House vacation rentals in Sheffield
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Top-rated house rentals in Sheffield
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Sheffield house rentals
House rentals with a pool
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Home in Ghent
4.87 out of 5 average rating, 274 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Home in New Paltz
4.98 out of 5 average rating, 444 reviewsmidcentury modern in ground pool walk 2 trail/town
Home in Woodstock
4.98 out of 5 average rating, 105 reviewsWoodstock Historic Artist Estate- The Museum House
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Home in Cottekill
4.95 out of 5 average rating, 248 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
Home in Litchfield
4.93 out of 5 average rating, 167 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Weekly house rentals
Home in Hudson
4.94 out of 5 average rating, 127 reviewsMain Street Cottage
Home in New Marlborough
4.89 out of 5 average rating, 122 reviewsLake House in the Berkshire (Access Dock & Canoe
Home in Great Barrington
4.95 out of 5 average rating, 116 reviewsThe Hideaway: Berkshire Home - village of Egremont
Home in Chatham
4.9 out of 5 average rating, 149 reviews2BR Chatham Vlg. Park@Door Keyless 100% Smoke Free
Home in Rhinebeck
4.91 out of 5 average rating, 262 reviewsArchitectural wonder in the woods
Home in Millerton
4.93 out of 5 average rating, 367 reviewsMountaintop Skyloft
Home in Ghent
4.9 out of 5 average rating, 261 reviewsRenovated guesthouse on 52 acres!
Home in Ancramdale
4.93 out of 5 average rating, 129 reviewsSki & unwind in the country, stargaze in hot tub
Private house rentals
Home in Sheffield
5 out of 5 average rating, 26 reviewsThe Kellogg House in the Heart of The Berkshires
Home in Sheffield
4.99 out of 5 average rating, 82 reviewsBelle Meade
Home in Sheffield
4.91 out of 5 average rating, 77 reviewsHouse Among Trees - A Perfect Getaway
Home in Sheffield
4.82 out of 5 average rating, 66 reviewsCharming Berkshires Cottage by Evergreen Home
Home in Copake
4.93 out of 5 average rating, 43 reviewsYellow Door House
Home in Salisbury
5 out of 5 average rating, 24 reviewsGreystone at Twin Lakes
Home in Sheffield
4.98 out of 5 average rating, 50 reviewsWalt's Place-Your Family Getaway
Home in Hillsdale
5 out of 5 average rating, 23 reviewsEnjoy all 4 Seasons
Quick stats about house rentals in Sheffield
Total rentals
50 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
1.9K reviews
Nightly prices starting at
$120 before taxes and fees
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