Berkshires is a stunning region in Massachusetts known for its quaint villages and towns that provide its visitors with spectacular natural attractions. This highland is in the northwest of Connecticut and west of Massachusetts. The region is also perfect if you want a getaway that involves lush woodlands, outdoor activities, and cultural immersion. Popular destinations include the National Historic Landmark of Jacob’s Pillow—home to one of the most famous dance training centers. Alternatively, you can visit the scenic Monument Mountain, once hiked by literary giants such as Nathaniel Hawthorne and Herman Melville. With the perfect blend of nature and culture, you’ll never run out of places to go. Heading home to cozy accommodation and dipping in a pool would be a perfect way to end the day. So, level up your comfort during your getaway by staying at one of these best Airbnbs with pool in Berkshires, Massachusetts.
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 13, 2024.
1. Cozy cabin with a fireplace, Sandisfield (from USD 849)
Berkshires is known for its picturesque outdoors, and one can appreciate it in comfort and style by staying in this homey cabin. This rental also has essential amenities, from its fully equipped kitchen to its spacious bedrooms.
Take a dip in the spa room’s indoor swimming pool or meditate in the yoga space. Note, though, that the pool amenity is not accessible during winter. Alternatively, you can cozy up in the stone fireplace or the reading nooks to maximize comfort during your stay. Moreover, an office is available in the rental for those on business trips.
Top guest reviews
Amenities & Room:
fabulous views and outdoor areas plenty of roomgreat outside spaces—a fire pit and an enormous sunny front deck and large very comfortable common areasit's a beautiful space with tons of roomthe rooms are beautifulCleanliness:
the cabin was beautiful it was clean and very spacious ana was quick to respond and assist with everythingHost:
the hosts were super prompt to get back to us with any questions we hadcolin a very responsive hostcolin and ana were amazing hosts extremely responsive and helpfulcolin was friendly and quick to respond to any of our questionsthe hosts were extremely responsive and the house was greatRead more reviewsLocation:
great place to go with family to get awaysuch a great scenic location and spacious house would highly recommend for a weekend awayit is somewhat remote but the property is so cool and you can walk arounda delightful place for a family vacation
2. Tranquil home near a river, Sandisfield (from USD 375)
Get away from all the hustle and bustle of the city and enjoy a stay in this private home. This residence features 8 acres (3 hectares) of lush nature and easy access to cultural sites and ski resorts that will bring out the adventurer in you.
You can enjoy a meal in the dining room with a view of the woods or cozy up in the living room, warmed by a fireplace. Take a dip in the fenced and in-ground swimming pool near the river, perfect for any and every season. This property also has essential amenities such as a fully equipped kitchen, a washer and dryer, and Wi-Fi, guaranteeing a convenient stay.
Top guest reviews
Amenities & Room:
no a/c but cools off very nicely in the eveningeven without air conditioning the house was comfortable day and nighttheir home provides comfort and guest amenities: well appointed kitchen linens comfortable furniturethe grounds large in-ground pool and surrounding nature tops it all offCleanliness:
place was very nice and very clean throughouther home was clean charming and well-appointedvery clean and lively house with a beautiful backyard with a river running through itgreat house comfortable clean great screened in porch and pool we had a fantastic stay hereclean comfortable and private home with big heated pool in a beautiful locationHost:
linda is a wonderful hostmarcella was a fantastic host and very responsivegreat hosts and a wonderful placemarcella was very friendly and helpful and made our stay extremely pleasantresponsive friendly and very understandingRead more reviewsLocation:
a lovely house in a great location close to great hiking trailsthis is a beautiful home in a wonderful locationif you're looking or a nice quiet getaway in a beautiful area this is a great place
Nearby Airbnbs with pool
3. Luxury home with fire pit, Great Barrington (from USD 545)
Indulge in a luxury home that’s only a two-and-a-half-hour drive from New York City. This stunning luxury home has a fully equipped gourmet kitchen and a dining room with an eight-seater farmhouse table. Plus, it has surrounding lush greeneries and parkland.
Level up your relaxation in the saltwater pool. The pool can also be heated at an additional fee. Diving and drinking are prohibited. Note, though, that you need to contact the hosts to confirm the pool’s availability since it’s seasonally open. Alternatively, stream some shows with the 55-inch TV and Amazon Fire Stick streaming service. The three-season porch allows guests to cook up some barbecue on the grill while overlooking the view of the trees. Guests can enjoy complimentary cocktails and coffee.
Top guest reviews
Amenities & Room:
the house is gorgeous; from the furniture to the light fixtures to the bathroom tiles everything was beautifulspeaking of work - wifi was also greatthe rooms were large and roomy perfect for families with small childrenthe house was filled with light really comfortable beautifully decorated and cleanthe pool was luxurious with beautiful landscapingCleanliness:
everything about this place feels luxurious clean and modernthe place is so spotless bright and freshit was very clean and had everything we needed to enjoy the weekendthis place was fantastic it was really clean and the layout is greatthe house is spacious beautiful and cleanHost:
the hosts were fantastic and accommodated our needsthe hosts were very helpful and communicative toothe hosts answered all our questions promptly and gave clear directions on how to use everythingthe hosts were quick to respond and so graciousthe hosts prem and mary were very kind and welcomingRead more reviewsLocation:
house is also located close to great barrington town which has many cute restaurants and shopsit is super close to ski butternut amazing hikes and the lovely shops & restaurants of great barringtonthe location is unbeatable and we loved relaxing in their poolall in all a roomy elegant family friendly house in a perfect location in the berkshiresbeautiful house cozy home great location exactly as described
4. Homey rental with an entertainment space, Sheffield (from USD 299)
Spend a vacation in complete intimacy by staying in this Airbnb rental surrounded by lush nature. Sandwiched between Butternut and Catamount, this place offers free Wi-Fi, parking, and a spacious entertainment area, to name a few.
Take a dip in the heated in-ground pool in the private yard or unwind on its sun loungers. You can also cook a meal for the entire family in the fully equipped kitchen area. A dedicated workspace is available for individuals on business trips.
Top guest reviews
Read more reviewsCleanliness:
the heated pool was beautiful and clean and where we spent most of our timecozy home on the hill clean & comfortable
5. Pet-friendly home, Great Barrington
Enjoy a getaway in luxury with high-end accommodation in this pet-friendly home. This property is on the borders of Great Barrington, allowing a perfect location for outdoor activities such as biking and kayaking.
A round outdoor pool lets guests have a relaxing dip in the waters and grants them a view of nature surrounding the home. It’s also heated upon request, and you can chill on its sun loungers. Additionally, this home houses a fitness area and a working station for working professionals and students. It is minutes away from Bash Bish Falls and Catamount Mountain Resort, perfect for the outdoorsman in you.
Great Barrington, Massachusetts, United States
13.73 km (8.6 mi) from Monument Mountain ReservationAccommodates: 6
Top guest reviews
Amenities & Room:
the area doesn’t have great service but wifi works without an issuethe house has everything needed for a very comfortable stayHost:
the owner is very very responsiveand julie is very responsivewe really enjoyed our stay and the hosts were extremely accommodating and communicativeRead more reviewsLocation:
the location is beautiful and close to great barringtonberkshire bliss is the perfect place to stay for a few couples or a large family
6. Private home on secluded hills, Great Barrington (from USD 540)
This rental, on a 19th-century barn, is the home for you if you want a quiet place with a spectacular mountain view. This home doesn’t miss out on modern comforts such as free Wi-Fi and an equipped kitchen.
Dip your toes in the nearby heated free-form pool surrounded by lush nature, unwind on the sun loungers, or try the trampoline. If indoor activities are your cup of tea, this home has a loft dedicated to TV and gaming purposes. Be one with nature in this property, which is close to the best hiking areas and restaurants.
7. Clayton Farm, Southfield
Live in luxury by staying in Clayton Farm, which has a majestic landscape. This rental sleeps a large group and has necessities such as free Wi-Fi, a fully-equipped kitchen, and an HDTV. You can dip in the heated pool with outdoor seating, a scenic view, and a stainless grill for barbecue parties.
Those in the mood for some sport can enjoy ping pong and air hockey in the playhouse. This property is less than 25 minutes from Ski Butternut, making it perfect for those who want to ski in the great outdoors. Moreover, this home has a pet fee for guests who wish to bring their furry friends.
Southfield, Massachusetts, United States
19.1 km (11.9 mi) from Monument Mountain ReservationSuperhost
Accommodates: 9
Top guest reviews
Read more reviewsLocation:
this is a great place for a family vacation in the berkshires
8. Family home with a hot tub, New Marlborough
This old-fashioned, New England-style family home is perfect for large families and groups. It is a tranquil and private rental with free Wi-Fi, a smart TV, and a game console.
Go for a dip in the fenced and in-ground pool with sun loungers or the hot tub with a scenic view, or enjoy outdoor activities in the yard. Keep in mind, though, that glasses are not allowed in and around the swimming pool or the hot tub. Movies and board games are available for those who prefer to stay indoors. Prepare a meal for the entire family in the fully equipped kitchen with a double oven. Public beach access is also available for those who wish to see the beach.
New Marlborough, Massachusetts, United States
14.67 km (9.2 mi) from Monument Mountain ReservationAccommodates: 10
Top guest reviews
Amenities & Room:
the pool hot tub and deck are fantasticthis is a very warm and comfortable house loaded with all you need for cooking and relaxingCleanliness:
comfortable and clean would definitely recommendRead more reviewsLocation:
if you are looking for an escape from the hustle and bustle this is an amazing place to staywonderful home in a great location
9. Stylish abode with wooden furnishings, Becket (from USD 374)
Spend your getaway being one with nature in this woodland haven only a few minutes from hiking trails and playgrounds. This cozy home has a stone fireplace, a chef’s kitchen, and a large outdoor deck.
Guests staying in the main house will have access to the heated in-ground swimming pool, which has a deep end of 8 feet (2 meters). The pool area is open between Memorial Day and Labor Day. Note also that one has to follow the swimming pool rules while using the amenity, and maintenance is conducted on some days.
Additionally, guests can engage in activities such as playing tennis or basketball, hiking, or swimming on the nearby beach. Two office spaces and Wi-Fi are available for those on a business trip to focus and get some work done.
Top guest reviews
Amenities & Room:
the wifi was strong enough for streaming and workingthe house was super comfortable and had everything we neededRead more reviewsHost:
the hosts were very helpful and attentivethe hosts were very friendly and extremely communicative if we had any questions during our stay
10. Spacious and modern house, Great Barrington (from USD 500)
Escape into the countryside and relax in this modern home in the woods. Despite being one with nature, it still has modern amenities such as free Wi-Fi and a TV for either work or entertainment. Guests can enjoy the home’s heated in-ground pool with outdoor seating. It’s also worth noting that the fenced swimming pool is free from chemicals.
The modern open kitchen has all the cooking essentials to prepare a nice family meal. Work out using the free Peloton or explore the great outdoors at the nearby hiking and horse trails. If you love skiing, know that Ski Butternut is just 10 minutes away. Plus, you can visit nearby restaurants and shops, about 25 minutes from this property.
Top guest reviews
Amenities & Room:
we loved the hill behind the house for sledding and appreciated the well-stocked kitchenCleanliness:
the house was spotless when we arrived and the bedrooms were very comfortablethe home was beautiful comfortable clean and the backyard and pool were so relaxingmy family and dog were able to enjoy a nice quiet weekend away at this spacious locationHost:
steven is an excellent host and responds promptly to any questionsstephen was a fantastic hoststephen was such a great hoststephen was a great hosthe was very responsive and even provided us with a bottle of champagne and a lovely candleRead more reviewsLocation:
the location is perfectspacious house in peaceful locationthere are interesting hiking trails all around the placeclose to ski mountains and town of great barrington with fabulous hiking nearbygreat barrington has so many good stores for amazing pastries bagels and coffee
Explore the majesty of the outdoors in Berkshires
A getaway to Berkshires and staying in an accommodation with cozy amenities might be what you need to escape the hustle and bustle of the city. With this rural region’s natural wonders, it isn’t surprising why so many tourists flock here. Make the most of your trip by staying in one of the best Airbnbs with a pool.
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