Holiday rentals with a hot tub in Great Barrington

4.99 out of 5 average rating, 252 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.

BathroomOutdoor spacesComfort

4.97 out of 5 average rating, 109 reviews

Cabin in East Nassau

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 tubBathroomTV

4.95 out of 5 average rating, 146 reviews

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

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.

Hot tubOutdoor spacesCleanliness

4.88 out of 5 average rating, 108 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!

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

Hot tubOutdoor spacesHospitality

4.99 out of 5 average rating, 379 reviews

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

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

SEPT. SPECIAL: Prosecco, s’mores kit & firepit supplies. Blush is a romantic boutique tiny-home getaway in Chatham, NY—just 2.5 hours from NYC. Enjoy a private hot tub, firepit, dreamy loft lounge, plush queen bed, full kitchen and curated luxe design. Tucked into a peaceful & private oasis yet just a 2-minute walk from Main Street: restaurants, brewery, shops, theater. Designed for quiet couples’ getaways, with low voices appreciated outdoors in and around the hot tub. @artparkhomes

Hot tubBathroomFamily

4.95 out of 5 average rating, 313 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.

Outdoor spacesHot tubSleep quality

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, 145 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.

BathroomOutdoor spacesLayout

4.96 out of 5 average rating, 310 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.

Outdoor spacesHot tubLayout

4.96 out of 5 average rating, 113 reviews

Home in Athens

Lake House close to Skiing & Indoor Hot Tub

Sleepy Hollow is a small community with lots to offer inside . This home offers so much entertainment you won't even have to leave the driveway . From a pool table, and video games to outside on a luxurious lawn overlooking this private lake. Sit down have a fire , cookout and watch the sun go down. Hunter and Windham mountain are both approx 40 minutes. Hudson is a skip away at 20-25 minutes putting you right on Main Street where all the action is.

Hot tubOutdoor spacesBackyard

4.9 out of 5 average rating, 101 reviews

Home in Sheffield

Berkshire Getaway~ No Pet Fee! Walk to Distillery

Hi! Welcome to the Berkshires! Enjoy total privacy on a full acre property overlooking 200 acres of conservation land. Warm nights by the fire & scenic views all in our fully stocked home 8 min from Great Barrington. Within steps of Big Elm Brewery & Berkshire Mountain Distillery. Peloton included. Pet-Friendly. Minutes to great hiking, skiing, antiquing & more Seasonal Hot Tub is not available until further notice, sorry for the inconvenience.

Outdoor spacesBathroomCondition

Barn in Town of Hillsdale

4.97 out of 5 average rating, 185 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.

Outdoor spacesBathroomAccuracy

4.95 out of 5 average rating, 115 reviews

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

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!

Outdoor spacesBathroomAccess

Popular amenities for Great Barrington hot tub accommodation

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a hot tub

4.87 out of 5 average rating, 171 reviews

Sunlight glimmers on the calm water surface at sunset, framed by tall trees. A hammock is visible on the ground, while a private dock with two Adirondack chairs provides a serene spot to relax. Colors of autumn foliage add warmth to the scene.

Home in Copake

Dreamy Hudson Valley Lakehouse with Hot Tub

BathroomOutdoor spacesCheck-in

4.98 out of 5 average rating, 134 reviews

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

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

Outdoor spacesBathroomAccuracy

4.98 out of 5 average rating, 241 reviews

Home in Craryville

Modern Home in Woods With Hot Tub

BathroomOutdoor spacesTV

4.88 out of 5 average rating, 221 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

Outdoor spacesBathroomAmenities

4.92 out of 5 average rating, 252 reviews

Home in Craryville

The City Farmers Upstate. Farm house with hot tub

BathroomHot tubKitchen

4.94 out of 5 average rating, 297 reviews

The exterior of a large farmhouse features a welcoming porch with a wooden bench and decorative elements. Lush greenery surrounds the pathway leading to the entrance, enhancing the inviting appearance of the dark wood siding and multiple windows reflecting natural light.

Home in Hudson

Livingston Farmhouse Escape with hot tub and sauna

Hot tubOutdoor spacesHiking

4.96 out of 5 average rating, 127 reviews

A wooden house is set against a wooded backdrop, featuring a dark facade with large windows. An outdoor fire pit is surrounded by seating arrangements on either side. The grassy area offers a natural and open invitation to enjoy the surrounding landscape.

Home in Catskill

Modern High-end 2BR2BATH in the woods of Catskills

BathroomOutdoor spacesLocation

4.85 out of 5 average rating, 215 reviews

An outdoor hot tub accommodates up to seven people, featuring a smooth surface and multiple jets. The setting includes lush green foliage in the background, with a clear sky above and natural light reflecting off the water's surface.

Home in Otis

The Meadows House @ Otis Ridge w/ 7-person hot tub

Hot tubBathroomCheck-in

Villa rentals with a hot tub

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.

4.75 out of 5 average rating, 146 reviews

Villa with Access to Amazing Amenities!

BathroomOutdoor spacesBarbecue

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 Town of Taghkanic

5.0 out of 5 average rating, 3 reviews

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

Hot tubFamilyIndoor spaces

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.

4.74 out of 5 average rating, 39 reviews

Spacious Villa with Access to Various Amenities!

BathroomOutdoor spacesView

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.

4.63 out of 5 average rating, 38 reviews

Villa with Access to Various Amenities

Hot tubBathroomFamily

4.75 out of 5 average rating, 4 reviews

Equipped Villa with Access to Amazing Amenities!

FamilyViewSkiing

Cabin rentals with a hot tub

4.96 out of 5 average rating, 125 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

Outdoor spacesBathroomKitchen

Cabin in Castleton-on-Hudson

The lodge cabin is presented against a vibrant sunset, illuminated by soft lights along the pathway leading to the entrance. The structure features a large deck with an overhanging roof, surrounded by trees and landscaped greenery.

4.94 out of 5 average rating, 127 reviews

Private Family Cabin w/ Hot Tub and Secluded Pond

Hot tubOutdoor spacesSleep quality

4.93 out of 5 average rating, 140 reviews

A cottage with a white exterior is set amidst trees with bare branches, indicating a winter landscape. A gravel path leads to the entrance, and a small porch is visible at the front. Snow lightly dusts the roof, enhancing the serene ambiance.

Cabin in Hinsdale

Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere

BathroomOutdoor spacesSkiing

4.94 out of 5 average rating, 109 reviews

The cabin's exterior is framed by lush greenery, featuring large windows that invite natural light. A deck extends from the side, offering a seamless connection to the surrounding woods. The dark wooden siding complements the serene outdoor environment.

Cabin in Red Hook

Secluded Cabin in Woods With Hot Tub

BathroomHot tubCondition

4.99 out of 5 average rating, 124 reviews

Cabin in Norfolk

The Red Cabin-Secluded Getaway with backyard Brook

BathroomHot tubWi-Fi

4.98 out of 5 average rating, 127 reviews

Cabin in Chesterfield

Hilltown Cabin Hideaway: A River Runs Through It!

Outdoor spacesBathroomNearby

Superhost

A hot tub is positioned on a wooden deck, inviting relaxation. A single chair sits nearby, offering a view of a lush landscape featuring trees with autumn foliage. Clear blue skies enhance the serene outdoor setting.

Cabin in Catskill

4.91 out of 5 average rating, 222 reviews

Cabin Oasis near Town

Hot tubBathroomBackyard