Find hotels in Sheffield, MA from ฿2,015

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
14 Sep - 15 Sep
Tomorrow
15 Sep - 16 Sep
Next weekend
19 Sep - 21 Sep
In two weeks
26 Sep - 28 Sep

Filter by

Guest rating
Guest rating
Star rating

Top 10 Sheffield hotels and places to stay

Our top choices for Sheffield hotels

Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (403)
"Peaceful area and great staff; Thank you for the service and experience "
The price is ฿3,332
฿3,832 total
includes taxes & fees
15 Sept - 16 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, (547)
"Excellent location, friendly service, clean, comfortable room."
The price is ฿2,380
฿2,659 total
includes taxes & fees
15 Sept - 16 Sept
Travelodge by Wyndham Great Barrington Berkshires
Pleasant Valley Motel West Stockbridge
Exterior

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (1001)
"Very nice staff!!"
The price is ฿2,206
฿2,420 total
includes taxes & fees
19 Sept - 20 Sept
Pleasant Valley Motel West Stockbridge
Wilder House Berkshires
Wilder House Berkshires Room 3 | 1 bedroom, premium bedding, individually decorated

Wilder House Berkshires

2.0 star property
9.8 out of 10, Exceptional, (31)
"Beautiful and very comfortable house. Our hosts were always friendly and accessible, breakfast was delicious!"
The price is ฿6,598
฿7,370 total
includes taxes & fees
24 Sept - 25 Sept
Wilder House Berkshires
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (636)
"Nice staff, clean, and lots of apace in the rooms."
The price is ฿4,831
฿6,106 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (135)
"Vintage antique home. Close to road, but was quiet at night."
The price is ฿5,216
฿5,998 total
includes taxes & fees
15 Sept - 16 Sept
Blackberry River Inn
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, (749)
"A great mom & pop motel. Clean and friendly "
Monument Mountain Motel
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, (1003)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is ฿3,911
฿4,369 total
includes taxes & fees
21 Sept - 22 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (720)
"We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise "
The price is ฿4,019
฿4,490 total
includes taxes & fees
15 Sept - 16 Sept
Berkshires Untold
Element Lenox Berkshires
Exterior

Element Lenox Berkshires

3.0 star property
9.6 out of 10, Exceptional, (4)
"New hotel very nice"
The price is ฿5,363
฿5,991 total
includes taxes & fees
21 Sept - 22 Sept
Element Lenox Berkshires
Quality Inn
Lobby

Quality Inn

2.5 star property
8.4 out of 10, Very good, (1005)
"Great location and close enough to walk to shops and restaurants. "
The price is ฿2,940
฿3,284 total
includes taxes & fees
28 Sept - 29 Sept
Quality Inn
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (802)
"My stay was perfect. I can't wait to stay there again. "
The price is ฿2,507
฿2,800 total
includes taxes & fees
16 Sept - 17 Sept
Howard Johnson by Wyndham Lenox
The Brooks Motel
Double Room | Egyptian cotton sheets, premium bedding, memory-foam beds, desk

The Brooks Motel

2.0 star property
7.8 out of 10, Good, (100)
"Excelente "
The Brooks Motel
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lobby sitting area

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (38)
"Hotel was clean, the rooms had good space, the breakfast was excellent and the team there was very friendly and accommodating "
The price is ฿4,492
฿5,018 total
includes taxes & fees
16 Sept - 17 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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, (1001)
"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 ฿4,052
฿5,767 total
includes taxes & fees
16 Sept - 17 Sept
The Cornell Inn, Lenox & The Berkshires
East Rock Inn
Premium Apartment | Private kitchen | Electric kettle

East Rock Inn

2.0 star property
9.4 out of 10, Exceptional, (32)
"Room was really comfortable and clean. Beautiful views from the main court yard during the day and at night the sky was full of stars. Amazing. "
The price is ฿4,886
฿5,458 total
includes taxes & fees
28 Sept - 29 Sept
East Rock Inn
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cots/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (631)
"This property seemed improved over my last stay. It was clean and convenient for access to the local area amenities. I would stay there the next time I am in the area."
The price is ฿2,015
฿2,251 total
includes taxes & fees
29 Sept - 30 Sept
Econo Lodge Lee - Great Barrington
Becket Motel
Front of property

Becket Motel

2.5 star property
6.6 out of 10, (58)
"Comfortable stay "
The price is ฿3,332
฿4,786 total
includes taxes & fees
15 Sept - 16 Sept
Becket Motel
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

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

3.5 star property
9.0 out of 10, Wonderful, (724)
"Pleasant stay"
The price is ฿3,685
฿4,559 total
includes taxes & fees
16 Sept - 17 Sept
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Little Cat Lodge
Seasonal outdoor pool

Little Cat Lodge

2.0 star property
9.4 out of 10, Exceptional, (59)
"Nice rooms"
Little Cat Lodge
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

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
"Staff were friendly, helpful, informative. Offered restaurant suggestion for breakfast. Rooms were spacious and clean. "
Tammy 1-night trip
Posted 7 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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 ฿2,940 per night from 28 Sept to 29 Sept
฿2,940
฿3,284 total
28 Sept - 29 Sept
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)

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 Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG. 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: Provides free self parking, an indoor pool and complimentary wireless Internet access. Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG and The Red Lion Inn 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 34 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.