The Berkshires Fishing Holidays

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Photo by Photo courtesy of Berkshire Visitors Bureau
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Top Fishing The Berkshires Hotels

Harbour House Inn

Harbour House Inn

3.5 out of 5
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 Wi-Fi 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 29 Sept 2026

Harbour House Inn
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

4.5 out of 5
26 Glendale Road, RR 183 Stockbridge MA
  • 46 min drive from Jiminy Peak Mountain Resort
Stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Tanglewood Music Center and Chesterwood are located ...
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
1896 House Country Inn & Motels

1896 House Country Inn & Motels

2.5 out of 5
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 centre 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 1 Nov 2026

1896 House Country Inn & Motels
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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.