Find Cheap Hotels in Cheshire, MA from CA $143
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Sep 8 - Sep 9Tomorrow
Sep 9 - Sep 10This weekend
Sep 11 - Sep 13Next weekend
Sep 18 - Sep 20Our top choices for Cheshire cheap hotels
CA $319
CA $337 total
includes taxes & fees
Sep 14 - Sep 15
2. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
Debra
CA $163
CA $182 total
includes taxes & fees
Sep 13 - Sep 14
3. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
Prasanna
CA $130
CA $145 total
includes taxes & fees
Oct 1 - Oct 2
CA $131
CA $162 total
includes taxes & fees
Sep 16 - Sep 17
CA $154
CA $169 total
includes taxes & fees
Sep 9 - Sep 10
CA $229
CA $256 total
includes taxes & fees
Sep 24 - Sep 25
7. Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection HotelNorth Adams
Basil
CA $198
CA $221 total
includes taxes & fees
Sep 29 - Sep 30
CA $138
CA $154 total
includes taxes & fees
Sep 9 - Sep 10
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Top Cheshire Hotel Reviews
Quality Inn Lee - Lenox South
8/10 Good
"Very clean property with kind staff. Nice room, decent complimentary coffee, breakfast offerings not for me."
Vacation Village in the Berkshires
10/10 Excellent
"Great location, fair price, clean and spacious"
Willows Motel Williamstown
10/10 Excellent
"Great location. Outside of hotel is a little dated but the room Amazing breakfast. The owners really take pride in providing fresh healthy options."
The Black Swan Lee - Lenox, an Ascend Collection Hotel
8/10 Good
"Black swann is great hotel with very helpful staff. They also have a Indian restaurant inside the hotel with lake view. It is a bit pricey but their fish curry is a must try!! I had it twice in a row and I am very picky eater."
The Yankee Inn
10/10 Excellent
"On an overpriced holiday weekend in the Berkshires, Yankee Inn was a great balance of price and amenities. The indoor pool was nicer than most, and the hot tub was great. Outdoor pool was a bit oddly placed between the parking lot and the main road, but nice as well. Both very clean. Room was spacious and clean, beds were comfortable, though I think they were doubles rather than queens. The included breakfast was on the very good end of standard - the fruit was fresh and delicious, there were both eggs and waffles, plus cereal, yogurt, bacon/sausage. Meh on the pastries, and the coffee was terribly watery. My true only gripe is that there was truly not a single place to hang wet bathing suits that didn't result in them dripping all over the floor. Had we been on the 2nd floor, we would have had an outside railing, but on the first floor there was none. With 4 people using the pool and hot tub, it was an annoyance. Overall, great place for a quick stay."
Hotel Downstreet, an Ascend Collection Hotel
8/10 Good
"Nice and conveniently located"
FairBridge Inn Express
8/10 Good
"great value"
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