Holiday rentals with a pool in Pioneer Valley

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Pioneer Valley

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

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Guest favourite

Bungalow in Easthampton

4.92 out of 5 average rating, 520 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

Top guest favourite

Home in Chesterfield

4.98 out of 5 average rating, 61 reviews

High Field Farm

Come to High Field Farm to getaway and unwind in a beautiful, classic New England farmhouse. Set on over 500 acres of land, enjoy a spacious, tasteful and pristine country vacation home, lovingly cared for by the same family for over 50 years. The house offers four bedrooms and two full bathrooms, and endless outdoor opportunities like hiking or fly-fishing. You'll enjoy spectacular mountain views in an idyllic and private country setting that will enchant and nourish your heart and soul.

Guest favourite

Guest house in Lenox

4.9 out of 5 average rating, 266 reviews

The Coach House | Modern 2BR Loft + Views & Pool

Restored coach barn with 25-ft cedar ceilings, skylights, and mountain views—part of House on Golden Hill, a historic Lenox farmhouse compound. This airy 2BR + loft retreat blends rustic charm with modern ease. Enjoy a full kitchen, cozy living space, and outdoor area. Set beside a stream with seasonal pool access, it’s perfect for families, couples, or creative escapes. Centrally located and just minutes to downtown Lenox, Tanglewood, and trails—your Berkshires base for rest and inspiration.

Top guest favourite

Guest suite in Enfield

5 out of 5 average rating, 145 reviews

Luxe 1822 Apt | Rain Shower | Plush beds | Firepit

Oversized 1800sf apartment is a 2-story unit, front half of a 200-year-old former schoolhouse in Enfield's historic district. The antique colonial is set up as a side-by-side duplex with private apartment occupying the front 1/2 of house & the owner's unit in the back with a separate driveway entrance & door. EXTRAS: ❋ PRIVATE USE OF POOL & PATIO ❋ KEYCODE CHECK-IN ANYTIME ❋ COFFEE/TEA BAR WITH EVERYTHING NEEDED ❋ POPCORN MACHINE, SNACKS & DRINKS ❋ 4 TVs: YOUTUBE TV, MAX, NETFLIX, WIFI

Superhost

Flat in Northampton

4.92 out of 5 average rating, 244 reviews

Wood, sunshine & movies in best downtown location

Sun-drenched 1st fl apt in 2-family Victorian, steps from Northampton's vibrant downtown. 2 spacious queen bedrooms, 1 bedroom/study with pull-out king. Pine-paneled kitchen with breakfast bar; open living/dining room; stereo with turntable and vintage record collection; home theater with projector. Private deck. Wood floors throughout apartment. 42" HDTV in master bedroom. Hi-speed Internet. Laundry room in basement with washer/dryer (shared with upstairs apt). Shared heated pool (Mar-Nov).

Superhost

Home in Deerfield

4.8 out of 5 average rating, 240 reviews

Perfectly Polished Deerfield Home 5 min to I-91

A perfectly polished home, nestled in the Sugarloaf Mountain Range with a view of Mount Toby! This property offers 4 bedrooms and 4 beds. With over 2000 sqft of living space, you will enjoy coming home to wind down after a day at Yankee Candle, hiking, or other event in the beautiful Pioneer Valley. The house has something for everyone, whether it’s streaming your favorite show on Netflix, Hulu or Prime Video or relaxing on the patio deck while the kids enjoy the huge pool and water slide!

Guest favourite

Home in Colrain

4.89 out of 5 average rating, 131 reviews

The 1770 House

Come and enjoy our country retreat with breathtaking mountain and valley views. This expanded 1770 farmhouse gives you 4,500 sq. ft. of space for large family and friend get togethers. The house overlooks the Green River Valley with views to Vermont. The end of a dirt road location provides an escape with views that are changing through the seasons. There are six bedrooms and three bathrooms. Have an event or special gathering from wedding to retirement let us know maybe we can help.

Guest favourite

Home in Williamstown

4.89 out of 5 average rating, 223 reviews

Hollywood Bungalow in the Berkshires #C0191633410

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 favourite

Flat in Otis

4.95 out of 5 average rating, 111 reviews

Enjoy every season the Berkshires have to offer.

Come enjoy the Berkshires any season you choose. We are close to local ski areas, with have access to snow shoeing, ice fishing and many more winter activities. Also located within minutes of the many cultural attractions the Berkshires have to offer, Jacob's Pillow, Shakespeare & Company, and Tanglewood. Enjoy the beautiful fall foliage on our small private pond. You can bring your kayak or canoe to enjoy the wildlife that abounds or catch & release in our pond.

Guest favourite

Cabin in Guilford

4.95 out of 5 average rating, 173 reviews

Silver Brook Cabin

Waterfront setting in a relaxing, but convenient, location in southeastern Vermont. Photos and captions do the best job of describing our cabin, adjacent brook, and very nearby Green River with its covered bridge and swimming holes. The cabin is 20 minutes from Brattleboro with its many restaurants, shops, movie theater, and galleries. Not only is the immediate area wonderful for swimming, biking, and hiking, you can also simply relax with a good book or two.

Guest favourite

Guest house in Williamstown

4.93 out of 5 average rating, 245 reviews

Perfect Base for Your Berkshire Adventure

Charming private guesthouse with shared pool use. Newly renovated, the space features high ceilings, queen sized bed, rustic Arts & Crafts furniture, heat/air conditioning, and kitchenette. Located in an outbuilding on the property, the guesthouse 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 favourite

Guest house in Enfield

4.96 out of 5 average rating, 45 reviews

Close BDL AirPort & SixFlags Free Private Parking

Escape to Pineside Retreat in Enfield, CT—a tranquil haven blending comfort and nature. Conveniently located 20 minutes from Bradley Airport and MGM Springfield Casino, 15 minutes from Six Flags, 22 minutes from Holyoke Mall, 5 minutes from Scantic River State Park, and 10 minutes from Windsor Locks Canal State Park. Perfect for professionals or adventurers seeking relaxation in a cozy, rustic-modern retreat.