An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.

Cheshire hotels from HK$544

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Our top choices for Cheshire hotels

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is HK$1,989
HK$2,102 total
includes taxes & fees
1 Jul - 2 Jul
Harbour House Inn

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is HK$1,123
HK$1,254 total
includes taxes & fees
7 Jul - 8 Jul
The Yankee Inn

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, (1,000 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
The price is HK$935
HK$1,044 total
includes taxes & fees
29 Jun - 30 Jun
Best Western Plus Berkshire Hills Inn & Suites

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,000 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is HK$1,184
HK$1,323 total
includes taxes & fees
7 Jul - 8 Jul
Quality Inn Lee - Lenox South

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (462 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is HK$1,607
HK$1,763 total
includes taxes & fees
29 Jun - 30 Jun
Shaker Mill Inn

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (917 reviews)
"Very clean! Friendly staff! Will stop there again!"
United States
Theresa
The price is HK$691
HK$813 total
includes taxes & fees
19 Jul - 20 Jul
Cozy Corner Motel

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (107 reviews)
"Wonderful stay! Our room was beautiful - clean and cozy. I had a drink at the outside bar - it was lovely. Highly recommend staying here. It’s a hidden gem."
United States
Michelle
The price is HK$882
HK$979 total
includes taxes & fees
28 Jun - 29 Jun
Gregory House Country Inn

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (115 reviews)
"Most comfortable hotel bed I've ever slept in"
United States
Matthew
The price is HK$1,341
HK$1,498 total
includes taxes & fees
6 Jul - 7 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (472 reviews)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
The price is HK$529
HK$593 total
includes taxes & fees
29 Jun - 30 Jun
Berkshire Travel Lodge

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (613 reviews)
"Very well run property with good amenities and a lovely pool and sitting area. Lots of good attention to detail to make it a desirable place to stay!"
United States
Carolyn
The price is HK$1,090
HK$1,217 total
includes taxes & fees
30 Jun - 1 Jul
Maple Terrace Motel

Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (914 reviews)
"clean; quiet; good breakfast; as advertised; easy check-in/check out; convenient parking; "
United States
Thomas
The price is HK$862
HK$963 total
includes taxes & fees
30 Jun - 1 Jul
Howard Johnson by Wyndham Williamstown

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,000 reviews)
"Clean room and breakfast"
United States
Raphael
The price is HK$1,286
HK$1,787 total
includes taxes & fees
8 Jul - 9 Jul
The Red Lion Inn

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,000 reviews)
"Spacious and clean room, great location, friendly staff"
United States
Theresa
The price is HK$1,206
HK$1,347 total
includes taxes & fees
30 Jun - 1 Jul
Hotel Downstreet, an Ascend Collection Hotel

Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown
3.0 star property
Williamstown
8.8 out of 10, Excellent, (415 reviews)
"We were very pleased with our stay. The staff at the desk when we checked in and again when we checked out were very accommodating and friendly. "
United States
Susan
The price is HK$1,584
HK$1,769 total
includes taxes & fees
13 Jul - 14 Jul
Fairfield Inn & Suites by Marriott Williamstown

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (831 reviews)
"Plenty of parking. Staff was friendly"
United States
William
The price is HK$487
HK$544 total
includes taxes & fees
12 Jul - 13 Jul
FairBridge Inn Express

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (669 reviews)
"Decent place.friendly, quiet"
United States
William
The price is HK$699
HK$780 total
includes taxes & fees
7 Jul - 8 Jul
Econo Lodge Lee - Great Barrington

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (794 reviews)
"The room was comfortable and clean, I will stay there again"
United States
Monica
The price is HK$698
HK$779 total
includes taxes & fees
30 Jun - 1 Jul
The Villager Motel

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (26 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is HK$1,591
HK$1,778 total
includes taxes & fees
19 Jul - 20 Jul
Element by Marriott Lenox Berkshires

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,002 reviews)
"Great breakfast and coffe is available 24 hours. Nice location to near by restaurants and great view by water."
United States
andrew
The price is HK$1,393
HK$1,556 total
includes taxes & fees
1 Jul - 2 Jul
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (991 reviews)
"Great lobby and dining room atmosphere!"
United States
Carin
The price is HK$1,307
HK$1,460 total
includes taxes & fees
29 Jun - 30 Jun
Berkshires Untold
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 wildlife.

An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.

Top Cheshire Hotel Reviews

More cheap stays in Cheshire

Frequently asked questions

What's the best place to stay in Cheshire?
Located 9.8 mi (15.7 km) from the heart of Cheshire, Hotel Downstreet, an Ascend Collection Hotel is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Berkshire Mountain Lodge and Vacation Village in the Berkshires. See all available top hotels, or vacation rentals in Cheshire.
What are some of the best holiday rentals that Cheshire has to offer?
Experience Three Sisters Sanctuary in Goshen, MA: This holiday home rental outside of Cheshire is equipped with a garden, air conditioning and WiFi to help you feel comfortable during your stay. See all 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?
Hotel Downstreet, an Ascend Collection Hotel: Features daily, an indoor pool and free self parking. Berkshire Mountain Lodge and Vacation Village in the Berkshires 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 6 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 Susan B. Anthony Birthplace Museum 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.

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