Holiday rentals with a hot tub in Berkshire County

Hilltop Ski and Sun Chalet with Hot Tub

Welcome to your Berkshires escape—a spacious 5-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.

Berkshire family getaway at Jiminy Peak!

Beautifully renovated space for a perfect getaway! Our home is a comfortable family space with ski-in/ski-out access to Jiminy Peak through an access trail at the end of our street, so you can skip the parking and shuttles. With four bedrooms spread over three floors for privacy, a brand new kitchen, and space to relax, there's room for everyone in your group to make the most of your time away. And with the charming towns of the Berkshires all around you, there's plenty to do all year round.

Art House! W Hot Tub 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

Best of the Berkshires + Hot Tub by Evergreen Home

Evergreen Home Vacation Rentals invites you to this stylish 2-bed, 1-bath cottage, just 10 minutes from Catamount and 7 minutes from Great Barrington. This renovated 50s gem features a chef’s kitchen and a 500 sq. ft. deck with a private hot tub. Enjoy thoughtful touches like yoga mats, a record player, and a backyard hammock. Whether you're here to ski, hike, or shop, it is the perfect Berkshires base. Monthly ski rental discounts are available! Inquire today to secure your winter escape.

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.

Stonebridge Cabin: Modern Amenities, Enjoy Nature!

Our quiet, peaceful and nestled in the woods, is a meticulously updated modern retreat offers the quiet comfort of a home away from home. Only 5 minutes from town and in the heart of the Berkshires, this cozy cabin is a perfect escape from everyday life. Enjoy the fully appointed trappings of modernity—high-speed internet, a beautifully updated and well-stocked kitchen, hot tub, brand new stylish and comfortable furnishings, TV room, and more! Find us on social media: @stonebridgecabin

Cabin with Hot Tub and Lake Access

Although we are new to Airbnb we have hosted 71 bookings, 259 nights rating 4.6 on Evolve and Booking websites. Escape to the Berkshires for serene stay at this 2 bed-2 bath, Tolland vacation rental. Perfect for relaxing with the whole family getaway or weekend with friends! The peaceful cabin boasts a lush yard, a private hot tub, access to Cranberry pond (four beaches) and kayaks. Explore the area world-class attractions , hikes, ski, or farm to table food and wine scene.

Amazing Berkshire Mountains Cabin

Our incredible 4-bedroom home is situated on 2 beautiful secluded acres in picture perfect Monterey - the quintessential 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.

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a 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, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relax by the firepit- we hope you enjoy your stay and will visit us again.

HOT TUB! Berkshires: Dog & Family Friendly!

Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Freshly painted & new floors for 2026! -Patio w/ Hot tub, fire pit, canoe use -Acre secluded lot -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Appalachian Trail hiking -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch -Generator on site

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.

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 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 nearby towns. Mini-splits provide AC in bedrooms and LVR/DR/Kitchen common area. Up to 6 guests (no exceptions). 1 house-trained dog ok.