
Fitness-friendly vacation rentals in Berkshire County
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Top-rated fitness-friendly rentals in Berkshire County
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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.

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2
Ski-in,ski-out! Unbeatable location for all seasons! Closest condo at JiminyPeak to the slopes and lifts. Located right at base of Mt. in JJ’sLodge in the heart of JiminyVillage. Mere steps to BerkshireExpress HighSpeed 6pack! Amazing pano views of the slopes surround. Designated pkg space in owner’s pkg lot. Unmatched access to all JP’s year-round activities. Skiing,MtBiking,hiking,tennis,swimming,fall foliage leaf peeping, shops,restaurants,MtAdventurePark w/ famous MtCoaster&AlpineSuperSlide.

"Hemlock Shadow" near Tanglewood on Six Acres
Hemlock Shadow is located on 6 acres of native and wild forest and features a small stream and pond located at the bottom of the property. It is centrally located near Lenox, MA and is only 1 mile up the hill from Tanglewood and all of the amenities the surrounding area offers. You will find excellent hiking trails within walking distance of the house. This minimalistic home offers an in-forest oasis where you can escape your troubles and enjoy the majestic nature afforded by the Berkshires.

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.

Serene+Stylish Mountain Retreat
Our beautifully-designed, comfortable, much-loved townhome is great for families or friends wanting an escape to the Berkshire mountains. Located up the hill from Jiminy Peak Village Center, the home has 4 bedrooms over 3 floors, an open plan living space, updated kitchen, family room, and new deck. A short walk to the slopes in winter and use of Jiminy Peak resort pools in the summer make it a year-round destination. Book your stay and find out why once you are here, it’s so hard to leave!

Cabin Retreat in the Berkshire Woods
Welcome to Hayscent Hollow, where you'll find seclusion and serenity in the Berkshire woods. Featuring 3 bedrooms and 2 bathrooms, this cabin offers a fully equipped kitchen, a spacious living room and an entertainment room with a pool table and home gym. Step outside to the expansive wraparound deck with a BBQ grill and backyard, or relax in the glassed-in porch and absorb the calm of the forest. Whether you're out exploring or staying in, this home offers comfort and convenience for all.

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!

Jiminy Peak Ski Loft with Hot Tub
This ski-in/ski-out loft at Jiminy Peak offers all of the amenities you could ever possibly ask for! A spacious 1 bedroom loft that sleeps up to 4 (1 Queen Bed, 1 Pullout Couch) is stylish and comfortable. We are the new owners and we are regularly updating the furniture and decor. A full kitchen, full bathroom with tub, ski locker / equipment storage, laundry in unit, dedicated parking spot, access to 2 pools and 2 hot tubs, a sauna, skiing, mountain cart, ropes course, and more!

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

Great 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. **Additional charge

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.

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.
Popular amenities for Berkshire County fitness-friendly rentals
Fitness-friendly apartment rentals

Mountainside Condo Ski on/off

Peaceful 2 BR apartment minutes from Tanglewood

Dream Vacation

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

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4

Cozy Ski Retreat

Lovely Condo w/ Resort Amenities

Must See Cabin Suite Jiminy Sleeps 4- Mountainview
Fitness-friendly condo rentals

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

Jiminy Peak Apartment

Jiminy Peak Country Inn 1 Bedroom Suite

Peaceful 1BR Condo with Pond View

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

Ski-in/Ski-Out on Jiminy Peak

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Jiminy Peak | 3BR 2 BA | 4-Season Mountain Retreat
Fitness-friendly house rentals

8 Mi to Tanglewood & Butternut Ski: Spacious Home!

Close to Catamount, Mini Gym, Big Views!

Snowdrop Lodge: Beautiful Condo at Jiminy Peak

Jiminy Peak Peaceful Home in Berkshires

Serene Berkshires Home On 5+ Acres, Rustic & Chic

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

Berkshire Retreat

All new mountain retreat near Great Barrington.
Destinations to explore
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- Fitness-friendly rentals Massachusetts
- Fitness-friendly rentals United States
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Thacher State Park
- Butternut Ski Area and Tubing Center
- Mount Snow Ski Resort
- Bash Bish Falls State Park
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Zoom Flume
- Mohawk Mountain Ski Area
- Taconic State Park
- Ski Sundown
- Norman Rockwell Museum
- Opus 40
- Naumkeag
- June Farms
- Berkshire Botanical Garden
- Hancock Shaker Village
- Millbrook Vineyards & Winery
- Poets' Walk Park
- MVP Arena
- Rensselaer Polytechnic Institute




