An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.

Cheshire hotels from RM287

  • 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
26 Jun - 28 Jun
Next weekend
3 Jul - 5 Jul

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Cheshire hotels

Exterior

1. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is RM1,050
RM1,109 total
includes taxes & fees
24 Jun - 25 Jun
Harbour House Inn
Jetted bathtub

2. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is RM594
RM664 total
includes taxes & fees
7 Jul - 8 Jul
The Yankee Inn
In-room safe, individually decorated, individually furnished, desk

3. 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, (1,001 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
The price is RM493
RM551 total
includes taxes & fees
25 Jun - 26 Jun
Best Western Plus Berkshire Hills Inn & Suites
Garden

4. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (462 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is RM798
RM876 total
includes taxes & fees
1 Jul - 2 Jul
Shaker Mill Inn
Front of property

5. Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (140 reviews)
"The room was clean and comfortable. It was a quiet night's sleep as I believe I was the only one there. Breakfast was very plain and simple: English muffins and cinnamon toast, with no fruit or juice. Coffee was plentiful"
United States
Sarah
The price is RM443
RM698 total
includes taxes & fees
30 Jun - 1 Jul
Blooming Inn
Indoor pool

6. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (111 reviews)
"Most comfortable hotel bed I've ever slept in"
United States
Matthew
The price is RM707
RM790 total
includes taxes & fees
8 Jul - 9 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Lobby

7. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,003 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is RM575
RM642 total
includes taxes & fees
24 Jun - 25 Jun
Quality Inn Lee - Lenox South
Reception

8. The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (793 reviews)
"The room was comfortable and clean, I will stay there again"
United States
Monica
The price is RM368
RM411 total
includes taxes & fees
29 Jun - 30 Jun
The Villager Motel
55-inch LCD TV with digital channels, printers

9. The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (34 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
The price is RM632
RM706 total
includes taxes & fees
20 Jul - 21 Jul
The Revival House
Gazebo

10. Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (916 reviews)
"Very clean! Friendly staff! Will stop there again!"
United States
Theresa
The price is RM365
RM429 total
includes taxes & fees
12 Jul - 13 Jul
Cozy Corner Motel
Desk, iron/ironing board, free WiFi, bed sheets

11. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (829 reviews)
"Plenty of parking. Staff was friendly"
United States
William
The price is RM257
RM287 total
includes taxes & fees
8 Jul - 9 Jul
FairBridge Inn Express
Property grounds

12. Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (612 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 RM534
RM596 total
includes taxes & fees
29 Jun - 30 Jun
Maple Terrace Motel
Front of property

13. Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (61 reviews)
"Comfortable stay "
United States
Paul
The price is RM434
RM624 total
includes taxes & fees
25 Jun - 26 Jun
Becket Motel
Lobby

14. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (997 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 RM582
RM743 total
includes taxes & fees
22 Jul - 23 Jul
Berkshire Mountain Lodge
Lake view

15. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
10.0 out of 10, Exceptional, (1 review)
"Everything was perfect!!"
United States
Grzegorz
The price is RM652
RM728 total
includes taxes & fees
25 Jun - 26 Jun
Berkshire Lake Lodge
Exterior

16. Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (216 reviews)
"The whole place was beautifully well kept and the view couldn't be beat. Would definitely recommend to others and hope to return in the future."
United States
Jared
The price is RM841
RM889 total
includes taxes & fees
24 Jun - 25 Jun
Blue Vista Motor Lodge
In-room dining

17. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (669 reviews)
"Decent place.friendly, quiet"
United States
William
The price is RM327
RM365 total
includes taxes & fees
24 Jun - 25 Jun
Econo Lodge Lee - Great Barrington
Exterior

18. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,005 reviews)
"Clean room and breakfast"
United States
Raphael
The price is RM627
RM886 total
includes taxes & fees
1 Jul - 2 Jul
The Red Lion Inn
View from property

19. Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (327 reviews)
"Clean rooms and the staff was extremely friendly and helpful"
United States
Graham
The price is RM368
RM411 total
includes taxes & fees
30 Jun - 1 Jul
Williamstown Motel
Courtyard

20. The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (102 reviews)
"We enjoyed our stay. Staff was nice and the motel is set between several different towns to explore. We plan to stay again soon!"
United States
Shakeila
The price is RM461
RM505 total
includes taxes & fees
24 Jun - 25 Jun
The Springs Motel
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

10.0/5 (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
An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.

Top Cheshire Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"I had an excellent experience with the Yankee Inn. The room was updated and the house keeping was excellent. The location was good and the staff was very nice. The breakfast was very good. I would definitely recommend staying here."
Nicolina 2-night trip
Posted 1 hour ago
The Yankee Inn

More cheap stays in Cheshire

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA
The price is RM493 per night from 25 Jun to 26 Jun
RM493
RM551 total
25 Jun - 26 Jun
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)

Frequently asked questions

What's the best place to stay in Cheshire?
Located 9.8 mi (15.7 km) from the heart of Cheshire, Hotel Downstreet, an Ascend Collection Hotel is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Berkshire Mountain Lodge and Vacation Village in the Berkshires. 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?
Hotel Downstreet, an Ascend Collection Hotel: Features daily, an indoor pool and free self parking. Berkshire Mountain Lodge and Vacation Village in the Berkshires 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?
A favourite place to visit is Mount Greylock State Reservation. You'll also find Mount Greylock State Reservation Visitor Center and Susan B. Anthony Birthplace Museum 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