Sheffield vacation rentals

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Best Sheffield vacation rentals

Most recommended vacation rentals in Sheffield

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Antique Farmhouse Totally Restored - Sheffield - Building
Antique Farmhouse Totally Restored
Sheffield, MA
Free Wi-Fi
Pet friendly
$893+
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Skiing and Hiking Water-View Home in the Berkshires - Sheffield - Living room
Skiing and Hiking Water-View Home in the Berkshires
Sheffield, MA
9.0Wonderful(15)
Free Wi-Fi
$418+
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Whitney by AvantStay Private Berkshires Estate - Sheffield - Bedroom
Whitney by AvantStay Private Berkshires Estate
Sheffield, MA
Parking
Free Wi-Fi
Pet friendly
$605+
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Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton! - Sheffield - Patio
Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton!
Sheffield, MA
Free Wi-Fi
Pet friendly
$369+
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Cheerful 3-bedroom cottage with woodstove - Sheffield - Living room
Cheerful 3-bedroom cottage with woodstove
Sheffield, MA
Free Wi-Fi
$465+
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Private Peninsula 2ac Surrounded By Water Min From Hiking Skiing Theater Music - Sheffield - Living room
Private Peninsula 2ac Surrounded By Water Min From Hiking Skiing Theater Music
Sheffield, MA
Pet friendly
$645+
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Come Stay At The Sheffield Chalet! - Sheffield - Bathroom
Come Stay At The Sheffield Chalet!
Sheffield, MA
Free Wi-Fi
$361+
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12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room - Sheffield - Living room
12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room
Sheffield, MA
Free Wi-Fi
$571+
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Little House in the Woods by Evergreen Home - Sheffield - Living room
Little House in the Woods by Evergreen Home
Sheffield, MA
Pet friendly
$681+
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the bunkhouse - Sheffield
the bunkhouse
Sheffield, MA
$258+
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Summer And Fall In Sheffield With Monthl - Sheffield
Summer And Fall In Sheffield With Monthl
Sheffield, MA
Free Wi-Fi
Pet friendly
$396+
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Close to everything Berkshire! - Sheffield
Close to everything Berkshire!
Sheffield, MA
Free Wi-Fi
Pet friendly
$351+
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Charming Berkshires Cottage by Evergreen Home - Sheffield
Charming Berkshires Cottage by Evergreen Home
Sheffield, MA
$344+
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Charming Berkshires cottage is your perfect ski vacation home! - Sheffield
Charming Berkshires cottage is your perfect ski vacation home!
Sheffield, MA
Free Wi-Fi
$326+
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Newly Renovated Country Retreat-Berkshires - Sheffield
Newly Renovated Country Retreat-Berkshires
Sheffield, MA
$205+
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Spacious Country Retreat With Secluded Tree Top Mountain Views - Sheffield
Spacious Country Retreat With Secluded Tree Top Mountain Views
Sheffield, MA
Pet friendly
$672+
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$0 - $291$291 - $582$582 - $873$873 - $1,164$1,164+ per night

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Low season

February

High season

February

Average price (weekend night)

$459
Cheapest month to stay with an average 0% drop in price.
Most expensive month to stay with an average 0% rise in price.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Sheffield vacation rental deals

  • Vacation rentals in Sheffield are around 128% cheaper than hotels on average. Search here to compare prices for all accommodation types in Sheffield.
  • The best vacation rental properties in Sheffield are Cheerful 3-bedroom cottage with woodstove (9.9, 24 reviews), Elterwater--Your lakefront oasis, a Berkshire getaway. Long term discount. (9.7, 44) and Elterwater--Your lakefront oasis, a Berkshire getaway. Long term discount. (9.7, 44), based on ratings and reviews from real travelers.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Sheffield for 2 days.

FAQs when booking a vacation home in Sheffield

  • What types of vacation rentals are available in Sheffield?

    There are loads of different property types that you can make your vacation home in Sheffield. You’ll find cottages, houses and luxury tents.

  • Are there any pet-friendly vacation rentals in Sheffield?

    There are a number of dog and pet-friendly Sheffield vacation rentals, with around 36% allowing you to bring your pet along with you.

  • How can I find vacation rentals near me in Sheffield?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Sheffield?

Our map will help you find the perfect place to stay in Sheffield by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Sheffield

Sheffield vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Sheffield. Find cheap vacation homes to rent in Sheffield. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Sheffield that suits you best.

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