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Fitness-friendly vacation rentals in Pioneer Valley

Find and book unique fitness-friendly rentals on Airbnb

Top-rated fitness-friendly rentals in Pioneer Valley

Guests agree: these fitness-friendly rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
Cottage in Brimfield
4.98 out of 5 average rating, 96 reviews

Cheerful cottage by Little Alum Lake & Sturbridge

Little Alum is a gorgeous spring-fed lake in the quintessential New England town of Brimfield, MA. Brimfield is known as home to the largest flea market in the country. Little Alum is regarded as one of the cleanest lakes in Massachusetts due to its pristine water quality. The charming cottage is a one level home within close proximity to highways & downtown Sturbridge and off route 20 just a few minutes to downtown Brimfield and Antique show/flea market. Partial water views, steps to the water.

Guest favorite
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
4.98 out of 5 average rating, 47 reviews

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.

Guest favorite
A bright and inviting open-concept living area features two vibrant blue armchairs adorned with floral patterns. A wooden dining table is visible in the background, with a fully equipped kitchen displaying colorful cabinetry and modern appliances. Soft light enhances a welcoming atmosphere.
Home in Ashford
4.87 out of 5 average rating, 127 reviews

Lake - King - Gym - Kayak - Fire Pit - Pets Allowed - WD

The Lake House, a two-story Designer's Dream, boasts scenic water and starry sky views. ● 397 Mbps Wi-Fi | 2x 55” Smart UHD TVs | Washer & Dryer | Indoor Fireplace ● Nintendo (NES) w/ 30 Games | Record Player w/ Vinyl Collection ● 3x Kayaks | 2x Stand Up Paddle Boards | 2x Cruiser Bikes | 2-Car Garage ● Gym (Bike, Yoga Mats, Weight Bands, Power Tower) ● Patio w/ Fire Pit & Grill| Full Kitchen | Coffee (Keurig) Drive to: ● UCONN (10 Mins) | Hartford (20 Mins) | Boston (1 Hour) | NYC (2 Hours)

Guest favorite
The exterior of a two-story house is displayed, featuring a wide front porch with multiple windows. A well-maintained lawn is positioned in front, bordered by shrubs. The home includes a stone accent and a double garage, all set against a backdrop of trees.
Guest suite in Granby
4.91 out of 5 average rating, 152 reviews

Whole place,staycation,3 bedrooms, spacious area

ENTIRE LIVING SPACE: Private spacious 3 bedroom lower level. Near MacDuffie Prep School & 5 prestigious colleges. Couples, solo adventurers, business travelers, families (with kids), and big groups. 14 acre. Private-golf course, pickleball, polypropylene basketball court, badminton, fishing, frisbee golf and tennis courts close by. Nature surrounds you with quiet locations to relax. 1 acre beach pond to cool off. If you are the person who likes to stay busy or relax, this is the place for you.

Top guest favorite
Home in Goshen
5 out of 5 average rating, 25 reviews

Waterfront Wonderland | Luxe Log Cabin (Sauna/Gym)

This large lakefront log home comes complete with a sauna, gym, private dock, kayak & canoe, hammock, grill, screen porch, wraparound deck, fireplace and spacious loft. The perfect place for summer rest and relaxation, autumn colors, or a Winter getaway in the foothills of the Berkshires. Cabin vibes meet modern furnishing and amenities. Enjoy beautiful sunsets by the lake, natural serenity, and exploration. 20 mins to charming Northampton attractions, 30 mins from Berkshire East ski resort ❄️

Guest favorite
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
4.92 out of 5 average rating, 108 reviews

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.

Guest favorite
Home in Pittsfield
4.97 out of 5 average rating, 149 reviews

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!

Top guest favorite
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
4.95 out of 5 average rating, 91 reviews

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

Relax with the family in this beautiful new home on the Farmington River, featuring open living spaces, a fireplace, full kitchen, two bedrooms, and a walk‑out deck to enjoy the sounds of the water. Explore nearby arts at Tanglewood, with musicians such as James Taylor, Bonnie Raitt, ++, Jacobs Pillow, and Becket, hike the Appalachian Trail, kayak on Otis Reservoir, and enjoy fall foliage or winter skiing (close by Butternut Ski Lodge) A perfect year‑round getaway for every traveler

Top guest favorite
Aerial view of a charming home nestled among vibrant autumn foliage, showcasing rich reds and yellows. Rolling hills and a serene green field extend in the background, while a quiet road meanders through the picturesque landscape.
Home in Whitingham
5 out of 5 average rating, 85 reviews

VT Outdoor Retreat-Fire Pit-Yard Games-Sleeps 11

Escape to our tranquil countryside retreat, a spacious Southern Vermont basecamp built for year-round adventure. Nestled among fields and forest, the home offers peace and privacy with direct access to the VAST snowmobile trail network and easy access to skiing at Mt. Snow. It sleeps 11 and is ideal for families or friends who want space and value without resort pricing. After a day outside, unwind by the fire pit, enjoy the arcade, or settle in with a good book.

Top guest favorite
Home in Sunderland
4.99 out of 5 average rating, 76 reviews

Historic 5-Bdrm Home Minutes from 5 College Area

Our historic five bedroom, 2.5 bath, 3200 square foot home sleeps 13 comfortably between two kings, three queens, a bunk, and a set of twin beds. 19 ppl with blow up & couches. Our home is a professionally designed combination of historic and modern, with original wood floors, as well as keypad entry and mini-split heating and cooling. Family groups of 3-4 couples with children will be most comfortable. We do not allow parties or events, or non-staying guests.

Top guest favorite
Apartment in Sandisfield
4.95 out of 5 average rating, 61 reviews

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.

Top guest favorite
An inviting kitchen features a central island with barstools and warm wood accents. Large windows allow natural light to fill the space, highlighting the modern appliances and tasteful decor. A dining area with additional seating is visible in the background, promoting a sense of openness.
Home in Lenox
5 out of 5 average rating, 16 reviews

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.

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