Hotels in Cheshire

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Check prices for these dates

Tonight
Feb 23 - Feb 24
Tomorrow
Feb 24 - Feb 25
This weekend
Feb 27 - Mar 1
Next weekend
Mar 6 - Mar 8

Where to stay in Cheshire?

Exterior
Harbour House Inn
Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 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
Feb 24 - Feb 25
Harbour House 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, (26 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 $150
$168 total
includes taxes & fees
Feb 25 - Feb 26
The Revival House
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, (144 reviews)
The price is $174
$194 total
includes taxes & fees
Feb 24 - Feb 25
The Trail in Adams - Berkshires’ Art Hotel
Courtyard
The Springs Motel
The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (92 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 $109
$119 total
includes taxes & fees
Feb 25 - Feb 26
The Springs Motel
Standard Room, 1 King Bed, Non Smoking | Minibar, iron/ironing board, free WiFi, bed sheets
Rodeway Inn
Rodeway Inn
2.0 star property
Adams
7.6 out of 10, Good, (236 reviews)
The price is $77
$85 total
includes taxes & fees
Mar 24 - Mar 25
Rodeway Inn
Exterior
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,261 reviews)
The price is $116
$141 total
includes taxes & fees
Feb 24 - Feb 25
Vacation Village in the Berkshires
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express
FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (811 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 $89
$99 total
includes taxes & fees
Feb 24 - Feb 25
FairBridge Inn Express
Exterior
Berkshire Valley Inn
Berkshire Valley Inn
2.5 star property
Williamstown
9.2 out of 10, Wonderful, (567 reviews)
Set in Williamstown, this welcoming hotel puts you 10 minutes from Jiminy Peak Mountain Resort and Brodie Mountain. Enjoy a seasonal outdoor pool, free breakfast, and WiFi. Travelers love the helpful staff, clean rooms, and nearby hiking trails.
The price is $125
$140 total
includes taxes & fees
Mar 8 - Mar 9
Berkshire Valley Inn
Exterior
Huttopia Berkshires
Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (9 reviews)
Surrounded by nature in the Berkshires, this campground offers an outdoor pool and convenient access to hiking and biking trails. Just a short drive from Jiminy Peak Mountain Resort and Mountain Coaster, you'll find the perfect basecamp for outdoor adventures.
The price is $168
$188 total
includes taxes & fees
Mar 8 - Mar 9
Huttopia Berkshires
Daily to-go breakfast for a fee
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very Good, (989 reviews)
Slope-side convenience awaits at this mountain resort with direct ski access. After hitting the trails, unwind in 2 hot tubs, grab dinner at John Harvard's, or enjoy the outdoor pool. With ski storage and lessons available, all your winter adventure needs are covered.
The price is $189
$211 total
includes taxes & fees
Mar 8 - Mar 9
Jiminy Peak Mountain Resort
Mountain view
Howard Johnson by Wyndham Williamstown
Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (904 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 $90
$101 total
includes taxes & fees
Feb 24 - Feb 25
Howard Johnson by Wyndham Williamstown
Miscellaneous
1896 House Country Inn & Motels
1896 House Country Inn & Motels
2.5 star property
Williamstown
6.6 out of 10, (448 reviews)
Escape to this charming country inn where Williamstown's natural beauty awaits. After exploring nearby Sheep Hill, unwind in the garden or sip drinks at the onsite bar. Free parking, business center, and restaurant make your Berkshires getaway complete.
The price is $125
$140 total
includes taxes & fees
Feb 24 - Feb 25
1896 House Country Inn & Motels
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, (1,002 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 $103
$115 total
includes taxes & fees
Feb 25 - Feb 26
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Property grounds
Maple Terrace Motel
Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (596 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 $99
$111 total
includes taxes & fees
Feb 24 - Feb 25
Maple Terrace Motel
Property grounds
Willows Motel Williamstown
Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,006 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 $85
$95 total
includes taxes & fees
Feb 24 - Feb 25
Willows Motel Williamstown
Seasonal outdoor pool
Berkshire Inn
Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (844 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
Feb 24 - Feb 25
Berkshire Inn
Terrace/patio
The Central Downtown Inn & Suites
The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (358 reviews)
The price is $102
$114 total
includes taxes & fees
Feb 25 - Feb 26
The Central Downtown Inn & Suites
Property entrance
Hotel On North
Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (825 reviews)
This boutique hotel combines business-friendly amenities with cozy accommodations near Barrington Stage Company. Enjoy thoughtful perks including complimentary WiFi, free parking, and convenient room service, all while exploring nearby cultural attractions.
The price is $149
$166 total
includes taxes & fees
Feb 24 - Feb 25
Hotel On North
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, (1,005 reviews)
The price is $114
$127 total
includes taxes & fees
Mar 23 - Mar 24
Hotel Downstreet, an Ascend Collection Hotel
View from property
Williamstown Motel
Williamstown Motel
2.0 star property
Williamstown
9.4 out of 10, Exceptional, (315 reviews)
The price is $80
$89 total
includes taxes & fees
Mar 15 - Mar 16
Williamstown 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.
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Top landmarks in Cheshire

St Mary's of the Assumption Church

This historic Catholic church 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

The region around Cheshire is home to attractions such as Mount Greylock State Reservation and Mount Greylock State Reservation Visitor Center.

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

Check out reviews of Cheshire hotels guests love

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"My wife and I just got back from a 2 night stay at the Hotel Downstreet in North Adams MA. We were very happy with this hotel and definitely plan to return! Several things stood out to us: first, upon checking in the front desk staff placed us in a quiet room located at the end of a hallway. This was very considerate, as there were numerous young families staying at this hotel (it was school vacation week). Second, our room was spotless and the bed was comfortable. The amenities at the hotel looked great - indoor pool, fitness center, and laundry (very useful if staying with young children). Location: walking distance to Mass MoCA, grocery store (Big Y), and pharmacy (CVS) and several restaurants; driving distance to attractions in the Berkshires, southern VT, and the NY capital region. And finally - an outstandingly reasonable price. Well worth a stay if you are looking for a trip in NW Massachusetts/the Berkshires."
David 2-night trip
Posted 1 day ago
Hotel Downstreet, an Ascend Collection Hotel

Frequently asked questions

What accommodations do travelers like in Cheshire?
Guests like Vacation Village in the Berkshires, Holiday Inn & Suites Pittsfield-Berkshires by IHG and Hotel Downstreet, an Ascend Collection Hotel.
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.