Photo by Ed Gaffny

Find hotels in Cheshire, MA from AED 248

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Tonight
4 Jun - 5 Jun
Tomorrow
5 Jun - 6 Jun
This weekend
6 Jun - 8 Jun
Next weekend
13 Jun - 15 Jun

Filter by

Guest rating
Guest rating
Star rating

Compare 987 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)
"Nice place for a weekend away."
The price is AED 867
AED 916 total
includes taxes & fees
12 Jun - 13 Jun
Harbour House Inn
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 location, friendly staff, and clean/comfortable room!"
The price is AED 468
AED 523 total
includes taxes & fees
10 Jun - 11 Jun
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1002)
"Convenient and reasonably priced."
The price is AED 403
AED 450 total
includes taxes & fees
11 Jun - 12 Jun
The Yankee, Trademark Collection by Wyndham
The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (466)
"Staff was incredibly nice & helpful, and the stay was very comfortable. We’d definitely stay there again."
The price is AED 527
AED 589 total
includes taxes & fees
16 Jun - 17 Jun
The Constance by the Lenox Collection
Berkshires Untold
Lobby

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (600)
"Amazing place . "
The price is AED 438
AED 489 total
includes taxes & fees
10 Jun - 11 Jun
Berkshires Untold
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout drapes

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1000)
"friendly staff nice area"
The price is AED 559
AED 624 total
includes taxes & fees
9 Jun - 10 Jun
Hotel Downstreet, Ascend Hotel Collection
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1004)
"Great place to stay "
The price is AED 372
AED 415 total
includes taxes & fees
15 Jun - 16 Jun
Best Western Plus Berkshire Hills Inn & Suites
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, (644)
"Wonderful property we’ve been coming here for years"
The price is AED 426
AED 528 total
includes taxes & fees
5 Jun - 6 Jun
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (789)
"Great place."
The price is AED 400
AED 447 total
includes taxes & fees
8 Jun - 9 Jun
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1001)
"Quintessential Berkshire Inn."
The price is AED 632
AED 870 total
includes taxes & fees
8 Jun - 9 Jun
The Red Lion Inn
Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (730)
"Wonderful stay, room was great and staff was friendly. "
The price is AED 650
AED 726 total
includes taxes & fees
30 Jun - 1 Jul
Hotel On North
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1817)
"Nice place"
The price is AED 354
AED 436 total
includes taxes & fees
17 Jun - 18 Jun
Vacation Village in the Berkshires
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1000)
"The Inn was beautiful and the staff were knowledgeable and friendly "
The price is AED 473
AED 672 total
includes taxes & fees
5 Jun - 6 Jun
The Cornell Inn, Lenox & The Berkshires
Williamstown Motel
Reception

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (265)
"It was a very clean and the gentleman was so nice and spent a lot of time helping us figure out what to see and gave great suggestions on where to eat also. "
The price is AED 345
AED 386 total
includes taxes & fees
9 Jun - 10 Jun
Williamstown Motel
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, (597)
"We stayed in this hotel for one night because of the Divine Mercy weekend. This hotel is near to the Divine Mercy complex. They also serve breakfast."
The price is AED 248
AED 277 total
includes taxes & fees
10 Jun - 11 Jun
Econo Lodge Lee - Great Barrington
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (712)
"Nice clean spot that was convenient and affordable."
The price is AED 327
AED 365 total
includes taxes & fees
5 Jun - 6 Jun
The Villager Motel
Fairfield Inn & Suites by Marriott Williamstown
Exterior

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
8.8 out of 10, Excellent, (345)
"Good option in North Adams area "
The price is AED 525
AED 587 total
includes taxes & fees
22 Jun - 23 Jun
Fairfield Inn & Suites by Marriott Williamstown
Berkshire Valley Inn
Exterior

Berkshire Valley Inn

2.5 star property
9.2 out of 10, Wonderful, (543)
"Great, and quiet place. Friendly staff!"
The price is AED 543
AED 607 total
includes taxes & fees
24 Jun - 25 Jun
Berkshire Valley Inn
The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (455)
"Great location and nice accommodations."
The price is AED 821
AED 917 total
includes taxes & fees
17 Jun - 18 Jun
The Williams Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (364)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
The price is AED 698
AED 779 total
includes taxes & fees
5 Jun - 6 Jun
Chambery Inn
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Cabins in Cheshire you'll enjoy

Bear Creek Cabin
Exterior

Bear Creek Cabin

9.8 out of 10, Exceptional, (30)
The price is AED 1,469
AED 2,154 total
includes taxes & fees
9 Jun - 10 Jun
Bear Creek Cabin

These pet-friendly hotels in Cheshire may fit your trip

LAKEFRONT OASIS w/ sauna + gym
Interior

LAKEFRONT OASIS w/ sauna + gym

10.0 out of 10, Exceptional, (1)
The price is AED 2,889
AED 4,950 total
includes taxes & fees
5 Jun - 6 Jun
LAKEFRONT OASIS w/ sauna + gym

Check out family-friendly hotels in Cheshire

Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (931)
The price is AED 526
AED 587 total
includes taxes & fees
5 Jun - 6 Jun
Jiminy Peak Mountain Resort
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.

Learn more about Cheshire

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

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 Berkshires Untold and Vacation Village in the Berkshires. See all available top hotels, or vacation rentals in Cheshire.

What are some of the best vacation rentals in Cheshire?

Deluxe Queen Room with 2 Queen Beds: This vacation home rental outside of Cheshire is equipped with an outdoor pool, air-conditioning, and cable TV to help you feel comfortable during your stay. 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.