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29 Aug - 30 Aug
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Top 10 Sheffield hotels and places to stay

Our top choices for Sheffield hotels

Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (787)
"My stay was perfect. I can't wait to stay there again. "
The price is ฿2,550
฿2,848 total
includes taxes & fees
1 Sept - 2 Sept
Howard Johnson by Wyndham Lenox
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1003)
"Great staff! Comfortable bed! "
The price is ฿4,637
฿5,180 total
includes taxes & fees
7 Sept - 8 Sept
Hampton Inn & Suites Berkshires-Lenox
Monument Mountain Motel
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

2.5 star property
8.8 out of 10, Excellent, (744)
"A great mom & pop motel. Clean and friendly "
Monument Mountain Motel
Wilder House Berkshires
Wilder House Berkshires Room 3 | 1 bedroom, premium bedding, individually decorated

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (29)
"Brads and Lara both served a fabulous breakfast. So friendly and welcoming! The bed was very comfortable. Only complaint was that the cabinet, closet door needs to be greased with WD 40 please on the hinges! A terrible & loud screeching noise!"
The price is ฿6,136
฿6,854 total
includes taxes & fees
28 Sept - 29 Sept
Wilder House Berkshires
Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (401)
"Peaceful area and great staff; Thank you for the service and experience "
The price is ฿3,390
฿3,898 total
includes taxes & fees
2 Sept - 3 Sept
Locust Tree Bed and Breakfast LLC
Travelodge by Wyndham Great Barrington Berkshires
In-room safe, desk, free cots/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.6 out of 10, Good, (546)
"Excellent location, friendly service, clean, comfortable room."
The price is ฿2,421
฿2,705 total
includes taxes & fees
14 Sept - 15 Sept
Travelodge by Wyndham Great Barrington Berkshires
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (127)
"We had a vey clean room with a comfortable bed The breakfast was awesome as was the entire staff. Enjoyed our stay"
The price is ฿5,305
฿6,101 total
includes taxes & fees
2 Sept - 3 Sept
Blackberry River Inn
The Little Lion
Pool

The Little Lion

3.0 star property
8.6 out of 10, Excellent, (529)
"Comfy, quiet, and clean "
The price is ฿4,810
฿5,373 total
includes taxes & fees
1 Sept - 2 Sept
The Little Lion
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1007)
"Wonderful place to stay"
The price is ฿4,038
฿4,511 total
includes taxes & fees
21 Sept - 22 Sept
The Yankee, Trademark Collection by Wyndham
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1004)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is ฿4,088
฿4,567 total
includes taxes & fees
7 Sept - 8 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is ฿4,122
฿5,866 total
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (422)
"Very casual and easy check in and out; lovely and substantial breakfast"
The price is ฿5,294
฿5,808 total
includes taxes & fees
4 Sept - 5 Sept
Shaker Mill Inn
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (482)
"Nice quaint out of the ordinary vacation experience. "
The price is ฿5,596
฿6,250 total
includes taxes & fees
1 Sept - 2 Sept
Whistler's Inn Bed & Breakfast
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1005)
"Great location and close enough to walk to shops and restaurants. "
The price is ฿2,991
฿3,341 total
includes taxes & fees
14 Sept - 15 Sept
Quality Inn
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hypo-allergenic bedding, iron/ironing board, free cots/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (29)
"Do hotel, very clean we had a great day"
The price is ฿4,569
฿5,104 total
includes taxes & fees
4 Sept - 5 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (159)
"Inn was gorgeous and staff exceptional!"
Brook Farm Inn
Little Cat Lodge
Seasonal outdoor pool

Little Cat Lodge

2.0 star property
9.4 out of 10, Exceptional, (58)
"Great place"
Little Cat Lodge
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (573)
"Fabulous place"
The price is ฿4,907
฿5,481 total
includes taxes & fees
1 Sept - 2 Sept
Courtyard by Marriott Lenox Berkshires
The Whitlock
Exterior

The Whitlock

2.0 star property
8.6 out of 10, Excellent, (264)
"Wonderful ambience and people!"
The price is ฿5,723
฿6,393 total
includes taxes & fees
2 Sept - 3 Sept
The Whitlock
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1007)
"Very comfortable and a nice breakfast "
The price is ฿3,540
฿3,954 total
includes taxes & fees
14 Sept - 15 Sept
Quality Inn
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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Learn more about Sheffield

Tucked in the Berkshires, this charming town offers scenic hikes at Bartholomew's Cobble and local art at the Sheffield Historical Society. Catch live performances at the Berkshire Theatre Festival in nearby Stockbridge or sample farm-fresh produce at the weekend farmers' market on the town green.

See all hotels in Sheffield

Top Sheffield Hotel Reviews

More cheap stays in Sheffield

More cheap stays in Sheffield

Quality Inn

Quality Inn

372 Main Street, Rte 7 and Main Street, Great Barrington, MA
The price is ฿2,991 per night from 14 Sept to 15 Sept
฿2,991
฿3,341 total
14 Sept - 15 Sept
includes taxes & fees

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Where is the best place to stay in Sheffield?

Wilder House Berkshires is one of the top choices for your stay based on our traveller data. This B&B offers free breakfast and free parking. Two other options for your trip to the area are Berkshire Mountain Lodge and Berkshires Untold. See all available top hotels, or vacation rentals in Sheffield.

If I need to cancel my hotel reservation in Sheffield, will I receive a refund?

Yes, the majority of hotel reservations are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If your reservation is non-refundable, it may still be possible to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Sheffield.

What are some accommodation options with pools in Sheffield?

Berkshire Mountain Lodge: Offers free self parking, an indoor pool and complimentary wireless Internet access. The Red Lion Inn and Howard Johnson by Wyndham Lenox are a couple of other choices that feature an on-site pool. View all hotels with pools in Sheffield.

What's it like staying in Sheffield?

Visitors can enjoy all that Sheffield has to offer, including the casinos and local tours. In Sheffield, there are 35 hotels and other accommodation options to choose from. Find out more about Sheffield.

What are the top places to visit in Sheffield?

Favourite places to visit include Housatonic River, Magnolia Bluffs Casino and Mount Everett State Reservation. A couple of additional sights to add to your itinerary are Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary. Take a look at what more there is to see and do in Expedia's Sheffield guide.

What's the seasonal weather like in Sheffield?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Sheffield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.