A lake surrounded by autumn-colored trees and hills.

Find hotels in Cheshire, MA from 1.823.876 ₫

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Cheshire hotels

1. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (55 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is 6.669.773 ₫
7.049.926 ₫ total
includes taxes & fees
18 Aug - 19 Aug
Harbour House Inn

2. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,009 reviews)
"A comfortable, clean place with good breakfast, good amenities, and a good hot tub."
United States
Michael
The price is 5.126.940 ₫
5.726.791 ₫ total
includes taxes & fees
23 Jul - 24 Jul
The Yankee Inn

3. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,463 reviews)
"Great and tranquil location, good sleeps, friendly and helpful staff, would do it again."
United States
Melanie
The price is 3.520.289 ₫
4.220.585 ₫ total
includes taxes & fees
10 Aug - 11 Aug
Vacation Village in the Berkshires

4. Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (624 reviews)
The price is 3.654.310 ₫
4.081.785 ₫ total
includes taxes & fees
18 Aug - 19 Aug
Maple Terrace Motel

5. Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (933 reviews)
"Loved this place"
United States
Jeremy
The price is 2.484.405 ₫
2.915.561 ₫ total
includes taxes & fees
11 Aug - 12 Aug
Cozy Corner Motel

6. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,002 reviews)
"Hotel was clean and staff helpful and courteous. Hotel is a little tired (showing it's age) but I would certainly not hesitate to book a future stay."
United States
Andrew
The price is 3.104.323 ₫
3.467.529 ₫ total
includes taxes & fees
2 Aug - 3 Aug
Best Western Plus Berkshire Hills Inn & Suites

7. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (1,004 reviews)
"Staff was fabulous and extremely helpful and friendly. Valey parking was terrific!!! and FREE Great to have since we had to park at the bank next to the hotel while there was construction in front of the building. Rooms were tidy and very clean Breakfast was excellent with a large variety of offerings"
United States
Margaret
The price is 3.410.602 ₫
3.809.643 ₫ total
includes taxes & fees
2 Aug - 3 Aug
Holiday Inn & Suites Pittsfield-Berkshires by IHG

8. The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (108 reviews)
"We enjoyed our stay. Staff was nice and the motel is set between several different towns to explore. We plan to stay again soon!"
United States
Shakeila
The price is 4.022.676 ₫
4.412.876 ₫ total
includes taxes & fees
27 Jul - 28 Jul
The Springs Motel

9. Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,003 reviews)
"Great value and excellent location"
United States
Truett
The price is 2.222.989 ₫
2.483.017 ₫ total
includes taxes & fees
22 Jul - 23 Jul
Willows Motel Williamstown

10. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,016 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is 3.513.361 ₫
4.511.786 ₫ total
includes taxes & fees
20 Aug - 21 Aug
Berkshire Mountain Lodge

11. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (858 reviews)
"Some of the furniture and rugs show age. The bed was comfortable and the staff was always available to help!"
United States
DAVID
The price is 1.632.733 ₫
1.823.876 ₫ total
includes taxes & fees
4 Aug - 5 Aug
FairBridge Inn Express

12. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,003 reviews)
"Quick check in and comfortable bed in a pretty New England town."
United States
William
The price is 4.521.961 ₫
5.051.030 ₫ total
includes taxes & fees
26 Jul - 27 Jul
Hotel Downstreet, an Ascend Collection Hotel

13. Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very good, (1,000 reviews)
"This was our third stay. we love the quiet, unusual for a large resort complex, the mountain views and the spacious and comfortable accommodations. On the Jiminy Peak property, so it's a two minute walk to all the Summer mountain activities."
United States
MARK
The price is 4.705.910 ₫
5.256.501 ₫ total
includes taxes & fees
16 Aug - 17 Aug
Jiminy Peak Mountain Resort

14. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (877 reviews)
"Beautiful room with an amazing lobby."
United States
Dragana
The price is 5.757.948 ₫
6.431.628 ₫ total
includes taxes & fees
3 Aug - 4 Aug
Hotel On North

15. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (888 reviews)
"Very clean and updated simple motel."
United States
christopher
The price is 2.365.837 ₫
2.642.639 ₫ total
includes taxes & fees
3 Aug - 4 Aug
Berkshire Inn

16. The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (646 reviews)
"amazing friendly and helpful staff perfect stay!"
United States
Thomas
The price is 7.548.433 ₫
8.431.600 ₫ total
includes taxes & fees
28 Jul - 29 Jul
The Williams Inn

17. Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown
3.0 star property
Williamstown
8.8 out of 10, Excellent, (421 reviews)
"clean room and fast response to request"
United States
hui
The price is 6.231.204 ₫
6.960.255 ₫ total
includes taxes & fees
16 Aug - 17 Aug
Fairfield Inn & Suites by Marriott Williamstown

18. The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (802 reviews)
"The price in this area is expensive and this motel provides a reasonable alternative!"
United States
qing
The price is 2.602.710 ₫
2.907.148 ₫ total
includes taxes & fees
26 Jul - 27 Jul
The Villager Motel

19. Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (221 reviews)
"Great facilities, fantastic views and neighborhood. Everything is so neat and clean. Live it and will come back."
United States
Meng
The price is 6.475.996 ₫
6.845.128 ₫ total
includes taxes & fees
28 Jul - 29 Jul
Blue Vista Motor Lodge

20. Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (334 reviews)
"Very clean room and friendly staff. Lots of great restaurants close by."
United States
Robert
The price is 2.602.908 ₫
2.907.448 ₫ total
includes taxes & fees
29 Jul - 30 Jul
Williamstown Motel
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.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Cheshire attractions

Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking and lake views.

A lake surrounded by autumn-colored trees and hills.

Top Cheshire Hotel Reviews

More cheap stays in Cheshire

Hotels in Cheshire with star rating

Frequently asked questions

What's the seasonal weather in Cheshire?
The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Cheshire are January, March, February and November, with each month seeing an average of 17 cm of snowfall.

Explore a world of travel with Expedia