A lake surrounded by autumn-colored trees and hills.

Find hotels in Cheshire, MA from Rp1.242.209

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
3 Jul - 5 Jul
Next weekend
10 Jul - 12 Jul

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Cheshire hotels

Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (54 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is Rp4.528.799
Rp4.786.940 total
includes taxes & fees
9 Jul - 10 Jul
Harbour House Inn
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,003 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
The price is Rp2.421.026
Rp2.704.286 total
includes taxes & fees
5 Jul - 6 Jul
Best Western Plus Berkshire Hills Inn & Suites
Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,014 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is Rp2.650.236
Rp2.960.385 total
includes taxes & fees
6 Jul - 7 Jul
The Yankee Inn
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,004 reviews)
"The staff was very helpful. It was very clean and the bed was comfortable. We would stay there again."
United States
Andrew
The price is Rp2.589.084
Rp3.292.049 total
includes taxes & fees
8 Jul - 9 Jul
Berkshire Mountain Lodge
Dining room

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (108 reviews)
"Wonderful stay! Our room was beautiful - clean and cozy. I had a drink at the outside bar - it was lovely. Highly recommend staying here. It’s a hidden gem."
United States
Michelle
The price is Rp2.008.237
Rp2.229.142 total
includes taxes & fees
14 Jul - 15 Jul
Gregory House Country Inn
Property grounds

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (613 reviews)
"Very well run property with good amenities and a lovely pool and sitting area. Lots of good attention to detail to make it a desirable place to stay!"
United States
Carolyn
The price is Rp2.481.289
Rp2.771.546 total
includes taxes & fees
9 Jul - 10 Jul
Maple Terrace Motel
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (837 reviews)
"Plenty of parking. Staff was friendly"
United States
William
The price is Rp1.112.025
Rp1.242.209 total
includes taxes & fees
15 Jul - 16 Jul
FairBridge Inn Express
Room, 1 King Bed, Accessible, Non Smoking (Transfer Shower) | Hypo-allergenic bedding, desk, laptop workspace, blackout curtains

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,000 reviews)
"Spacious and clean room, great location, friendly staff"
United States
Theresa
The price is Rp3.045.981
Rp3.402.360 total
includes taxes & fees
15 Jul - 16 Jul
Hotel Downstreet, an Ascend Collection Hotel
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (478 reviews)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
The price is Rp1.204.764
Rp1.349.357 total
includes taxes & fees
6 Jul - 7 Jul
Berkshire Travel Lodge
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (920 reviews)
"Very clean! Friendly staff! Will stop there again!"
United States
Theresa
The price is Rp1.574.458
Rp1.850.613 total
includes taxes & fees
12 Jul - 13 Jul
Cozy Corner Motel
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,005 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is Rp2.420.131
Rp2.703.287 total
includes taxes & fees
27 Jul - 28 Jul
Quality Inn Lee - Lenox South
Property grounds

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,001 reviews)
"The property was nice and the staff enthusiastic"
United States
Matt
The price is Rp1.684.153
Rp1.881.130 total
includes taxes & fees
6 Jul - 7 Jul
Willows Motel Williamstown
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,004 reviews)
"Clean room and breakfast"
United States
Raphael
The price is Rp3.323.539
Rp4.512.477 total
includes taxes & fees
20 Jul - 21 Jul
The Red Lion Inn
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (1,000 reviews)
"Quiet room. Comfortable bed linens"
United States
Margo
The price is Rp2.784.756
Rp3.110.573 total
includes taxes & fees
7 Jul - 8 Jul
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Reception

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (795 reviews)
"The room was comfortable and clean, I will stay there again"
United States
Monica
The price is Rp1.767.249
Rp1.973.964 total
includes taxes & fees
9 Jul - 10 Jul
The Villager Motel
Mountain view

Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (915 reviews)
"clean; quiet; good breakfast; as advertised; easy check-in/check out; convenient parking; "
United States
Thomas
The price is Rp1.790.521
Rp2.000.033 total
includes taxes & fees
5 Jul - 6 Jul
Howard Johnson by Wyndham Williamstown
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,001 reviews)
"Great breakfast and coffe is available 24 hours. Nice location to near by restaurants and great view by water."
United States
andrew
The price is Rp3.062.097
Rp3.420.416 total
includes taxes & fees
6 Jul - 7 Jul
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,412 reviews)
"Property is great and stay was great"
United States
Isha
The price is Rp2.129.715
Rp2.575.332 total
includes taxes & fees
14 Jul - 15 Jul
Vacation Village in the Berkshires
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (996 reviews)
"Great lobby and dining room atmosphere!"
United States
Carin
The price is Rp2.952.464
Rp3.297.903 total
includes taxes & fees
12 Jul - 13 Jul
Berkshires Untold
Free daily buffet breakfast

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Good location and great breakfast."
United States
Linda
The price is Rp3.094.330
Rp3.456.367 total
includes taxes & fees
8 Jul - 9 Jul
Hampton Inn & Suites Berkshires-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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Cheshire attractions

St Mary's of the Assumption Church

10.0/10 (1 review)
This historic Catholic parish has served Cheshire's community since 1879, offering a serene space for reflection. Visit during religious holidays to experience special services in its traditional architectural setting.
See properties

Learn more about Cheshire

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

See all hotels in Cheshire
A lake surrounded by autumn-colored trees and hills.

Top Cheshire Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Nice place to stay."
Debra 1-night trip
Posted 1 hour ago
Berkshires Untold

More cheap stays in Cheshire

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
The price is Rp1.112.025 per night from 15 Jul to 16 Jul
Rp1.112.025
Rp1.242.209 total
15 Jul - 16 Jul
includes taxes & fees
5.4/10 (837 reviews)

Frequently asked questions

What's the best place to stay in Cheshire?
Located 12.2 mi (19.6 km) from the heart of Cheshire, The Yankee Inn is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Vacation Village in the Berkshires and Berkshire Mountain Lodge. See all available top hotels, or vacation rentals in Cheshire.
If I need to cancel my hotel reservation in Cheshire, will I receive a refund?
Yes! Most room reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Cheshire.
What's the best LGBTQ-friendly place to stay in Cheshire?
Harbour House Inn is a top LGBTQ-friendly B&B, and features free breakfast and free WiFi. See all available hotels listed as LGBTQ-friendly in Cheshire.
What are some hotels with pools in Cheshire?
The Yankee Inn: Features a seasonal outdoor pool, an indoor pool and buffet. Vacation Village in the Berkshires and Berkshire Mountain Lodge are two additional hotels that feature an on-site pool. View all hotels with pools in Cheshire.
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 6 hotels and other accommodation options to choose from. Find out more about Cheshire.
What is there to see in Cheshire?
The picturesque setting of Mount Greylock State Reservation and Cheshire Reservoir exemplify the area's natural beauty. You'll also find Mount Greylock State Reservation Visitor Center and Mount Greylock in the area. Take a look at what more there is to see and do in Expedia's Cheshire guide.
What's the seasonal weather in Cheshire?
The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Cheshire are January, March, February and November, with each month seeing an average of 17 cm of snowfall.

Explore a world of travel with Expedia