Photo by Ed Gaffny

Find hotels in Cheshire, MA from AED 228

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Check prices for these dates

Tonight
10 Apr - 11 Apr
Tomorrow
11 Apr - 12 Apr
This weekend
11 Apr - 13 Apr
Next weekend
18 Apr - 20 Apr

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Compare 954 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Harbour House Inn
Exterior

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
14 Apr - 15 Apr
Harbour House Inn
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (83)
"We stayed one night, everything was as described . "
The price is AED 257
AED 430 total
includes taxes & fees
15 Apr - 16 Apr
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 349
AED 513 total
includes taxes & fees
13 Apr - 14 Apr
Becket Motel
Blue Vista Motor Lodge
Single Room | In-room safe, desk, free WiFi, bed sheets

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (167)
"We had such a great stay at the Blue Vista Motor Lodge. The staff we encountered were welcoming and lovely. The room was super clean and had everything we needed for a comfortable stay. And the view! Incredible. "
The price is AED 656
AED 693 total
includes taxes & fees
13 Apr - 14 Apr
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, (128)
"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
11 Apr - 12 Apr
The Trail in Adams - Berkshires’ Art Hotel
The Revival House
55-inch LCD TV with digital channels, printers

The Revival House

3.0 star property
The price is AED 505
AED 565 total
includes taxes & fees
4 May - 5 May
The Revival House
Hotel Downstreet, Ascend Hotel Collection
Exterior

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1000)
"We have been here about 5 times. Greay location. Good price."
The price is AED 465
AED 520 total
includes taxes & fees
27 Apr - 28 Apr
Hotel Downstreet, Ascend Hotel Collection
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (381)
"love porches!"
The price is AED 625
AED 853 total
includes taxes & fees
24 Apr - 25 Apr
The Porches Inn at Mass MoCA
Pilgrim Inn
Individually decorated, individually furnished, desk, laptop workspace

Pilgrim Inn

2.5 star property
5.8 out of 10, (304)
"Very comfortable and in a convenient location"
The price is AED 253
AED 283 total
includes taxes & fees
4 May - 5 May
Pilgrim Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1001)
"affordable hotel"
The price is AED 340
AED 380 total
includes taxes & fees
23 Apr - 24 Apr
Quality Inn
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (380)
"Quick and easy check in! The manager was friendly and helpful. "
The price is AED 307
AED 343 total
includes taxes & fees
11 Apr - 12 Apr
Sunset Inn
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

2.5 star property
5.4 out of 10, (711)
"Friendly staff and quick checkin "
The price is AED 261
AED 292 total
includes taxes & fees
23 Apr - 24 Apr
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 881
AED 985 total
includes taxes & fees
11 Apr - 12 Apr
Chambery Inn
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (587)
"While the gentleman at the front desk can be a bit cold, the women that work at the property are very pleasant. They were super accommodating and did a nice job cleaning the room during our stay. The room was a good value and provided a nice place for our family of 5 plus a small dog to lay our heads at night."
The price is AED 228
AED 255 total
includes taxes & fees
16 Apr - 17 Apr
Econo Lodge Lee - Great Barrington
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (123)
"Fantastic in every way! We highly recommend the inn for the warm atmosphere, superb service and lovely facilities. First rate!"
The price is AED 915
AED 1,022 total
includes taxes & fees
11 Apr - 12 Apr
Devonfield Inn B&B
The Black Swan Lee - Lenox, Ascend Hotel Collection
Lobby

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Great customer service. Greeted me right away and were very friendly."
The price is AED 340
AED 380 total
includes taxes & fees
16 Apr - 17 Apr
The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

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

3.5 star property
9.0 out of 10, Wonderful, (616)
"Condo built in 90's - good condition. Didn't know unit was two floors with spiral staircase - we are in our 60's so that wasn't great. "
The price is AED 393
AED 491 total
includes taxes & fees
28 Apr - 29 Apr
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (629)
"Very clean and comfortable with great restaurant and bar downstairs"
The price is AED 514
AED 575 total
includes taxes & fees
4 May - 5 May
Hilton Garden Inn Lenox Pittsfield
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (601)
"Great location. Pleasant staff."
The price is AED 253
AED 283 total
includes taxes & fees
11 Apr - 12 Apr
Wagon Wheel Inn
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (717)
"Staff friendly. Room comfortable. Location great."
The price is AED 275
AED 308 total
includes taxes & fees
1 May - 2 May
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 lake views.

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 13.4 mi (21.6 km) from the heart of Cheshire, Life House Berkshires is a top choice for your stay based on our traveler data. Other good options for your stay in the area are The Yankee, Trademark Collection by Wyndham and Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG. 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.