Vacation rentals in Sheffield
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Top-rated vacation rentals in Sheffield
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Sheffield vacation rentals
Stay near Sheffield's top sights
Other great vacation rentals in Sheffield
Guest favourite
Vacation home in Great Barrington
4.94 out of 5 average rating, 139 reviewsHome in Great Barrington. Steps from downtown!
Dec. 12 – 19
$366 CAD per night
Guest favourite
Home in Great Barrington
4.96 out of 5 average rating, 212 reviewsJaw dropping mountain & lake views
Jan. 22 – 29
$1,231 CAD per night
Guest favourite
Cottage in Hillsdale
4.94 out of 5 average rating, 171 reviewsCozy Cottage Catamount, Berkshires Walk to Brewery
Feb. 3 – 10
$184 CAD per night
Guest favourite
Cottage in Great Barrington
4.93 out of 5 average rating, 234 reviewsArtist Cottage
Nov. 9 – 16
$358 CAD per night
Guest favourite
Farm stay in Ancram
4.95 out of 5 average rating, 264 reviewsRelaxing secluded stay with loving social animals.
Feb. 25 – Mar. 4
$224 CAD per night
Guest favourite
Barn in Hillsdale
4.97 out of 5 average rating, 116 reviewsHudson Valley Hilltop Barn
Aug. 31 – Sep. 7
$1,603 CAD per night
Guest favourite
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Jun. 20 – 27
$883 CAD per night
Guest favourite
Guest suite in Sheffield
5.0 out of 5 average rating, 59 reviewsThe Sunset Suite~Great South Berkshire Location!
Dec. 17 – 24
$274 CAD per night
Quick stats about vacation rentals in Sheffield
Total rentals
90 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
3.8K reviews
Nightly prices starting at
$137 CAD before taxes and fees
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- Monthly Rentals Sheffield
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