Photo by Ed Gaffny

Find hotels in Cheshire, MA from £56

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Property class

Top 10 Cheshire hotels and places to stay

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"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 £185
includes taxes & fees
18 Aug - 19 Aug
Harbour House Inn

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Had a wonderful time "
The price is £105
includes taxes & fees
1 Sept - 2 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1001)
"Wonderful place to stay"
The price is £111
includes taxes & fees
8 Sept - 9 Sept
The Yankee, Trademark Collection by Wyndham

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1938)
"It was a beautiful property with lots to do"
The price is £98
includes taxes & fees
27 Aug - 28 Aug
Vacation Village in the Berkshires

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (666)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is £133
includes taxes & fees
1 Sept - 2 Sept
Berkshires Untold

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (510)
"Property was excellent "
The price is £127
includes taxes & fees
3 Sept - 4 Sept
The Constance by the Lenox Collection

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1003)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is £135
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1001)
"Clean,friendly staff and great location."
The price is £119
includes taxes & fees
7 Sept - 8 Sept
Hotel Downstreet, Ascend Hotel Collection

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

3.5 star property
9.0 out of 10, Wonderful, (688)
"Had a great time"
The price is £91
includes taxes & fees
8 Sept - 9 Sept
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

FairBridge Inn Express

2.5 star property
5.4 out of 10, (764)
"Close to our target event a plus"
The price is £56
includes taxes & fees
27 Aug - 28 Aug
FairBridge Inn Express

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (853)
"Consistently a clean room with welcoming staff."
The price is £95
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1002)
"Loved our visit"
The price is £186
includes taxes & fees
11 Aug - 12 Aug
The Red Lion Inn

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (622)
"It was lovely!"
The price is £53
includes taxes & fees
24 Aug - 25 Aug
Econo Lodge Lee - Great Barrington

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (548)
"Amazing place to stay. Can’t wait to go again. "
Berkshire Mountain Lodge

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1002)
"Very clean rooms and excellent staff."
The price is £99
includes taxes & fees
1 Sept - 2 Sept
Best Western Plus Berkshire Hills Inn & Suites

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (431)
"Beautiful scenery. Room was not fancy but comfortable and clean. "
The price is £56
includes taxes & fees
11 Aug - 12 Aug
Berkshire Travel Lodge

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (282)
"Small comfortable room, accommodating staff, very close to Williams College."
The price is £69
includes taxes & fees
2 Sept - 3 Sept
Williamstown Motel

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (862)
"Humble little hotel. Ideal for a visit to nearby Mass MOCA."
The price is £91
includes taxes & fees
11 Aug - 12 Aug
Howard Johnson by Wyndham Williamstown

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (726)
"Great quiet stay. "
The price is £74
includes taxes & fees
1 Sept - 2 Sept
The Villager Motel

Berkshire Valley Inn

2.5 star property
9.2 out of 10, Wonderful, (554)
"Very clean and very nice staff. Breakfast was great"
The price is £138
includes taxes & fees
10 Aug - 11 Aug
Berkshire Valley 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

Learn more about Cheshire

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

Photo by Ed Gaffny
Open Photo by Ed Gaffny

Top Cheshire Hotel Reviews

Frequently asked questions

When is the best time to go to Cheshire?
The most popular time to visit Cheshire is during the summer months, particularly July and August. At this time, the climate is pleasantly warm, with average temperatures ranging from 17 to 22°C, making it superb for exploring the stunning countryside and charming towns.

During the peak season of June to August, Cheshire comes alive with a variety of outdoor activities and events. Attractions such as the beautiful Tatton Park and the historic Chester Zoo are bustling with families and nature enthusiasts alike. The delightful weather lends itself to leisurely walks along the picturesque canals or through the scenic gardens, allowing you to fully immerse yourself in the region's natural beauty.

For couples seeking romance, these summer months offer vibrant festivals, open-air concerts, and various local events that showcase Cheshire's rich heritage. Imagine indulging in al fresco dining at one of the many quaint bistros, where you can enjoy seasonal dishes made from local produce while soaking up the lively atmosphere.

If you're looking for a slightly quieter experience, consider visiting in September. This month often sees fewer crowds while still enjoying lovely weather and the beautiful autumn colours beginning to emerge. You'll be able to explore the area at a more leisurely pace and perhaps take advantage of some off-peak pricing on accommodations and activities.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Cheshire.
How can I save on a Cheshire hotel booking with Expedia?
Before booking your Cheshire hotel, remember to join Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. You could also enjoy savings by bundling together your hotel and flights on Expedia.
How much is the nightly rate at a Cheshire hotel?
Prices for hotels in Cheshire often vary, but you can find a great deal from £56 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.