Find Hotel Wedding Venues in Cheshire, MA
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Our top choices for Cheshire wedding hotels
9.4 out of 10, Exceptional, (53)
"The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people."
alton
The price is NT$6,781
NT$7,168 total
includes taxes & fees
Jan 7 - 2026/1/8
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very Good, (997)
"Very clean and timely and efficient and the lady who checked me in named Valerie did an amazing job and was very informative and helpful . "
Dwight
The price is NT$3,091
NT$3,453 total
includes taxes & fees
Jan 2 - 2026/1/3
8.8 out of 10, Excellent, (1002)
"Old time charm and hot tub under the stars"
Lori
The price is NT$4,731
NT$6,694 total
includes taxes & fees
Jan 14 - 2026/1/15
The price is NT$4,695
NT$4,962 total
includes taxes & fees
Jan 1 - 2026/1/2
9.6 out of 10, Exceptional, (553)
"staff was great"
Tim
The price is NT$6,900
NT$7,707 total
includes taxes & fees
Jan 11 - 2026/1/12
6.6 out of 10, (448)
"The price is good. It's a classic motel from the '50's, but gets the job done."
edson
8.0 out of 10, Very Good, (193)
"Very well kept property, nice restaurant and is in a great area"
Josephine
The price is NT$5,267
NT$6,146 total
includes taxes & fees
Jan 4 - 2026/1/5
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 ChesterwoodStockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
Robert
The price is NT$12,033
NT$14,557 total
includes taxes & fees
Jan 7 - 2026/1/8
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.
Top Cheshire Hotel Reviews
The Yankee, Trademark Collection by Wyndham
10/10 Excellent
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- Visit Dalton
- Williamstown Historical Museum
- Massachusetts Museum of Contemporary Art
- Visit North Adams
- Visit Lenox
- The Clark Art Institute
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