
Vacation rentals with a pool in Western Massachusetts
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Top-rated rentals with a pool in Western Massachusetts
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Popular amenities for Western Massachusetts rentals with a pool
House rentals with a pool

The 1770 House
Historic house on a beautiful property. Kitchen had all the equipment you could need along with top of the line stove and oven. Make cooking for a large group easy and enjoyable!

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace
We were in town for my daughter’s wedding and I was looking for a place that had outdoor space to enjoy and this house did not disappoint. Everything was spectacular! It was lovely to have the pool, we enjoyed our coffee in the morning and wine at night surrounded by peaceful lighting. The kitchen is beautiful (exactly) like the pictures and so many extras. The host who lives downstairs was very helpful and thoughtful. We appreciated all the special touches and look forward to finding a reason to return.

Stunning luxury home with pool
beautiful well maintained house, supremely functional as well as spacious. very clear instruction all over the house. 5 bathrooms to go with each of 4 bedrooms. multiple lounge areas. fully equipped kitchen with anything once could need.

Beautiful Pool Home between Lk George/Saratoga
This was my first ever experience with AirBNB. I couldn't have stayed at a better location for my first experience! Melissa's home was warm welcoming and beautiful. I stayed for four nights with my four children. There was plenty of space for all of us. Although my youngest still chose to sleep with me lol the bed was still big enough for the two of us. The pool was absolutely perfect, my kids loved it! The hot tub was very relaxing and very easy to use. My kids really enjoyed it too. The grill worked wonderfully and the fire pit was great for smores. The covered patio made watching my kids enjoy the pool even more relaxing for me, I'm a ginger so if I can be outside and out of direct sunlight that's a huge bonus for me. The kitchen had everything we needed as well. Melissa was very responsive when I had questions and I cannot thank her enough for the great week. We'll be back next June for another week! Can't wait to return to this fantastic vacation spot!

Stunning Views, Bucolic Bliss in 1790s Farmhouse
We really enjoyed our time at Elizabeth Jane's place. The home is spacious and quaint, with nice furnishings, a tasteful colonial feel and easy access to downtown Litchfield and the Berkshires. The bucolic setting is lovely - scenic, relaxing and peaceful.

Stylish Rural Sanctuary with POOL!
We had a wonderful stay at this beautiful property! The location is close to plenty to do and great dining but also feels very private. The home is absolutely beautiful as pictured. The pool was a real treat to have and half of the pool is a shallow end which was a bonus for us traveling with a child. The beds are very comfortable which is always a huge plus when traveling. The hosts were responsive with any questions that came up. We would happily stay again!

Berkshire County modern home + pool
We had a wonderful stay at this adorable home in the Berkshires! The house was very comfortable and cozy, and the backyard with the deck and pool provided a wonderful space to hang out day and night. The house was situated 20-30 minutes from so many places - downtown Lenox, Miraval Spa and Ballderdash Winery. We can’t wait to come back!!

Pool*Hot Tub*Pirate Ship*Fire Pit*Luxury Farmhouse
Arps place was Superb to say the least. Me and my family had a great time. The home is beautifully designed and decorated, very homey. All my friends are asking me to send them arps place they also want to experience what I had experienced.
Condo rentals with a pool

Seasons on Mt Snow Condo - Ski/Hike/Bike/Swim
We stayed at Julia's vacation rental for a 3-day weekend with our four children under the age of 12. The things that were great: 1) the unit is 150 foot walk in ski boots from a ski trail that will take you to the Mount Snow lift, which was great because we didn't have to shlep 4 kids ski gear, 2) the four kids loved the bunk bed room and were comfortable, 3) there are two large shelves of board games the kids enjoyed, 4) the access to the Sports Center which has a heated indoor pool and hot tubs were a great way to end the day after skiing, 5) the outdoor locker was a great place to dump all the ski gear (much better storage location than inside the car or inside the unit) and 6) very nice fluffy towels and bed sheeting was comfortable. A combined liquid shampoo and body soap is provided in each bathroom, which is the same that we use to bath our kids at home.

Mt Snow Ski In/Out at Seasons
The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.

Summer Dream! The Handle Lodge at Snowtree Condos
Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.

CASiNO, Spa, Hot Tub, Pool, King bed, sauna
An excellent stay!

Peaceful Oasis steps from Mohegan Sun
We absolutely loved our stay here. The house was comfortable and clean. The amenities are perfect. It is such a perfect place to stay. Christina was very helpful, kind, personable and always quick to reply. Would definitely recommend staying here.

The Vacay Villa
Wonderful location! Beautiful pool! Perfect hot tub! My family loved our visit!

Walk to Mt. Snow-Spa-Summer Pool
Great little studio spot to use as your Basecamp for activities in the area!

Premier Stratton Village Location - Pool & Hot Tub
The place was cozy and comfortable, with great amenities like a parking garage, pool, and sauna. The WiFi was excellent, and the unit was clean and well-equipped for a relaxing stay. There wasn’t much to do since it was the off-season, but it’s a great spot if you’re looking for a quiet retreat. Would recommend for a peaceful getaway.
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- Six Flags New England
- Bushnell Park
- Taconic State Park
- Jiminy Peak Mountain Resort
- Albany Center Gallery
- Berkshire East Mountain Resort
- Bash Bish Falls State Park
- Catamount Mountain Ski Resort
- Kent Falls State Park
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Brimfield State Forest
- Norman Rockwell Museum
- Beartown State Forest
- Dinosaur State Park
- Mohawk Mountain Ski Area
- Bigelow Hollow State Park
- Hartford Golf Club
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Clarksburg State Park
- Pineridge Cross Country Ski Area
- Naumkeag