Photo by Ed Gaffny

Find hotels in Cheshire, MA from AED 228

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Check prices for these dates

Tonight
19 Feb - 20 Feb
Tomorrow
20 Feb - 21 Feb
This weekend
21 Feb - 23 Feb
Next weekend
28 Feb - 2 Mar

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Compare 944 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 AED 978
AED 1,034 total
includes taxes & fees
24 Feb - 25 Feb
Harbour House Inn
Blooming Inn
Room

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (78)
"This is a great venue. It is affordably priced, conveniently located, artfully maintained in accordance with it original style (wooden floors and picket rail porch, antique furniture, etc.). I felt unique and pampered in my room. I even heard a train whistle nearby in the early wee hours of the morning, reassuring and comforting rather than disturbing. I hope to return for a longer stay."
The price is AED 301
AED 479 total
includes taxes & fees
3 Mar - 4 Mar
Blooming Inn
Becket Motel
Front of property

Becket Motel

2.5 star property
6.6 out of 10, (55)
"I liked how there was walking trails and shopping near by. "
The price is AED 338
AED 501 total
includes taxes & fees
21 Feb - 22 Feb
Becket Motel
Blue Vista Motor Lodge
Front of property

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (165)
"I rarely take the time to review anywhere I’ve stayed, but this place has stolen my heart! Its absolutely breathtaking property is second only to the friendliness of the staff. We couldn’t get enough of the sauna and hot tub with a view of the mountains, as well ans the evening firepit surrounded by andirondak chairs. The rooms and building is well maintained seemingly brand new. One of very few places I would stay again over and over! "
The price is AED 578
AED 611 total
includes taxes & fees
23 Feb - 24 Feb
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 AED 638
AED 713 total
includes taxes & fees
21 Feb - 22 Feb
The Trail in Adams - Berkshires’ Art Hotel
Hotel Downstreet, Ascend Hotel Collection
Exterior

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.6 out of 10, Excellent, (1002)
"We love this hotel! Our room was clean and spacious, the staff members we interacted with were friendly and helpful, the lobby/common and art galleries were very interesting, and there is so much to do within easy walking distance. "
The price is AED 459
AED 513 total
includes taxes & fees
25 Feb - 26 Feb
Hotel Downstreet, Ascend Hotel Collection
The Porches Inn at Mass MoCA
Outdoor pool

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (376)
"Lovely place to stay. Wonderful breakfast."
The price is AED 621
AED 775 total
includes taxes & fees
23 Feb - 24 Feb
The Porches Inn at Mass MoCA
Pilgrim Inn
Front of property

Pilgrim Inn

2.5 star property
5.8 out of 10, (302)
"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 AED 253
AED 283 total
includes taxes & fees
24 Feb - 25 Feb
Pilgrim Inn
Quality Inn
Exterior

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1001)
"Nice place. Made fresh waffle mix when I asked. No complaints"
The price is AED 309
AED 345 total
includes taxes & fees
9 Mar - 10 Mar
Quality Inn
Sunset Inn
Outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (379)
"I think some of the unfavorable reviews I have seen are unfair. Everything is relative and, yes, this is clearly an older property that appears to be privately owned. Notwithstanding its age and some of the dated decor and furnishing, my room was very clean (cleaner than some I have stayed in at upscale hotels). It was one of the coldest nights of the year and the heat worked well and the water was hot. The television and WiFi worked and for my purposes (a one night layover on my way to visit...
The price is AED 264
AED 295 total
includes taxes & fees
1 Mar - 2 Mar
Sunset Inn
FairBridge Inn Express
Room

FairBridge Inn Express

2.5 star property
5.4 out of 10, (703)
"Quiet "
The price is AED 228
AED 255 total
includes taxes & fees
5 Mar - 6 Mar
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 AED 698
AED 779 total
includes taxes & fees
23 Feb - 24 Feb
Chambery Inn
Econo Lodge Lee - Great Barrington
Exterior

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (585)
"It was close to Butternut on a snowy day. Very good for the value and what it is."
The price is AED 253
AED 283 total
includes taxes & fees
23 Feb - 24 Feb
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 AED 915
AED 1,022 total
includes taxes & fees
4 Mar - 5 Mar
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, (1000)
"Clean. Very nice location. Would be beautiful in the summer. Would go there again "
The price is AED 390
AED 436 total
includes taxes & fees
26 Feb - 27 Feb
The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires

3.5 star property
9.0 out of 10, Wonderful, (595)
"It was a great little getaway from the city, service was great and helpful nothing to complain about this spot"
The price is AED 437
AED 540 total
includes taxes & fees
24 Feb - 25 Feb
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
Lakehouse Inn
Lake

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (245)
"We loved the history of the hotel and how well they preserved many features of the property. Loved the suite and view of the lake. Everyone that works there was very kind and attentive."
The price is AED 463
AED 543 total
includes taxes & fees
21 Feb - 22 Feb
Lakehouse Inn
Hilton Garden Inn Lenox Pittsfield
Exterior

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (627)
"Very clean and comfortable with great restaurant and bar downstairs"
The price is AED 480
AED 536 total
includes taxes & fees
23 Feb - 24 Feb
Hilton Garden Inn Lenox Pittsfield
Wagon Wheel Inn
Exterior

Wagon Wheel Inn

2.0 star property
7.2 out of 10, Good, (599)
"Great location. Pleasant staff."
The price is AED 253
AED 283 total
includes taxes & fees
21 Feb - 22 Feb
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, (713)
"spacious room. "
The price is AED 290
AED 324 total
includes taxes & fees
23 Feb - 24 Feb
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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Learn more about Cheshire

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

See all hotels in Cheshire
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

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, Ascend Hotel Collection 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 Life House Berkshires. 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.