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Cottages in Sheffield

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Recommended hotels in Sheffield

Wilder House Berkshires

2.0 star property
Sheffield
9.8 out of 10, Exceptional, (38)
"Highly recommend this beautiful bed & breakfast! The room was wonderful and overlooked the property, the breakfast was delicious, and the hospitality was amazing. I had a fantastic stay, and will definitely stay at The Wilder House again when I'm in the area."
United States
Marina
$153 nightly
The price is $171
Nov 17 - Nov 18
Total with taxes and fees
Wilder House Berkshires

Cheerful 3-bedroom cottage with woodstove

Sheffield
10.0 out of 10, Exceptional, (40)
"we had a wonderful time staying at the house, very comfortable and well equipped and responsive host."
United States
lisa s.
$404 nightly
The price is $451
Nov 11 - Nov 12
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield
10.0 out of 10, Exceptional, (9)
"Two very comfortable nights. Cabin is well appointed. Great kitchen and outdoor space. Tremendous views, amazing star gazing. Very private. "
United States
Robert B.
$617 nightly
The price is $689
Nov 12 - Nov 13
Total with taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (434)
"Nice place, easy check in"
United States
Robert
$101 nightly
The price is $111
Nov 12 - Nov 13
Total with taxes and fees
Shaker Mill Inn

Monument Mountain Motel

2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (783)
"This was an older property, but room was nice and bathroom was updated. "
United States
Martha
$67 nightly
The price is $74
Nov 11 - Nov 12
Total with taxes and fees
Monument Mountain Motel

Quality Inn

2.5 star property
Lee
8.4 out of 10, Very Good, (1003)
"Clean room and good breakfast "
United States
Kelly
$87 nightly
The price is $98
Dec 1 - Dec 2
Total with taxes and fees
Quality Inn

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1002)
"Great place. Friendly staff and very well located. Great breakfast options. "
United States
Abiezer
$101 nightly
The price is $113
Nov 18 - Nov 19
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
Great Barrington
8.8 out of 10, Excellent, (692)
"Solid location, great room, good breakfast. Fair Price. Been 3 different times and look forward to returning again "
United States
Jamie
$102 nightly
The price is $114
Nov 16 - Nov 17
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1005)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
$110 nightly
The price is $122
Dec 1 - Dec 2
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (751)
"Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome. "
United States
Jeff
$113 nightly
The price is $126
Nov 11 - Nov 12
Total with taxes and fees
Berkshire Mountain Lodge

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (819)
"Staff was very friendly and helpful."
United States
Pamela
$79 nightly
The price is $88
Nov 11 - Nov 12
Total with taxes and fees
Howard Johnson by Wyndham Lenox

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
Great Barrington
7.6 out of 10, Good, (556)
"I loved the stay people were nice loved the pool and internet was great "
United States
Jennifer
$75 nightly
The price is $84
Nov 11 - Nov 12
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.6 out of 10, Exceptional, (10)
"Very friendly with dog. No complaints with accommodations "
United States
Lilian
$135 nightly
The price is $151
Nov 20 - Nov 21
Total with taxes and fees
Element Lenox Berkshires

Locust Tree Bed and Breakfast LLC

3.0 star property
East Canaan
9.0 out of 10, Wonderful, (410)
"Peaceful area and great staff; Thank you for the service and experience "
United States
Andre
$105 nightly
The price is $121
Nov 12 - Nov 13
Total with taxes and fees
Locust Tree Bed and Breakfast LLC

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (794)
"Easy parking, great community spaces, beautiful decor! "
United States
Kerry
$93 nightly
The price is $104
Nov 17 - Nov 18
Total with taxes and fees
Berkshires Untold

Quality Inn

2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1003)
"Nice and clean would stay again."
United States
Stephen
$84 nightly
The price is $94
Nov 24 - Nov 25
Total with taxes and fees
Quality Inn

Sunset Inn

2.0 star property
Lee
7.6 out of 10, Good, (409)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
$86 nightly
The price is $97
Dec 2 - Dec 3
Total with taxes and fees
Sunset Inn

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (57)
"Bright new hotel with very friendly and helpful staff. "
United States
Mary
$118 nightly
The price is $132
Dec 2 - Dec 3
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
$183 nightly
The price is $205
Nov 12 - Nov 13
Total with taxes and fees
The Red Lion Inn

Hilton Garden Inn Lenox Pittsfield

3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (656)
"Lovely hotel, room was great along with the staff and the grounds where beautiful. Thank you."
United States
Vicki
$111 nightly
The price is $124
Nov 23 - Nov 24
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
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

Find out more about Sheffield

Sheffield Cottages information

Number of reviews
11,433
Accommodation
109 Cottages
Lowest Price
$74
Highest Price
$689

Frequently asked questions

How much do cottages in Sheffield cost?
Cottages in Sheffield range between $74 and $689 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 109 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.
How can I find cheap cottages in Sheffield?
With Expedia's handy filter tool, booking cheap cottages in Sheffield has never been simpler. To find accommodations that are very pocket friendly, tailor your search results by budget, amenities and star rating.
What is there to do in Sheffield near my cottage?
After you've checked in to your hotel, get out and discover the incredible things Sheffield has for you to experience. Magnolia Bluffs Casino is a great attraction to add to your itinerary.

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