Photo by Ed Gaffny

Find hotels in Cheshire, MA from CNY572

Check Cheshire hotel prices

Tonight
May 23 - May 24
Tomorrow night
May 24 - May 25
This weekend
May 24 - May 26
Next weekend
May 31 - Jun 2

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Compare 870 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Exterior
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1001)
"The omelette bar with the continental breakfast was killer."
The price is $110
$122 total
includes taxes & fees
30 May - 31 May
The Yankee, Trademark Collection by Wyndham
Fridge, microwave, stovetop, coffee/tea maker
Berkshire Mountain Lodge
3.0 star property
8.8 out of 10, Excellent, (311)
"A good stay. Clean and quite. Nice pool and fun for the Kidspiration "
The price is $165
$204 total
includes taxes & fees
27 May - 28 May
Berkshire Mountain Lodge
Lobby
Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, (245)
"Love the lobby (even smells great!) Love the decor and the outdoor patio. Happy with entire stay."
The price is $99
$111 total
includes taxes & fees
28 May - 29 May
Life House Berkshires
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Front of property - evening/night
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (586)
"Very unique venue rooms were awesome staff was incredibly personable will certainly stay there again"
The price is $169
$189 total
includes taxes & fees
27 May - 28 May
Hotel On North
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (857)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is $159
$174 total
includes taxes & fees
23 Jun - 24 Jun
Jiminy Peak Mountain Resort
Indoor pool
Courtyard by Marriott Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, (510)
"Room was so nice. Bed was comfortable. Overall glad we stayed here. "
The price is $152
$170 total
includes taxes & fees
30 May - 31 May
Courtyard by Marriott Lenox Berkshires
Front of property - evening/night
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (294)
"Love the Williams Inn"
The price is $269
$300 total
includes taxes & fees
27 May - 28 May
The Williams Inn
Exterior
Hampton Inn & Suites Berkshires-Lenox
2.5 star property
9.2 out of 10, Wonderful, (1000)
"No water for drinking on each floor, only in lobby. Some updates could be done. Lovely people."
The price is $135
$151 total
includes taxes & fees
30 May - 31 May
Hampton Inn & Suites Berkshires-Lenox
Hypo-allergenic bedding, laptop workspace, blackout drapes
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, (923)
"A great place to stay in North Adams. Clean, friendly and located just a couple of miles from an outstanding breakfast restaurant. "
The price is $149
$166 total
includes taxes & fees
27 May - 28 May
Hotel Downstreet
Lobby
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.4 out of 10, Very Good, (945)
"The hotel was farther off of the freeway than I thought it would be. But it was a nice quiet room with a good breakfast. The workout room had a decent treadmill. The stepper needed a battery and the Peloton needed help from the employee to connect to the internet so we didn't ask. The staff was super friendly and jumping to help with any issues. A very good experience."
The price is $101
$113 total
includes taxes & fees
30 May - 31 May
Best Western Plus Berkshire Hills Inn & Suites
Indoor pool
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3.0 star property
7.8 out of 10, Good, (580)
"loved how close to downtown the property is, we walked whwre we could. parking garage is closed for renovations but the staff was great and provided free valet and parked our car close or in front of the doors most days to help with us having a small child and my husband using a cane. loved the bar and pool as well. the hallways smelled strongly of weed but thankfully the smell stayed in the halls "
The price is $101
$113 total
includes taxes & fees
29 May - 30 May
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Exterior
Fairfield Inn & Suites by Marriott Williamstown
2.5 star property
8.8 out of 10, Excellent, (270)
"Cleanliness. Conenience. Lobby decor. Friendly service. Late model hi def TV. Comfy bed."
The price is $161
$180 total
includes taxes & fees
28 May - 29 May
Fairfield Inn & Suites by Marriott Williamstown
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
8.8 out of 10, Excellent, (103)
"It was clean and quiet good Breakfast "
The price is $219
$244 total
includes taxes & fees
27 May - 28 May
The Trail in Adams - Berkshires’ Art Hotel
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn
2.0 star property
7.6 out of 10, Good, (661)
"I liked how quiet it was. I liked the town"
The price is $81
$91 total
includes taxes & fees
27 May - 28 May
Berkshire Inn
Exterior
Berkshire Valley Inn
2.5 star property
9.0 out of 10, Wonderful, (502)
"Very comfortable stay. Hotel as a lot of charm, staff was friendly and accommodating. Breakfast had healthy options. Also appreciated accommodations for pets, including the dog park and dog bowls/treats. Highly recommend!"
The price is $164
$180 total
includes taxes & fees
24 May - 25 May
Berkshire Valley Inn
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express
2.5 star property
5.2 out of 10, (554)
"The staff."
The price is $79
$88 total
includes taxes & fees
26 May - 27 May
FairBridge Inn Express
Property grounds
Wagon Wheel Inn
2.0 star property
7.2 out of 10, Good, (546)
"Deff stay again if in the area "
The price is $99
$111 total
includes taxes & fees
26 May - 27 May
Wagon Wheel Inn
Exterior
Howard Johnson by Wyndham Lenox
2.0 star property
7.6 out of 10, Good, (610)
"Convenient "
The price is $79
$88 total
includes taxes & fees
27 May - 28 May
Howard Johnson by Wyndham Lenox
Lake view
Stay Berkshires
2.0 star property
8.4 out of 10, Very Good, (336)
"The staff went to great lengths to solve a problem that arose with my reservation. I would strongly recommend Stay Berkshire for a visit to the Williamstown area. "
The price is $160
$179 total
includes taxes & fees
27 May - 28 May
Stay Berkshires
Exterior
Willows Motel Williamstown
2.0 star property
8.8 out of 10, Excellent, (795)
"The breakfast was excellent, with a wide variety of fruits and baked items."
The price is $79
$88 total
includes taxes & fees
27 May - 28 May
Willows Motel Williamstown
Don't see what you're looking for?
See all available properties in Cheshire
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.

More cheap stays in Cheshire

Quality Inn

Quality Inn

170 Housatonic Street, Lee, MA
The price is CNY862 per night from Jun 2 to Jun 3
CNY862
CNY963 total
includes taxes & fees
Jun 2 - Jun 3
8/10 Very Good! (896 reviews)

Stay near popular Cheshire attractions

Image for St Mary's of the Assumption Church

St Mary's of the Assumption Church

5/5(1 review)

Learn about the local history of Cheshire with a stop at St Mary's of the Assumption Church. Discover the area's mountain views, or seek out its ski slopes.

See properties
St Mary's of the Assumption Church

Cheshire Travel Info

Number of reviews
4,720
Accommodation
870 hotels
Highest price
CNY1,948
Lowest price
CNY572
Reasons to visit
Jiminy Peak Mountain Resort, Colonial Theater and Williamstown Theatre Festival
Hotels with dining
3
Hotels with family-friendly amenities
5

Frequently asked questions

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'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, April, March, and February, with each month seeing an average of 8 inches of snowfall.

Recent reviews of Cheshire hotels
Expedia 亿客行 verified reviews

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

5/5 Excellent
"Nice & quiet property. Will love the food at the restaurant, JAE. "
A verified traveler stayed at Hilton Garden Inn Lenox Pittsfield
Posted 22 hours ago
Hilton Garden Inn Lenox Pittsfield