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Stephentown – 36 hotels and places to stay
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Disney Magic at Jiminy Mountain, hotel in Stephentown

Located 20 miles from Tanglewood, Disney Magic at Jiminy Mountain offers 4-star accommodations in Hancock and has a shared lounge, a restaurant and a bar.

This is a great location. We loved being able to walk to the ski lifts and restaurants. The bed was comfortable and the kitchenette was handy for making meals. We had great skiing weather, but if we did not, there was a heated outdoor pool and hot tub we would have enjoyed. Our young daughter appreciated the Disney decorations.
9.6
Scored 9.6
Exceptional
Rated exceptional
14 reviews
Price from$205.16per night
Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy, hotel in Stephentown

Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy is located in Hancock, just 20 miles from Tanglewood and 20 miles from Cranwell Spa & Golf Club.

Loved the small (and large!) details that create the relaxing environment
9.0
Scored 9.0
Wonderful
Rated wonderful
6 reviews
Price from$211.85per night
Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4, hotel in Stephentown

Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 offers accommodations in Hancock, 21 miles from Cranwell Spa & Golf Club and 21 miles from Tanglewood Musical Center.

Everything was incredibly well done. The checkin was simple and contactless.
9.1
Scored 9.1
Wonderful
Rated wonderful
14 reviews
Price from$211.85per night
Vacation Village in the Berkshires, hotel in Stephentown

Nestled in the scenic hills and countryside of the Berkshires in Hancock, Massachusetts, this hotel offers recreational activities.

We liked the indoor pool and the room was very private and we felt like we were in our own place !
8.5
Scored 8.5
Very Good
Rated very good
1,307 reviews
Price from$135per night
Jiminy Peak Mountain Resort, hotel in Stephentown

Nestled on Hancock, Massachusetts’ ski slopes, Jiminy Peak Mountain Resort offers a restaurant, adventure parks and ski-to-door access.

The hotel is right on the mountain. If you get a room with a view, it is a nice sight. You get free coffee and tea in the lobby, and free parking on the premises.
7.6
Scored 7.6
Good
Rated good
239 reviews
Price from$159per night
The Yankee, Trademark Collection by Wyndham, hotel in Stephentown

Nestled on a 111-acre wildlife sanctuary and surrounded by the beauty of the Berkshires, The Yankee, Trademark Collection by Wyndham provides a welcoming stay by the famous Appalachian Trail in...

My husband and I just returned from a 2 night stay at The Yankee. We absolutely loved every aspect of this wonderful hotel. The front desk staff was friendly and knowledgeable. You could tell that cleanliness was a priority. The room was large and the bed was wonderfully comfortable. Breakfast, which was included, was very good and there was even the ability to have a freshly made omelet. My husband and I love a good hot tub and pool. The pool was the perfect temperature as was the hot tub. Many times you go away only to find a cold pool and a lukewarm hot tub. Not here. They were both perfect. Location is good, service is good, and the facilities are wonderful. We will be back and when we are in the area will not stay anywhere else.
8.3
Scored 8.3
Very Good
Rated very good
942 reviews
Price from$106.25per night
Best Western Plus Berkshire Hills Inn & Suites, hotel in Stephentown

Located off Route 20, this Pittsfield hotel is 3.5 miles from Lichtenstein Center for the Arts. The hotel features a hydro-massage tub and a gym as well as traditional rooms with free Wi-Fi.

The room was spacious.
7.9
Scored 7.9
Good
Rated good
248 reviews
Price from$122.18per night
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, hotel in Stephentown

Welcome to the Holiday Inn and Suites Pittsfield-Berkshires Centrally located in downtown Pittsfield Massachusetts.

The staff is super kind and responsive. Love the breakfast in the morning.
7.3
Scored 7.3
Good
Rated good
274 reviews
Price from$118per night
Howard Johnson by Wyndham Lenox, hotel in Stephentown

This Lenox, Massachusetts hotel is just one mile from Bousquet Ski Area. Howard Johnson Lenox offers an outdoor pool, mountain views and guest rooms with free Wi-Fi and cable TV.

Nice
6.7
Scored 6.7
Pleasant
Rated pleasant
342 reviews
Price from$79per night
Hilton Garden Inn Lenox Pittsfield, hotel in Stephentown

Hilton Garden Inn Lenox/Pittsfield/Berkshires offers accommodations in Pittsfield. The hotel has a fitness center and indoor pool, and guests can enjoy a meal at the restaurant or a drink at the bar.

Breakfast sandwich was excellent
8.6
Scored 8.6
Excellent
Rated excellent
190 reviews
Price from$188.19per night
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