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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 loved the room and the kids enjoyed the pool
8.5
Scored 8.5
Very Good
Rated very good
1,302 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
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
8.5
Scored 8.5
Very Good
Rated very good
191 reviews
Price from$188.19per night
Life House, Berkshires, hotel in Stephentown

Located in Lenox, 3.4 miles from Tanglewood, Life House, Berkshires has accommodations with a shared lounge, free private parking, a restaurant and a bar. This 4-star hotel offers free WiFi.

Staff were very friendly. Room was very clean. My husband thought the bed was a little lumpy. Excellent value for the price.
8.0
Scored 8.0
Very Good
Rated very good
203 reviews
Price from$118.89per 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...

Nice Large Room with fireplace and hottub.
8.3
Scored 8.3
Very Good
Rated very good
940 reviews
Price from$106.25per night
Hampton Inn & Suites Berkshires-Lenox, hotel in Stephentown

This Lenox, Massachusetts hotel is situated only a short distance from area attractions, including historic downtown Lenox and features a variety of free amenities along with comfortable and modern...

Loved the breakfast options, especially the waffles. Loved the pool hours.
8.7
Scored 8.7
Excellent
Rated excellent
346 reviews
Price from$132.93per night
The Springs Motel, hotel in Stephentown

Located in New Ashford, 19 miles from Tanglewood, The Springs Motel provides accommodations with a seasonal outdoor swimming pool, free private parking, a garden and a terrace.

Perfect location! Exactly as described. Nice renovated motel, comfortable bed, clean.
8.2
Scored 8.2
Very Good
Rated very good
62 reviews
Price from$150per night
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