Fitness-friendly holiday rentals in Stockbridge

4.98 out of 5 average rating, 47 reviews

A hot tub is surrounded by wooden fencing and greenery. The water appears inviting against a backdrop of trees and a clear blue sky, creating a private outdoor space for relaxation.

Home in Great Barrington

Berkshires Family Oasis with Hot Tub, Patio, Gym

All seasons family retreat in PRIME Berkshires location. Located adjacent to the famous Appalachian trail, 5 minutes from downtown Great Barrington, 2 minutes from Ski Butternut and 15 minutes from Tanglewood in Lenox. Easy access to sensational hiking, dining, lakes and museums. The home is spacious and open with 4 BR, 7 beds, a large finished basement TV & game room space and backyard patio and hot tub. A perfect spot to enjoy the spectacular beauty and unlimited activities of the Berkshires.

5 out of 5 average rating, 116 reviews

A wooden deck features a hot tub, gently steaming in the evening air. String lights illuminate the surrounding area, casting a warm glow over the autumn foliage. Two Adirondack chairs are positioned nearby, inviting relaxation in the serene, wooded setting.

Home in Taghkanic

Sunbeam Lodge: Pool+Sauna, 50 Acres, ‘70s Oasis

Our peaceful, skylit, 3-bed 2-bath lodge is a totally private woodland paradise on a quiet country lane. Part secluded retreat, part rustic resort, part '70s-style cottage, it's only 2 hours from NYC & 20 minutes from Hudson. Unwind in 50 acres of untouched forest & grounds, a seasonal saltwater pool & cabana bar, a Finnish sauna & 7-person hot tub (open year-round), an open chef's kitchen & living room, & a sunny deck overlooking endless natural splendor. See more @sunbeamlodge on Instagram.

5 out of 5 average rating, 33 reviews

New! Gemini House 1892 Farmhouse w/ Pool - Hudson

Introducing Gemini House, a lovingly restored 1892 Farmhouse w/ Pool, on 2 acres in the scenic Hudson Valley. This charming 3 BR, 2.5 BA home is an Ideal Escape in the Perfect Location! Relax and enjoy the lovely living spaces, warm wood stove, fully-equipped kitchen, comfy beds, claw-foot tub, Pool, outdoor fire pit, dedicated work spaces, gardens plus a Bonus Room w/ Ping Pong table and workout space - minutes from the bustle of downtown Hudson, the train station, and only 2 hrs from NYC!

4.92 out of 5 average rating, 108 reviews

A bright and open living area is showcased with high ceilings and large windows. A comfortable seating arrangement is positioned near a fireplace, while a dining table set for six is visible. Wood accents and neutral tones contribute to a cozy, inviting space.

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.

4.99 out of 5 average rating, 336 reviews

A bright and inviting living area features large windows that offer views of the surrounding greenery. A comfortable sofa and chairs surround a coffee table, while a desk with a chair is positioned near the window for a productive workspace.

Cabin in Ghent

Cozy chalet w/ deck, fire pit, by Hudson & hiking

Cozy 3-bedroom (5-beds), 2-bathroom home on 4 private acres in charming Ghent, NY. Recently renovated, Arch Bridge Chalet offers modern clean comfort with an open floor plan, luxury bathrooms, high-end appliances and cookware, a wood-burning fireplace, outdoor deck, and fire pits. Surrounded by trees, trails, and streams, yet close to Hudson Valley farms, breweries, Berkshires skiing, and the vibrant town of Hudson. Perfect for hiking, biking, kayaking, skiing, and year-round getaways.

4.78 out of 5 average rating, 18 reviews

Hotel room in Lee

Beautiful place|2 BD|Kitchen| Pool

After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar. • Pools, Gym, Movie Theater and mini golf  • Accommodate up to 6 people  • One guest in the party, must be at least 21 y/o or older.    * U$10 PER NIGHT OF RESORT FEE(WAIVED) .  **Additional charge .

4.97 out of 5 average rating, 148 reviews

A hot tub sits under a wooden pergola, with soft lighting creating a warm ambiance. In the background, a fire pit glows softly, surrounded by lush gardens and a stone wall, providing a peaceful setting for evening relaxation.

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!

4.95 out of 5 average rating, 138 reviews

An inviting outdoor seating area is featured under a pergola adorned with warm string lights. The space includes a circular table surrounded by a sectional couch, creating a cozy spot for relaxation among lush greenery.

Home in Albany

Boho-Chic Cape Conveniently Located

Enjoy a spacious yet cozy home in a quiet neighborhood with off-street parking. Minutes from restaurants, shopping, universities (UAlbany, Sage, St. Rose), parks, museums, hospitals(Albany Med, St.Peters) and State Capital Offices for those traveling for business. We’re right off the main highway leading to the World Famous Saratoga Race Track (30 min) and Adirondack Mountains/Lake George (50 min)! From this Air Force Family to yours, welcome to our home.

4.95 out of 5 average rating, 61 reviews

Apartment in Sandisfield

Sweet Dreams Retreat

Romantic weekend getaway, featuring fireplaces, hot tub, swimmingpool, and outdoor decks . The Berkshire's, a popular vacation location. This is the perfect spot to unwind and recharge. Sweet Dreams Retreat is kept spotlessly clean and generiously stocked with everything you might need, including a full kitchen, washer and dryer, luggage racks and much more. Enjoy hiking, skiing, and a great selection of resturaunts and unique shops and more.

4.97 out of 5 average rating, 171 reviews

An outdoor hot tub is surrounded by softly glowing string lights, set against a backdrop of lush green grass and distant hills. A wooden swing is visible in the foreground, inviting relaxation in this tranquil hilltop setting.

Barn in Hillsdale

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.

The exterior of the two-story home is shown, featuring a covered patio with a white pergola adorned with string lights. A seating area is visible on the patio, while large windows in the upper story invite ample natural light. The greenery surrounds the property.

4.82 out of 5 average rating, 280 reviews

Bright, Airy Home in Hudson w/ TONS of Character!

Welcome to 514 Route 66! Conveniently located 5 min from historic Warren St, this bright and stylish country home is just minutes from downtown Hudson, where you can enjoy fine-dining restaurants, hip cocktail bars, art galleries, antique shopping, and more. Or, just relax, stay home, and sip coffee or wine in the sun-drenched living area, beneath the vaulted ceiling. A perfect mix of town and country, for a perfect upstate weekend.

5 out of 5 average rating, 16 reviews

Home in Lenox

Spacious Lenox Farmhouse | Retreat Near Tanglewood

Welcome to Green Garden! This charming 3 bedroom, 2.5 bathroom New England farmhouse is your new favorite retreat in the Berkshires. After a day of exploring, kick back by the glow of the fire pit or relax inside. Minutes from Tanglewood and downtown Lenox, you’ll enjoy farmer’s markets, great dining, and peaceful star-filled nights. The house is kid-friendly with a Pack ’n Play, Tripp Trapp high chair, and Inglesina Fast Table.

Popular amenities for Stockbridge fitness-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-Friendly apartment accommodation

An indoor pool area features calm blue waters under soft lighting. Large windows allow natural light to fill the space, and potted plants add greenery around the edges. Lounge chairs are arranged around the pool for relaxation, maintaining a peaceful atmosphere.

Apartment in Pittsfield

Charming 1 Bedroom - 4 Star Resort w/ pool

5 out of 5 average rating, 77 reviews

A charming entrance is framed by blooming pink shrubs and lush greenery, standing in front of a dark-colored home. The wooden fence complements the natural setting, with a soft pathway leading to the welcoming door. Sunlight filters through the trees, enhancing the peaceful ambiance.

Apartment in Lenox

Peaceful 2 BR apartment minutes from Tanglewood

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.

Apartment in Hancock

Mountainside Condo Ski on/off

An outdoor pool is featured at the resort, surrounded by lounge chairs and umbrellas for shade. Views of the well-maintained grounds and pool area are available, with trees and hills in the background. Nearby buildings provide accommodations for guests.

Apartment in Lee

4.92 out of 5 average rating, 25 reviews

Dream Vacation

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.

Apartment in Hancock

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

The living room features two reclining sofas positioned around a coffee table. A soft area rug adds comfort underfoot. A floor lamp provides ambient lighting, and wall art adds character to the neutral-toned space.

Apartment in Latham

Track Season Ready! Saratoga!

Apartment in Hancock

4.74 out of 5 average rating, 31 reviews

Central Berkshires Artsy Loft with Pool & Hot Tub

4.87 out of 5 average rating, 15 reviews

Apartment in Albany

Private Apartment Sleeps 6+

Fitness-friendly condo rentals

An aerial view of a multi-level green house surrounded by vibrant autumn foliage. The property is set against a backdrop of rolling hills, with pathways leading toward the house. A gravel driveway and landscaped areas enhance the outdoor space.

4.94 out of 5 average rating, 71 reviews

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

The exterior of the Country Inn at Jiminy Peak Mountain Resort is shown, featuring a traditional design with a large entryway supported by columns. A stone facade complements the light-colored siding, and multiple windows reflect the surrounding landscape. The entrance is accessible with a gentle ramp.

4.86 out of 5 average rating, 37 reviews

Jiminy Peak Apartment

An outdoor pool is surrounded by a wooden deck, offering lounge chairs and tables for relaxation. The area features a heated pool and a hot tub, framed by the building's façade, with large windows visible in the background. An umbrella provides shade near the seating area.

4.61 out of 5 average rating, 162 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

A lush green lawn frames a serene pond, reflecting the surrounding landscape. The two-story condo units are visible in the background, showcasing a harmonious blend with the natural setting. Towering trees provide a calming backdrop, enhancing the peaceful atmosphere of the area.

Condo in Lenox

4.7 out of 5 average rating, 10 reviews

Peaceful 1BR Condo with Pond View

The exterior of the Country Inn is displayed, featuring a covered entrance supported by columns and a stone base. A two-story structure showcases multiple windows, providing ample natural light. The building is surrounded by a parking area and nestled against a mountainous backdrop.

4.91 out of 5 average rating, 81 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

Condo in Williamstown

Vacation Village in Berkshires 12/28/25-1/4/26

A heated outdoor pool is seen surrounded by a patio area. Lush green hills and trees create a scenic backdrop. Nearby recreational areas can be observed, emphasizing the inviting outdoor atmosphere for relaxation and leisure.

4.79 out of 5 average rating, 14 reviews

Ski-in/Ski-Out on Jiminy Peak

4.74 out of 5 average rating, 31 reviews

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Fitness-Friendly Holiday House

A bright bedroom features a four-poster bed draped with crisp white bedding. A patterned rug lies beneath the bed. Artwork adorns the walls, complemented by a sleek black lamp and wooden furniture. Natural light streams through a shuttered window, with a radiator adding warmth.

4.98 out of 5 average rating, 50 reviews

3BR Stylish Hudson House w Fenced Backyard

4.83 out of 5 average rating, 18 reviews

Home in Becket

Secluded Berkshires Cabin | Deck, BBQ & Town Beach

4.77 out of 5 average rating, 70 reviews

A spacious living area showcases a blue sectional sofa with decorative pillows, paired with an orange armchair. A central coffee table holds magazines and snacks, while large windows invite natural light. A brick fireplace and an open steel staircase add character to the room.

Home in Otis

Serene Berkshires Home On 5+ Acres, Rustic & Chic

4.96 out of 5 average rating, 52 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

An aerial view of a spacious Hudson farmhouse is presented, surrounded by lush greenery and a manicured lawn. The property features a large patio area with outdoor seating, and the landscaped grounds provide a serene setting. The home showcases a charming roof and ample outdoor space.

5 out of 5 average rating, 17 reviews

Stylish farmhouse w/fireplace by downtown & nature

4.97 out of 5 average rating, 97 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!

4.95 out of 5 average rating, 91 reviews

A serene riverside scene features a seated statue surrounded by natural elements. Colorful fallen leaves blanket the ground, and trees provide a lush backdrop. A gentle stream flows nearby, enhancing the peaceful ambiance of the setting.

Home in Sandisfield

Lux on the River near Tanglewood w/220v EV charge