Vacation rentals with a pool in Western Massachusetts

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Western Massachusetts

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Bungalow in Easthampton

4.92 out of 5 average rating, 430 reviews

The Creation Station

Welcome to The Creation Station. I am your host John. The Creation Station was built with love and care by me with my friends and family. Amenities? Update! We just installed an 8 person hot tub! Plus our pool, jacuzzi tub, projector, giant deck and a stage with sound system, drums amps and karaoke input. The most unique amenity though is The Enchanted Forest. A lit trail surrounding the property. Fun for kids of all ages! Please let me know how I can make your stay amazing. See you soon! John

Superhost

Cabin in Stephentown

4.84 out of 5 average rating, 238 reviews

Cabin in the woods w cedar Hot Tub + private pond

The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.

Superhost

Apartment in Northampton

4.88 out of 5 average rating, 136 reviews

Luxury w sunny balcony in best downtown location

Bright, newly renovated, luxuriously furnished, tree-lined flat a few steps from Northampton's vibrant downtown. Sliding glass doors open to a lovely balcony overlooking trees and roofs. Open floor plan, eat-in butcher-block kitchen, dishwasher, living room with movie projector, home theater system, queen pullout sofa. Spacious queen bedroom with 42" HDTV, private study nook. Access to yard areas with outdoor dining table, heated 36-ft pool, play gym. Basement washer/dryer. Off-street parking.

Guest favorite

Guesthouse in Belmont

4.99 out of 5 average rating, 200 reviews

Charming Pool/Garden Guest House

A little Paradise! Charming pool and guesthouse in country setting, birds and flowers galore. Much to do in the area, or just quiet, settling into some refresh-your-soul time. The guesthouse has all you need to feel at home. Within 15 minutes you'll find Gunstock Recreational Area, Highlands Mtn. Bike Park, Hermit Woods Winery, Funspot bowling and arcades, hiking, fishing, Shaker Village, Lakes Region Casino, NH Speedway, Bank of America Pavillion (concerts) and Tanger Outlet Shopping.

Guest favorite

Guesthouse in Granville

4.9 out of 5 average rating, 785 reviews

Moon Valley Country Retreat no clean fee pets yes

Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Near Lk George, Lk Champlain, Saratoga, Manchester & Rutland, VT. Hiking, fishing and swimming nearby. Air conditioners on the main floor for the summer months. Our 9120 watt solar array powers our property. During the cold months enjoy the wood stove. All wheel drive recommended in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

Guest favorite

Farm stay in Thompson

4.99 out of 5 average rating, 133 reviews

Rustic Farmette Studio w/ Hot Tub & seasonal pool

Relax and rejuvenate at this unique getaway on 20 acres in CT’s Quiet Corner. Just an hour from Boston, Providence, & Hartford, enjoy this private in-law studio with beautiful forest views. Lounge in bath robes & soak in the hot tub, take a walk along the trails, enjoy local vineyards, or explore antiques. Folks from all backgrounds and identities are welcome at The Farmette. Ideal for couples, solo travelers, a small family. Please include all individuals (&pets) in your booking.

Guest favorite

Guesthouse in Williamstown

4.93 out of 5 average rating, 219 reviews

Perfect Base for Your Berkshire Adventure

Charming private cottage with shared pool use. This newly renovated garden studio features high ceilings, a separate kitchenette with granite counters, mini fridge, microwave, queen sized bed, and rustic Arts & Crafts furniture. Located in a separate outbuilding, the cottage is close to woodland hikes, excellent biking, as well as many other attractions in the Berkshires. The beautiful in-ground pool is perfect for an afternoon dip - guest hours are usually between 3-5.

Guest favorite

Bungalow in Williamstown

4.89 out of 5 average rating, 202 reviews

Hollywood Bungalow in the Berkshires

Cool Cozy Rustic Country Bungalow with Screening Room on filmmakers/artists' enclave that's well-located in clean and beautiful Williamstown, near incredible Hiking Trails, Farms, Skiing, MASS MoCA, Clark Art Institute, Williams College, with Pool access, Cable & Smart TV, Porch and Patio, Grill, Fire Pit, Piano Bar Outbuilding with stereo & its own WIFI, First Floor Bathroom with Jacuzzi Bathtub, Laundry, fast WIFI, and lots of outlets in a quiet area on a quiet street.

Guest favorite

Apartment in Brookfield

4.94 out of 5 average rating, 186 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Guest favorite

Guesthouse in Lenox

4.95 out of 5 average rating, 283 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Guest favorite

Barn in Hillsdale

4.97 out of 5 average rating, 117 reviews

Hudson Valley Hilltop Barn

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & on a 15-acre hilltop with views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking and tons of games. Perfect for winter sledding right on our hill. 100 acres of untouched nature around property. Near great shops & restaurants in Hudson & Great Barrington. *Pets must get written approval*

Guest favorite

Guest suite in Amherst

4.95 out of 5 average rating, 270 reviews

Sunlit Clean Amherst Cozy Log Cabin

Peaceful log cabin on an 8 acre property. Truly a gem to enjoy: a quiet, relaxing, cozy, sunlit cabin with a vaulted ceiling. Beautiful gardens, warm electric fireplace, and steps away from Atkins Reservoir and hiking trails. You will feel secluded but close to local attractions. Umass only 7 minutes away and close to Amherst College, Hampshire College, Smith College, and Mount Holyoke as well.