Photo by Ed Gaffny
Find 4 Star Hotels in Cheshire, MA from SAR 388
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check availability on Cheshire 4 Star Hotels
Tonight
Tomorrow
This weekend
Next weekend
Compare Cheshire 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

The Williams Inn
The Williams Inn
9.6 out of 10, Exceptional, (449)
The price is SAR 998
SAR 1,115 total
includes taxes & fees
13 May - 14 May

Lakehouse Inn
Lakehouse Inn
9.6 out of 10, Exceptional, (257)
The price is SAR 728
SAR 853 total
includes taxes & fees
25 May - 26 May

The Central Downtown Inn & Suites
The Central Downtown Inn & Suites
8.8 out of 10, Excellent, (279)
The price is SAR 388
SAR 434 total
includes taxes & fees
25 May - 26 May

33 Main
33 Main
10.0 out of 10, Exceptional, (70)
The price is SAR 1,471
SAR 1,644 total
includes taxes & fees
15 May - 16 May

Devonfield Inn B&B
Devonfield Inn B&B
10.0 out of 10, Exceptional, (125)
The price is SAR 1,009
SAR 1,127 total
includes taxes & fees
14 May - 15 May

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
9.2 out of 10, Wonderful, (105)
The price is SAR 2,584
SAR 3,126 total
includes taxes & fees
15 May - 16 May

Seven Hills Inn
Seven Hills Inn
7.8 out of 10, Good, (467)

The Inn at Stockbridge
The Inn at Stockbridge
9.8 out of 10, Exceptional, (98)
Save an average of 15% on thousands of hotels when you're signed in
Learn more about Cheshire
Get away to romantic Cheshire! Enjoy the skiing, hiking, and lake views.

Photo by Ed Gaffny
Open Photo by Ed Gaffny
Recent reviews of Cheshire hotels
Recent reviews of Cheshire hotels

The Williams Inn
5/5 Excellent
"A delightful property in every way. We had comfy beds, lots of quiet (our rooms were adjacent to the elevator and we never heard a peep), loved the complimentary coffee, tea, and water. Enjoyed the public spaces and the restaurant. Easy parking, steps from Spring Street. I could go on and on, but the summary is I’d be so pleased to stay here again. "
A verified traveler stayed at The Williams Inn
Posted 1 day ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Cheshire Hotels by Star Rating
Stay near popular Cheshire attractions
- Hotels near St Mary's of the Assumption Church
- Hotels near Tanglewood Music Center
- Hotels near Williams College
- Hotels near Jiminy Peak Mountain Resort
- Hotels near National Shrine of the Divine Mercy
- Hotels near Green Mountain National Forest
- Hotels near Massachusetts Museum of Contemporary Art
- Hotels near Lee Premium Outlets
- Hotels near Mount Greylock
- Hotels near The Clark Art Institute
- Hotels near The Mount
- Hotels near Norman Rockwell Museum
- Hotels near Jacob's Pillow
- Hotels near Berkshire East Ski Resort
- Hotels near Hancock Shaker Village
- Hotels near Bousquet Ski Area
- Hotels near Mount Greylock State Reservation Visitor Center
- Hotels near Berkshire Botanical Garden
- Hotels near Shakespeare and Company
- Hotels near Williamstown Theatre Festival
More Hotel Options in Cheshire
More Accommodation Types in
- Vacation Homes in Cheshire
- Apartments in Cheshire
- Cottages in Cheshire
- Condo Rentals in Cheshire
- Resorts in Cheshire
- B&B in Cheshire
- Cabin Rentals in Cheshire
- Farmstay in Cheshire
- Motels in Cheshire
- Guest Houses in Cheshire
- Chalets in Cheshire
- Inns in Cheshire
- Aparthotels in Cheshire
- Condo Resorts in Cheshire
- Lodges in Cheshire
- Villas in Cheshire
Explore more hotels
- Hotel On North
- Holiday Inn & Suites Pittsfield-Berkshires by IHG
- Best Western Plus Berkshire Hills Inn & Suites
- The Porches Inn at Mass MoCA
- Courtyard by Marriott Lenox Berkshires
- The Cornell Inn, Lenox & The Berkshires
- Quality Inn
- Fairfield Inn & Suites by Marriott Williamstown
- Howard Johnson by Wyndham Lenox
- Hampton Inn & Suites Berkshires-Lenox
- Club Wyndham Bentley Brook
- Gregory House Country Inn
- The Central Downtown Inn & Suites
- Williamstown Motel
- Blooming Inn
- The Villager Motel
- Jiminy Peak Mountain Resort
- Willows Motel Williamstown
- Berkshire Inn
- Hilton Garden Inn Lenox Pittsfield