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Check prices for these dates

This weekend
May 22 - May 24
Next weekend
May 29 - May 31

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Our top choices for Cheshire hotels

Exterior

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 ￥37,111
￥39,226 total
includes taxes & fees
May 25 - May 26
Harbour House Inn
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (136 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 ￥16,517
￥26,241 total
includes taxes & fees
Jun 2 - Jun 3
Blooming Inn
Front of property

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (60 reviews)
"Comfortable stay "
United States
Paul
The price is ￥15,105
￥22,200 total
includes taxes & fees
Jun 2 - Jun 3
Becket Motel
Exterior

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (211 reviews)
"Great stay! "
United States
ALEKSey
The price is ￥29,712
￥31,406 total
includes taxes & fees
May 28 - May 29
Blue Vista Motor Lodge
Comfort Double Room, Lake View | Desk, laptop workspace, free WiFi

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
The price is ￥23,748
￥26,526 total
includes taxes & fees
May 26 - May 27
Berkshire Lake Lodge
Standard Room, 1 King Bed, Non Smoking | Minibar, iron/ironing board, free WiFi, bed sheets

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (243 reviews)
"Found dead flies in the beds and the sheets were stained. I would not expect much from an inexpensive room but I do expect it to be clean."
United States
Heidi
The price is ￥12,720
￥14,208 total
includes taxes & fees
May 24 - May 25
Rodeway Inn
Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.0 out of 10, Wonderful, (150 reviews)
"Incredible staff, free parking and cute rooms!"
Canada
Priscilla
The price is ￥24,873
￥27,784 total
includes taxes & fees
May 28 - May 29
The Trail in Adams - Berkshires’ Art Hotel
55-inch LCD TV with digital channels, printers

The Revival House

The Revival House
3.0 star property
Adams
9.2 out of 10, Wonderful, (29 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
The price is ￥24,685
￥27,574 total
includes taxes & fees
May 24 - May 25
The Revival House
Room, 1 King Bed, Accessible, Non Smoking (Transfer Shower) | Hypo-allergenic bedding, desk, laptop workspace, blackout drapes

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,002 reviews)
"Loved our stay. This property is very clean, well-maintained, and had everything we needed for a comfortable stay."
United States
Brianna
The price is ￥24,453
￥27,314 total
includes taxes & fees
May 25 - May 26
Hotel Downstreet, an Ascend Collection Hotel
Exterior

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (473 reviews)
"Very beautiful hotel! The room was very clean."
United States
Daniel
The price is ￥31,339
￥38,558 total
includes taxes & fees
May 31 - Jun 1
The Porches Inn at Mass MoCA
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,002 reviews)
"Great location "
United States
Edith
The price is ￥17,975
￥20,077 total
includes taxes & fees
May 25 - May 26
Quality Inn Lee - Lenox South
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (413 reviews)
"Nice place for a stay"
United States
Jay
The price is ￥15,741
￥17,583 total
includes taxes & fees
May 26 - May 27
Sunset Inn
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (819 reviews)
"Scammers!! I booked a night just to shower and refresh. An abandoned public bathroom is 100 times cleaner than their room"
United States
Elie
The price is ￥10,909
￥12,184 total
includes taxes & fees
Jun 22 - Jun 23
FairBridge Inn Express
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (376 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is ￥27,187
￥30,369 total
includes taxes & fees
May 27 - May 28
Chambery Inn
In-room dining

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (663 reviews)
"Good to stay. "
United States
Ibinabo
The price is ￥12,017
￥13,423 total
includes taxes & fees
Jun 10 - Jun 11
Econo Lodge Lee - Great Barrington
Front of property - evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is ￥52,311
￥58,431 total
includes taxes & fees
May 27 - May 28
Devonfield Inn B&B
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,002 reviews)
"Clean rooms and lovely view"
Canada
Laraib
The price is ￥19,637
￥21,935 total
includes taxes & fees
May 25 - May 26
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Property amenity

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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.2 out of 10, Wonderful, (898 reviews)
"Family friendly resort with amenities the whole family can enjoy!"
United States
Justina
The price is ￥18,460
￥23,728 total
includes taxes & fees
May 25 - May 26
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is ￥53,183
￥62,375 total
includes taxes & fees
Jun 2 - Jun 3
The Inn at Stockbridge
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (96 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
The price is ￥20,193
￥22,556 total
includes taxes & fees
May 28 - May 29
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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.
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Stay near popular Cheshire attractions

St Mary's of the Assumption Church

5.0/5 (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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Nice staff, nice room and facilities. Having stayed there several times happily and will be back again in June. Thanks."
David 2-night trip
Posted 9 hours ago
Vacation Village in the Berkshires

More cheap stays in Cheshire

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
The price is ￥12,561 per night from May 25 to May 26
￥12,561
￥14,031 total
May 25 - May 26
includes taxes & fees
7.6/10 Good! (855 reviews)

Frequently asked questions

What's the best place to stay in Cheshire?
Located 11.5 mi (18.6 km) from the heart of Cheshire, Berkshire Mountain Lodge 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?
Peace and quiet on the lake: This vacation home rental outside of Cheshire is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind. 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. See all available hotels listed as LGBTQ-friendly in Cheshire.
What are some hotels with pools in Cheshire?
Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. Vacation Village in the Berkshires and Hotel Downstreet, an Ascend Collection Hotel are two additional hotels with an onsite pool. View all hotels with pools in Cheshire.
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 6 hotels and other accommodations to choose from. Find out more about Cheshire.
What are the top places to visit in Cheshire?
A favorite place to visit is Mount Greylock State Reservation. You'll also find Susan B. Anthony Birthplace Museum 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.

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