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Vacation Rentals in Cheshire, Massachusetts

about Cheshire

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Cheshire, Massachusetts vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Cheshire are added and updated every week!

Compared to hotels, Cheshire vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Cheshire, Massachusetts Vacation Rentals and Tourism

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Check out more areas which feature homes, villas, cabins, cottages, or condos.

Cheshire things to do

 

Mass Museum of Contemporary Art

I was with a friend on a day trip to North Adams and she took me to MASS MoCA. Entry was $10 with a college ID, free for her as a student of Williams...read more

 

Mount Greylock State Reservation

Whether you hike or drive, you have to get to the top of this mountain. You will be rewarded with spectacular views, the Memorial tower and Bascom Lodge...read more

 

Beacon Cinema

Great old building that is beautiful. Been here twice, one on a holiday, one not. Both times the lines were ridiculous. The front of the house management...read more

 

Clark Art Institute

Sterling Clark, you were one hell of an early 20th century baller. I challenge my fellow yelpers to find a more affluent collection in New England. This...read more

 

The Colonial Theatre

A beautiful theatre just outside of Lenox. I saw The Crucible here and was really impressed by the acoustics and the caliber of acting displayed by a very...read more

 

Barrington Stage Company: Mainstage

Saw an incredible production of Fiddler on the Roof here this weekend. And while the show was a little long for me, clocking in at three hours, I enjoyed...read more

 

Berkshire Hills Country Club

I also recently attended a wedding here. This seems to be quite the place to attend weddings. This seemed like a pretty good venue to use for a wedding....read more

 

Bakers Golf Center

This is a pretty fun mini golf spot. There's quite a bit of skill involved in this course, including avoiding stuff that moves, water hazards, windmills,...read more

 

Berkshire Museum

I really like this museum. My toddler had a blast. It is a fun way to spend a couple hours. The Dino dig is perfect for toddlers & the Christmas tree...read more

 

Mt Greylock Bowl

Wow.... how many teenage nights did I spend at this place when I should have been studying for AP whatever? Too many. Aside from the smoke (which is...read more

 

Onota Boat Livery

Wonderful experience!! They were very helpful and informative. We went fishing on Lake Onota and row boated for 4 hours for $60... they helped us set up our...read more

 

Radiance Yoga

An AMAZING yoga studio if you're in the Berkshires! The studio is clean and pretty, uncluttered, calming, easy. The yoga room itself is quite beautiful,...read more

 

Images Cinema

This is a fantastic little theatre in Williamstown! From blankets to organic popcorn and butter and candy this great theatre has it all... except multiple...read more

 

Natural Bridge State Park

PHENOMENAL. And, like, $2. Seriously. Just go see. So lovely.read more

 

Herman Melville's Arrowhead

Arrowhead is amazing! The tour guide we had was enthusiastic and very kind! You can tell he really loves his job. This is not your everyday run of the...read more

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