Photo by Ed Gaffny

Find hotels in Cheshire, MA from SAR 287

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Check Cheshire hotel prices

Tonight
23 Dhuʻl-Q. - 24 Dhuʻl-Q.
Tomorrow night
24 Dhuʻl-Q. - 25 Dhuʻl-Q.
Next weekend
29 Dhuʻl-Q. - 1 Dhuʻl-H.

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Compare 904 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (371)
"A lovely hotel in close proximity to the Clark. Highly recommended!"
The price is SAR 740
SAR 827 total
includes taxes & fees
10 Dec - 11 Dec
The Williams Inn
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1746)
"Property was beautiful, great staff "
The price is SAR 634
SAR 733 total
includes taxes & fees
26 Nov - 27 Nov
Vacation Village in the Berkshires
Life House Berkshires
Lobby

Life House Berkshires

3.5 star property
9.0 out of 10, Wonderful, (442)
"Staff were very friendly and the rooms were decorated adorably! We absolutely enjoyed our stay! "
The price is SAR 449
SAR 502 total
includes taxes & fees
25 Nov - 26 Nov
Life House Berkshires
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1005)
"Staff was very nice, friendly and accommodating. The room was nice, clean, comfortable and spacious. "
The price is SAR 351
SAR 392 total
includes taxes & fees
1 Dec - 2 Dec
The Yankee, Trademark Collection by Wyndham
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Exterior

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3.0 star property
8.0 out of 10, Very Good, (682)
"We stayed for two weeks and couldn’t have been happier with the service. Such nice people, and so understanding. Six stars if I could!"
The price is SAR 371
SAR 414 total
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is SAR 559
SAR 614 total
includes taxes & fees
26 Nov - 27 Nov
Jiminy Peak Mountain Resort
Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (650)
"Beautiful room & exceptional staff. Highly recommend!"
The price is SAR 544
SAR 608 total
includes taxes & fees
26 Nov - 27 Nov
Hotel On North
Hotel Downstreet
Exterior

Hotel Downstreet

3.0 star property
8.6 out of 10, Excellent, (1043)
"Great location, wonderful staff, fun pool and cool art. Would definitely stay again! "
The price is SAR 436
SAR 487 total
includes taxes & fees
8 Dec - 9 Dec
Hotel Downstreet
Berkshire Mountain Lodge
Exterior

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (411)
"Loved our room. Very clean"
The price is SAR 619
SAR 767 total
includes taxes & fees
25 Nov - 26 Nov
Berkshire Mountain Lodge
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1030)
"The staff were so friendly and helpful. I found this a perfect place to stay where you could relax and recharge. Just keep in mind, technology isn't their top priority, but the front desk clerk was so kind, as he let us borrow his lap top to watch the Eagles play Thursday night football. "
The price is SAR 444
SAR 495 total
includes taxes & fees
1 Dec - 2 Dec
Hampton Inn & Suites Berkshires-Lenox
Best Western Plus Berkshire Hills Inn & Suites
Exterior

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.4 out of 10, Very Good, (1010)
"Room was clean, comfortable, and convenient. Dog Friendly! Will stay again!"
The price is SAR 339
SAR 378 total
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Berkshire Hills Inn & Suites
Courtyard by Marriott Lenox Berkshires
Lobby lounge

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (533)
"Nice, friendly staff. large lobby area with multiple seating areas. Coffee over priced. "
The price is SAR 458
SAR 512 total
includes taxes & fees
5 Dec - 6 Dec
Courtyard by Marriott Lenox Berkshires
Berkshire Inn
Outdoor pool

Berkshire Inn

2.0 star property
7.6 out of 10, Good, (747)
"Nice area "
The price is SAR 323
SAR 361 total
includes taxes & fees
25 Nov - 26 Nov
Berkshire Inn
The Porches Inn at Mass MoCA
Outdoor pool

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (369)
"We had an excellent time and loved all the beautiful details. Will definitely stay here again."
The price is SAR 603
SAR 737 total
includes taxes & fees
23 Dec - 24 Dec
The Porches Inn at Mass MoCA
FairBridge Inn Express
Room

FairBridge Inn Express

2.5 star property
5.4 out of 10, (678)
"I don’t know so many complaints. Bed was good, clean. Plenty of park. Provided what we paid for and was expecting. "
The price is SAR 297
SAR 331 total
includes taxes & fees
25 Nov - 26 Nov
FairBridge Inn Express
Howard Johnson by Wyndham Lenox
Outdoor pool

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (701)
"It served our needs"
The price is SAR 297
SAR 331 total
includes taxes & fees
25 Nov - 26 Nov
Howard Johnson by Wyndham Lenox
Hilton Garden Inn Lenox Pittsfield
Exterior

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (618)
"Check in and check out where quick and easy. The room was comfortable and clean. The staff were nice and accommodating. Central location to surrounding attractions. "
The price is SAR 512
SAR 572 total
includes taxes & fees
22 Dec - 23 Dec
Hilton Garden Inn Lenox Pittsfield
Howard Johnson by Wyndham Williamstown
Exterior

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (824)
"Very nice, very convenient."
The price is SAR 375
SAR 419 total
includes taxes & fees
25 Nov - 26 Nov
Howard Johnson by Wyndham Williamstown
Fairfield Inn & Suites by Marriott Williamstown
Exterior

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
8.8 out of 10, Excellent, (308)
"It was a wonderful stay, the staff was ready to help and it was a quiet clean place to do work and also go enjoy the beautiful town of Williamstown"
The price is SAR 503
SAR 562 total
includes taxes & fees
8 Dec - 9 Dec
Fairfield Inn & Suites by Marriott Williamstown
1896 House Country Inn & Motels
Exterior

1896 House Country Inn & Motels

2.5 star property
6.6 out of 10, (404)
"Excellent experience for the price. Lovely area next to creek. Helpful staff"
The price is SAR 287
SAR 321 total
includes taxes & fees
5 Dec - 6 Dec
1896 House Country Inn & Motels
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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Frequently asked questions

What's the best place to stay in Cheshire?

Located 20.8 mi (33.4 km) from the heart of Cheshire, The Red Lion Inn is a top choice for your stay based on our traveler data. Other good options for your stay in the area are Life House Berkshires and The Yankee, Trademark Collection by Wyndham. See all available top hotels, or vacation rentals in Cheshire.

What are some of the best vacation rentals in Cheshire?

Berkshire Village Carriage House - Super Private!!: This vacation home rental outside of Cheshire is located in the mountains and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind. See all 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.

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.