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Search hotels in Cheshire, Massachusetts

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Cheshire – 37 hotels and places to stay

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The Springs Motel, hotel in Cheshire

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£117.91per night
The Trail in Adams - Berkshires' Art Hotel, hotel in Cheshire

Located in the heart of the Berkshires, this eco-friendly bed and breakfast offers on-site massage services. Massachusetts Museum of Contemporary Art is 6 miles away.

Absolutely loved the shower!
8.2
Scored 8.2
Very Good
Rated very good
20 reviews
Price from£171.95per night
The Yankee, Trademark Collection by Wyndham, hotel in Cheshire

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...

Beds very comfortable. Clean facilities. Staff helpful and friendly.
8.3
Scored 8.3
Very Good
Rated very good
925 reviews
Price from£83.52per night
Tourists, hotel in Cheshire

Located in North Adams, 17 miles from Bennington Battle Monument, Tourists has accommodations with a seasonal outdoor swimming pool, free private parking, a garden and a shared lounge.

The design, heated floors
9.1
Scored 9.1
Wonderful
Rated wonderful
27 reviews
Price from£231.10per night
Hotel on North, hotel in Cheshire

Located in Pittsfield and within 8.1 miles of Tanglewood, Hotel on North has a bar, non-smoking rooms, and free WiFi throughout the property.

Love this beautiful old building that they turned into a hotel. The room was spacious and the bathroom was huge. Love that they have free parking also.
9.0
Scored 9.0
Wonderful
Rated wonderful
205 reviews
Price from£147per night
The Williams Inn, hotel in Cheshire

The Williams Inn has a fitness center, shared lounge, a restaurant and bar in Williamstown.

Staff at desk, restaurant, and on the floors treated us kindly and competently. Location is unbeatable when visiting Williams.
9.2
Scored 9.2
Wonderful
Rated wonderful
174 reviews
Price from£180.01per night
Disney Magic at Jiminy Mountain, hotel in Cheshire

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.

The theme was nice and the facilities were pretty
9.3
Scored 9.3
Wonderful
Rated wonderful
16 reviews
Price from£96.91per night
Hilton Garden Inn Lenox Pittsfield, hotel in Cheshire

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.

The staff was very friendly and helpful. They have an indoor pool.
8.5
Scored 8.5
Very Good
Rated very good
189 reviews
Price from£130.19per night
Hampton Inn & Suites Berkshires-Lenox, hotel in Cheshire

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...

Location , very clean breakfast could have been better , the lady said she had no more scrambled eggs ??
8.7
Scored 8.7
Excellent
Rated excellent
337 reviews
Price from£112.49per night
Hotel Downstreet, hotel in Cheshire

Steps from the Massachusetts Museum of Contemporary Art and placed in North Adams city center, this hotel offers a spacious on-site health club and easy access to local attractions.

Large room, extremely clean
8.1
Scored 8.1
Very Good
Rated very good
152 reviews
Price from£234.25per night
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