Vacation Rentals in Sheffield, Massachusetts
Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Sheffield, 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 Sheffield are added and updated every week!
Compared to hotels, Sheffield 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.
Sheffield, Massachusetts Vacation Rentals and Tourism
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Sheffield things to do
Bartholomew's Cobble
A series of well-marked hiking trails snake through some strikingly massive and odd-looking stones, many of them topped with moss so soft-looking you'll be...read more
Ski Butternut Ski Area & Ski & Board Shop
Me and the posse came here for a hardcore day of.....TUBING. Actually it was more like an hour and a half until we were freezing and were in need of some...read more
Bash Bish Falls
Pretty much an amazing waterfall. My parents used to bring me here as a small child, and gasp, allowed us to swim. I'm not sure if swimming was actually...read more
Norman Rockwell Museum
Great visit today. Went especially to see the Heroes & Villains Alex Ross exhibit. A very cool show for a comic book nerd like me. I really enjoyed...read more
Cove Bowling Lanes
Clean, cheap, good selection of balls, very pleasant staff and a great way to spend a couple of hours. A great rainy day activity!read more
Charter The Berkshires
Yesterday I went on my second ice fishing excursion with Paul, and was once again impressed with the experience! I'd never been ice fishing before my...read more
Lime Rock Park
Amazing Park! Highly suggested to any race fan or even anyone partial. Great place to spend a day. Tickets are cheap and the sights are amazing. My father...read more
Bear Mountain
Bear Mountain is one of the best places to go hiking in Connecticut. It's classic New England...nice and rocky with thick treecover. I have always gone up...read more
Triplex Cinema
Never sit in theatre 3 on a saturday night. The sound of third rate street musicians comes through the wall and is more than distracting. The manager...read more
Monument Mountain
The blizzard of '10 thwarted my plans to leave this country and spend some time recharging. Heartbroken and listless though I was, the need to exit stage...read more
Catamount Aerial Adventure Park
Big kids, listen up. This is our jungle gym, our playground, our adrenaline ride. A ski/snowboard resort converted into a Summer obstacle course park,...read more
Kilpatrick Athletic Center
The KIlpatrick is the woefully under-utilized athletic center at Simon's Rock. (At least by the students.) Beautiful and new, it features a lap pool, a...read more
Artful Mind Artzine
Great local Art magazine for the Berkshires Connecticut and Hudson Valley.read more





