Vacation rentals with a hot tub in Great Barrington

The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.

5 out of 5 average rating, 104 reviews

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

4.99 out of 5 average rating, 235 reviews

A cozy living room features a brown sofa positioned centrally, paired with an ottoman. Striped armchairs flank the space, with two lamps providing soft illumination. Warm wood paneling and large windows contribute to a welcoming ambiance, complemented by a decorative area rug underneath.

Home in Colebrook

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

Rustic getaway in the beautiful Litchfield Hills of Northwestern Connecticut featuring a 2-acre pond and access to 9 miles of unique hiking trails on 450+ wooded acres. Cozy 1700's farmhouse comfortably sleeps 4 adults in 2 bedrooms, with an additional kids room that has a fold-out double futon and loft with one double air-mattress, perfect for children's sleeping bags. There is a pull out sofa in the living room. Dogs welcome! The house is next to Norbrook Farm Brewery, which you can walk to.

4.96 out of 5 average rating, 101 reviews

The kitchen features deep black cabinetry paired with warm wood countertops. A window above the sink allows natural light to illuminate the floral wallpaper. Modern fixtures and a stylish faucet enhance the space, offering a functional area for meal preparation.

Cabin in Hudson

Cozy Grove Luxury Cabin

Luxurious, lovingly-appointed mid-century country retreat located less than 15 minutes from restaurants, galleries, and shopping in downtown Hudson, nestled between farmers’ markets, breweries, cideries, distilleries, hiking, and more! Recently-renovated 1958 cabin features a deep soaking tub, outdoor hot tub, woodstove, and upscale amenities. Set back from the road amidst a grove of pine and apple trees, it's the perfect spot for kicking back in luxury after a day exploring local attractions.

4.99 out of 5 average rating, 114 reviews

Cabin in Norfolk

The Red Cabin-Secluded Getaway with backyard Brook

Welcome to our secluded mid-century cabin nestled in the foothills of the Berkshires in Northwestern CT! When you stay here you'll find over three private acres of ferns, forests, wild flowers and a native trout brook a stone's throw from the backdoor with your private hot tub to relax in. Beyond the brook are hundreds of acres of state forest preserve. Enjoy great hiking, fishing, skiing, antiques and restaurants minutes away. Only 2 hours from NYC and 8 minutes to Historic Norfolk Center.

Two Adirondack chairs and a small side table are positioned on a grassy area, overlooking a serene lake. The water reflects the surrounding trees and hills, creating a peaceful atmosphere. The scene is complemented by gentle slopes of greenery in the background.

4.96 out of 5 average rating, 187 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.

4.99 out of 5 average rating, 473 reviews

Tiny home in Chatham

Sugar Shack | Romantic Tiny Home + Hot Tub

Sugar Shack | Romantic Tiny Home + Hot Tub. Celebrate Valentine’s all of FEB with complimentary roses-prosecco-robes-slippers! Escape to this 300 sq ft tiny home with private hot tub and she-shed. A peaceful, romantic getaway in the heart of Chatham—just steps from shops, dining, and theater. Only 2.5 hrs from NYC & Boston. Hike, explore, soak under the stars, or cozy up by the firepit. Thoughtfully designed for privacy, comfort, and indulgence. A blissful upstate NY retreat at @artparkhomes.

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, 132 reviews

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.

4.96 out of 5 average rating, 100 reviews

Home in Becket

HOT TUB! Spring Time! Berkshires! Dog-Friendly!

Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Patio w/ Hot tub, fire pit, canoe use -Acre wooded/secluded lot -Ski Otis Ridge 15 min or Butternut 30 min -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Naumkeag Lights -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

4.95 out of 5 average rating, 297 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 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.

4.99 out of 5 average rating, 306 reviews

Home in Lee

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.

4.83 out of 5 average rating, 133 reviews

Bungalow in Craryville

Lakeview Bungalow w/ Hot Tub, Fireplace & Lake

Relax and recharge at this charming 2BR lakeview bungalow in Copake Lake, NY. Just steps from the water, it features a private deck, firepit, cozy fire stove, two paddle boards, and a brand-new hot tub. Enjoy hiking, boating, skiing at nearby Catamount Mountain, winter walks around the lake, or simply unplugging. Close to Hudson and Great Barrington with easy access to trails, dining, and more — a stylish year-round retreat for couples, families, or friends.

4.96 out of 5 average rating, 295 reviews

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

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.

Popular amenities for Great Barrington hot tub rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a hot tub

4.95 out of 5 average rating, 115 reviews

A charming colonial home is depicted, featuring white siding and a green front door. Potted flowers decorate the entryway, and several windows provide natural light. The well-maintained lawn is surrounded by colorful blooms, contributing to the home's inviting curb appeal.

Home in Kinderhook

Modern and cozy 3 bedroom with outdoor oasis

4.89 out of 5 average rating, 183 reviews

A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.

Home in Rhinebeck

4Br Mountain Brook House on 130 acres w/ trails

Superhost

The exterior view highlights a modern two-story home surrounded by lush landscaping. A spacious deck is visible on the upper level, complemented by outdoor seating below. A hot tub and dining area with a patio umbrella can be seen on the stone patio, creating inviting spaces for relaxation.

Home in Cementon

4.88 out of 5 average rating, 130 reviews

Upstate Riverfront Getaway with Hot tub

4.99 out of 5 average rating, 139 reviews

Home in Kingston

Antique Uptown Charmer w/ Five-Star Modern Kitchen

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, 51 reviews

Sauna + Hot Tub Escape | Private & Pet Friendly

5 out of 5 average rating, 163 reviews

An aerial view captures the expansive landscape surrounding the barn, featuring vibrant autumn foliage and rolling mountains in the background. A serene pond is nestled among the trees, with the property’s expansive lawn visible in the foreground, emphasizing the natural beauty of the 12-acre site.

Home in Saugerties

Upstate Modern Scandinavian Barn in the Catskills

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.

4.98 out of 5 average rating, 45 reviews

Berkshires Family Oasis with Hot Tub, Patio, Gym

4.88 out of 5 average rating, 85 reviews

A charming gray house is depicted in a snowy landscape, with soft light emanating from a front window. The driveway and yard are covered in fallen leaves, while a wooden fence outlines the property, and a dusting of snow adds a serene touch.

Home in Sheffield

Berkshire Getaway~ No Pet Fee! Walk to Distillery

Villa rentals with a hot tub

4.99 out of 5 average rating, 94 reviews

The exterior of a spacious country estate is depicted, featuring a large infinity pool in the foreground. The house is framed by lush gardens and tall trees, with patio seating and blue umbrellas near the pool. Bright skies enhance the overall serene atmosphere.

Villa in Coxsackie

Magnificent Hudson River Estate with Infinity Pool and Spa

An arcade room features a variety of games, including a vibrant green air hockey table at the center. Nearby, colorful games and a television surround comfortable seating, providing an inviting space for entertainment and enjoyment.

Villa in South Lee

4.74 out of 5 average rating, 39 reviews

Spacious Villa with Access to Various Amenities!

The exterior of the spacious home is viewed from the lawn, showcasing a large stone chimney at the center. Two levels of balconies and decks are visible, bordered by lush greenery, creating a welcoming outdoor space. The structure features wooden siding and multiple entrances.

Villa in Taghkanic

5 out of 5 average rating, 3 reviews

Retreat to 56 Acres w/ Hot Tub, 2 Acre Pond, Pool

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

4.77 out of 5 average rating, 136 reviews

Villa with Access to Amazing Amenities!

A view of the resort grounds showcases well-maintained tennis courts, surrounded by lush greenery. Mountainous terrain rises in the background, providing natural beauty to the setting. The architecture includes several buildings, featuring balconies and clustered lights that enhance the outdoor space.

Villa in South Lee

4.65 out of 5 average rating, 37 reviews

Villa with Access to Various Amenities

Cabin rentals with a hot tub

A cabin nestled among tall trees is gently illuminated at dusk. Soft light streams through the open sliding door, revealing a cozy sleeping area with a person resting on a bed. The surrounding forest is lush with greenery, enhancing the serene atmosphere.

4.86 out of 5 average rating, 327 reviews

40-Foot Container Cabin in the Catskills

4.95 out of 5 average rating, 168 reviews

An open living area features high ceilings with exposed wooden beams. A comfortable gray sofa and a round coffee table sit on a traditional rug. A kitchen island with bar seating is visible, along with a modern television mounted on the wall.

Cabin in Catskill

Modern cabin retreat

4.96 out of 5 average rating, 367 reviews

A renovated Airstream is nestled among lush greenery, featuring large windows and a deck with dining setup. Soft lighting from overhead string lights adds a warm ambiance, while surrounding trees enhance the peaceful, natural setting.

Cabin in West Sand Lake

The Airstream at June Farms

The exterior of a modern cabin is showcased, featuring dark wood siding and large windows that invite natural light. A pair of black rocking chairs sits on the deck, complemented by a small metal table and logs stacked nearby. Lush green grass and scattered yellow wildflowers enhance the outdoor setting.

4.98 out of 5 average rating, 140 reviews

Modern Cabin in the Woods with Hot Tub

4.97 out of 5 average rating, 119 reviews

Cabin in Chesterfield

Hilltown Cabin Hideaway: A River Runs Through It!

An outdoor deck features a hot tub alongside a shaded seating area with blue cushions. A patio umbrella provides cover, while the surrounding greenery adds to the serene atmosphere. The wooden deck is spacious and inviting for relaxation.

4.88 out of 5 average rating, 203 reviews

Private Woodstock Getaway w Hot Tub

4.95 out of 5 average rating, 118 reviews

The kitchen features green cabinetry with a white countertop. Shelves above hold various jars and glasses. A window allows natural light to brighten the space, with a view of nature visible outside. Additional storage includes a fridge and a stainless steel trash bin.

Cabin in Athens

Charming Lakefront Cabin with Hot Tub