Holiday rentals with a hot tub in Stockbridge

Find and book unique hot tub accommodation on Airbnb

Quick stats about holiday rentals with a hot tub in Stockbridge

Total holiday rentals
Explore 20 holiday rentals in Stockbridge
Nightly prices starting at
Stockbridge holiday rentals start at $334 AUD per night before taxes and fees
Verified guest reviews
Over 310 verified reviews to help you choose
Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 10 rentals that welcome pets
Holiday rentals with a pool
20 properties feature pools
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wi-Fi availability
20 of Stockbridge holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Stockbridge rentals
5 Average rating
Stockbridge stays are highly rated by guests—averaging 5 out of 5!
Nearby attractions
Stockbridge's top spots, include Norman Rockwell Museum, Naumkeag, and Berkshire Botanical Garden

Top-rated hot tub accommodation in Stockbridge

Guests agree: These hot tub accommodation options are highly rated for location, cleanliness and more.

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Top Guest favourite

A tiny home features a private hot tub on the deck, illuminated by soft LED lights. The structure is surrounded by natural wood paneling, with doors leading into the cozy interior, where warm light spills out, creating an inviting ambiance.

Tiny home in Chatham

4.99 out of 5 average rating, 375 reviews

Boutique TINY home+private HOT TUB-walk to Main St

Sept. SPECIAL(Mon-Thurs): Includes Prosecco, s’mores kit, firepit supplies. Blush is a romantic boutique tiny home getaway in Chatham, NY—just 2.5 hrs from NYC. Enjoy a private hot tub, firepit, dreamy loft lounge, plush queen bed, full kitchen & curated luxe design throughout. Tucked into a peaceful private oasis, yet only a 2-min walk to Main St. restaurants, brewery, shops & theater. Perfect for couples seeking a unique Hudson Valley getaway near hiking, galleries, great dining. @artparkhomes

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Guest favourite

Cabin in East Nassau

4.97 out of 5 average rating, 106 reviews

Fall Foliage Luxury Cabin & View 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, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

Hot tubBathroomSkiing

Guest favourite

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

4.96 out of 5 average rating, 106 reviews

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!

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Guest favourite

A serene view of a winding driveway surrounded by vibrant perennial gardens. Colorful flowers grow abundantly along the path, leading to a scenic landscape of rolling hills and distant mountains under a partly cloudy sky.

Home in Pittsfield

4.97 out of 5 average rating, 156 reviews

Hidden Oasis in the Mountains by Evergreen Home

Evergreen Home Vacation Rentals invites you to this hidden oasis in the heart of the Berkshires. This attractive 5-bedroom home features a large, fully-outfitted kitchen, Tuft & Needle mattresses, and stunning mountain views. Relax in the hot tub, enjoy the perennial gardens, or gather on the stone patio by the fire pit. Just 7 minutes to Bousquet Mountain and minutes from Lenox and Tanglewood, this is the perfect retreat for family and friends. Experience luxury and comfort—book today!

Outdoor spacesBathroomGetting around

Guest favourite

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

4.88 out of 5 average rating, 107 reviews

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

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Top Guest favourite

Home in Lee

4.99 out of 5 average rating, 316 reviews

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 relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

Outdoor spacesBathroomCleanliness

Guest favourite

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, 310 reviews

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.

Outdoor spacesHot tubWalkability

Superhost

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

4.81 out of 5 average rating, 144 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.

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Top Guest favourite

The spacious kitchen features an island with a wood countertop and built-in storage. Mint green cabinetry offers a serene ambiance. Natural light flows through large windows, illuminating the dining area with a wooden table and cozy seating, creating an inviting space for gatherings.

Home in Ghent

4.98 out of 5 average rating, 133 reviews

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

At the end of a dead end road on 12 acres, you'll find the perfect retreat. Highlights include a natural swimming pool, yoga deck, outdoor Japanese hot tub and sauna. Chef's kitchen, grill and smoker. Living room has a piano and seats a large group. Outside there's a 3 level stone patio, deck and firepit w/outdoor sound system. Private yoga & in-home massage. Peloton bike, Temperpedic & saatva mattress, beautiful linens! *extra 6 guests w/rental of guest house!

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Top Guest favourite

The spacious living room features large windows that provide scenic views of the mountains and lake. A comfortable sectional sofa is complemented by a decorative throw and cushions. The ceiling is elevated with wooden beams, and stylish decor enhances the inviting atmosphere.

Home in Monterey

4.96 out of 5 average rating, 307 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.

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Top Guest favourite

Barn in Town of Hillsdale

4.97 out of 5 average rating, 183 reviews

Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & hot tub & stock tank pool on a 15-acre hilltop w/ views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking & tons of games. Near great shops & restaurants in Hudson & Great Barrington. We can point you to the best people to book for private massages or yoga classes right at the house.

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Top Guest favourite

A striking red barn-style building is surrounded by lush greenery and autumn-colored trees. Stone pathways lead to the entrance, complemented by a wooden deck that extends from the structure. Large windows allow natural light to enter, enhancing the home’s inviting exterior.

Barn in Copake Lake

4.95 out of 5 average rating, 115 reviews

The Barn at Copake Country Club

Completely refurbished 1827 post & beam barn featuring an Adirondack-chic style. Surrounded by the original wood floors & walls, this 3,000 sq ft 3-bed/3-bath space feels spacious yet cozy & offers fabulous views of Zeky's Pond across the street. Located just a stones throw from Copake Lake & Copake Country Club, you will never run out of things to do; it's the perfect spot for a family vacation, golf trip, celebration or couples getaway!

Hot tubOutdoor spacesAir conditioning