Fitness-friendly vacation rentals in Berkshire County

Find and book unique fitness-friendly rentals on Airbnb

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Popular amenities for Berkshire County fitness-friendly rentals

Fitness-friendly apartment rentals

Top guest favorite
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
5 out of 5 average rating, 72 reviews

Peaceful 2 BR apartment minutes from Tanglewood

LironRating, 5 stars9 months ago
Wonderful place to stay in Lenox! Approximately 10min drive to Tanglewood and downtown. Fully decked out apartment with all the amenities: full kitchen, toiletries stocked in the bathroom, lovely outdoor patio space. Relatively good value for the Berkshires, which of course, skews expensive. Jack and Tania were very responsive by text but respected our space and privacy in-person. Would absolutely stay again!
Superhost
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
4.86 out of 5 average rating, 29 reviews

Mountainside Condo Ski on/off

ThomasRating, 5 stars2 months ago
A great place for a skiing getaway at Jiminy Peek Resort! Ski - in, ski -out, a lovely appointed condo, with access to a hot tub. Frank was most helpful and friendly. I highly recommend his place.
Guest favorite
The living room features a cozy sofa and an armchair with a checkered pattern. A large window allows natural light to fill the space, complemented by soft drapery. An entertainment unit with a TV is situated near a decorative mirror and a wooden coffee table.
Apartment in Hancock
5 out of 5 average rating, 6 reviews

Mountain View Jiminy Peak Ski On Off sleeps 4

StaceyRating, 5 stars2 months ago
We had a lovely stay. The location can’t be beat. We were able to ski in and out, walk to village area and the restaurant was down the hall. It was so convenient yet even with everything so close- it was so peaceful and quiet. The directions and communications were detailed making it easy to get in and around once there. The bed was extremely comfortable!! The condo itself was immaculate and the view out to the slopes was fantastic. It had everything we needed! Everyone we encountered was so friendly and helpful! Howie was flexible with the checkin- making it much easier for us to get out onto the slopes! He communicated throughout our stay to be sure we were having a great time! Couldn’t ask for a better stay! Thank you! We will definitely be back!
Guest favorite
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
4.97 out of 5 average rating, 38 reviews

Ski-InSki-Out Loft Lift&MT.Views

ShawnRating, 5 stars1 month ago
My stay was smooth and the condo was nice. I was on a business trip so I didn't have much time in the room besides sleeping which was quiet
Superhost
The game room features comfortable seating with colorful cushions and a spacious, low-profile table. A large television is positioned on a stand, while shelves are filled with various board games. Vibrant wall art depicting gaming characters adds a playful atmosphere to the space.
Apartment in Hancock
4.6 out of 5 average rating, 5 reviews

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

CassandraRating, 5 stars1 month ago
We had a great time in this suite for 2 nights during Easter Weekend . This was a surprise gift for my boys .they absolutely loved the decor/gamers & Minecraft .they already asked to go back .host was very responsive and made sure we had everything we needed .we will definitely be back!
Guest favorite
A cozy living area features a tall Christmas tree adorned with lights and ornaments next to a glass-top coffee table. A fireplace with built-in decor sits beneath a mounted television. Velvety blue chairs complement an orange accent pillow on the nearby couch, surrounded by large windows with sheer curtains.
Apartment in Hancock
5 out of 5 average rating, 10 reviews

Artsy loft near MassMoCA with pool and hot tubs

NicoleRating, 5 stars2 months ago
We had a great stay at the end of ski season; the place was quiet and relaxing. We will definitely return!
Superhost
A welcoming living space is presented, featuring a dark stone fireplace as a focal point. Two armchairs with deer motifs complement a plush sofa, while a coffee table sits centrally. Soft light enters through partially open shades, enhancing the cozy atmosphere.
Apartment in Hancock
4.72 out of 5 average rating, 18 reviews

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

ShawnRating, 5 stars1 month ago
I rented this condo for some of my staff who said their stay was great. Four mechanics sharing a condo at a ski resort, they were easy to please.
Guest favorite
A spacious living and dining area features a large wooden table and a cozy seating arrangement. A flat-screen TV is mounted above a fireplace, and natural light flows through windows, creating a bright environment. Textured rugs add warmth to the hardwood flooring.
Apartment in Hancock
5 out of 5 average rating, 18 reviews

All-Season Condo at Jiminy Peak (Berkshires)

RobynRating, 5 stars3 months ago
Second year in a row staying here. And another perfect vacation. Great location, amenities are perfect, clean condo, and the owner is responsive when needed. Can't wait to stay here again.

Fitness-friendly condo rentals

Guest favorite
A cozy living area features a stone fireplace, a flat-screen television mounted on the wall, and a dark leather sofa. A wooden coffee table is positioned in the center, with decorative items displayed. Light filters through large glass doors, leading to an outdoor balcony.
Condo in Hancock
4.95 out of 5 average rating, 58 reviews

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

EladRating, 5 stars1 month ago
A Perfect Stay at Elisa's! Elisa's place was absolutely magical! Located in a charming yet convenient resort, this beautifully designed space instantly felt like home. Sunlight streams through the windows, illuminating tasteful décor that balances style and comfort. What truly stands out is Elisa's hospitality. Her communication was warm and helpful, and her local recommendations led us to hidden gems throughout the area. The spotless cleanliness and private garden oasis for morning coffee or evening drinks made everything perfect. This place represents exceptional value—not just accommodation but an experience connecting you to the local community.
Superhost
Condo in New Ashford
5 out of 5 average rating, 5 reviews

Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8

MichelleRating, 5 stars3 months ago
Great stay! Listing as described. My family really enjoyed our stay.
A nighttime view of a ski resort is depicted, showcasing well-lit ski slopes winding down a mountain. The landscape is illuminated with bright lights, highlighting the fresh snow. Several ski runs are visible, creating a serene and lively winter atmosphere.
Condo in Hancock
4.88 out of 5 average rating, 33 reviews

Unique - Country suite @ Jiminy Peak

BrentRating, 5 stars17 months ago
We had a fabulous time up at Jiminy Peak and being right on the mountain at Shana’s place made it very easy to enjoy the many things to do. Shana is a great host and her unit was perfect for our family of 5. Our younger two tried counting all of the gnomes in every room. We definitely recommend staying at Shana’s place, she is very easy to work with and quick to answer any questions. Thanks again A+
The entrance of the Country Inn is showcased, featuring a large, sloped roof and welcoming porch. Decorative lighting fixtures are positioned at the entrance, and the name 'Country Inn' is prominently displayed above the door. Lush shrubs frame the front of the building, enhancing the inviting appearance.
Condo in Hancock
4.6 out of 5 average rating, 148 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

BenRating, 5 stars3 months ago
We had a great stay here. It was very close to the ski lifts, and the ski locker was directly across the hall. It made for a very enjoyable and easy skiing experience. Jiminy Peak is a great place to ski at with a variety of trails for all skill levels, and even though it was a school vacation week/weekend, the lift lines were never long. Margaret was very responsive to any questions we had and made the process easy. We loved it!
Superhost
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
4.63 out of 5 average rating, 8 reviews

Peaceful 1BR Condo with Pond View

VeraRating, 5 stars5 months ago
Very nice and clean 1-bedroom apartment with a great view and everything you need for cooking meals. Wonderful location and very kind hosts
Superhost
Icicles hang from a structure in the foreground, with a view of snow-covered ski slopes illuminated by soft lights in the distance. The landscape is blanketed in fresh snow, creating a serene winter atmosphere.
Condo in Hancock
5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook

Ashley And NathanielRating, 5 stars15 months ago
We had a wonderful time staying at Paul’s place! We had easy access to the mountain for skiing. It was wonderful to have a ski locked to store our stuff outside of the room. In addition to the wonderful accommodation our kids loved the indoor/outdoor pool after a long day on the slopes. Highly recommend Paul and his accommodation!!!
A detailed trail map illustrates the ski terrain and features at Jiminy Peak Mountain Resort. The layout highlights various trails of differing difficulty levels, lifts, and key landmarks within the resort, providing a clear overview for winter activities.
Condo in Hancock
4.9 out of 5 average rating, 10 reviews

Ski-in/Ski-Out on Jiminy Peak

BiancaRating, 5 stars4 months ago
Perfect home base for skiing at Jiminy! It was great for me and my kid plus we got to enjoy the hot tub, pool, breakfast at the country store and dinner at bluebird & co. Justine was a great and communicative host - we hope to return soon!
Children are observed playing at a sandy beach by a tranquil lake. Some are digging in the sand while others are engaged in water play. The background features calm water reflecting the trees and a clear sky, enhancing the outdoor natural setting.
Condo in Great Barrington
4.85 out of 5 average rating, 41 reviews

Gem of the Berkshires, walkable to lake & downdown

TaranRating, 5 stars7 months ago
I cannot speak highly enough of Ephrat - she was a wonderful host and even let us stay later as we had family visiting. I had arranged a weekend for family and friends at this house, and she made the experience just as special as I had hoped for. On top of the stellar hosting and lovely home, the view is simply gorgeous. Best home to stay in during the fall in Great Barrington, hands down!

Fitness-friendly house rentals

Guest favorite
A modern cabin nestled among tall trees showcases a large deck with expansive glass windows reflecting the surrounding greenery. A stone pathway leads from the foreground to the entrance, framed by lush foliage and natural landscaping, enhancing the connection to nature.
Home in Sandisfield
4.92 out of 5 average rating, 26 reviews

Luxury Lake Home/ Ski House (on lake) All Seasons

JeanneRating, 5 stars6 months ago
Beautiful location. The lake, stream, and woods are pretty. The house is well-stocked and was perfect for our large group. The host Sean was very helpful before and during our stay.
Superhost
A private backyard features a heated pool surrounded by a stone patio. Lounge chairs with striped cushions line the deck, and a screened sunroom provides additional outdoor comfort. Lush greenery and blooming flowers add to the serene atmosphere, while awnings offer shade from the sun.
Home in Egremont
5 out of 5 average rating, 4 reviews

Fabulous Heated Pool, Screen Porch, Ping Pong!

AmyRating, 5 stars11 months ago
We had a wonderful family vacation staying at Stone Hill. The house is absolutely perfect, literally a dream house. The pool and landscaping are beautiful and peaceful. The kitchen has everything you could ever need for cooking big meals. We thoroughly enjoyed the basket with s’mores ingredients and the fire pit. The screened-in porch was the perfect spot to enjoy morning coffee and look out at the scenery and pool. The ping-pong table in the basement was fun for the whole family, as well as a great selection of games and cards in the TV room. These came in handy on our 2 rainy days. The owner was super responsive to a few questions we had. It’s the perfect location, only a short drive to Great Barrington and grocery shopping at Guido’s. There’s also a great dog park in GB if you’re traveling with a dog. We hope to come back to Stone Hill many times in the future.
A well-lit living area features large windows allowing natural light, with a cozy plaid sofa and two armchairs positioned around a modern fireplace. A rustic wooden coffee table is placed in the center, complementing the warm tones of the room.
Home in Hancock
4.83 out of 5 average rating, 12 reviews

Beautiful 4 Bedroom Townhouse in the Berkshires

LindaRating, 5 stars3 months ago
This home was the perfect place for our family/friends gathering. Location was fantastic - just a short 1-2 min walk to the ski-in spot, making it incredibly convenient for hitting the slopes with little ones. The host was exceptionally informative and friendly, ensuring we had everything for a comfy stay. Kids had fun sledding between the houses and grownups loved the hot tub.
An open living area features a light wood floor and large windows allowing natural light to fill the space. Comfortable couches are positioned around a woven coffee table, with artwork displayed on the walls, providing a welcoming environment for relaxation and entertainment.
Home in Great Barrington
4.84 out of 5 average rating, 43 reviews

Modern Escape in the Woods of the Berkshires - 4br

StevenRating, 5 stars12 months ago
Our family of 7 + 2 dogs found this to be the perfect trip to kick off summer. Space feels larger than the photos portray and is open enough for gatherings while allowing privacy for a few of us who worked remotely. The outdoor areas are perfect, complimented with pristine outdoor furniture. Everything is well maintained both inside and out. Everyone enjoyed the pool with enough room for all and being fenced in for our dogs was a welcome bonus! Our family was able to take advantage of the great hiking & biking nearby and enjoy Great Barrington for dinner. The host Steve was appropriately communicative and responsive throughout. If he’ll have us, we look forward to returning. We highly recommend this Airbnb.
The home's exterior is framed by vibrant red foliage, creating a striking entryway. A path made of stone leads to the entrance, while steps adorned with leaves provide access. Surrounding greenery enhances the natural setting, offering a serene and inviting atmosphere.
Home in Richmond
4.9 out of 5 average rating, 10 reviews

"Hemlock Shadow" near Tanglewood on Six Acres

VictoriaRating, 5 stars5 months ago
We gathered for New Year's with all our kids and a grandchild. The place is very well setup with bedrooms on 3 levels, so wonderful privacy for all. The living space is cozy with lots of comfortable seating. All the holiday decorations were a nice surprise and put us in a festive mood as soon as we got there. The whole house feels lived in and we immediately felt at home. Kitchen has a huge variety of small appliances and an amazing coffee machine. We'll be back!
Guest favorite
A serene view of the surrounding mountains is captured during sunset, with soft sunlight illuminating the landscape. A grassy area is visible, framed by trees, and a wooden deck extends into the view, creating a peaceful outdoor space.
Home in Hancock
4.88 out of 5 average rating, 48 reviews

Jiminy Peak Peaceful Home in Berkshires

EllenRating, 5 stars3 months ago
We had a great stay at Michelle’s place. It was very conveniently located to the base of Jiminy Peak, which made getting to and from the mountain very easy. The house was very well appointed and had everything we needed. We used the fireplace twice and it was super easy. Having access to the facilities at The Country Inn at Jiminy Peak was great as I am injured and can’t ski currently, so instead I went to the gym each day. My family didn’t want to leave and my kids are asking when we can go back!
Superhost
Home in Otis
4.74 out of 5 average rating, 47 reviews

Serene Berkshires Home On 5+ Acres, Rustic & Chic

MarvinRating, 5 stars2 weeks ago
Beautiful home, very spacious. Peaceful. Amazing yard for outdoor activities. Plenty of parking. Would definitely come again
Guest favorite
A charming two-story house is surrounded by greenery, featuring a classic red exterior with white trim. A spacious porch runs along the front, while manicured grounds and a wooden fence enhance the property’s inviting appeal. Trees in the background provide a natural backdrop.
Home in Canaan
4.99 out of 5 average rating, 90 reviews

Berkshire Lake House, gunite pool, Chef's Kitchen

AlexandraRating, 5 stars3 days ago
This was our second stay at the Queechy Lake house and it did not disappoint! The home is wonderfully maintained, fully equipped and cozy - we appreciated the new additions of the pool and backyard activities. It rained most of the weekend but we utilized Meredith and Jason’s local recommendations and had a blast.

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