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Vacation Rentals in Sheffield, Massachusetts

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about Sheffield

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


Ski Butternut Ski Area & Ski & Board Shop

It was my first time going to Butternut even though it is fairly close to me, a little over an hour away. I'm glad we went(myself, 13 yr old daughter and more


Bash Bish Falls

The name alone had me hooked. So I thought as I went through a nearby list of attractions while visiting Stockbridge last weekend. Little did I know more


Norman Rockwell Museum

My husband, my mother, and I visited here in May 2013 and it was 100% worth the drive. Even just the drive to the museum is beautiful and humbling. more


Monument Mountain

The views at the top of the trail make this a five-star review. That and the condition of the trails. On a recent visit to the Great Barrington area, more


Charter The Berkshires

My wife and I decided to try ice fishing with Charter the Berkshires, it we're bot very glad we did! It was a super fun day and we both learned a lot. more


Cove Bowling Lanes

"there's a beverage here man" I heard a rumor that the cove bowling lanes was the inspiration for the movie "the Big Lebowski", maybe it's because 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 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, more


Berkshire Functional Fitness

As someone who works in the fitness world, I can tell you that this is a greatly place to go. I was in the area for the holidays and stopped by 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 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 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, more



OK- So here I go.. Everybody can have things framed, heck most people do it themselves! Erica the owner and the framer- is wonderful, she took the more


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 more

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New Listing! Delightful 4BR Apartment at Historic Inn Sleeps 12 - Enjoy Community Game Room + On-Site Restaurant & Day Spa!
Sheffield Apartment Rental Picture
  • bedrooms 4
  • rental type Apartment
  • sleeps 12
  • baths 3
  • rates (USD) $350 - $400 /nt
    $2,500 /wk
    $9,000 /mth

write a review

Antique Farmhouse Totally Restored & Crafted
Sheffield House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 16
  • baths 3
  • rates (USD) $350 - $600 /nt
    $2,500 - $3,400 /wk
    $10,000 - $12,400 /mth

21 reviews write a review

Completely private home set on 4 acres along the banks of the Housatonic River.
Sheffield House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $243 - $275 /nt
    $1,200 - $1,700 /wk
    $5,600 /mth

3 reviews write a review

Beautiful Berkshire Country House, Views-Summer Specials!!!
Sheffield House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $279 - $295 /nt
    $1,750 - $1,950 /wk
    $6,950 - $6,975 /mth

4 reviews write a review

The Perfect Berkshire Mountain Escape With An Epic View and Direct Trail Access
Sheffield House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 15
  • baths 3
  • rates (USD) $450 - $1,000 /nt
    $2,000 - $4,000 /wk

8 reviews write a review

Gateway To The Berkshires
Sheffield House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD)

17 reviews write a review