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Featured Cottages in Sheffield

Stylish Pine Plains Home Near Parks & Hiking!
Interior

Stylish Pine Plains Home Near Parks & Hiking!

3.0 star property
10.0 out of 10, Exceptional, (2)
"Extra clean, private and lots of thoughtful extras like cell phone chargers, etc. "
Stylish Pine Plains Home Near Parks & Hiking!
A-frame Cabin w/ Furnished Deck in Becket!
Interior

A-frame Cabin w/ Furnished Deck in Becket!

3.0 star property
A-frame Cabin w/ Furnished Deck in Becket!
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Front of property

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

3.0 star property
10.0 out of 10, Exceptional, (1)
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Pondfront Gem Minutes From Hudsons Best Shops & Cafes The Stillwater House
Interior

Pondfront Gem Minutes From Hudsons Best Shops & Cafes The Stillwater House

3.0 star property
6.0 out of 10, (1)
"The location of the house was very near for food and supplies,yet very private. The inside was very clean and well kept. We enjoyed the quietness and surrounding grounds with views of local wild life. The things that we did not like was the musty - moldy smell when we first got there. Every time you used the water it smelled. Red light on fridge for changing filter. Bought spring water to use for drinking, coffee, and cooking. All reported to host upon departure."
Pondfront Gem Minutes From Hudsons Best Shops & Cafes The Stillwater House
Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!
Interior

Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

3.0 star property
Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!
Peaceful Goshen Cottage w/ Screened Porch & Views!
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Peaceful Goshen Cottage w/ Screened Porch & Views!

3.0 star property
Peaceful Goshen Cottage w/ Screened Porch & Views!
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Terrace/patio

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Skiing & Hiking: Water-view Home in the Berkshires
Interior

Skiing & Hiking: Water-view Home in the Berkshires

3.0 star property
Skiing & Hiking: Water-view Home in the Berkshires
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Interior

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Charming Sharon Dwelling w/ Deck & Fire Pit!
Front of property

Charming Sharon Dwelling w/ Deck & Fire Pit!

3.0 star property
Charming Sharon Dwelling w/ Deck & Fire Pit!
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Interior

West Cornwall Cabin ~ 4 Mi to Covered Bridge!

3.0 star property
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Private Hot Tub: Hudson Valley Cabin Retreat!
Interior

Private Hot Tub: Hudson Valley Cabin Retreat!

3.0 star property
Private Hot Tub: Hudson Valley Cabin Retreat!
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay
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Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

3.0 star property
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay
Serene Salisbury Rental Home on 26 Acres w/ Deck!
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Serene Salisbury Rental Home on 26 Acres w/ Deck!

3.0 star property
Serene Salisbury Rental Home on 26 Acres w/ Deck!
Ashley Falls Home w/ Fire Pit: Hike & Ski!
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Ashley Falls Home w/ Fire Pit: Hike & Ski!

3.0 star property
8.0 out of 10, Very Good, (1)
"Nice location. Spacious with ample bedrooms. Would have been nice if there was a second bathroom on the second floor. It might be time to freshen the furniture in the sitting area."
Ashley Falls Home w/ Fire Pit: Hike & Ski!
Waterfalls and Trails at 'the Mills At Green Hole'
Front of property

Waterfalls and Trails at 'the Mills At Green Hole'

3.0 star property
Waterfalls and Trails at 'the Mills At Green Hole'
Lakefront Otis Home w/ Stunning Views & Boats!
Interior

Lakefront Otis Home w/ Stunning Views & Boats!

3.0 star property
Lakefront Otis Home w/ Stunning Views & Boats!
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Interior

Cozy Stockbridge Cabin - Walk to Beach & Lake!

3.0 star property
2.0 out of 10, (1)
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Whitney by Avantstay Private Berkshires Estate
Interior

Whitney by Avantstay Private Berkshires Estate

3.0 star property
Whitney by Avantstay Private Berkshires Estate
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Interior

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

3.0 star property
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Sheffield Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"The staff was helpful, friendly. Nice location. The room was very clean and quiet, but so much of the place is brown. Brown carpet, brown paneled walls, brown chair, brown furniture, brown lamps. A minor detraction, but I look at hotel decor with a discerning eye and I like things to be less bland/mundane."
Elizabeth 1-night trip
Posted 1 day ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Sheffield

Find out more about Sheffield

Sheffield Cottages information

Number of reviews
5
Accommodation
68 Cottages
Lowest Price
Highest Price

Frequently asked questions

How much do cottages in Sheffield cost?
Cottages in Sheffield range between and per night. These stays offer a chance to touch base with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Sheffield?
There are 68 cottages in Sheffield. No matter if you're taking a trip with the kids or planning a getaway with your besties, Expedia can help you find the ideal space to get back to nature.
Why book your cottage in Sheffield with Expedia?
We think a getaway should be a walk in the park, so if you're in search of cottages in Sheffield at a nice price, Expedia has your back. Save money and check in to an economical option far from the downtown buzz, or book a 5-star cottage to pamper your loved ones.

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