Cheshire, MA Inns from $127

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Inns in Cheshire

La Perla Italian Restaurant offers Italian cuisine and wood-fired pizzas.

"Big rooms, very friendly staff and great pizza!"

$125 nightly

Aug 13 - Aug 14

Total includes taxes and fees

Welcome to The 1896 House, a serene retreat managed by Brookside Accommodations.

"Near hiking for Mt. Greylock and the Appalachian Trail. Nice walking area close by at Lamb's Hill. Clean Older mattress, was OK, but could feel springs a little. If you like a tub, it is tiny. The shower is OK"

$113 nightly

Aug 12 - Aug 13

Total includes taxes and fees

Relax by the serene pool surrounded by lush greenery and a picturesque view.

"I loved the pool and the wonderful view from the pool. I felt very safe here and there was an overall sense of being welcomed."

$121 nightly

Sep 7 - Sep 8

Total includes taxes and fees

Stately building with a neoclassical facade, featuring a central entrance and columns, set amidst a well-manicured lawn.

"Memorable. A wonderful hotel I every aspect. Faultless service from Scoyt and the team"

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Top Cheshire Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"This Vacation Village is amazing, returning this week for a little time away. Stayed last week for work and came home and planned a 3 day trip based on the location. "