Photo by Ed Gaffny

Find hotels in Cheshire, MA from SAR 239

    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
14 Jul - 15 Jul
Tomorrow
15 Jul - 16 Jul
This weekend
18 Jul - 20 Jul
Next weekend
25 Jul - 27 Jul

Filter by

Guest rating
Guest rating
Star rating

Compare 994 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, (50)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
The price is SAR 885
SAR 936 total
includes taxes & fees
16 Jul - 17 Jul
Harbour House Inn
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1014)
"Great service and a wonderful place to stay"
The price is SAR 475
SAR 531 total
includes taxes & fees
27 Jul - 28 Jul
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, (492)
"Had a fantastic stay, love this property. Cant wsit to go back"
The price is SAR 649
SAR 725 total
includes taxes & fees
22 Jul - 23 Jul
The Constance by the Lenox Collection
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, (1004)
"Beautiful location!"
The price is SAR 730
SAR 815 total
includes taxes & fees
21 Jul - 22 Jul
The Black Swan Lee - Lenox, Ascend Hotel Collection
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, (1002)
"Fantastic place"
The price is SAR 539
SAR 602 total
includes taxes & fees
12 Aug - 13 Aug
Hotel Downstreet, Ascend Hotel Collection
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1875)
"Very nice places "
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, (1002)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
The price is SAR 605
SAR 822 total
includes taxes & fees
21 Jul - 22 Jul
The Cornell Inn, Lenox & The Berkshires
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (632)
"Great place stay after an evening at Tanglewood!"
The price is SAR 672
SAR 750 total
includes taxes & fees
16 Jul - 17 Jul
Berkshires Untold
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (741)
"A total dump !"
The price is SAR 267
SAR 298 total
includes taxes & fees
28 Jul - 29 Jul
FairBridge Inn Express
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, (673)
"We love this place. It's a wonderful location in the Berkshires, easy to get to all of the surrounding towns and attractions. The amenities are awesome, the units are spotless, and the service is friendly and prompt. Have stayed twice and cannot wait to return again!"
The price is SAR 605
SAR 728 total
includes taxes & fees
23 Jul - 24 Jul
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (821)
"Very convenient location, downtown, short drive to local attractions "
The price is SAR 483
SAR 540 total
includes taxes & fees
21 Jul - 22 Jul
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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, (1012)
"Very nice stay"
The price is SAR 475
SAR 531 total
includes taxes & fees
27 Jul - 28 Jul
Best Western Plus Berkshire Hills Inn & Suites
Williamstown Motel
Exterior detail

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (276)
"room was spotless, staff friendly, dining easy walkable distance, although older, well maintained. good choice for overnight stay, price reasonable."
The price is SAR 402
SAR 449 total
includes taxes & fees
6 Aug - 7 Aug
Williamstown Motel
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1004)
"I had excellent stay at the Red Lion Inn "
The price is SAR 697
SAR 946 total
includes taxes & fees
4 Aug - 5 Aug
The Red Lion 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, (608)
"It is clean and reasonably priced. We were comfortable and close to Tanglewood. "
The price is SAR 239
SAR 267 total
includes taxes & fees
3 Aug - 4 Aug
Econo Lodge Lee - Great Barrington
Berkshire Travel Lodge
Outdoor pool

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (424)
"No hot water. Limited TV, coffee was burnt tar, musty smell, hideous very dark green wall. Yikes!"
The price is SAR 263
SAR 284 total
includes taxes & fees
16 Jul - 17 Jul
Berkshire Travel Lodge
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (720)
"Great quiet stay. "
The price is SAR 371
SAR 415 total
includes taxes & fees
16 Jul - 17 Jul
The Villager Motel
Howard Johnson by Wyndham Williamstown
Pool

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (850)
"The rooms were tasteful, cheerful and emaculate. We have been searching for lovely, reasonably priced accommodations for our annual trips to Williamstown and we have definitely found them here. The beds were so comfortable, the room felt spacious and the bathroom had extra perks. We will return , highly recommend!"
The price is SAR 413
SAR 461 total
includes taxes & fees
16 Jul - 17 Jul
Howard Johnson by Wyndham Williamstown
Berkshire Valley Inn
Exterior

Berkshire Valley Inn

2.5 star property
9.2 out of 10, Wonderful, (552)
"Very clean and very nice staff. Breakfast was great"
The price is SAR 694
SAR 775 total
includes taxes & fees
27 Jul - 28 Jul
Berkshire Valley Inn
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (513)
"Clean, comfortable and great staff. Highly recommend and will be staying there again in the future."
Berkshire Mountain Lodge
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

Learn more about Cheshire

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

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 6.5 mi (10.5 km) from the heart of Cheshire, Vacation Village in the Berkshires is a top choice for your stay based on our traveler data. Other good options for your stay in the area are The Williams Inn and Hotel Downstreet, Ascend Hotel Collection. See all available top hotels, or vacation rentals in Cheshire.

What are some of the best vacation rentals in Cheshire?

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. : This vacation home rental outside of Cheshire offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. 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.