Hotels in Cheshire

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Next weekend
Aug 7 - Aug 9
In two weeks
Aug 14 - Aug 16

Where to stay in Cheshire?

Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (55 reviews)
This charming B&B offers free breakfast, WiFi, and parking in scenic Cheshire. Explore nearby attractions like Adams Theater and Mount Greylock State Reservation, then return to this welcoming inn. Pittsfield Station is just a 16-minute drive away.
The price is $254
$268 total
includes taxes & fees
Aug 4 - Aug 5
Harbour House Inn
Desk, iron/ironing board, WiFi (free), bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (863 reviews)
Tucked away in a peaceful corner of Pittsfield, this quiet motel offers free WiFi and parking with a 24-hour front desk. Nearby Crane Museum of Papermaking awaits exploration, while winter enthusiasts will love the downhill skiing options just moments away.
The price is $69
$77 total
includes taxes & fees
Aug 4 - Aug 5
FairBridge Inn Express
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
Discover this Lenox retreat with stunning mountain views, year-round swimming options, and fireplaces in select rooms. Just minutes from Bousquet Ski Area and local attractions, enjoy free breakfast and helpful staff after a day exploring.
The price is $175
$195 total
includes taxes & fees
Aug 4 - Aug 5
The Yankee Inn
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, desk, laptop workspace, blackout drapes

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)
Escape to this Pittsfield hotel near the train station, with Tanglewood Music Center nearby. After enjoying the complimentary breakfast, explore local skiing trails or workout in the fitness center. Clean rooms and attentive staff create a welcoming mountain getaway.
The price is $114
$127 total
includes taxes & fees
Aug 5 - Aug 6
Best Western Plus Berkshire Hills Inn & Suites
Standard Room, 1 King Bed, Non Smoking | Minibar, iron/ironing board, WiFi (free), bed sheets

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (266 reviews)
The price is $72
$81 total
includes taxes & fees
Sep 1 - Sep 2
Rodeway Inn
55-inch LCD TV with digital channels, printers

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (36 reviews)
Wake up to a complimentary self-serve breakfast at this charming Adams guesthouse. Enjoy free WiFi and parking while exploring nearby Adams Theater and Berkshire Scenic Railway Museum. Just a 22-minute drive from Pittsfield Station.
The price is $166
$185 total
includes taxes & fees
Aug 17 - Aug 18
The Revival House
Courtyard

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (111 reviews)
Tucked in New Ashford, this welcoming motel provides a refreshing seasonal outdoor pool, terraced grounds, and garden spaces. Just 15 minutes from skiing at Jiminy Peak and Brodie Mountain with free WiFi and convenient parking.
The price is $152
$167 total
includes taxes & fees
Aug 5 - Aug 6
The Springs Motel
Reception

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,003 reviews)
The price is $149
$166 total
includes taxes & fees
Sep 1 - Sep 2
Hotel Downstreet, 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, (2,493 reviews)
The price is $118
$143 total
includes taxes & fees
Aug 31 - Sep 1
Vacation Village in the Berkshires
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, (152 reviews)
The price is $205
$229 total
includes taxes & fees
Aug 4 - Aug 5
The Trail in Adams - Berkshires’ Art Hotel
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (935 reviews)
The price is $95
$111 total
includes taxes & fees
Aug 5 - Aug 6
Cozy Corner Motel
Mountain view

Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (927 reviews)
Wake up to complimentary breakfast before exploring Williamstown's attractions. Located near Colonial Plaza and Lower Linear Park, this clean, comfortable motel offers free WiFi and parking. Fellow travelers consistently praise the friendly, attentive staff.
The price is $100
$112 total
includes taxes & fees
Aug 4 - Aug 5
Howard Johnson by Wyndham Williamstown
Property grounds

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,004 reviews)
Immerse in the Berkshire charm at this Williamstown motel featuring an outdoor pool with pool bar. Rooms offer refrigerators and microwaves for convenience, while free breakfast, WiFi, and parking enhance your visit. Nearby Colonial Plaza awaits exploration.
The price is $99
$111 total
includes taxes & fees
Aug 6 - Aug 7
Willows Motel Williamstown
Property grounds

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (629 reviews)
Escape to this Williamstown motel in the entertainment district with a seasonal pool. Clean rooms await after exploring nearby Linear Park. Friendly staff, free breakfast, WiFi and parking enhance your value-packed stay.
The price is $129
$144 total
includes taxes & fees
Aug 5 - Aug 6
Maple Terrace Motel
Desk, iron/ironing board, WiFi (free), bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (901 reviews)
Enjoy a serene retreat in Pittsfield with a seasonal outdoor pool and proximity to Colonial Theater and Berkshire Museum. This motel offers clean rooms, free WiFi, and parking. Just a 2-minute drive from the transportation hub for your Tanglewood adventures.
The price is $90
$101 total
includes taxes & fees
Aug 4 - Aug 5
Berkshire Inn
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,007 reviews)
Unwind at this centrally located Pittsfield hotel with an indoor pool and health club. Just 15 minutes from Tanglewood Music Center and a quick 6-minute walk to transportation. Enjoy quiet rooms with microwaves, refrigerators, and a bar on-site.
The price is $119
$133 total
includes taxes & fees
Aug 31 - Sep 1
Holiday Inn & Suites Pittsfield-Berkshires by IHG
View from property

Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (335 reviews)
The price is $109
$122 total
includes taxes & fees
Aug 9 - Aug 10
Williamstown Motel
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,039 reviews)
The price is $122
$158 total
includes taxes & fees
Sep 1 - Sep 2
Berkshire Mountain Lodge
Exterior

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (384 reviews)
The price is $109
$122 total
includes taxes & fees
Aug 4 - Aug 5
The Central Downtown Inn & Suites
Outdoor pool

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (489 reviews)
The price is $186
$230 total
includes taxes & fees
Sep 1 - Sep 2
The Porches Inn at Mass MoCA
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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Top landmarks in Cheshire

St Mary's of the Assumption Church

10.0/10 (1 review)
St Mary's of the Assumption Church is in the heart of Cheshire, so why not stop by during your stay.
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Learn more about Cheshire

Cheshire is well-known for its attractions such as Mount Greylock State Reservation and Cheshire Reservoir.

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

Check out reviews of Cheshire hotels guests love

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

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

10/10 Excellent
"Very nice, clean and quiet hotel with good location."
Leonid 1-night trip
Posted 3 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Frequently asked questions

What accommodations do travelers like in Cheshire?
Guests like Vacation Village in the Berkshires, Hotel Downstreet, an Ascend Collection Hotel and FairBridge Inn Express.
Can I book a refundable hotel in Cheshire?
If you're looking for the flexibility to change your travel plans to Cheshire, most hotels offer refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Cheshire if I want a vacation home instead of a traditional hotel?
Browse 5 vacation homes on our site.
What will the weather in Cheshire be like during my vacation?
July and August are typically the warmest months in Cheshire when the average temp is 63°F. January and February are the coldest months when the average temperature is 25°F. July and August are the months with the most rain.
Why should I book my Cheshire hotel with Hotels.com?
There are lots of reasons to book your Cheshire trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.