Holiday rentals with a hot tub in Berkshire County

Canoe Use, HOT TUB, Private, Berkshires!

Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Patio w/ Hot tub, fire pit -Acre wooded/secluded lot -8 Private beaches (NOT beach front) -Private Canoe -Appalachian Trail hiking -Wineries/Breweries -Master w/Queen. -2nd bed with 1 Twin/Full Bunk -Full size pull out couch - Kitchen w/utensils, pans, appliances, condiments. -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Generator on site

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.

NEW! Hilltop Ski and Sun Chalet with Hot Tub

Welcome to your Berkshires escape—a spacious 4-bedroom, 3.5-bath home that offers the best of both worlds: tranquil seclusion but close to downtown Great Barrington and charming Sheffield. The home’s location is a dream for outdoor enthusiasts, with Butternut and Catamount ski mountains just a short drive away. Rest and unwind in the hot tub after a wonderful day on the mountain. Whether you’re here to ski, hike, or simply relax, you’ll feel right at home in this idyllic Berkshires getaway.

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

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.

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.

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.

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!

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.