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Vacation Rentals in Sheffield, Massachusetts

$243 $100
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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Weekly rate:

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$2,000
$4,000+

Bedrooms: Min 0, Max 5

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

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

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

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
 
 
 
 
 

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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

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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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

Beautiful Sheffield Barn on 20 Acres with Hiking Trails!
Sheffield House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 12
  • baths 3
  • rates (USD) $357 - $386 /nt
    $2,700 /wk
    $5,500 - $9,500 /mth
 
 
 
 
 

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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