Fitness-friendly vacation rentals in Pioneer Valley

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Popular amenities for Pioneer Valley fitness-friendly rentals

Fitness-friendly apartment rentals

Top guest favorite
Apartment in Lenox
5 out of 5 average rating, 72 reviews

Peaceful 2 BR apartment minutes from Tanglewood

LironRating, 5 stars10 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
Apartment in Wilmington

Luxury 2 Bedroom Suite 202B

BenRating, 5 stars3 months ago
Steven was a great host. My friends and I booked here for the weekend to go skiing at Mt Snow, and this was a short distance away. Our room had a spot in the hallway to place skis and boots, which was convenient for our stay. Our rooms were clean and the whole place was exactly like the photos. Steven was quick to respond when we had questions and was very generous to provide a bigger room for our group. Overall Steven is a great and caring host who shows pride in taking care of the lodge as well as the guests that stay there.
Superhost
Apartment in Hancock
4.86 out of 5 average rating, 29 reviews

Mountainside Condo Ski on/off

ThomasRating, 5 stars3 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
Apartment in Hancock
4.97 out of 5 average rating, 38 reviews

Ski-InSki-Out Loft Lift&MT.Views

ShawnRating, 5 stars2 months 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
Guest favorite
Apartment in Hancock
5 out of 5 average rating, 11 reviews

Artsy loft near MassMoCA with pool and hot tubs

GinaRating, 5 stars1 week ago
The absolute perfect location at the heart of the Berkshire Yoga Festival! Loved the location. Very comfortable for two people. The host was very quick to respond and was accommodating. I would definitely recommend and would stay there again.
Top guest favorite
Apartment in Keene
5 out of 5 average rating, 10 reviews

Privacy, View, Amenities, Gym, Garage included too

AndreaRating, 5 stars1 month ago
Laura’s place was better than expected. The pictures don’t do it justice. I wish I knew about it 4 years ago when my son started college. I would’ve stayed there every year. They are very welcoming. The suite is amazing and the scenery is beautiful. I wish we could’ve stayed there longer.
Guest favorite
Apartment in Hancock
5 out of 5 average rating, 18 reviews

All-Season Condo at Jiminy Peak (Berkshires)

RobynRating, 5 stars4 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.
Apartment in Dover
4.66 out of 5 average rating, 122 reviews

2BD 1BA | Mount Snow VT | Ski-Back Trail | Shuttle

ArielleRating, 5 stars3 weeks ago
Wonderful location and home, bring earplugs or noise cancelling devices as you can hear everything from floor above. Still well worth the price!

Fitness-friendly condo rentals

Guest favorite
Condo in Hancock
4.95 out of 5 average rating, 59 reviews

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

EladRating, 5 stars2 months 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, 4 reviews

Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8

DanielRating, 5 stars4 months ago
Jiminy Peak is a great family mountain. Christina's place is perfectly located to do everything right out your back door. Christina was an excellent host. Thank you.
Guest favorite
Condo in Dover
5 out of 5 average rating, 18 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

JosephRating, 5 starstoday
Outstanding stay at Erin’s beautiful place. Immaculately clean. Perfectly remodeled with all high end fixtures and decorations. Plenty of accommodations in the condo. Very quiet in the summer. Facilities are top notch with indoor and outdoor pool. Grill and fire pit in the common area that you can reserve as well as gorgeous common area with games activities and a nice gym. Walk or ski to mount snow Sundance area. Can’t say enough and can’t wait to return. Thankyou for hosting.
Guest favorite
Condo in Dover
4.91 out of 5 average rating, 110 reviews

Seasons on Mt Snow Condo - Ski/Hike/Bike/Swim

MichaelRating, 5 stars3 months ago
We stayed at Julia's vacation rental for a 3-day weekend with our four children under the age of 12. The things that were great: 1) the unit is 150 foot walk in ski boots from a ski trail that will take you to the Mount Snow lift, which was great because we didn't have to shlep 4 kids ski gear, 2) the four kids loved the bunk bed room and were comfortable, 3) there are two large shelves of board games the kids enjoyed, 4) the access to the Sports Center which has a heated indoor pool and hot tubs were a great way to end the day after skiing, 5) the outdoor locker was a great place to dump all the ski gear (much better storage location than inside the car or inside the unit) and 6) very nice fluffy towels and bed sheeting was comfortable. A combined liquid shampoo and body soap is provided in each bathroom, which is the same that we use to bath our kids at home.
Guest favorite
Condo in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars2 months ago
The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.
Guest favorite
Condo in Dover
4.95 out of 5 average rating, 61 reviews

Condo w/ great amenities 4-seasons! Ski in Ski out

BrianRating, 5 stars1 week ago
Christine was a great host. The condo was as described. The place was clean and well organized, very cute and cozy. Christine was very responsive and helpful. I will definitely stay here again.
Top guest favorite
Condo in Dover
5 out of 5 average rating, 58 reviews

Four Seasons Slope-side Getaway at Mount Snow

AlexRating, 5 stars3 months ago
Dean and Tina are excellent hosts! We had a great weekend on the mountain. Their home is very comfortable and awesome location.
Superhost
Condo in Hancock
5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook

Ashley And NathanielRating, 5 stars16 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!!!

Fitness-friendly house rentals

Guest favorite
Home in Great Barrington
4.91 out of 5 average rating, 77 reviews

Charming, view, large deck, private/walk downtown

BrianRating, 5 stars3 months ago
We stayed for a ski weekend and found the house perfect fit for a group 3 kids skiing and snowboarding. There’s plenty of room in the kitchen in the living room all all we came away extremely satisfied.
Guest favorite
Home in Dover
5 out of 5 average rating, 5 reviews

Mins. to Mt. Snow! Spacious! Game room/hot tub!

KimberlyRating, 5 stars1 month ago
Stayed here over the weekend for a wedding in May. The house is even more stunning than the photos show. Everything was as described or better, and Emilio was responsive and accommodating when we realized the coffee pot was missing and had a new one dropped off within a matter of hours. Only thing was that the house was pretty warm and wasn’t easy to cool down, but in May in Vermont keeping the windows open did enough to solve that. We’d love to come back again during ski season for our annual family trip instead of where we usually go because the house is so amazing!
Guest favorite
Home in Wilmington
5 out of 5 average rating, 11 reviews

Outdoor Enthusiasts Paradise!

EmilyRating, 5 stars5 months ago
Our family had a beautiful, peaceful ski/snowboard vacation at Samantha’s home. The house was exceptionally clean and Samantha was an attentive host. We’ll hopefully visit again!
Superhost
Home in Otis
4.74 out of 5 average rating, 47 reviews

Serene Berkshires Home On 5+ Acres, Rustic & Chic

MarvinRating, 5 stars3 weeks ago
Beautiful home, very spacious. Peaceful. Amazing yard for outdoor activities. Plenty of parking. Would definitely come again
Top guest favorite
Home in Dover
5 out of 5 average rating, 21 reviews

Alpine Chalet: Hot Tub,GameRoom,Theatre,Gym,Sauna

EmeriaRating, 5 stars3 weeks ago
We had such a lovely time! The home was even bigger than we thought and it was so much fun. We will definitely be back in the future!
Guest favorite
Home in Dover
4.9 out of 5 average rating, 30 reviews

Family Vaca! 11minMtSnow-HotTub-GameRm-FirePit

AnthonyRating, 5 stars2 months ago
Great house to stay with friends and children. Managers were very responsive to questions. We would definitely stay there again.
Guest favorite
Home in Wilmington
5 out of 5 average rating, 12 reviews

4bed, 2bath @ Chimney Hill w/Hot Tub & EV Charger

YoniRating, 5 stars3 months ago
Lovely home. Hopefully I can stay here next year.
Guest favorite
Home in Great Barrington
4.97 out of 5 average rating, 33 reviews

All Seasons Berkshires Family Retreat with Hot Tub

CathyRating, 5 stars2 months ago
This lovely home provided the perfect backdrop to our Easter gathering. Comfortable amenities inside and out with a large yard, play set, hot tub, ping pong, etc. Home was very clean and kitchen was well stocked. Gary was an excellent host with great communication and suggestions for local activities. We would definitely love to return.

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