Vacation Rentals & House Rentals in Sheffield

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Parking
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Beach or lakeside relaxation
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26 Houses

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Private Berkshire County Retreat

Sheffield house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$686

Great rentals within 20 miles that match your search

Newly Renovated Lakefront Getaway on Robinson Pond

Copake house

3 bedrooms
1 bathroom

sleeps 5

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$287

Berkshires Spacious Comfortable Charming Farmhouse

Lee apartment

3 bedrooms
2 bathrooms

sleeps 8

“lovely stay” The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.

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$373

Hillhouse Log Cabin

Hillsdale log cabin

3 bedrooms
2 bathrooms

sleeps 13

“rest,relax,recharge” It's a Beautiful home that has all the modern conveniences. It's quiet, quaint and had just what I needed to get away from it all. I enjoyed morning coffee on the back deck among the trees and afternoon walks in the woods. A perfect place to recharge.

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$487

Berkshire Farmhouse Vacation

West Stockbridge house

5 bedrooms
2 bathrooms

sleeps 15

“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the living room and paneled walls in the dining room. We were there on a rainy, cold weekend, so did not have an opportunity to enjoy the grounds or porch, but imagine it would be lovely in the warmer weather. Elaine (and her shop) were on the same grounds and she was available for questions about the area. Overall a very relaxing & convenient experience.

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$298