Vacation rentals with a hot tub in Berkshire County

4.86 out of 5 average rating, 290 reviews

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

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.

5 out of 5 average rating, 56 reviews

A cozy corner features a small electric fireplace and a comfortable chair, accented by a light throw blanket. The wall is adorned with textured wooden panels, while shelves display decorative plants. Natural light filters through the sliding doors, enhancing the inviting atmosphere.

Home in Becket

Berkshires! Canoe Use, HOT TUB, Private

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.

4.96 out of 5 average rating, 168 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.

4.97 out of 5 average rating, 77 reviews

A bright loft space features a spacious queen bed with light linens and decorative throw pillows. Skylights open the room to natural light, illuminating the cozy seating area and a kitchenette. A small dining table sits nearby, while a fireplace adds warmth to the ambiance.

Loft in Austerlitz

The Lookout Loft @Moonbeams: stay on 38 acres

The Lookout Loft at Moonbeams: a light-filled loft with a private bath & kitchenette on 38 acres in the Taconic Mountains. Relax & listen to the birds on your private outdoor deck. Cozy up by the gas indoor fireplace in the winter. Explore the property, located on a quiet, idyllic gravel road. Enjoy our wood fired hot tub (inquire about it for an additional set-up fee), hiking trails & tranquility brook-side lawn with multiple fire pits. A nature oasis perfect for the weekend or longer stays!

Cottage in Great Barrington

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.

4.94 out of 5 average rating, 295 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.

5 out of 5 average rating, 46 reviews

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

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, optional Tiny Home, and EV charging!

4.89 out of 5 average rating, 168 reviews

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

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

4.96 out of 5 average rating, 27 reviews

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

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.

Place to stay in North Adams

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.

4.93 out of 5 average rating, 155 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.

4.82 out of 5 average rating, 111 reviews

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

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.

4.94 out of 5 average rating, 118 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!

4.95 out of 5 average rating, 282 reviews

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

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.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

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A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Berkshire County hot tub rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a hot tub

4.85 out of 5 average rating, 78 reviews

A spacious living area features a modern sectional sofa adorned with various cushions, positioned around a round coffee table. Exposed wooden beams and high ceilings create an open atmosphere. A staircase leads to an upper level, and natural light illuminates the well-equipped kitchen visible in the background.

Home in Lee

Stonebridge Cabin: Modern Amenities, Enjoy Nature!

KateRating, 5 stars3 weeks ago

The location was great! The house accommodation was as show and very comfortable beds. We cannot wait to come back

5 out of 5 average rating, 31 reviews

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

The Catamount Ski Haus w. Pool/Hot Tub

JulieRating, 5 stars4 weeks ago

This house was perfect for our needs. We were in town for Berkshires graduation. It was 15 min from the school and 15 min from Great Barrington. Wish the weather would have been better for the pool! They were very available for any of our questions and needs. Definitely recommend!

4.94 out of 5 average rating, 32 reviews

The open living area showcases a modern curved sectional sofa in dark leather, adorned with cream and patterned pillows. A sleek chandelier hangs from the high ceiling, complemented by a wall-mounted TV and a wooden fireplace. Large sliding doors lead to the outdoor patio.

Home in Hancock

Bougie B’s Mountainside Getaway

TheresaRating, 5 stars3 months ago

Absolutely beautiful space. Spotlessly clean. Full kitchen amenities plus a little coffee station. Fabulously comfortable beds and living room furniture. Deliciously soft towels. Just an overall great experience and peaceful stay!!

5 out of 5 average rating, 20 reviews

A spacious house is surrounded by tall trees, showcasing a blend of gray siding and large windows. Lush greenery and ornamental grasses frame the property, while a cozy outdoor barrel sauna and a patio umbrella add inviting touches to the serene landscape.

Home in Canaan

The Little Yellow Door

RachelRating, 5 stars1 day ago

An incredible house for a group trip. More gorgeous and spacious than the photos made it seem — both inside and outdoors! Incredibly decorated, too!

An outdoor area features a wooden barrel sauna alongside a modern hot tub. The hot tub's white surface contrasts with the natural wood of the sauna, set against a backdrop of lush green trees and a wooden fence, creating a serene environment for relaxation.

5 out of 5 average rating, 41 reviews

Sauna + Hot Tub Escape | Private & Pet Friendly

AmyRating, 5 stars2 weeks ago

Loved the sauna and hot tub! The place is lovely, spacious, well stocked and very comfortable. We appreciated the bottled water that was left out for us. Very thoughtful and friendly host and caretaker/cleanup team. Will definitely stay again if in the area!

5 out of 5 average rating, 56 reviews

A serene lakeside setting is presented, featuring two metal chairs positioned near the water's edge. A small picnic table is nearby, surrounded by lush green grass and shaded by overhanging tree branches. The calm lake reflects the clear sky and distant hills.

Home in Lanesborough

Guest Fave, 15 Min Jiminy, Large Open LR, Hot Tub

KarleneRating, 5 stars3 weeks ago

Kristine was great! She was responsive to any concerns, candidly answered questions and gave recommendations, and the house and location were beautiful. Would love to go back, and cannot recommend enough!

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.

5 out of 5 average rating, 18 reviews

NEW! Hilltop Ski and Sun Chalet with Hot Tub

SarahRating, 5 stars4 days ago

Such a perfect house and a perfect stay! We did a midweek stay just to relax and couldn’t have had a better place to do so! The house is beautiful and so clean. The kitchen and everything you need to cook or grill (or make cheeseboards which is what we did). It’s super private and quiet and the back porch is the best. We loved having coffee on the porch every morning. Very close to downtown GB and plenty to do and see! Clear instructions and details about everything in the house and we got to check-in a little bit early. Hope to stay again!

5 out of 5 average rating, 49 reviews

The exterior of a newly renovated home is shown, featuring a light-colored façade and numerous large windows. A spacious deck with steps leads to the entrance, surrounded by a well-maintained lawn and trees. The peaceful setting is complemented by glimpses of the lake in the background.

Home in Becket

Lakeside 3-BR Berkshires Residence

LindaRating, 5 stars2 weeks ago

The house was just as described. The view of lake fabulous. It was easy to launch our kayaks from dock. Nice chairs on dock. The screen porch had very comfortable furniture. We enjoyed the hot tub. We celebrated our 45 th anniversary with our adult daughters and spouses. The grill was large and easy to use. Also enjoyed the ping pong table. Easy drive to Lee and restaurants and Big Y

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Cabin rentals with a hot tub

Cabin in Austerlitz

Private Hot Tub: Hudson Valley Cabin Retreat!

HanRating, 5 stars4 months ago

We had a wonderful time at the place. House was warm and clean. Kids had a lot of stuff to do and rooms to play in. Joy was so accommodating and responsive. I would highly recommend the place to other families looking for private place for wonderful time together.

KimRating, 5 stars34 months ago

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

Can’t say enough good things about our stay at Moonbeams. The house was so clean and had all the amenities you could ask for. We are a family of 4 with a 21 and 15 year old. We really enjoyed the expansive deck overlooking the beautiful forest where we hung out and grilled. They have a record player and we all liked listening to the records so much that we are going to get one at home. We enjoyed hanging out at the 2 fire pits. There is one near the house and another down by the stream. The house even has its own trail that we enjoyed. A few nights we watched movies on the large tv projector screen. The house had the perfect amount of space with the 3 bedrooms. We enjoy hiking and loved the 2 nearby trails up the road. The house is centrally located. Took about 20 min to get to everything we wanted to see. Great Barrington, Lenox, Chatham (the cidery is a must go to), Stockbridge and more. Graham and Alex were the perfect hosts and always helpful and available. We felt lucky to stay at such a special place that they have created! They made it so easy to relax and just enjoy the outdoors!

4.92 out of 5 average rating, 39 reviews

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

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

MadisonRating, 5 stars4 months ago

AMAZING! Some friends and I escaped the city for 3 days and stayed at this cabin. We will definitely be returning. The place was huge and so cute. Joy was more than accommodating. The hot tub was huge and clean. The wood burning fire places were so cute. Overall amazing place to say I would 1000% recommend.