Find hotels in Cheshire, MA from ₩109,394

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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 ₩395,300
₩417,832 total
includes taxes & fees
Jun 8 - Jun 9
Harbour House 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, (1,001 reviews)
"Breakfast was reasonable. We had issue with our room and the staff helpfully moved us to another room. Would stay again"
United States
Anandaraja
The price is ₩173,265
₩193,537 total
includes taxes & fees
Jun 8 - Jun 9
Best Western Plus Berkshire Hills Inn & Suites

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is ₩347,777
₩388,460 total
includes taxes & fees
Jun 19 - Jun 20
The Yankee Inn

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,004 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is ₩190,950
₩213,294 total
includes taxes & fees
Jun 10 - Jun 11
Quality Inn Lee - Lenox South

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, (100 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
The price is ₩210,349
₩234,968 total
includes taxes & fees
Jun 14 - Jun 15
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (863 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
The price is ₩123,093
₩137,495 total
includes taxes & fees
Jun 8 - Jun 9
Howard Johnson by Wyndham Lenox

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (912 reviews)
"Facilities were excellent. Staff was very helpful and very efficient & courteous in taking care of any concerns I had."
United States
Barbara J
The price is ₩131,819
₩155,097 total
includes taxes & fees
Jun 17 - Jun 18
Cozy Corner Motel

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (821 reviews)
"Quiet"
United States
William
The price is ₩110,784
₩123,748 total
includes taxes & fees
Jun 21 - Jun 22
FairBridge Inn Express

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (468 reviews)
"The breakfast was not diabetic friendly. They stated pet friendly but no place for dog to go to the bathroom. Had to walk dog through garbage . Cigarette butts all over very the place. Beds were terrible. My towels had clumps of black hair on them. Lotion and shampoos left in room were used not new ones. Will not go back"
United States
Stacy
The price is ₩102,354
₩114,648 total
includes taxes & fees
Jun 8 - Jun 9
Berkshire Travel Lodge

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (611 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 ₩179,186
₩200,159 total
includes taxes & fees
Jun 10 - Jun 11
Maple Terrace Motel

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (137 reviews)
"The room was clean and comfortable. It was a quiet night's sleep as I believe I was the only one there. Breakfast was very plain and simple: English muffins and cinnamon toast, with no fruit or juice. Coffee was plentiful"
United States
Sarah
The price is ₩162,670
₩258,051 total
includes taxes & fees
Jun 10 - Jun 11
Blooming Inn

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (666 reviews)
"Decent place.friendly, quiet"
United States
William
The price is ₩110,784
₩123,746 total
includes taxes & fees
Jun 15 - Jun 16
Econo Lodge Lee - Great Barrington

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (975 reviews)
"Very nice hotel. Highly recommend the restaurant."
United States
Thomas
The price is ₩194,560
₩217,324 total
includes taxes & fees
Jun 9 - Jun 10
Berkshires Untold

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (789 reviews)
"The room was comfortable and clean, I will stay there again"
United States
Monica
The price is ₩138,674
₩154,894 total
includes taxes & fees
Jun 10 - Jun 11
The Villager Motel

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (460 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is ₩232,163
₩254,683 total
includes taxes & fees
Jun 10 - Jun 11
Shaker Mill Inn

Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (910 reviews)
"clean; quiet; good breakfast; as advertised; easy check-in/check out; convenient parking; "
United States
Thomas
The price is ₩171,380
₩191,433 total
includes taxes & fees
Jun 8 - Jun 9
Howard Johnson by Wyndham Williamstown

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
The price is ₩208,246
₩232,611 total
includes taxes & fees
Jun 8 - Jun 9
Berkshire Lake Lodge

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (97 reviews)
"Comfy, cozy, quiet stay in this lovely property full of character! Thank you, hard-working staff."
United States
Leslieann H
The price is ₩175,291
₩194,574 total
includes taxes & fees
Jun 8 - Jun 9
Gregory House Country Inn

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (212 reviews)
"We loved the clean, casual relaxing atmosphere and the VIEW was amazing. Sunrise and sunset!"
United States
Laura
The price is ₩316,770
₩334,829 total
includes taxes & fees
Jun 9 - Jun 10
Blue Vista Motor Lodge

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (859 reviews)
"Great stay "
United States
Brian
The price is ₩133,984
₩149,659 total
includes taxes & fees
Jun 9 - Jun 10
Berkshire Inn
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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 11.5 mi (18.6 km) from the heart of Cheshire, Berkshire Mountain Lodge is a top choice for your stay based on our traveler data. Other good options for your stay in the area are Vacation Village in the Berkshires and Berkshires Untold. 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 hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might be able to still cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Cheshire.
Where can I learn more about changing or cancelling my trip to Cheshire?
To find more details about updating your trip to Cheshire or cancelling it, click here.
What is the favorite LGBTQ-friendly accommodation 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?
Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. Vacation Village in the Berkshires and The Yankee Inn are two additional hotels with an onsite pool. View all hotels with pools in Cheshire.
What is the best hotel near Albany International Airport (ALB)?
Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.
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 accommodations to choose from. Find out more about Cheshire.
What are the top places to visit in Cheshire?
A favorite place to visit is Mount Greylock State Reservation. You'll also find Mount Greylock State Reservation Visitor Center and Adams Theater in the area. Check out what more to see and do in Expedia's Cheshire guide.
What's the seasonal weather like in Cheshire?
The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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