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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 11...read 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 that...read 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, a...read more

 

Norman Rockwell Museum

Norman Rockwell now is viewed as an American icon whose illustrations -- mostly for the Saturday Evening Post from the 1920s to the early '60s -- created a...read 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. You...read more

 

Cove Bowling Lanes

I came here for a state tournament, this is a dilapidated old building. On a Saturday night there are more people sitting in the bar then on the lanes. The...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

 

Catamount Aerial Adventure Park

This is an adventure park in the woods that is supposedly suitable for ages 7 and up (though I think the younger you are, the better - way more fearless!)....read 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 several...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

 

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

 

Triplex Cinema

The Triplex has long been the best movie theatre in the area; however they managed to alienate myself and many other long time customers, by not informing...read more

 

Framed

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 business...read 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 be...read more

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Beautiful Berkshire Home W Tennis Court; Close to Skiing!
Sheffield House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 9
  • baths 3
  • rates (USD) $500 - $525 /nt
    $3,100 - $3,500 /wk
 
 
 
 
 

31 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) $500 - $1,000 /nt
    $2,200 - $4,000 /wk
 
 
 
 
 

8 reviews 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
 
 
 
 
 

22 reviews write a review

Beautiful Sheffield Barn on 20 Acres with Hiking Trails!
Sheffield House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 12
  • baths 3
  • rates (USD) $314 - $343 /nt
    $2,400 /wk
    $5,000 - $8,500 /mth
 
 
 
 
 

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Beautiful Renovated Farmhouse on Eight Acres with Views of Mount Everett
Sheffield House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $314 - $343 /nt
    $2,400 /wk
    $4,500 - $8,500 /mth
 
 
 
 
 

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Summer Availability! 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
 
 
 
 
 

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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
    $8,500 /mth
 
 
 
 
 

3 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

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