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Hotels in Cheshire

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Choose from 985 Cheshire Hotel Deals

Hotel Downstreet, Ascend Hotel Collection
Hotel Downstreet, Ascend Hotel Collection
3 out of 5
40 Main St, North Adams, MA
  • 23 min drive from St Mary's of the Assumption Church
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,006 reviews)
"Very nice hotel - simple and clean rooms and nicer lobby"

Reviewed on May 19, 2025

Hotel Downstreet, Ascend Hotel Collection
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
  • 29 min drive from St Mary's of the Assumption Church
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (588 reviews)
"A great spot for resting between long hike days. Clean, modern and enjpyable. Great to have coffee every morning as well as cold citrus water available. Well done!"

Reviewed on May 16, 2025

Life House Berkshires
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
  • 27 min walk from St Mary's of the Assumption Church
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and in-room massages. Our guests praise the helpful staff in ...
8.6/10 Excellent! (1,805 reviews)
"Excellent stay- wonderful indoor pool and outdoor hot tub. Next week I’m sure the huge outdoor pool and kiddie pool will be open. Also great kids playground, basketball court, volleyball and gym. No breakfast or food available but you have a fridge and ability to cook. Coffee maker in the room. Highly ..."

Reviewed on May 17, 2025

Vacation Village in the Berkshires
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
3 out of 5
435 Laurel St, Lee, MA
  • 40 min drive from St Mary's of the Assumption Church
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
9/10 Wonderful! (1,006 reviews)
"Very friendly staff and well-equipped room."

Reviewed on May 16, 2025

The Black Swan Lee - Lenox, Ascend Hotel Collection
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
  • 27 min drive from St Mary's of the Assumption Church
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,002 reviews)
"I had a wonderful stay at The Yankee, Trademark Collection by Wyndham. The room was beautiful and comfortable, making for a very relaxing experience. The staff was incredibly kind, welcoming, and made check-in and check-out effortless. However, during my visit, there was construction happening nearby, ..."

Reviewed on May 7, 2025

The Yankee, Trademark Collection by Wyndham
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
  • 47 min drive from St Mary's of the Assumption Church
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,005 reviews)
"Helpful check-in. Charming inn. Fascinating nooks, crannies, antiques, and paintings. The porch is great."

Reviewed on May 17, 2025

The Red Lion Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
190 Meadow Street, South Lee, MA
  • 48 min drive from St Mary's of the Assumption Church
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (636 reviews)
"Perfect nature getaway"

Reviewed on May 16, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Williams Inn
The Williams Inn
4 out of 5
101 Spring Street, Williamstown, MA
  • 25 min drive from St Mary's of the Assumption Church
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
9.6/10 Exceptional! (449 reviews)
"A delightful property in every way. We had comfy beds, lots of quiet (our rooms were adjacent to the elevator and we never heard a peep), loved the complimentary coffee, tea, and water. Enjoyed the public spaces and the restaurant. Easy parking, steps from Spring Street. I could go on and on, but ..."

Reviewed on May 8, 2025

The Williams Inn
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3 out of 5
8 Dan Fox Dr, Pittsfield, MA
  • 25 min drive from St Mary's of the Assumption Church
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (478 reviews)
"NO NOISE CLEAN PLACE"

Reviewed on May 12, 2025

Berkshire Mountain Lodge
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
  • 22 min drive from St Mary's of the Assumption Church
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,005 reviews)
"Everything was in order just as I expected"

Reviewed on May 17, 2025

Best Western Plus Berkshire Hills Inn & Suites
The Constance, The Whitlock, & The Dewey By The Lenox Collection
The Constance, The Whitlock, & The Dewey By The Lenox Collection
3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
  • 34 min drive from St Mary's of the Assumption Church
Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.6/10 Excellent! (395 reviews)
"First time visit but will return. Charming property, helpful staff and great location and breakfast!"

Reviewed on May 12, 2025

The Constance, The Whitlock, & The Dewey By The Lenox Collection
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox
2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
  • 27 min drive from St Mary's of the Assumption Church
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.6/10 Good! (724 reviews)
"Loved the room with the big tub."

Reviewed on May 15, 2025

Howard Johnson by Wyndham Lenox
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find cheap hotels in Cheshire

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