Vacation Rentals in Sheffield, Massachusetts
We feature rental homes, villas, cabins, cottages, and condos in destinations all over the world. If you're looking for Sheffield, Massachusetts vacation rentals, click the "rental results" tab and inquire about your favorite listings. Browse Sheffield vacation deals, family-friendly amenities, and more. If you can't find what you're looking for, remember that vacation rentals in Sheffield, Massachusetts are added and updated every week, so please bookmark us and come back for a visit! Feel free to peruse other destinations as well, as we've got everything from large family vacation rentals to lake cabins to luxury beach houses.
Sheffield, Massachusetts Vacation Rentals and Tourism
more destinations
Check out more areas which feature homes, villas, cabins, cottages, or condos.
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
Norman Rockwell Museum
My aunt and uncle took me here while I was visiting them in Connecticut. They were really excited about it (they'd been here before), but we all had a...read more
Bash Bish Falls
To get to Bash Bish Falls, there is a nearby dedicated free parking lot that is only about a 15-20 minute hike generally downhill. The hike to get back to...read more
Ski Butternut Ski Area & Ski & Board Shop
I Love it here!!! The views alone are worth the trip. Lots of long trails and the perfect place to learn or just have a relaxing day skiing. Good also...read more
Bear Mountain
This, yelp hiking friends, is an absolutely fantastic hike. You can trek the entire Lion's Head to Bear Mountain, or you can do as we did (because of...read more
Cove Bowling Lanes
Good time--cheap bowling, and a little mini golf course too. Wasn't crowded when we were there at 8pm.read more
Triplex Cinema
The Triplex Cinema is my go-to theater when I don't feel like driving an hour to Albany to go to the Spectrum. Triplex is a small, independent theater...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
Naumkeag House
After years of seeing Naumkeag's gardens and home in various books and publications, it was a thrill to finally see it in person! Naumkeag is a classic...read more
Santarella Museum & Gardens
Oh my good God. This place is beautiful. This place is amazing. I want to get married here. http://www.santarella.us/home.htm Look at those pictures!...read more
Charer The Berkshires!
I first met Paul on January 30th 2010. My now fiancée had booked an ice fishing trip for me as a birthday present. As an avid fisherman I was eager to...read more
CrossFit Great Barrington
BizFit is the Great Barrington crossfit gym, however, unlike many Crossfit gyms it's run by Mike Bissalon a guy who's been involved in extreme fitness for...read more
Kilpatrick Athletic Centers
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
Chesterwood
I didn't expect much from this place and was quickly put in a foul mood because of the higher-than-expected admission price. I had driven a long way,...read more
O'hara's Landing Marina
Ahhhh, the majesty that IS Twin Lakes. Got a boat? Pop it here, yo. Want to drive a boat around for a few hours but don't own one? Rent one here,...read more
- bedrooms 3
- community Sheffield
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$950
- $1,200
/wk
$3,500 - $4,500 /mth
- bedrooms 5
- community
- rental type House
owner badge
- sleeps 12
- baths 3
- rates (USD)
$545
- $545
/nt
$3,540 - $3,540 /wk
$9,800 - $9,800 /mth





