Photo by Ed Gaffny

Find hotels in Cheshire, MA from NT$1,893

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Compare 1,006 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Huttopia Berkshires

1.0 star property
The price is NT$3,623
NT$4,047 total
includes taxes & fees
Aug 24 - Aug 25
Huttopia Berkshires

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (106)
"Lovely Inn and very responsive and approachable staff. "
The price is NT$2,806
NT$4,293 total
includes taxes & fees
Aug 20 - Aug 21
Blooming Inn

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (725)
"Great quiet stay. "
The price is NT$2,940
NT$3,284 total
includes taxes & fees
Aug 3 - Aug 4
The Villager Motel

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"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!! "
The price is NT$7,790
NT$8,234 total
includes taxes & fees
Aug 5 - Aug 6
Harbour House Inn

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (653)
"It's a clean, nice place. And easy to get to the surrounding towns."
The price is NT$16,811
NT$18,779 total
includes taxes & fees
Aug 8 - Aug 9
Berkshires Untold

The Revival House

3.0 star property
9.6 out of 10, Exceptional, (7)
"Beautifully renovated historical bed and breakfast that offers historical details along with modern touches. Our room was spacious and very clean and common areas are appointed with great attention to detail. "
The price is NT$5,345
NT$5,971 total
includes taxes & fees
Jul 31 - Aug 1
The Revival House

Becket Motel

2.5 star property
6.6 out of 10, (58)
"Comfortable stay "
The price is NT$2,821
NT$4,146 total
includes taxes & fees
Aug 3 - Aug 4
Becket Motel

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (932)
"Breakfast had lots of fresh fruit. Staff was very friendly and helpful. "
The price is NT$2,913
NT$3,254 total
includes taxes & fees
Aug 11 - Aug 12
Willows Motel Williamstown

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1002)
"Clean,friendly staff and great location."
The price is NT$5,051
NT$5,642 total
includes taxes & fees
Aug 3 - Aug 4
Hotel Downstreet, Ascend Hotel Collection

The Springs Motel

2.0 star property
9.0 out of 10, Wonderful, (52)
"Love this renovated motel. They made it cute and trendy"
The price is NT$3,723
NT$4,084 total
includes taxes & fees
Aug 4 - Aug 5
The Springs Motel

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (771)
"Was great loved the jacuzzi tub "
The price is NT$2,929
NT$3,271 total
includes taxes & fees
Aug 4 - Aug 5
Howard Johnson by Wyndham Lenox

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1000)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
The price is NT$3,958
NT$5,582 total
includes taxes & fees
Aug 27 - Aug 28
The Cornell Inn, Lenox & The Berkshires

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (534)
"Excellent stay!"
The price is NT$3,112
NT$4,139 total
includes taxes & fees
Aug 17 - Aug 18
Berkshire Mountain Lodge

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (567)
"The staff, room and property was wonderful! "
The price is NT$3,341
NT$3,732 total
includes taxes & fees
Aug 17 - Aug 18
Maple Terrace Motel

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (4)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is NT$4,722
NT$5,274 total
includes taxes & fees
Jul 31 - Aug 1
Holiday Inn Express & Suites Pittsfield - Berkshires

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (837)
"We thoroughly enjoyed our 1-night stay at the Cozy Corner! Rooms were very clean, and beds very comfortable! They also had a great breakfast, and I loved the outdoor seating area by the babbling brook!"
The price is NT$3,088
NT$3,617 total
includes taxes & fees
Aug 6 - Aug 7
Cozy Corner Motel

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1018)
"Very nice stay"
The price is NT$4,014
NT$4,483 total
includes taxes & fees
Aug 3 - Aug 4
Best Western Plus Berkshire Hills Inn & Suites

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (615)
"It was a clean, well-run, low cost option. "
The price is NT$1,893
NT$2,115 total
includes taxes & fees
Aug 12 - Aug 13
Econo Lodge Lee - Great Barrington

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (179)
"Clean, beautiful view wonderful service"
The price is NT$7,187
NT$7,596 total
includes taxes & fees
Aug 4 - Aug 5
Blue Vista Motor Lodge
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

St Mary's of the Assumption Church

St Mary's of the Assumption Church

Learn about the local history of Cheshire with a stop at St Mary's of the Assumption Church. Discover the area's mountain views, or seek out its ski slopes.

Learn more about Cheshire

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

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

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 traveler data. This B&B offers free breakfast and free parking. Other good options for your stay in the area are Vacation Village in the Berkshires and Hotel Downstreet, Ascend Hotel Collection. 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 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 3 hotels and other accommodations to choose from. Find out more about Cheshire.

What are the top places to visit in Cheshire?

A couple of favorite places to visit are Mount Greylock State Reservation and St Mary's of the Assumption Church. You'll also find Mount Greylock State Reservation Visitor Center and Mount Greylock 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.