Holiday rentals with a hot tub in Berkshire County

Find and book unique rentals with a hot tub on Airbnb

Top-rated rentals with a hot tub in Berkshire County

Guests agree: these rentals with a hot tub are highly rated for location, cleanliness and more.

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Superhost

Cabin in Stephentown

4.86 out of 5 average rating, 297 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.

Guest favourite

Home in Great Barrington

4.96 out of 5 average rating, 170 reviews

Elegant Year-Round Lakeside Retreat with AC

The Haven, an elegant cottage surrounded by woods, located on a pristine lake with private dock. 4 bedrooms, 3 baths. This year-round vacation cottage with hot tub provides an experience in the Berkshires you won’t forget! Leaf-peep in fall, ski in winter, hike in spring, kayak & swim in summer, or browse the boutique shops in quaint towns like Great Barrington, Lenox and Stockbridge. Newly installed mini-splits provide AC in all bedrooms and LVR/DR/Kitchen common area. 1 house-trained dog ok.

Guest favourite

Cottage in Great Barrington

4.93 out of 5 average rating, 305 reviews

Artist Cottage

Enchanting, private, romantic, retro style, artsy, cottage & lodge building with fireplaces and outdoor hot tub and shower area in a quaint, quiet, neighborhood nested at the base of Flag Rock and near nature trails and downtown Great Barrington. Perfect for a romantic get-away. Open retro style kitchen with wood stove and TV is stocked with utensils and pans for cooking with gas oven and retro appliances. Upstairs bedroom with ensuite large bathroom with soaking tub and message chair.

Superhost

Home in North Adams

4.89 out of 5 average rating, 171 reviews

Art House! Spacious Getaway By Mass Moca

This newly renovated Victorian curated by the local Grant Larkin Design Team is a great space for large groups, with easy access to Berkshire Art Museum & outdoor fun! Nearby: Mass Moca 2 min Big Y 2 min MCLA 5 min Clarksburg State Park 7 min Hairpin Turn 8 min Williams College 10 min Susan B Anthony Museum 12 min Ashuwillticook Rail Trail 13 min Clark Art Institute 14 min Mt. Greylock Gould Trailhead 14 min Mohawk State Forest 23 min Jiminy Peak Resort 29 min Bright Ideas Brewing 2 min

Top guest favourite

Cabin in Stockbridge

4.97 out of 5 average rating, 33 reviews

Stockbridge Snug- cabin luxury just steps to lake!

The Snug (an energy efficient home) was designed, renovated, and completed in June 2022. It serves as a cozy haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, attend a Tanglewood concert, take in a play, or just hot tub amongst the trees- we hope you enjoy your stay and will visit us again.

Guest favourite

Place to stay in North Adams

4.93 out of 5 average rating, 163 reviews

Berkshire Mountain Top Chalet

Amazing mountain top lodge with beautiful views, and majestic log interior. Soaring ceilings, dramatic stone fireplace, and many more amazing amenities such as blazing fast internet, multiple decks, and hot tub. This gorgeous lodge is located near all The Berkshires has to offer—resplendent nature with waterfalls, hiking trails; cultural institutions such as Mass MoCA, and the Clark Institute; adventures such as zip-lining, white-water rafting, and skiing—it is the ultimate place for you.

Top guest favourite

Cabin in East Nassau

5 out of 5 average rating, 58 reviews

Luxury Cabin | Fall Foliage, & Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit and chairs, Webber Grill, radiant floor, WFH space, and EV charging!

Superhost

Home in Tyringham

4.84 out of 5 average rating, 122 reviews

Treetop Hideaway in Tyringham

For your upcoming stay, look no further than this airy, secluded log cabin overlooking the beautiful Tyringham Valley. On the first floor, you will find a great room with vaulted ceilings and a fireplace, as well as a master suite, second bedroom, half bath and recently renovated kitchen. The second floor includes two more bedrooms and a bathroom. The exterior offers a screen porch with hot tub, wraparound deck and 35+ acres of woods bordering conservation land in Monterey.

Guest favourite

Home in Great Barrington

4.94 out of 5 average rating, 123 reviews

Best of the Berkshires + Hot Tub by Evergreen Home

Ski, hike, shop, and dine with this beautiful 2-bed, 1-bath Berkshires cottage as your home base. 7 minutes to downtown Great Barrington, this stylish, cozy rental has everything you need for a great getaway. A new renovation brings modern amenities to this classic 50’s cottage. Enjoy a chef’s kitchen, 500 sq-foot deck with hot tub, and thoughtful touches like yoga mats, a record player, board games, and a backyard hammock. Monthly ski rental discounts are available!

Top guest favourite

Cabin in Monterey

4.95 out of 5 average rating, 286 reviews

Amazing Berkshire Mountains Cabin

Our incredible 4 bedroom home is situated on 2 beautiful secluded acres in picture perfect Monterey - the ultimate Berkshire County getaway, with modern kitchen, screened porch, 2 fireplaces a fabulous outdoor hot tub and a beautiful brook on the property. Enjoy hiking the Appalachian Trail in nearby Beartown State Forest or kayaking and swimming in the incomparable Lake Garfield. We are a quick ride to Ski Butternut, Catamount, Tanglewood, Lenox and Great Barrington.

Guest favourite

Home in Canaan

4.95 out of 5 average rating, 61 reviews

A/C! Hot Tub, Movie Room, & Private Beach Access!

Welcome to your all-season escape in the heart of the Berkshires & Hudson Valley! Stretch out and relax in this cozy, stylish home that feels worlds away—yet is just minutes from everything. Whether you’re here for skiing, concerts at Tanglewood, wine tasting, or farm-fresh markets, you’re perfectly positioned to enjoy it all. ☀️ SUMMER BONUS: Your stay includes exclusive access to Queechy Lake’s private beach—perfect for sunbathing, swimming, and lakeside lounging.

Guest favourite

Home in Monterey

4.96 out of 5 average rating, 271 reviews

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.