Photo by Photo courtesy of Berkshire Visitors Bureau

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Fishing Hotels in The Berkshires

Harbour House Inn

725 North State Road Cheshire MA

5 min drive from Jiminy Peak Mountain Resort

Stay at this B&B in Cheshire. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Cheshire Reservoir and Adams Theater are located ...

9.8/10 Exceptional! (58 reviews)

"EVERYTHING about this hotel experience was ten stars, from Brandy meeting us at the door with homemade treats to the elegant and welcoming decor to the relaxing front porch looking out on the impeccable grounds to the cozy clean room and delicious breakfast. Thank you, Brandy and Daryl, for the incredible ..."

Reviewed on Sep 29, 2026

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

26 Glendale Road, RR 183 Stockbridge MA

46 min drive from Jiminy Peak Mountain Resort

Book a stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood ...

1896 House Country Inn & Motels

910 Cold Spring Road Williamstown MA

23 min drive from Jiminy Peak Mountain Resort

Stay at this hotel in Williamstown. Enjoy free parking, a business center, and a garden. Popular attractions Sheep Hill and Bullock Ledge Wildlife Management ...

6.8/10 (459 reviews)

"The beds in our room were so old and uncomfortable we got no sleep. There was no staff in the office or maid service—so we got no clean towels or beds made…we ran out of toilet paper, and our shower was literally falling apart—there was duct tape holding the floor together! And not only was there ..."

Reviewed on Nov 1, 2026

See all 1,079 properties in The Berkshires

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.