A covered wooden structure with a sloped roof, surrounded by greenery and trees.

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Check prices for these dates

Next weekend
Jul 24 - Jul 26
In two weeks
Jul 31 - Aug 2
In one month
Aug 14 - Aug 16
In two months
Sep 11 - Sep 13
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, (57 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is CA $268
CA $299 total
includes taxes & fees
Jul 19 - Jul 20
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, (12 reviews)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
United States
Tom S.
The price is CA $562
CA $986 total
includes taxes & fees
Jul 21 - Jul 22
Guesthouse Cabin vacation rentals in Berkshire County
2 bedrooms, WiFi (free), bed sheets

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is CA $152
CA $285 total
includes taxes & fees
Jul 28 - Jul 29
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Front of property

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (61 reviews)
"Comfortable stay "
United States
Paul
The price is CA $148
CA $213 total
includes taxes & fees
Jul 20 - Jul 21
Becket Motel
Interior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is CA $187
CA $551 total
includes taxes & fees
Jul 22 - Jul 23
Real Estate: Therapy - Lake, Laundry, Love it
Outdoor spa tub

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is CA $317
CA $671 total
includes taxes & fees
Jul 28 - Jul 29
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is CA $287
CA $633 total
includes taxes & fees
Jul 28 - Jul 29
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Front of property

Manor House Inn

Manor House Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (139 reviews)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
The price is CA $446
CA $495 total
includes taxes & fees
Jul 29 - Jul 30
Manor House Inn
Lake view

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.4 out of 10, Exceptional, (6 reviews)
"Everything was perfect!!"
United States
Grzegorz
The price is CA $286
CA $319 total
includes taxes & fees
Jul 19 - Jul 20
Berkshire Lake Lodge
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (193 reviews)
"Excellent breakfast, very nice staff."
United States
Leslie
The price is CA $192
CA $221 total
includes taxes & fees
Jul 21 - Jul 22
Blackberry River Inn
Front of property

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (139 reviews)
"Gedney Farm is a good place to stay for travelers looking for a spot a bit off the beaten track. The style is very informal, property beautiful, and the restaurant is excellent."
United States
Sarah
The price is CA $338
CA $371 total
includes taxes & fees
Aug 5 - Aug 6
Gedney Farm
Breakfast, lunch, dinner and brunch served

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (91 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is CA $448
CA $540 total
includes taxes & fees
Jul 21 - Jul 22
The Old Inn On The Green
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is CA $527
CA $969 total
includes taxes & fees
Aug 17 - Aug 18
Treetop Hideaway in Tyringham
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (434 reviews)
"Below average B&B"
United States
Larry
The price is CA $147
CA $170 total
includes taxes & fees
Jul 21 - Jul 22
Locust Tree Bed and Breakfast LLC
WiFi (free), bed sheets

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.8 out of 10, (98 reviews)
"Clean...cheap and comfortable bed"
United States
leo
The price is CA $183
CA $210 total
includes taxes & fees
Jul 21 - Jul 22
Hitching Post Country Motel
Desk, laptop workspace, blackout drapes, soundproofing

Pilgrim Inn

Pilgrim Inn
2.5 star property
Lee
5.8 out of 10, (332 reviews)
"Wonderful fantastic "
United States
Bryron
The price is CA $239
CA $267 total
includes taxes & fees
Aug 1 - Aug 2
Pilgrim Inn
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,000 reviews)
"Great place"
United States
Michelle
The price is CA $185
CA $207 total
includes taxes & fees
Jul 20 - Jul 21
Quality Inn Lee - Lenox South
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (425 reviews)
"It was a great stay, close to many amenities. The room was clean, with a comfortable bed."
Canada
Kevin
The price is CA $125
CA $140 total
includes taxes & fees
Jul 22 - Jul 23
Sunset Inn
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (381 reviews)
"Location is convenient to walk through downtown Lee and to get to a show at Tanglewood."
United States
Joseph
The price is CA $379
CA $423 total
includes taxes & fees
Jul 22 - Jul 23
Chambery Inn
In-room dining

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (676 reviews)
"Good location to towns in area"
United States
William
The price is CA $118
CA $132 total
includes taxes & fees
Aug 11 - Aug 12
Econo Lodge Lee - 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
"The staff were very friendly and helpful. It’s a rustic style hotel room but having the full kitchen was amazing! Great location and cozy room."
Jamie 2-night trip
Posted 15 hours ago
Berkshire Mountain Lodge

Find out more about Sheffield

Sheffield Resorts information

Number of reviews
3,293
Accommodation
8 Resorts
Lowest Price
CA $132
Highest Price
CA $986

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 Bartholomew's Cobble are a few of the interesting sights to visit. Bartholomews Cobble and Thom Reed UFO Monument Park 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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