Holiday rentals with a hot tub near Jiminy Peak Mountain Resort

4.96 out of 5 average rating, 112 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, 154 reviews

The exterior of the lakefront home showcases a vibrant blue facade, framed by well-maintained green lawns and leafy trees. A spacious deck is visible, along with multiple large windows that enhance the inviting appearance of the property.

Home in Valatie

Escape to Lakefront Leisure—Amazing views!

Welcome to this beautiful lake-front home on Kinderhook Lake, NY. Totally rebuilt in 2018, this home is designed to maximize the incredible view of the lake. Cool and sunny in the summer, and warm and cozy in the winter. Come and relax on Lake Kinderhook!! Brand new 6 person hot tub. Relax and unwind while 45 jets massage your muscles, summer or winter! Ever sit in the steaming hot water while snow falls around you? Upgraded 400/100 internet for work/school! About 2 hrs from New York City!

4.93 out of 5 average rating, 128 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

Welcome to Lake Ashmere! Our newly and completely renovated cottage features two bedrooms with comfy queen size beds, a loft with two full size beds, cathedral ceilings, a year-round six person hot tub and a large working kitchen stocked with everything you need. The living space is bright and airy. WiFi in the cottage is over 500 mbps, making it ideal for longer stays. The spectacular lake is just a three-minute walk from the cottage and has a kayak and inner tubes available to our guests.

4.92 out of 5 average rating, 108 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.

4.94 out of 5 average rating, 182 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.

Flat 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.

4.97 out of 5 average rating, 150 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!

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

4.98 out of 5 average rating, 129 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!

4.96 out of 5 average rating, 299 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.

4.99 out of 5 average rating, 357 reviews

Tiny home in Chatham

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

Blush at Art Park Homes is a romantic boutique tiny home getaway in Chatham, NY—just 2.5 hrs from NYC & Boston. 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

4.96 out of 5 average rating, 114 reviews

Home in Becket

HOT TUB! Dog & Family Friendly in the Berkshires!

Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Freshly painted & new floors for 2026! -Patio w/ Hot tub, fire pit, canoe use -Acre secluded lot -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Appalachian Trail hiking -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch

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.

4.93 out of 5 average rating, 339 reviews

Artist Cottage

Artsy vintage cottage with a private lodge in a quiet Berkshire neighborhood. Backyard opens to woods with trails nearby. Enjoy fireplaces and hot tub in winter, waterfall and outdoor shower in summer. Upstairs queen ensuite with bathroom and soaking tub; downstairs retro kitchen, living room, and full bath with shower. Lodge offers comfy seating, farm table, and big-screen TV. High-speed internet, Prime & Spectrum TV.

Popular amenities for rentals with a hot tub near Jiminy Peak Mountain Resort

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a hot tub

4.95 out of 5 average rating, 120 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

4.87 out of 5 average rating, 102 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!

4.95 out of 5 average rating, 189 reviews

A spacious outdoor area is surrounded by vibrant planters filled with blooming flowers. Comfortable seating is arranged around a fire pit, with a green umbrella providing shade. A pink flamingo float is set nearby, alongside a wooden hot tub and a stock tank plunge pool.

Home in Hudson

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

4.88 out of 5 average rating, 200 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 With Hot Tub Near MASS MoCA

4.97 out of 5 average rating, 99 reviews

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.

Home in Brunswick

Eclectic Troy Retreat w/ Hot Tub & Sauna!

4.92 out of 5 average rating, 249 reviews

Home in Craryville

The City Farmers Upstate. Farm house with hot tub

4.91 out of 5 average rating, 169 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

4BR Cabin with Hot Tub & Pools –15 mins to Mt Snow

4.94 out of 5 average rating, 101 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

Villa rentals with a hot tub

4.94 out of 5 average rating, 90 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

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!

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.

4.75 out of 5 average rating, 140 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.

4.63 out of 5 average rating, 38 reviews

Villa with Access to Various Amenities

4.75 out of 5 average rating, 4 reviews

Equipped Villa with Access to Amazing Amenities!

Cabin rentals with a hot tub

Cabin in Castleton-on-Hudson

Two colorful kayaks, one blue and one bright green, rest on a wooden dock beside a serene green pond. A paddle boat is occupied by two individuals, while a gentle fountain adds a soothing element to the lush surroundings, featuring a vibrant yellow slide in the background.

4.95 out of 5 average rating, 121 reviews

Private Family Cabin w/ Hot Tub and Secluded Pond

4.87 out of 5 average rating, 60 reviews

Cabin in Valatie

Private Cabin w/ Pool & Hot Tub near Hudson

4.96 out of 5 average rating, 372 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

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

4.93 out of 5 average rating, 46 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!

4.99 out of 5 average rating, 86 reviews

A modern chalet is nestled among trees, showcasing a large wrap-around deck adorned with outdoor seating. A fire pit with seating is situated in the grassy backyard, highlighted by warm evening lights. The architectural design features a steep roof and large windows that enhance the natural surroundings.

Cabin in Wilmington

Modern Chalet-private deck/firepit/ clubhouse pool

4.88 out of 5 average rating, 69 reviews

The exterior of the chalet showcases a warm wooden facade with large windows, allowing natural light to fill the interior. A spacious deck wraps around the front, accompanied by a neatly stacked pile of firewood. Surrounding trees provide a secluded atmosphere.

Cabin in Readsboro

Chalet with Amazing views+ Hot Tub + privacy

5 out of 5 average rating, 45 reviews

A cozy living room features a large leather sectional sofa adorned with colorful throw pillows. Natural light streams through a large window above, highlighting the warm wood paneling and decorative curtains. A comfortable armchair and a coffee table complete the inviting space.

Cabin in Wilmington

Serene Getaway•Hot Tub•Pool•Game Room•Mt Snow

Other holiday rentals with a hot tub

4.84 out of 5 average rating, 44 reviews

An outdoor pool area is surrounded by several lounge chairs and umbrellas, offering a view of vibrant autumn foliage on the hills. The pool is partially covered, and a building is visible in the background, enhancing the resort-like atmosphere.

Flat in Hancock

Mountainside Condo Ski on/off

4.94 out of 5 average rating, 71 reviews

A spacious living area features an arrangement of dark leather seating and a wooden dining table. Natural light streams through sliding glass doors that open to a balcony. A stone fireplace adds character, while decorative plants and artwork enhance the inviting ambiance.

Apartment in Hancock

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

4.96 out of 5 average rating, 54 reviews

A view from the condo showcases snow-covered slopes leading up to the mountain, with ski lifts operating in the distance. The landscape is framed by the rustic stone chimney of the adjacent building, creating a serene winter scene.

Flat in Hancock

Ski-In Ski-Out Loft Lift & MT. Views

4.79 out of 5 average rating, 14 reviews

A comfortable living area features a plaid armchair and a beige sofa beside a wooden coffee table. A television is positioned near large windows that provide natural light. Decorative wall art and a potted plant enhance the inviting atmosphere.

Flat in Hancock

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4

4.96 out of 5 average rating, 54 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

Corey Road Condo | @ Jiminy Peak • Pool • Hot Tub

5 out of 5 average rating, 10 reviews

Townhouse in Hancock

Jiminy Peak Slopeside Getaway • Ski & Adventure

4.96 out of 5 average rating, 51 reviews

An outdoor deck features a pair of unique swinging chairs and a dining set under a large umbrella. Lush greenery surrounds the area, with a backdrop of tall trees and a manicured lawn. Colorful lawn furniture is visible in the distance, inviting relaxation.

Home in Hancock

Grand 6BR Home by Jiminy | Hike • Hot Tub • Games