Find hotels in Sheffield, MA from ฿2,857

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
30 Oct - 31 Oct
Tomorrow
31 Oct - 1 Nov
This weekend
31 Oct - 2 Nov
Next weekend
7 Nov - 9 Nov

Filter by

Guest rating
Guest rating
Star rating

Top 10 Sheffield hotels and places to stay

Wilder House Berkshires Room 3 | 1 bedroom, premium bedding, individually decorated
Wilder House Berkshires
Wilder House Berkshires
2.0 star property
9.8 out of 10, Exceptional, (37)
"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
The price is ฿5,245
฿5,858 total
includes taxes & fees
5 Nov - 6 Nov
Wilder House Berkshires
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.0 out of 10, Wonderful, (1002)
"Great Indian restaurant in the hotel!"
United States
Chris
The price is ฿3,440
฿3,842 total
includes taxes & fees
5 Nov - 6 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Interior
Berkshires Untold
Berkshires Untold
3.5 star property
9.0 out of 10, Wonderful, (786)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is ฿2,999
฿3,350 total
includes taxes & fees
4 Nov - 5 Nov
Berkshires Untold
Exterior
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1023)
"Fresh breakfast menu, clean and great location."
United States
Gail
The price is ฿3,470
฿3,876 total
includes taxes & fees
2 Nov - 3 Nov
The Yankee, Trademark Collection by Wyndham
Front of property
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1001)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is ฿4,170
฿5,923 total
includes taxes & fees
4 Nov - 5 Nov
The Cornell Inn, Lenox & The Berkshires
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (740)
"Great stay, perfect "
United States
Lawrence
Berkshire Mountain Lodge
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.0 out of 10, Wonderful, (773)
"We enjoyed our stay and will definitely be back."
United States
Howard
The price is ฿3,791
฿4,687 total
includes taxes & fees
18 Nov - 19 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Double Room | Egyptian cotton sheets, premium bedding, memory-foam beds, desk
The Brooks Motel
The Brooks Motel
2.0 star property
7.6 out of 10, Good, (112)
"The room was very comfortable & clean. It had a really nice shower, which is very important for us when travelling. Thank you! See you again some time."
United States
Robert
The Brooks Motel
Outdoor pool, pool loungers
The Red Lion Inn
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1022)
"Picture perfect Inn"
United States
jeff
The price is ฿4,824
฿6,835 total
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
9.4 out of 10, Exceptional, (55)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
United States
Marti
The price is ฿4,100
฿4,580 total
includes taxes & fees
4 Nov - 5 Nov
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
American cuisine
the Alander
the Alander
2.5 star property
9.0 out of 10, Wonderful, (178)
"Very nice clean place in a beautiful area. "
United States
Wayne
The price is ฿5,180
฿5,801 total
includes taxes & fees
4 Nov - 5 Nov
the Alander
Front of property
The Constance by the Lenox Collection
The Constance by the Lenox Collection
3.5 star property
8.4 out of 10, Very good, (557)
"Everything was very nice. A very simple experience."
United States
Anthony
The price is ฿4,172
฿4,660 total
includes taxes & fees
3 Nov - 4 Nov
The Constance by the Lenox Collection
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8 out of 10, Excellent, (683)
"This motel was easy access right off the highway, super clean, and the staff was great. We would definitely stay here again. Breakfast options were good as well. "
United States
Tina
The price is ฿3,464
฿3,869 total
includes taxes & fees
11 Nov - 12 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Lobby
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.4 out of 10, Exceptional, (747)
"The property is very nice and the staff was extremely friendly and helpful."
United States
Greg
The price is ฿4,629
฿5,171 total
includes taxes & fees
4 Nov - 5 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Library
Blackberry River Inn
Blackberry River Inn
3.0 star property
9.4 out of 10, Exceptional, (151)
"Very good breakfast.excellent waiter.love the atmosphere."
United States
Marc
The price is ฿5,321
฿6,119 total
includes taxes & fees
4 Nov - 5 Nov
Blackberry River Inn
Front of property
Chambery Inn
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (371)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Egyptian cotton sheets, premium bedding, down duvets, minibar
Prospect Berkshires
Prospect Berkshires
3.0 star property
9.4 out of 10, Exceptional, (12)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is ฿8,595
฿10,686 total
includes taxes & fees
9 Nov - 10 Nov
Prospect Berkshires
Exterior
Chatham Travel Lodge
Chatham Travel Lodge
2.5 star property
7.8 out of 10, Good, (208)
" Nice"
United States
Katherine
The price is ฿3,755
฿4,206 total
includes taxes & fees
1 Nov - 2 Nov
Chatham Travel Lodge
Terrace/patio
Locust Tree Bed and Breakfast LLC
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (409)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is ฿3,399
฿3,909 total
includes taxes & fees
2 Nov - 3 Nov
Locust Tree Bed and Breakfast LLC
Property amenity
Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, (584)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is ฿4,115
฿4,597 total
includes taxes & fees
23 Nov - 24 Nov
Courtyard by Marriott Lenox Berkshires
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Sheffield attractions

Ashley House

You can learn about the history of Sheffield when you stop by Ashley House. Discover the area's breweries or seek out the hiking trails.
See properties

Bartholomew's Cobble

You can take time to visit Bartholomew's Cobble during your travels to Sheffield. Make some time to visit the casinos while you're in the area.
See properties

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
FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA

Top Sheffield Hotel Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"Very clean and roomy lodge (2 bedrooms); conveniently located; has kitchen; recreational facilities a bit dated. Will come back again. "
Mona 3-night trip
Posted 3 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

More cheap stays in Sheffield

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
The price is ฿2,558 per night from 4 Nov to 5 Nov
฿2,558
฿2,857 total
4 Nov - 5 Nov
includes taxes & fees
7.4/10 Good! (815 reviews)

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: Features 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 32 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.

Explore a world of travel with Expedia