Best Resorts in Sheffield

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Check prices for these dates

Next weekend
May 29 - May 31
In two weeks
Jun 5 - Jun 7
In one month
Jun 19 - Jun 21
In two months
Jul 17 - Jul 19
No exact matches found, but these alternatives could be just right

Recommended hotels in Sheffield

Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (49 reviews)
"the breakfast is from heaven. the house is beautiful. love the stay."
United States
Catherine
$176 nightly
The price is $197
May 27 - May 28
Total with taxes and fees
Wilder House Berkshires
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
$612 nightly
The price is $684
May 26 - May 27
Total with taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$451 nightly
The price is $504
May 25 - May 26
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
"Breakfast ok, coffee good, staff great"
United States
Peter
$106 nightly
The price is $119
May 29 - May 30
Total with taxes and fees
The Yankee Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (457 reviews)
"Wonderful place to stay!"
United States
Mervin
$98 nightly
The price is $108
May 25 - May 26
Total with taxes and fees
Shaker Mill Inn
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,002 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
$85 nightly
The price is $94
May 27 - May 28
Total with taxes and fees
Quality Inn Great Barrington
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (946 reviews)
"Clean and great job staffing "
United States
Pedro
$113 nightly
The price is $126
May 25 - May 26
Total with taxes and fees
Berkshire Mountain Lodge
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (856 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
$76 nightly
The price is $85
May 25 - May 26
Total with taxes and fees
Monument Mountain Motel
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (96 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
$127 nightly
The price is $142
May 28 - May 29
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (958 reviews)
"Great stay!"
United States
Aditya
$116 nightly
The price is $129
Jun 4 - Jun 5
Total with taxes and fees
Berkshires Untold
In-room safe, desk, free cribs/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (580 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
$75 nightly
The price is $84
May 25 - May 26
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
BBQ/picnic area

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.0 out of 10, Very Good, (2 reviews)
"After a little snafu with check-in (we had completed the form in advance and never received the room number text), we were able to get checked in with the virtual front desk. The inn was clean and well appointed and centrally located. The common areas felt inviting and useful for both the adults and kids. We would stay again."
United States
Samantha
$133 nightly
The price is $149
May 31 - Jun 1
Total with taxes and fees
Hideaway Inn Lenox
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (182 reviews)
"beautiful inn"
United States
Maura
$143 nightly
The price is $164
May 25 - May 26
Total with taxes and fees
Blackberry River Inn
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (561 reviews)
"Avoid this place."
United States
Carole
$95 nightly
The price is $106
Jun 11 - Jun 12
Total with taxes and fees
The Little Lion
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (417 reviews)
"Clean, good breakfast, friendly staff"
United States
Debra
$105 nightly
The price is $121
May 25 - May 26
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,002 reviews)
"Great location "
United States
Edith
$110 nightly
The price is $122
Jun 15 - Jun 16
Total with taxes and fees
Quality Inn Lee - Lenox South
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,006 reviews)
"Clean rooms and lovely view"
Canada
Laraib
$116 nightly
The price is $130
Jun 1 - Jun 2
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (855 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
$79 nightly
The price is $88
May 25 - May 26
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Exterior

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (766 reviews)
"Above average hotel breakfast. Very clean hotel."
United States
Helen
$124 nightly
The price is $139
Jun 1 - Jun 2
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (223 reviews)
"Alander was a nice stay with a very comfortable clean room. The simple accents and renovations to this property give it the tasteful environment I prefer over most large commercial properties."
United States
Arin
$137 nightly
The price is $153
May 26 - May 27
Total with taxes and fees
the Alander
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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"The hotel was funky is a good way, I liked the design and layout of the room and the dining area."
Daniel 2-night trip
Posted 9 hours ago
Berkshires Untold

Find out more about Sheffield

Sheffield Resorts information

Number of reviews
9,051
Accommodation
7 Resorts
Lowest Price
$84
Highest Price
$684

Frequently asked questions

What can I expect from a resort vacation in Sheffield?
Longing for a relaxing getaway? Indulge in all the comforts of a resort, where you can find everything you need for your stay from convenient food and drink options to activities and shopping. Browse the resort options in the area and discover the right one for you, whether you envision yourself sipping drinks by a sprawling pool or hitting the golf course for an afternoon game.
What's a top resort in Sheffield?
Our highest-rated resort near Sheffield: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 12.2 mi (19.6 km) from Sheffield. Has a sauna, a fitness center, and a terrace.
What can I do in Sheffield?
Housatonic River, Magnolia Bluffs Casino, and Mount Everett State Reservation are a few of the interesting sights to visit. Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary are a few additional attractions in the area that you might like.
What's the weather like in Sheffield?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to and around Sheffield?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 22 mi (35.4 km) from the city center. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 22.3 mi (35.9 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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