Photo by Ed Gaffny

Find hotels in Cheshire, MA from SAR 184

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Check prices for these dates

Tonight
27 Muh. - 28 Muh.
Tomorrow
28 Muh. - 29 Muh.
This weekend
31 Muh. - 2 Saf.
Next weekend
7 Saf. - 9 Saf.

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Guest rating
Star rating

Compare 941 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Harbour House Inn
Room

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Lovely space and welcoming host."
The price is SAR 964
SAR 1,019 total
includes taxes & fees
28 Jan - 29 Jan
Harbour House Inn
Blooming Inn
Room

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (75)
"Totally enjoyed our stay here. Just a short walk to a lovely downtown area with various dining options. We will definitely stay here again "
The price is SAR 307
SAR 489 total
includes taxes & fees
30 Jan - 31 Jan
Blooming Inn
Blue Vista Motor Lodge
Front of property

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (161)
"Clean. Quiet"
The price is SAR 532
SAR 562 total
includes taxes & fees
28 Jan - 29 Jan
Blue Vista Motor Lodge
The Trail in Adams - Berkshires’ Art Hotel
Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (127)
"The Trail in Adams offered me exactly what I needed: a quiet and convenient place prepare for a day in the woods the next day. Very convenient walking to nearby restaurants, right in the middle of Adams. There was a snowstorm that night, and the walks were shoveled several times that evening and the next morning. "
The price is SAR 605
SAR 676 total
includes taxes & fees
28 Jan - 29 Jan
The Trail in Adams - Berkshires’ Art Hotel
Hotel Downstreet
Exterior

Hotel Downstreet

3.0 star property
8.6 out of 10, Excellent, (1002)
"Easy to get to, nice location "
The price is SAR 435
SAR 486 total
includes taxes & fees
10 Feb - 11 Feb
Hotel Downstreet
The Porches Inn at Mass MoCA
Outdoor pool

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (374)
"The historical significance and what they have done to make it look like a rooming house for workers from the 1930's etc was done really well. Staff was nice and the breakfast was very organized and had good options. "
The price is SAR 539
SAR 686 total
includes taxes & fees
25 Feb - 26 Feb
The Porches Inn at Mass MoCA
Pilgrim Inn
Front of property

Pilgrim Inn

2.5 star property
5.8 out of 10, (300)
"room was clean heater was noisy bed was too soft pillow mattress no shampoo dont think they checked on our room after 1st night no coffee, cups room 101"
The price is SAR 184
SAR 205 total
includes taxes & fees
5 Feb - 6 Feb
Pilgrim Inn
Quality Inn
Exterior

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1003)
"Good basic overnight lodging. No issues other than that there was no TV channel guide and it was difficult to navigate the on-screen guide."
The price is SAR 316
SAR 353 total
includes taxes & fees
23 Feb - 24 Feb
Quality Inn
Sunset Inn
Outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (378)
"Quick and easy check in! The manager was friendly and helpful. "
The price is SAR 288
SAR 322 total
includes taxes & fees
28 Jan - 29 Jan
Sunset Inn
FairBridge Inn Express
Room

FairBridge Inn Express

2.5 star property
5.4 out of 10, (698)
"Stay was good as usual, other than a single person hanging out on balcony pacing back and forth making it uncomfortable room was clean other than food found left in microwave. Overall have had good stays and would keep booking"
The price is SAR 259
SAR 289 total
includes taxes & fees
28 Jan - 29 Jan
FairBridge Inn Express
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (363)
"Chamberry Inn was a nice, quiet, relaxing stay. Enjoyed every second of it. The staff were kind and helpful. Would definitely stay again if I was in the area."
The price is SAR 713
SAR 796 total
includes taxes & fees
29 Jan - 30 Jan
Chambery Inn
Econo Lodge Lee - Great Barrington
Exterior

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (583)
"Was convenient and inexpensive. The back stairs were a little rickety. Also had to ring the bell to check in later in the evening, but was fine. Room was just the basics, but served the purpose for my one night stay. "
The price is SAR 259
SAR 289 total
includes taxes & fees
28 Jan - 29 Jan
Econo Lodge Lee - Great Barrington
Devonfield Inn B&B
Room

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (122)
"Beautiful property, great service "
The price is SAR 1,047
SAR 1,169 total
includes taxes & fees
28 Jan - 29 Jan
Devonfield Inn B&B
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Excellent affordable option with a very pretty view of the lake. The 24 hour coffee and tea stand was also great. Staff were very polite and helpful. Room was very clean. Would definitely stay here again. "
The price is SAR 348
SAR 388 total
includes taxes & fees
2 Feb - 3 Feb
The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

3.5 star property
9.0 out of 10, Wonderful, (590)
"Plenty of room. Good location to local skiing. Clean."
The price is SAR 484
SAR 593 total
includes taxes & fees
28 Jan - 29 Jan
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Lakehouse Inn
Lake

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (239)
"Amazing breakfast!"
The price is SAR 473
SAR 554 total
includes taxes & fees
31 Jan - 1 Feb
Lakehouse Inn
The Ponds at Foxhollow by Capital Vacations
Property grounds

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is SAR 867
SAR 969 total
includes taxes & fees
14 Feb - 15 Feb
The Ponds at Foxhollow by Capital Vacations
Hilton Garden Inn Lenox Pittsfield
Exterior

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (624)
"Comfortable room and beds. Great hot shower. "
The price is SAR 490
SAR 547 total
includes taxes & fees
30 Jan - 31 Jan
Hilton Garden Inn Lenox Pittsfield
Wagon Wheel Inn
Exterior

Wagon Wheel Inn

2.0 star property
7.2 out of 10, Good, (597)
"Great location. Pleasant staff."
The price is SAR 259
SAR 289 total
includes taxes & fees
28 Jan - 29 Jan
Wagon Wheel Inn
Howard Johnson by Wyndham Lenox
Outdoor pool

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (708)
"The room was clean, and the staff was helpful and friendly. The location was great, and parking was convenient. However, the bathroom was extremely disappointing. There were stains and hairs on the toilet seat, and the overall cleanliness was far below acceptable standards."
The price is SAR 296
SAR 331 total
includes taxes & fees
28 Jan - 29 Jan
Howard Johnson by Wyndham Lenox
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 9.8 mi (15.8 km) from the heart of Cheshire, Hotel Downstreet 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.