Best Resorts in Sheffield

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Check prices for these dates

Next weekend
Jun 5 - Jun 7
In two weeks
Jun 12 - Jun 14
In one month
Jun 26 - Jun 28
In two months
Jul 24 - Jul 26
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 28 - May 29
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.
$617 nightly
The price is $689
Jun 1 - Jun 2
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.
$452 nightly
The price is $505
May 27 - May 28
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
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, (857 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
$76 nightly
The price is $85
May 27 - May 28
Total with taxes and fees
Monument Mountain Motel
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
$108 nightly
The price is $118
May 27 - May 28
Total with taxes and fees
Shaker Mill Inn
Standard Room, 2 Double Beds | Desk, laptop workspace, blackout drapes, iron/ironing board

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"The property is in terrible condition."
United States
Olga V
$61 nightly
The price is $67
May 27 - May 28
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (950 reviews)
"Clean and great job staffing "
United States
Pedro
$127 nightly
The price is $142
May 27 - May 28
Total with taxes and fees
Berkshire Mountain Lodge
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, (1,008 reviews)
"Breakfast ok, coffee good, staff great"
United States
Peter
$109 nightly
The price is $122
May 27 - May 28
Total with taxes and fees
The Yankee Inn
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (467 reviews)
"The breakfast was not diabetic friendly. They stated pet friendly but no place for dog to go to the bathroom. Had to walk dog through garbage . Cigarette butts all over very the place. Beds were terrible. My towels had clumps of black hair on them. Lotion and shampoos left in room were used not new ones. Will not go back"
United States
Stacy
$66 nightly
The price is $74
Jun 19 - Jun 20
Total with taxes and fees
Berkshire Travel Lodge
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,005 reviews)
"Great location "
United States
Edith
$110 nightly
The price is $122
Jun 16 - Jun 17
Total with taxes and fees
Quality Inn Lee - Lenox South
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
$74 nightly
The price is $82
May 27 - May 28
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
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, (856 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
$78 nightly
The price is $87
May 27 - May 28
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (959 reviews)
"Great stay!"
United States
Aditya
$116 nightly
The price is $129
May 27 - May 28
Total with taxes and fees
Berkshires Untold
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (413 reviews)
"Nice place for a stay"
United States
Jay
$103 nightly
The price is $115
May 27 - May 28
Total with taxes and fees
Sunset Inn
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 29 - May 30
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (183 reviews)
"beautiful inn"
United States
Maura
$140 nightly
The price is $161
Jun 2 - Jun 3
Total with taxes and fees
Blackberry River Inn
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, (99 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
$135 nightly
The price is $151
May 31 - Jun 1
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (562 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
Front of property

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (61 reviews)
"Best that can be said is that it was clean. The shower was ok. No on-site staff, we had to check in using a Ring doorbell and bad phone connection. The baseboard heat control required me to get on the floor and crawl into the corner of the room behind the fridge. And the room didn’t look at all like the picture on Expedia. Stay here if you have no other choice."
United States
Andrew
$125 nightly
The price is $140
Jun 2 - Jun 3
Total with taxes and fees
Becket Motel
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,004 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 31 - Jun 1
Total with taxes and fees
Quality Inn Great Barrington
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Clean room. Very well equipped. It is a hidden gem, close to everything. Great experience"
Carlos 3-night trip
Posted 10 hours ago
Berkshire Mountain Lodge

Find out more about Sheffield

Sheffield Resorts information

Number of reviews
10,981
Accommodation
7 Resorts
Lowest Price
$67
Highest Price
$689

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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