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Vacation rentals with a hot tub in Berkshire County

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Top-rated hot tub rentals in Berkshire County

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An old-fashioned cedar hot tub is positioned on a wooden deck, surrounded by trees displaying autumn foliage. The peaceful outdoor setting offers a serene atmosphere for relaxation.

Cabin in Stephentown

4.85 out of 5 average rating, 295 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.

A gravel patio features bright turquoise Adirondack chairs arranged around a fire pit, set against a backdrop of lush green trees. A hot tub is situated nearby, with a shaded seating area under a canopy. The peaceful surroundings enhance the outdoor space.

4.98 out of 5 average rating, 61 reviews

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

An aerial view showcases a serene lake bordered by lush greenery and trees, with the elegant cottage nestled among them. A private dock extends into the calm waters, reflecting the surrounding nature. The expansive landscape emphasizes the cottage's tranquil, waterfront location.

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.

A charming cottage is framed by vibrant flowering shrubs and greenery. The front porch is adorned with decorative elements, while large windows invite natural light into the space. A wooden fence encloses the front garden, enhancing the quaint and inviting atmosphere.

Cottage in Great Barrington

4.93 out of 5 average rating, 300 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.

The inviting living area features intricate wood detailing and an ornamental ceiling. Two comfortable armchairs flank a round marble coffee table, positioned over a traditional area rug. A decorative fireplace and a flat-screen TV offer cozy amenities, while natural light fills the space through nearby windows.

Home in North Adams

4.89 out of 5 average rating, 170 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 favorite

A living area is designed with an inviting leather sofa and two cozy armchairs arranged around a central coffee table. A media console displays framed artwork, and large windows offer views of the surrounding trees, creating a bright and airy atmosphere.

Cabin in Stockbridge

4.97 out of 5 average rating, 31 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.

A spacious mountain lodge is depicted, featuring a striking stone chimney and expansive decks. Large windows frame the scenic landscape, while lush green grass surrounds the building. The warm tones of the log exterior harmonize with the natural setting, inviting outdoor relaxation.

Place to stay in North Adams

4.93 out of 5 average rating, 158 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 favorite

A modern cabin features a striking facade with large windows, surrounded by colorful trees. An outdoor deck contains multiple seating areas, including lounge chairs and a dining table. A wood-fired hot tub is situated nearby, surrounded by landscaped greenery and gravel pathways.

Cabin in East Nassau

5 out of 5 average rating, 51 reviews

Luxury Cabin | Breathtaking Views & Outdoor Fun

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, freshwater lake only locals know about. 2.5 hrs from NYC and from Boston. Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit and chairs, Webber Grill, radiant floor, WFH space, and EV charging!

A bright great room features large windows that offer expansive views of the surrounding valley. Vaulted wooden ceilings enhance the airy feel, while a comfortable gray sofa and a white couch are positioned to invite relaxation. Natural light fills the space, showcasing the warm wooden walls.

Home in Tyringham

4.83 out of 5 average rating, 119 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.

A hot tub sits on a polished wooden deck, surrounded by greenery. Soft lighting from string lights illuminates the area. A colorful striped pillow rests on a lounge chair, with a patterned plate and drink placed nearby, creating a relaxing outdoor retreat.

Home in Great Barrington

4.94 out of 5 average rating, 121 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 favorite

A spacious log cabin with a metal roof is surrounded by trees. The front porch is lined with a railing, and large windows invite natural light. A gravel driveway leads up to the cabin, with a small shed visible to the side.

Cabin in Monterey

4.95 out of 5 average rating, 284 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.

A hot tub is positioned outdoors on a wooden deck, surrounded by tall trees. Fresh towels are neatly arranged on a small table nearby. The serene lake, framed by lush greenery, is visible in the background, indicating a peaceful outdoor retreat.

4.95 out of 5 average rating, 57 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.

Vacation rentals for every style

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Popular amenities for Berkshire County hot tub rentals

Free parking on premises

Air conditioning

House rentals with a hot tub

Top guest favorite

A spacious open-plan living area is showcased, featuring large windows that invite natural light. A modern sectional sofa in warm tones is arranged around a low table. A dining area with a long table and dining chairs is visible in the background, enhancing the inviting atmosphere.

Home in Egremont

5 out of 5 average rating, 36 reviews

The Catamount Ski Haus with Pool & Hot Tub

A spacious outdoor area features a circular stone fire pit surrounded by a sectional seating arrangement. A gazebo and hot tub are visible in the background, along with scenic views of rolling hills under an expansive sky.

Home in Hillsdale

4.96 out of 5 average rating, 23 reviews

Hillsdale Escape | Pool, Hot Tub, Game Room

A spacious white two-story house is set against a backdrop of lush greenery. The yard is framed by trees, featuring a patio area with seating and flags. A gravel driveway leads to the home, which offers a welcoming view of the outdoor space.

Home in Hancock

4.95 out of 5 average rating, 37 reviews

Berkshire Retreat: Huge Home W/Hot Tub & Yard

A large country estate is presented, featuring an orange exterior surrounded by lush greenery. The home includes a spacious front entryway with steps leading to double doors, while an expansive driveway and two-car garage are visible on the right.

Home in East Chatham

4.9 out of 5 average rating, 31 reviews

10 Acre Country Estate with Pool, Hot Tub & Views!

The living room features a bright and airy design with large windows that provide natural light. A soft sectional sofa offers ample seating, facing a cozy fireplace surrounded by stone. Decorative art pieces and a wooden ceiling enhance the room's warmth and character.

Home in Great Barrington

5 out of 5 average rating, 18 reviews

NEW! Hilltop Ski and Sun Chalet with Hot Tub

Top guest favorite

The exterior of the home is surrounded by lush greenery, featuring a spacious wooden deck. Large windows allow for ample natural light, while the grey siding complements the serene woodland setting. Steps lead to a well-maintained lawn, enhancing the inviting appearance of the property.

4.98 out of 5 average rating, 53 reviews

Lakeside 3-BR Berkshires Residence

A modern home with a dark exterior features large windows and a welcoming entrance. The surrounding landscape includes lush greenery and well-maintained plants, complemented by a gravel pathway leading to the front door, set against a backdrop of a clear blue sky.

Home in Great Barrington

4.97 out of 5 average rating, 34 reviews

All Seasons Berkshires Family Retreat with Hot Tub

The spacious living area features vaulted ceilings with exposed beams and large windowed doors that lead to the outdoor deck. A comfortable sectional sofa surrounds a coffee table, while a natural fiber rug adds texture to the hardwood floor. A wood fireplace is visible for warmth.

Home in West Stockbridge

4.95 out of 5 average rating, 41 reviews

Beautiful And Private Home Centrally Located

Cabin rentals with a hot tub

Cabin in Austerlitz

Private Hot Tub: Hudson Valley Cabin Retreat!

An open concept dining area features a round wooden table surrounded by white chairs. Large glass doors offer views of the outdoor deck and lush greenery, allowing natural light to fill the space. A plant adds a touch of nature inside.

Cabin in Austerlitz

Quiet nature retreat with a brook on 38 acres

A spacious log cabin is set against a backdrop of trees, featuring a well-kept lawn and a large front deck with seating. The structure includes multiple windows and a welcoming entryway, inviting guests to explore the tranquil surroundings and enjoy the natural light.

Cabin in Austerlitz

4.93 out of 5 average rating, 41 reviews

Cabin w/hot tub/fire pit/hiking/skiing!

Top guest favorite

A charming red house with a stone foundation is set amidst lush greenery. A wooden porch with railings is visible, complemented by an American flag hanging from the eaves. The driveway is gravel, leading to a garage with a white door.

Cabin in Egremont

4.98 out of 5 average rating, 80 reviews

Cozy cabin near Catamount&Butternut w workout rm

Other vacation rentals with a hot tub

Top guest favorite

A charming two-story home is set amidst lush greenery, featuring a spacious front porch with seating. The house is flanked by trees, and a large lawn is visible in front, complemented by a gravel driveway leading towards an attached garage.

Home in Lanesborough

5 out of 5 average rating, 24 reviews

Berkshire Mountain House

A view of the resort's outdoor area showcases green tennis courts surrounded by trees and grass. Multiple buildings featuring wooden exteriors are positioned in the background, with gentle hills covered in lush greenery rising beyond.

Villa in South Lee

4.78 out of 5 average rating, 131 reviews

Villa with Access to Amazing Amenities!

Top guest favorite

An aerial view captures the easy living ranch surrounded by expansive green trees. The spacious property reveals a long private driveway leading to the home, with natural forested hills in the background. The scene conveys a sense of privacy and tranquility.

Home in Great Barrington

5 out of 5 average rating, 14 reviews

Great Barrington Ranch. Sleeps 10,Hot Tub, 5 acres

A tranquil evening scene captures a blue house surrounded by tall trees as the sky displays shades of orange and pink during sunset. A spacious lawn leads to the home, with a hint of landscaping elements visible in the background.

Home in Great Barrington

4.81 out of 5 average rating, 16 reviews

Berkshire Retreat with Hot Tub

A contemporary black house is nestled among vibrant autumn foliage. The sloped roof and large windows create an inviting silhouette. Adirondack chairs are arranged on the grassy lawn, surrounded by lush greenery and colorful shrubs, enhancing the natural, tranquil setting.

Home in Tolland

4.95 out of 5 average rating, 64 reviews

Spacious Home w/ Hot Tub in Private Lake Community

A resort-style building features three levels with balconies, framed by lush green grass and a serene pond reflecting the structure. The surrounding area is dotted with a few rocks and landscaping, creating a peaceful outdoor environment.

Hotel room in Lee

5 out of 5 average rating, 11 reviews

Great place for family |2 BD|Kitchen| Pool

The spacious great room features comfortable seating arrangements, including armchairs and a sofa. A large flat-screen TV is mounted above a classic stone fireplace. Natural light floods in through multiple large windows, enhancing the neutral color palette and charming decor.

Home in New Marlborough

4.89 out of 5 average rating, 38 reviews

Berkshires Colonial Farmhouse

Top guest favorite

A mid-century modern house is set against a backdrop of lush trees and vibrant autumn foliage. The exterior features large windows and a welcoming entrance. A spacious lawn surrounds the property, complemented by neatly trimmed shrubs and a driveway leading to the two-car garage.

5 out of 5 average rating, 16 reviews

The Maple House - Modern Retreat Near Town

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