Vacation rentals with a hot tub in Lanesborough

4.99 out of 5 average rating, 378 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(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

BathroomHot tubLocation

4.97 out of 5 average rating, 107 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!

BathroomHot tubView

4.92 out of 5 average rating, 115 reviews

A peaceful scene reveals a winding road leading through a residential area with well-maintained homes. Snow-covered mountain slopes are visible in the background, flanked by trees that display early signs of changing seasons.

Townhouse in Hancock

Berkshire family getaway at Jiminy Peak!

Beautifully renovated space for a perfect getaway! Our home is a comfortable family space with ski-in/ski-out access to Jiminy Peak through an access trail at the end of our street, so you can skip the parking and shuttles. With four bedrooms spread over three floors for privacy, a brand new kitchen, and space to relax, there's room for everyone in your group to make the most of your time away. And with the charming towns of the Berkshires all around you, there's plenty to do all year round.

BathroomHot tubCleanliness

4.94 out of 5 average rating, 192 reviews

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.

Apartment in North Adams

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.

BathroomOutdoor spacesSleep quality

5.0 out of 5 average rating, 116 reviews

Treehouse in Wilmington

Beautiful timber-frame treehouse

The timber frame treehouse is a perfect couples retreat. The home is custom built with hardwood maple trees cut down and milled right on the property. The deck has a barrel sauna, cold or hot cedar soaking tub, a propane fire pit, a wood burning chiminea fire pit, and a bar top for outdoor dinning. The inside has a stone fireplace, fully equipped kitchen, tile shower, projector with dvds, books, board games, chandelier, and dimmable lighting for any mood. This home is truly one of a kind.

Hot tubOutdoor spacesSleep quality

4.97 out of 5 average rating, 157 reviews

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

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!

Hot tubBathroomCheckout

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

BathroomHot tubLaundry

4.99 out of 5 average rating, 318 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 relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

Hot tubOutdoor 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

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!

Hot tubBathroomLong stay

4.96 out of 5 average rating, 309 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.

BathroomOutdoor spacesTV

Superhost

A uniquely designed raised container home features multiple levels and large windows that offer expansive views of the surrounding landscape. The structure includes a covered outdoor area below, and the combination of dark wood and metal creates a striking exterior appearance.

Shipping container in Whitingham

4.88 out of 5 average rating, 121 reviews

The House of Pi

WE now pay your 15.5% Guest Service fee!!! Welcome to The House of Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock and Kayaks. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views. Hot Tub and Custom Cedar Sauna!

BathroomOutdoor spacesHospitality

4.96 out of 5 average rating, 112 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.

Outdoor spacesBathroomAmenities

Popular amenities for Lanesborough 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, 111 reviews

A bright living area features large glass doors that open to a wooden deck. Two green chairs flank a modern coffee table, while a basket sits in the corner. Natural light fills the space, illuminating the wooden floor and surrounding greenery outside.

Home in West Stockbridge

Berkshires-Enjoy The Peak, private home

Outdoor spacesBathroomAccess

Home in Town of Brunswick

A bright living area features large windows allowing natural light to fill the space. Comfortable seating arrangements include two armchairs and a vintage-style sofa. A small bookshelf displays assorted books, while a decorative mirror and plants add touches of character to the room.

4.96 out of 5 average rating, 106 reviews

Eclectic Troy Retreat w/ Hot Tub & Sauna!

Outdoor spacesHot tubGetting around

4.95 out of 5 average rating, 194 reviews

Aerial view of the Catskills lake-front house surrounded by greenery, showcasing the serene lake and lush forested area. The property features a large driveway, with the house positioned near the water's edge. Tranquil lake views extend into the distance.

Home in Athens

Private lakefront home, hot tub & resort amenities

Hot tubOutdoor spacesQuiet

4.98 out of 5 average rating, 108 reviews

A spacious hot tub is positioned under a wooden pavilion, surrounded by string lights. Water cascades gently inside, with soft lighting reflecting on the surface. In the background, a tranquil view of the lake and nearby seating areas can be seen, inviting relaxation.

Home in Athens

Hudson Valley Lake · Hot Tub · Dock · Games · View

Hot tubOutdoor spacesTV

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 spacesCheckout

4.95 out of 5 average rating, 171 reviews

An outdoor area is illuminated by warm lights, featuring a hot tub nestled beneath a canopy. Comfortable seating is arranged nearby, surrounded by lush greenery. A wooden deck provides a relaxing space, with a partially enclosed yard that enhances privacy.

Home in Hudson

Vibing Hot Tub Cottage | Pet-Friendly | Hudson, NY

BathroomOutdoor spacesCondition

4.89 out of 5 average rating, 180 reviews

A large outdoor pool is surrounded by a wooden deck with lounge chairs and umbrellas. The background features a multi-story building with expansive windows. Vibrant autumn trees with colorful foliage frame the scene, providing a serene and inviting atmosphere.

Home in Wilmington

Family-friendly 4BR | Pools Hot Tub | Near Mt Snow

BathroomOutdoor spacesQuiet

4.95 out of 5 average rating, 125 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

BathroomOutdoor spacesWalkability

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.

4.76 out of 5 average rating, 144 reviews

Villa with Access to Amazing Amenities!

Hot tubOutdoor spacesFamily

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 tubHospitalityFamily

4.9 out of 5 average rating, 21 reviews

A spacious living area features a large sectional sofa positioned around a warming fireplace, with logs neatly stacked beside it. Natural light fills the space through multiple windows, while a spiral staircase leads to the upper level. Soft area rugs add comfort to the wooden floor.

Villa in Dover

Huge Stunning Mt Snow Villa Jacuzzi/Hot Tub/GameRm

Hot tubValueCheckout

4.95 out of 5 average rating, 99 reviews

An aerial view captures the spacious villa surrounded by vibrant autumn foliage and rolling hills. The property features a pool nestled among trees, with expansive lawns and a gravel driveway leading up to the home, offering a serene retreat in nature.

Villa in Pownal

Vermont Vacation Villa—Grapevine Getaway

Outdoor spacesHot tubLocation

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!

Hot tubBathroomKitchen

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 tubBathroomLayout

4.75 out of 5 average rating, 4 reviews

Equipped Villa with Access to Amazing Amenities!

FamilyCheck-inCleanliness

Cabin rentals with a hot tub

4.98 out of 5 average rating, 126 reviews

Cabin in Chesterfield

Hilltown Cabin Hideaway: A River Runs Through It!

BathroomOutdoor spacesHospitality

4.93 out of 5 average rating, 139 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

Outdoor spacesHot tubAmenities

4.95 out of 5 average rating, 312 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

BathroomHot tubFamily

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, 126 reviews

Private Family Cabin w/ Hot Tub and Secluded Pond

Outdoor spacesHot tubHeating

4.96 out of 5 average rating, 375 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

Outdoor spacesHot tubHeating

4.96 out of 5 average rating, 124 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

Hot tubOutdoor spacesSkiing

5.0 out of 5 average rating, 136 reviews

Cabin in Wilmington

Mid-mod VT Dream Chalet near skiing, lake & forest

Hot tubBathroomHeating