Top 18 Vacation Rentals With Private Pool In Massachusetts, USA - Updated 2024

Nikki
Nikki 
Contributing Writer
Updated
| 5 min read

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 July 07, 2024.

1. Spacious four-bedroom retreat in the Berkshires, Richmond (from USD 417)

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.

Stayed at this property?
Richmond, Massachusetts, United States
PRIVATE VACATION HOME 10 Guests 4 Bedrooms 3 Bathrooms

2. Expansive house with ample driveway parking, Bourne (from USD 475)

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.

Stayed at this property?
Bourne, Massachusetts, United States
PRIVATE VACATION HOME 10 Guests 3 Bedrooms 2 Bathrooms

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.

Stayed at this property?
Sandwich, MA, US
6 Guests 3 Bedrooms 3 Bathrooms

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.

Stayed at this property?
36 reviews   Wifi Available
House 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
) our only suggestion is we could have used one more comfortable chair in the living room
the home is quite spacious with all the amenities to make a very comfortable stay
this was a very well kept house with a pleasant outdoor area and a very nice pool
Cleanliness:
not only was it exceptionally clean there was an attention to details (e
the house and pool were clean and a perfect size for our family of four
lovely clean comfortable well-equipped patio home with pool
Host:
dealing with the owner is also very easy and problem free
nice condo with everything you could need provided by owner
larry the owner was extremely communicative and helpful making our stay a memorable one
the extra condiments in the kitchen are very helpful salt container was empty
larry was very responsive and helpful
Location:
the location was ideal for location to beaches
super close to the beach
close to beaches golf mashpee commons and the bike trail for a nice ride to woods hole
the house is close to shopping and fun cape things to do
perfectly located near shopping/outlets short drive to beaches and falmouth (with nice shops and restaurants)
Read more reviews

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.

Stayed at this property?
67 reviews   Wifi Available
House 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
loved all of the extra amenities including the patio heater fire pit and corn hole
Cleanliness:
clean and had everything we needed
place was so clean and inviting
the house was exceptionally clean
the house was clean and very well stocked
the home was spotless and we were welcomed with cape cod chips and a bottle of wine
Host:
we enjoyed all the owner was terrific & responded to all questions very fast
eli was easy to communicate with and responsive
the property is exactly as pictured and communication with the owners was excellent
communication with the owners was great and we appreciated the sweet welcome surprise
Location:
beautiful property in a quiet neighborhood close to johns pond
quite location makes for a good nights sleep
excellent location great cleanliness and reasonably priced
Read more reviews

6. Beautiful oasis with a hot tub and sauna, Provincetown (from USD 1131)

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.

Stayed at this property?
Provincetown, Massachusetts, United States
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 5 Bathrooms

Top guest reviews
Amenities & Room:
the kids enjoyed floating in the pool and sitting out on the deck in the evenings
great amenities from pool to hot tub to sauna
Cleanliness:
it is super clean and is stocked with all you will need
Host:
the owner was very responsive
the owner is very responsive
our host was so welcoming and helpful
ted was an excellent host
owner ted was very welcoming and friendly
Location:
great location walk to town and beach
had amazing walks into the dunes with main trail entrances literally 5 minutes away from the house
Read more reviews

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.

Stayed at this property?
Nantucket, MA, US
House 7 Guests 4 Bedrooms 4 Bathrooms

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.

Stayed at this property?
24 reviews   Wifi Available
House 6 Guests 3 Bedrooms 1 Bathroom

Accommodates: 6
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
our family enjoyed the spaciousness of the home large kitchen comfortable beds and soothing outdoor water feature
we appreciated the well-equipped kitchen the very comfortable beds and the projection tv
the yard was beautiful with waterfall budda outdoor fire pit hammock gazebo and of course the pool
the backyard and the pool provided hours of fun for the family
Cleanliness:
this is our 3rd stay at tania's beautiful house; it's clean modern and cozy
Host:
the vrbo site was user friendly and detailed
tania the owner is wonderful
tania was extremely helpful and hospitable and responded to texts within minutes
tania was always friendly and super responsive to any issues that we had
and she was very helpful in getting our roku unit working with it
Location:
the location is very safe and quiet
you can get around from this location very well
well appointed and in a lovely peaceful location
and oh yes the neighborhood is wonderfully quiet at night
i also realized it was an ideal location for negotiating worcester where the traffic is pretty bad
Read more reviews

9. Spacious four-bedroom flat near the beach, Falmouth (from USD 664)

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.

Stayed at this property?
Falmouth, Massachusetts, United States
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 5 Bathrooms

Top guest reviews
Amenities & Room:
gorgeous the decor the natural light the warm pool large table for family dinners the amazing grill
the pool is lovely and totally secluded from the neighbor’s view
the other 2 rooms were perfect for the kids with one having a bunk bed with trundle
Cleanliness:
extremely clean which is very important to me
the house was beautiful very clean comfortable and private
plenty of space very clean and well furnished with well outfitted kitchen
the beds are very comfortable and both primary suites are spacious
Host:
they were lovely hosts
owner is very positive and communicative
the host family kate and frank are very thoughtful and responsive
kate and frank are incredibly friendly kind and prompt in responses
they also left the most kind welcome basket with items for us and our daughter
Location:
location is great - private but close to everything definitely a great vacation spot
it’s in a great location a short walk to wood neck beach and a quick drive into town
warm pool spacious rooms comfy linens … and a great secluded spot close to town
Read more reviews

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.

Stayed at this property?
Oak Bluffs, MA, US
23 reviews  
House 10 Guests 5 Bedrooms 4 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

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.

Stayed at this property?
32 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

12. Katama Luxury, Edgartown (from USD 607)

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.

Stayed at this property?
Edgartown, Massachusetts, United States
PRIVATE VACATION HOME 14 Guests 5 Bedrooms 6 Bathrooms

Top guest reviews
Amenities & Room:
the kitchen was well stocked and made cooking easy
Cleanliness:
the home has comfortable beds clean bathrooms and a nice sized side yard with heated pool
Host:
spotlessly clean and a friendly host/owner who checked in to make sure all was well
Location:
in summer it would be ideal positioned close to the bike path
what a joy perfect location to the beach and to downtown we rode bikes everywhere
an easy 10 min cycle to both locations
Read more reviews

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.

Stayed at this property?
43 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

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.

Stayed at this property?
32 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

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.

Stayed at this property?
102 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

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.

Stayed at this property?
Cummington, Massachusetts, United States
cottage 4 Guests 1 Bedroom 1 Bathroom

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.

Stayed at this property?
28 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

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.

Stayed at this property?
7 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

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


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.

History


Get Trip101 in your inbox

Unsubscribe in one click. See our Privacy Policy for more information on how we use your data

A former tv scriptwriter and flight attendant whose main mission is to explore every corner of the world and thinks that the best way to know a place and its culture is through local food and...Read more

 Want to contribute as a Local Expert?
Explore Massachusetts
x
Good things are meant to be shared!
Back to top
Visited any of these places? Click this button to activate our "Add a Tip" feature to share your experience.