Find hotels in Sheffield, MA from ฿2,266

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Our top choices for Sheffield hotels

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (45 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is ฿5,181
฿5,787 total
includes taxes & fees
26 Apr - 27 Apr
Wilder House Berkshires

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1,001 reviews)
"Very friendly staff and conviently located"
United States
Dawn
The price is ฿2,416
฿2,699 total
includes taxes & fees
29 Apr - 30 Apr
Quality Inn Great Barrington

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is ฿2,289
฿2,511 total
includes taxes & fees
26 Apr - 27 Apr
Pleasant Valley Motel West Stockbridge

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (416 reviews)
"Clean, good breakfast, friendly staff"
United States
Debra
The price is ฿3,380
฿3,888 total
includes taxes & fees
28 Apr - 29 Apr
Locust Tree Bed and Breakfast LLC

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (851 reviews)
"Staff was super nice! Everything was clean and neat. "
United States
Elizabeth
The price is ฿2,543
฿2,841 total
includes taxes & fees
26 Apr - 27 Apr
Howard Johnson by Wyndham Lenox

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (576 reviews)
"Clean"
United States
Brian
The price is ฿2,415
฿2,697 total
includes taxes & fees
26 Apr - 27 Apr
Travelodge by Wyndham Great Barrington Berkshires

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is ฿3,216
฿3,593 total
includes taxes & fees
26 Apr - 27 Apr
The Yankee Inn

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (912 reviews)
"Such a cool and affordable place to stay in the Berkshires. Great lobby/bar with a good restaurant."
United States
Kathy
The price is ฿2,758
฿3,081 total
includes taxes & fees
28 Apr - 29 Apr
Berkshires Untold

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (844 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is ฿2,028
฿2,266 total
includes taxes & fees
29 Apr - 30 Apr
Monument Mountain Motel

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (758 reviews)
"Nice clean room, clean and well maintained breakfast was tasteful each day. Desk Clerk very helpful in giving out direction, Breaksfast person, very friendly. Hotel is centrally located, shop and restaurant nearby"
United States
Berdest
The price is ฿3,574
฿3,992 total
includes taxes & fees
4 May - 5 May
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (915 reviews)
"Spacious, clean, and the pool was warm and perfect for family swimming "
United States
Danielle
The price is ฿2,672
฿3,710 total
includes taxes & fees
30 Apr - 1 May
Berkshire Mountain Lodge

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,001 reviews)
"Great location "
United States
Edith
The price is ฿3,313
฿3,700 total
includes taxes & fees
19 May - 20 May
Quality Inn Lee - Lenox South

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is ฿5,719
฿6,389 total
includes taxes & fees
3 May - 4 May
Element Lenox Berkshires

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (447 reviews)
"Everything was great— the cleanliness, the plentiful breakfast, the character and coziness, and the proximity to Amici across the street (free dessert with your room key)."
United States
Patrick
The price is ฿3,509
฿3,850 total
includes taxes & fees
27 Apr - 28 Apr
Shaker Mill Inn

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,000 reviews)
"Beautiful place- beautiful views "
United States
Yanis
The price is ฿3,683
฿4,114 total
includes taxes & fees
3 May - 4 May
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (556 reviews)
"A nice safe and quiet place to stay. Park right in front of your door. My dog loved the large grass area. The room was large and the beds very comfortable. The heat was on when we arrived which was great . It was cold and snowy that day. I loved having the self check-in and check out. We plan on going back the next time we are in the area. "
United States
SUSAN
The price is ฿3,541
฿3,956 total
includes taxes & fees
27 Apr - 28 Apr
The Little Lion

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Good location and great breakfast."
United States
Linda
The price is ฿4,132
฿4,616 total
includes taxes & fees
10 May - 11 May
Hampton Inn & Suites Berkshires-Lenox

Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (218 reviews)
"Very clean. Updated "
United States
jennifer
The price is ฿3,734
฿4,182 total
includes taxes & fees
30 Apr - 1 May
Chatham Travel Lodge

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (173 reviews)
"Charming, quiet, clean very clean with a beautiful dining room for breakfast and very respectful service."
United States
Mara
The price is ฿5,013
฿5,765 total
includes taxes & fees
28 Apr - 29 Apr
Blackberry River Inn

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (91 reviews)
"Clean rooms, friendly staff, pool was very clean and so is the hot tub. Breakfast was okay. Overall our stay was excellent. Highly recommended."
United States
Camille
The price is ฿4,185
฿4,675 total
includes taxes & fees
25 May - 26 May
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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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Stay near popular Sheffield attractions

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.

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

Top Sheffield Hotel Reviews

More cheap stays in Sheffield

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 Berkshires Untold and Berkshire Mountain Lodge. 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 Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG 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 Three Mile Pond Wildlife Management Area. A couple of additional sights to add to your itinerary are Mount Everett State Reservation and Thom Reed UFO Monument Park. 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.

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