10 Best Airbnbs With Pool In Massachusetts, USA - Updated 2024

Contributing Writer
| 6 min read

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 July 08, 2024.

1. Spacious five-bedroom home, East Sandwich (from USD 650)

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.

Stayed at this property?
East Sandwich, Massachusetts, United States
104.6 km (65.0 mi) from Sri Lakshmi Temple
55 reviews   Superhost Wifi Available
ENTIRE HOME 7 Beds 12 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 12

Top guest reviews
Amenities & Room:
the wifi was great and the space is lovely
pool is heated and great patio
couch was so comfortable that i'm going to buy one
the house is as described and we really enjoyed the swimming pool
the heated pool is always amazing too
everything was very clean and had an abundance of nice towels which i loved
the house is very comfortable and clean
weiguo was a nice host
weiguo is a great host he is quick to answer any questions and fix any issues
weiguo is a fantastic host
weiguo was a great host very quick to respond to any questions
weiguo was a fantastic host
great location short walk to a private beach great back yard with fantastic pool with 100%privacy
amazing house 3 minute walk to the beach and plenty of room for two families
amazing home with a great pool and perfect location near a private beach
and with the beach so close to the house it was easy to setup the perfect family photoshoot
beautiful for taking a walk or sitting for a while and taking pictures
Read more reviews

2. Spacious family-friendly home with sunroom, Dalton (from USD 620)

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.

Stayed at this property?
Dalton, Massachusetts, United States
139.64 km (86.8 mi) from Sri Lakshmi Temple
84 reviews   Superhost Wifi Available
ENTIRE HOME 5 Beds 8 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
the house is beautifully decorated lots of cosy furniture really well equipped kitchen
this house is perfect for groups - very spacious with plenty of living rooms (plural ) to spread out in
the kitchen is really well stocked with plates cups utensils etc
the house is clean roomy and well appointed
we loved our stay very clean and lots of nice touches
the pool was clean and lots of pool toys to play with
very clean and welcoming home
very clean comfortable and stylish we had a great time
she is very responsive and easy to communicate with
min ji was also a great host
the house is great cozy and spacious and a great location for cute berkshire dining/shopping and outdoor fun
very peaceful setting well stocked close to town
the house felt secluded but within close proximity to lenox jimmy peak and other berkshire attractions
Read more reviews

3. Craigsville, Barnstable (from USD 600)

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.

Stayed at this property?
Barnstable, Massachusetts, United States
114.68 km (71.3 mi) from Sri Lakshmi Temple
79 reviews   Wifi Available
ENTIRE HOME 6 Beds 10 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
there are a lot of amenities and the pool/outdoor space was fantastic
get the pool heated the extra 6 degrees is well worth it especially in the winter months
wifi and multiple tv's were also appreciated
air hockey table in the room adjacent to the pool is a nice touch
for an extra fee kirill will heat it to 84 degrees which was quite comfortable
the house was very clean and spacious
- house is very clean
the whole house was very clean
beds were so comfortable and entire house was very clean
kirill's place is nice and clean and spacious
kirill was a great host
great host and super responsive
host was available and very responsive
the host was extremely responsive and friendly in his communications
great host everything you need is there
the location was fantastic
great location we would definitely consider staying here again
great location for delicious food and activities
kids loved the indoor pool and the location was perfect
it's also easy to get to martha's vineyard or nantucket from this location
Read more reviews

4. Private suite near North Shore beaches, Beverly (from USD 110)

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.

Stayed at this property?
Beverly, Massachusetts, United States
57.42 km (35.7 mi) from Sri Lakshmi Temple
682 reviews   Superhost Wifi Available
Entire guest suite 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
coffee was great bed was huge and comfortable
the bed is incredibly comfortable and the whole space is big buy cozy
wonderful comfortable and fantastic location stayed here with my sister and niece for a weekend whale watching trip
this is a nice little space with it's own living room
very clean interior great communication and kind hosts
the suite was clean and cozy
the place was spotless and the bed was very comfortable
veronica's place was quaint clean and affordable
the rental was very clean and had a great bed
veronica was very helpful and kind
the host communicated very well
veronica was easy to communicate with and was a great host
veronica is incredibly friendly and very helpful with quick responses every time
host was very friendly and quick to respond
wow great location near gordon college
also very close to a beautiful walking park along the coast
good location to the highway
great location with quiet surroundings
the house was great and location was ideal
Read more reviews

5. Country Cottage in the City, Dedham (from USD 155)

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.

Stayed at this property?
Dedham, Massachusetts, United States
24.48 km (15.3 mi) from Sri Lakshmi Temple
178 reviews   Superhost Wifi Available
Entire guesthouse 1 Bed 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
cozy space in a lovely wooded setting comfortable bed and furniture pleasant decor friendly and helpful hosts nearby
pool and patio seating for good weather beautiful garden
wonderful charming rustic cottage with a pool fishpond and waterfall
the setting overlooking the pool is lovely and the garden meticulously maintained
a small fridge coffeemaker toaster and misc kitchen utensils were helpful to have on hand
the cottage was clean and cozy
clean quiet and conveniently located
it is clean inside with everything you could want for your stay
a quiet space that is clean comfortable and feels like home
it was clean comfortable and mark was a wonderful host
exceptionally nice and helpful hosts
highly recommend great hosts
he was a super friendly host without being overbearing and made sure we had everything we needed
the hosts were very friendly overall a great experience
mark is great host
great location nestled away in the woodland but a short drive to everything you could need
this was in a great location
not walking distance from town thus very peaceful and quiet
i would recommend anyone visiting to consider this location
mark's place is so cute and such a great value
Read more reviews

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.

Stayed at this property?
Rutland, Massachusetts, United States
42.34 km (26.4 mi) from Sri Lakshmi Temple
326 reviews   Superhost Wifi Available
Farm stay 5 Beds 5 Guests 1 Bedroom 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
the small apartment is comfortable for a weekend stay
the property is great with lots of activities for kids like trampolines swings pool etc
apartment is clean and well furnished
the room was updated and clean
the space is clean and has everything you'll need
clean spacious and a lot of fun highly recommended
the apartment was clean and just right for us
the hosts are wonderful
the farm is delightful and roger was a consummate host
excellent and helpful hosts
me and my family had a great time everyone is so friendly and welcoming
we enjoyed feeding animals beautiful and friendly atmosphere vegetables roger let us pick for cooking
lovely peaceful location for a quick getaway from boston with the family
the are has many interesting places
super cool to walk around and see all the farm animals
great place to stay and get away
super friendly clean great location to get out and unwind
Read more reviews

7. Three-bedroom property with private balcony, Hopkinton (from USD 120)

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.

Stayed at this property?
Hopkinton, Massachusetts, United States
9.58 km (6.0 mi) from Sri Lakshmi Temple
140 reviews   Superhost Wifi Available
ENTIRE HOME 3 Beds 15 Guests 4 Bedrooms 1 Bathrooms

Accommodates: 15

Top guest reviews
Amenities & Room:
it was just as described in the listing and very comfortable
very comfortable place to stay in a beautiful wooded area
great place to stay lost of room and comfortable
the pool is the awesome but the best part of the house was the deck and the bbq
we almost felt like this airbnb was more of a shared space private room type of airbnb
everything was very clean and organized when we arrived
the space is clean and has everything you would need
the pool was the best thing it was very clean inside and the area around the pool aswell
his house is very nice and clean
his place is great too everything was clean & convenient
wonderful home and a hospitable host
great host and beautiful property
wonderful place with great host
such an accommodating and gracious host
brad is welcoming friendly and a great host
the location was just perfect for my purposes
brad’s place is in an excellent location right between boston and worcester
great place to stay will stay again if we are in the area
all in all i highly recommend this place
my boyfriend and i wanted a nice relaxing weekend away and brads place was the perfect fit
Read more reviews

8. Cozy accommodation for five guests, Holliston (from USD 195)

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.

Stayed at this property?
Holliston, Massachusetts, United States
6.12 km (3.8 mi) from Sri Lakshmi Temple
113 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 4 Beds 5 Guests 2 Bedrooms 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
fresh flowers were left on table
the apartment was beautiful and perfectly equipped with the delight of having coffee machine and supplies on arrival
it was very comfortable and easily fit our family of 4
beautiful yard and pool too
the place was fully equipped and comfortable
very clean and quiet
space was very clean and neat
very clean and enjoyed the dog and cat too
the apartment is beautiful and extremely clean and comfortable
the house was clean with plenty of space
mike is a great host
mike was a great host both welcoming and friendly and we enjoyed our interaction with him
mike was very accommodating and helpful as a host
great host and easy to communicate with
mike was a great host everything was as promised in the description
love the location of the house
walking distance to some good restaurants
great location with shopping and places to eat
michael's place was perfect for us the ideal place for kids
great location beautiful yard and pool
Read more reviews

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.

Stayed at this property?
Medford, Massachusetts, United States
31.54 km (19.6 mi) from Sri Lakshmi Temple
688 reviews   Superhost Wifi Available
ENTIRE HOME 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the large sectional couch in the living room was extremely comfortable for lounging and napping
the accommodation is roomy with a comfortable sofa and beds
the set up is great with 2 beds in one room and one more private room
very clean and spacious
very clean and quiet
super clean and super easy
everything was clean and comfy
steve's place is clean and comfortable
the host was helpful
stephen was a wonderful host
stephen was a great host
steve is a fantastic host
the host also give you your privacy and let you enjoy your stay
close to public transportation and tons of great restaurants close by
the location is great
great location not too far from boston
perfect location for a tufts visit
great place walking distance to downtown
Read more reviews

10. Studio apartment with lots of recreational spaces, Middleborough

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.

Stayed at this property?
Middleborough, Massachusetts, United States
68.17 km (42.4 mi) from Sri Lakshmi Temple
21 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the studio was very clean and we enjoyed the amenities including wifi large-screen television and pool
we were really impressed by the kitchen as it had enough equipment for some more complex meals
both the bed and hide-a-bed are very comfortable
extremely clean and comfortable unit where our family was able to relax
it was very clean lots of space and a great yard with pool and more
paul was so helpful
paul’s hospitality was excellent and he and his wife are very accommodating host
great little touches from the host
paul is a great host who is informative polite and communicates great
paul is an incredible host and the apartment was lovely
the location is convenient to the freeway quiet and safe
quiet neighborhood but connects to major roads easily
if you are looking for a place to stay this is definitely where you want to be
Read more reviews

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.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Bettina is a Behavioral Science graduate with a versatile background spanning human resources, management, sales, and marketing. Her love for travel matches her passion for coffee and wine. She...Read more

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