRead more reviewsLocation:
lovely peaceful location for a quick getaway from boston with the familythe are has many interesting placessuper cool to walk around and see all the farm animalsgreat place to stay and get awaysuper friendly clean great location to get out and unwind
7. Three-bedroom property with private balcony, Hopkinton (from USD 127)
Ideal for a big group of travelers, this three-bedroom property features plenty of spaces where you can relax and have fun with the whole gang. There is a furnished private balcony, a great spot to lounge, enjoy nice outdoor views, and listen to some good music. You can also go for a quick dip at the property’s hot tub while sipping on your favorite wine.
If you are visiting during summer and want to cool off for a bit, you can use the on-site outdoor swimming pool. A fully equipped kitchen where you can prepare delicious meals is also available. Note that the host stays on the property, so you can easily communicate with him whenever you need assistance.
Top guest reviews
Amenities & Room:
it was just as described in the listing and very comfortablevery comfortable place to stay in a beautiful wooded areagreat place to stay lost of room and comfortablethe pool is the awesome but the best part of the house was the deck and the bbqwe almost felt like this airbnb was more of a shared space private room type of airbnbCleanliness:
everything was very clean and organized when we arrivedthe space is clean and has everything you would needthe pool was the best thing it was very clean inside and the area around the pool aswellhis house is very nice and cleanhis place is great too everything was clean & convenientHost:
wonderful home and a hospitable hostgreat host and beautiful propertywonderful place with great hostsuch an accommodating and gracious hostbrad is welcoming friendly and a great hostRead more reviewsLocation:
the location was just perfect for my purposesbrad’s place is in an excellent location right between boston and worcestergreat place to stay will stay again if we are in the areaall in all i highly recommend this placemy boyfriend and i wanted a nice relaxing weekend away and brads place was the perfect fit
8. Cozy accommodation for five guests, Holliston (from USD 143)
This homey accommodation for five guests features two bedrooms and plenty of modern conveniences for an enjoyable stay. It has central air conditioning and heating facilities to keep you comfortable in any weather. A washer and a dryer are also available to ensure that you do not run out of clean clothes.
You can also access various amenities on the premises, such as a shared swimming pool with a waterfall and a hot tub if you want to unwind and have fun with your loved ones. There are also loungers by the pool if you want to relax and enjoy the warmth of the sun.
Top guest reviews
Amenities & Room:
fresh flowers were left on tablethe apartment was beautiful and perfectly equipped with the delight of having coffee machine and supplies on arrivalit was very comfortable and easily fit our family of 4beautiful yard and pool toothe place was fully equipped and comfortableCleanliness:
very clean and quietspace was very clean and neatvery clean and enjoyed the dog and cat toothe apartment is beautiful and extremely clean and comfortablethe house was clean with plenty of spaceHost:
mike is a great hostmike was a great host both welcoming and friendly and we enjoyed our interaction with himmike was very accommodating and helpful as a hostgreat host and easy to communicate withmike was a great host everything was as promised in the descriptionRead more reviewsLocation:
love the location of the housewalking distance to some good restaurantsgreat location with shopping and places to eatmichael's place was perfect for us the ideal place for kidsgreat location beautiful yard and pool
9. Two-bedroom rental near public transportation, Medford
Situated near public transportation, restaurants, and bars, this three-bedroom property is a great choice for guests looking to have a great time in Medford. It features two bedrooms with comfortable beds and quality beddings to ensure a good night’s rest. The rental also has a private bathroom with towels and bath essentials for a hassle-free stay.
For guests who want to stay active during their vacation, there is a swimming pool here where you can do laps. If you prefer a quiet night inside, there are plenty of books that you can read while lounging on the living room’s plush couch.
Medford, Massachusetts, United States
31.54 km (19.6 mi) from Sri Lakshmi TempleSuperhost
Accommodates: 4
Top guest reviews
Amenities & Room:
the large sectional couch in the living room was extremely comfortable for lounging and nappingthe accommodation is roomy with a comfortable sofa and bedsthe set up is great with 2 beds in one room and one more private roomCleanliness:
very clean and spaciousvery clean and quietsuper clean and super easyeverything was clean and comfysteve's place is clean and comfortableHost:
the host was helpfulstephen was a wonderful hoststephen was a great hoststeve is a fantastic hostthe host also give you your privacy and let you enjoy your stayRead more reviewsLocation:
close to public transportation and tons of great restaurants close bythe location is greatgreat location not too far from bostonperfect location for a tufts visitgreat place walking distance to downtown
10. Studio apartment with lots of recreational spaces, Middleborough (from USD 105)
If you want to go on a romantic getaway where recreational facilities are right under your nose, this studio apartment might be a great choice. Enjoy bonding with your loved one at the on-site swimming pool with a slide and a diving board. Then, roast some s'mores on the firepit by the pool. If you want to stay on track with your fitness goals, there are tennis and basketball courts that you can use.
For some quality time indoors, there is a TV with Netflix and other streaming services where you can watch your favorite shows. In the morning, enjoy some freshly brewed coffee and muffins from the fully stocked kitchen. If you want a memorable dining experience, you can use the barbecue facilities by the pool to prepare savory meals for your partner.
Top guest reviews
Amenities & Room:
the studio was very clean and we enjoyed the amenities including wifi large-screen television and poolwe were really impressed by the kitchen as it had enough equipment for some more complex mealsboth the bed and hide-a-bed are very comfortableCleanliness:
extremely clean and comfortable unit where our family was able to relaxit was very clean lots of space and a great yard with pool and moreHost:
paul was so helpfulpaul’s hospitality was excellent and he and his wife are very accommodating hostgreat little touches from the hostpaul is a great host who is informative polite and communicates greatpaul is an incredible host and the apartment was lovelyRead more reviewsLocation:
the location is convenient to the freeway quiet and safequiet neighborhood but connects to major roads easilyif you are looking for a place to stay this is definitely where you want to be
Enjoy the outdoors at Massachusetts
There are plenty of gorgeous places to visit in Massachusetts that are perfect for travelers of all ages. Popular attractions here also showcase the beauty of nature, making it an ideal destination for those who love the outdoors. Make sure to book one of the best Airbnbs with pool in Massachusetts, USA, for a memorable stay.
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
Create an account to