Photo by Ed Gaffny
Find hotels in Cheshire, MA from $69
Check Cheshire hotel prices
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Compare 873 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
9.0 out of 10, Wonderful, 1,001 reviews
The price is $125
$140 total
includes taxes & fees
26 Jun - 27 Jun
Berkshire Mountain Lodge
Berkshire Mountain Lodge
8.8 out of 10, Excellent, 316 reviews
The price is $185
$227 total
includes taxes & fees
23 Jun - 24 Jun
Life House Berkshires
Life House Berkshires
9.0 out of 10, Wonderful, 268 reviews
The price is $119
$133 total
includes taxes & fees
24 Jun - 25 Jun
The price is $189
$211 total
includes taxes & fees
23 Jun - 24 Jun
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very Good, 860 reviews
The price is $153
$168 total
includes taxes & fees
24 Jun - 25 Jun
Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires
9.2 out of 10, Wonderful, 512 reviews
The price is $199
$222 total
includes taxes & fees
11 Jul - 12 Jul
The price is $220
$246 total
includes taxes & fees
26 Jun - 27 Jun
Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox
9.2 out of 10, Wonderful, 1,000 reviews
The price is $187
$209 total
includes taxes & fees
10 Jul - 11 Jul
The price is $149
$166 total
includes taxes & fees
23 Jun - 24 Jun
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
8.4 out of 10, Very Good, 956 reviews
The price is $134
$150 total
includes taxes & fees
24 Jun - 25 Jun
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
7.8 out of 10, Good, 591 reviews
The price is $141
$157 total
includes taxes & fees
23 Jun - 24 Jun
Fairfield Inn & Suites by Marriott Williamstown
Fairfield Inn & Suites by Marriott Williamstown
8.8 out of 10, Excellent, 273 reviews
The price is $179
$200 total
includes taxes & fees
14 Jul - 15 Jul
The Trail in Adams - Berkshires’ Art Hotel
The Trail in Adams - Berkshires’ Art Hotel
8.8 out of 10, Excellent, 106 reviews
The price is $218
$244 total
includes taxes & fees
22 Jun - 23 Jun
The price is $90
$101 total
includes taxes & fees
10 Jul - 11 Jul
The price is $144
$158 total
includes taxes & fees
23 Jun - 24 Jun
The price is $69
$77 total
includes taxes & fees
23 Jun - 24 Jun
The price is $69
$77 total
includes taxes & fees
1 Jul - 2 Jul
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox
7.6 out of 10, Good, 619 reviews
The price is $89
$99 total
includes taxes & fees
24 Jun - 25 Jun
The price is $160
$179 total
includes taxes & fees
23 Jun - 24 Jun
Willows Motel Williamstown
Willows Motel Williamstown
8.8 out of 10, Excellent, 802 reviews
The price is $99
$111 total
includes taxes & fees
23 Jun - 24 Jun
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.
Stay near popular Cheshire attractions
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.
Cheshire Travel Info
Number of reviews | 11,692 |
---|---|
Accommodation | 873 hotels |
Highest price | $189 |
Lowest price | $69 |
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
Recent reviews of Cheshire hotelsExpedia 亿客行 verified reviews
![The Black Swan Lee - Lenox, Ascend Hotel Collection](http://images.trvl-media.com/lodging/1000000/30000/20500/20447/874e3696_y.jpg)
The Black Swan Lee - Lenox, Ascend Hotel Collection
5/5 Excellent
"Loved the lake in the back !!!"
A verified traveler stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection
Posted 1 day ago
Stay near popular Cheshire attractions
- Hotels near St Mary's of the Assumption Church
- Hotels near Tanglewood Music Center
- Hotels near Jiminy Peak Mountain Resort
- Hotels near Williams College
- Hotels near National Shrine of the Divine Mercy
- Hotels near Massachusetts Museum of Contemporary Art
- Hotels near Norman Rockwell Museum
- Hotels near Lee Premium Outlets
- Hotels near Jacob's Pillow
- Hotels near Mount Greylock
- Hotels near The Clark Art Institute
- Hotels near The Mount
- Hotels near Berkshire East Ski Resort
- Hotels near Bousquet Ski Area
- Hotels near Shakespeare and Company
- Hotels near Hancock Shaker Village
- Hotels near Mohawk Trail State Forest
- Hotels near Mount Greylock State Reservation Visitor Center
- Hotels near October Mountain State Forest
- Hotels near Ventfort Hall Mansion and Gilded Age Museum
More Accommodation Types in Cheshire
- Vacation Homes in Cheshire (226)
- Apartments in Cheshire (70)
- Cottages in Cheshire (49)
- Condo Rentals in Cheshire (43)
- B&B in Cheshire (27)
- Cabin Rentals in Cheshire (26)
- Resorts in Cheshire (24)
- Motels in Cheshire (20)
- Farmstay in Cheshire (13)
- Aparthotels in Cheshire (5)
- Guest Houses in Cheshire (5)
- Villas in Cheshire (3)
- Condo Resorts in Cheshire (2)
- Lodges in Cheshire (2)
Hotels near Cheshire Airports
Other Hotels near Cheshire, Massachusetts
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- Lenox Hotels
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- The Berkshires Hotels
- Pittsfield Hotels
- Hudson Valley Hotels
- Williamstown Hotels
- Great Barrington Hotels
- Stockbridge Hotels
- Lee Hotels
- Bennington Hotels
- North Adams Hotels
- Wilmington Hotels
- Hancock Hotels
- Appalachian Mountains Hotels
- Nassau Hotels
- Otis Hotels
- West Stockbridge Hotels
- Becket Hotels
- Western Massachusetts Hotels
Explore more hotels
- The Williams Inn
- Berkshire Mountain Lodge
- Best Western Plus Berkshire Hills Inn & Suites
- Berkshire Inn
- Club Wyndham Bentley Brook
- Courtyard by Marriott Lenox Berkshires
- Hampton Inn & Suites Berkshires-Lenox
- Fairfield Inn & Suites by Marriott Williamstown
- The Cornell Inn, Lenox
- Hilton Garden Inn Lenox Pittsfield
- Jiminy Peak Mountain Resort
- Hotel On North
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