Photo by Ed Gaffny

Find hotels in Cheshire, MA from ฿2,462

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Top 10 Cheshire hotels and places to stay

Harbour House Inn
3.5 star property
9.4 out of 10, Exceptional, (52)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
United States
Lorie
The price is ฿8,565
฿9,054 total
includes taxes & fees
11 Nov - 12 Nov
Harbour House Inn
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.0 out of 10, Wonderful, (1009)
"Great Indian restaurant in the hotel!"
United States
Chris
The price is ฿3,470
฿3,876 total
includes taxes & fees
3 Nov - 4 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very good, (928)
"Friendly staff and clean rooms. Loved the onsite restaurant & bar."
United States
Carmen
The price is ฿3,363
฿3,757 total
includes taxes & fees
23 Nov - 24 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1020)
"Fresh breakfast menu, clean and great location."
United States
Gail
The price is ฿3,497
฿3,907 total
includes taxes & fees
2 Nov - 3 Nov
The Yankee, Trademark Collection by Wyndham
Berkshires Untold
3.5 star property
9.0 out of 10, Wonderful, (781)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is ฿3,025
฿3,379 total
includes taxes & fees
2 Nov - 3 Nov
Berkshires Untold
Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2108)
"Great place!"
United States
Nicole
The price is ฿3,000
฿3,710 total
includes taxes & fees
12 Nov - 13 Nov
Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
8.8 out of 10, Excellent, (1003)
"Staff was very nice!"
United States
David
The price is ฿5,106
฿5,703 total
includes taxes & fees
26 Nov - 27 Nov
Hotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (736)
"Great stay, perfect "
United States
Lawrence
Berkshire Mountain Lodge
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1001)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is ฿4,176
฿5,943 total
includes taxes & fees
29 Oct - 30 Oct
The Cornell Inn, Lenox & The Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.0 out of 10, Wonderful, (769)
"We enjoyed our stay and will definitely be back."
United States
Howard
The price is ฿3,581
฿4,455 total
includes taxes & fees
30 Oct - 31 Oct
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
9.4 out of 10, Exceptional, (55)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
United States
Marti
The price is ฿4,142
฿4,627 total
includes taxes & fees
4 Nov - 5 Nov
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1021)
"Picture perfect Inn"
United States
jeff
The price is ฿4,866
฿6,894 total
includes taxes & fees
12 Nov - 13 Nov
The Red Lion Inn
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (529)
"Nice place to stay for a wedding "
United States
Timothy
The price is ฿6,436
฿7,189 total
includes taxes & fees
23 Nov - 24 Nov
The Williams Inn
FairBridge Inn Express
2.5 star property
5.4 out of 10, (799)
"Good service and people"
United States
Jerod
The price is ฿2,204
฿2,462 total
includes taxes & fees
23 Nov - 24 Nov
FairBridge Inn Express
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (786)
"Clean room, great location. Restaurant phenomenal "
United States
Mary
The price is ฿3,303
฿3,690 total
includes taxes & fees
3 Nov - 4 Nov
Hotel On North
The Constance by the Lenox Collection
3.5 star property
8.4 out of 10, Very good, (557)
"Everything was very nice. A very simple experience."
United States
Anthony
The price is ฿4,237
฿4,733 total
includes taxes & fees
24 Nov - 25 Nov
The Constance by the Lenox Collection
The Porches Inn at Mass MoCA
3.5 star property
9.4 out of 10, Exceptional, (431)
"peaceful"
United States
Jose
The price is ฿5,555
฿6,934 total
includes taxes & fees
29 Oct - 30 Oct
The Porches Inn at Mass MoCA
Williamstown Motel
2.0 star property
9.4 out of 10, Exceptional, (309)
"Was upgraded to a larger room for no special reason. Very nice proprietor. For budget priced accommodations, this is an excellent value. Would definitely stay here again if I am in the area."
United States
DAVID
The price is ฿3,233
฿3,611 total
includes taxes & fees
5 Nov - 6 Nov
Williamstown Motel
The Central Downtown Inn & Suites
4.0 star property
8.8 out of 10, Excellent, (333)
"The rooms were large and well appointed! You could easily stay for a while and cook in the room. Nice balcony, nice living room area and very comfy bed and pillows. We enjoyed our stay very much"
United States
Candee
The price is ฿3,164
฿3,534 total
includes taxes & fees
26 Nov - 27 Nov
The Central Downtown Inn & Suites
Howard Johnson by Wyndham Williamstown
2.0 star property
6.6 out of 10, (895)
"Great affordable place to stay while in the northern Berkshires."
United States
PAUL
The price is ฿3,924
฿4,384 total
includes taxes & fees
29 Oct - 30 Oct
Howard Johnson by Wyndham Williamstown
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.
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Stay near popular Cheshire attractions

Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking and natural setting.

The road less traveled sometimes is absolutely beautiful. In a month this will be a great spot for Autumn. I will repost the exact same foliage shot and see if I am correct. Excited to do it actually..
Photo by Ed Gaffny
Open Photo by Ed Gaffny

Top Cheshire Hotel Reviews

More cheap stays in Cheshire

Frequently asked questions

What's the best place to stay in Cheshire?
Harbour House Inn is one of the top choices for your stay based on our traveller data. This B&B offers free breakfast and free parking. Two other choices for your trip to the area are Vacation Village in the Berkshires and Berkshire Mountain Lodge. See all available top hotels, or vacation rentals in Cheshire.
If I need to cancel my hotel reservation in Cheshire, will I receive a refund?
Yes! Most room reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Cheshire.
What's the best LGBTQ-friendly place to stay in Cheshire?
Harbour House Inn is a top LGBTQ-friendly B&B, and features free breakfast and free WiFi. See all available hotels listed as LGBTQ-friendly in Cheshire.
What are some hotels with pools in Cheshire?
Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool and free self parking. Berkshire Mountain Lodge and Holiday Inn & Suites Pittsfield-Berkshires by IHG are two additional hotels that feature an on-site pool. View all hotels with pools in Cheshire.
What is staying in Cheshire like?
Visitors can enjoy all that Cheshire has to offer, including the ski areas, restaurants and lake views. Tourists can also enjoy so much more including its shopping. In Cheshire, there are 5 hotels and other accommodation options to choose from. Find out more about Cheshire.
What is there to see in Cheshire?
A favourite place to visit is Mount Greylock State Reservation. You'll also find Mount Greylock State Reservation Visitor Center and Mount Greylock in the area. Take a look at what more there is to see and do in Expedia's Cheshire guide.
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.