Find hotels in Sheffield, MA from 2.197.993 ₫

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

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Sheffield hotels

Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished
Wilder House Berkshires

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (38)
Escape to Sheffield's serene countryside in this inviting B&B. Enjoy complimentary WiFi, parking, and a delicious cooked-to-order weekend breakfast. Nearby attractions include the unique UFO Monument Park and peaceful Lime Kiln Farm Wildlife Sanctuary.
"Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you! "
United States
Allison
The price is 4.261.734 ₫
4.760.356 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Wilder House Berkshires
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1002)
Immerse yourself in mountain vistas at this Lenox hotel, where peaceful accommodation include refrigerators and microwaves. Unwind in the hot tub, swim in the indoor or seasonal outdoor pool, and enjoy complimentary breakfast before exploring nearby attractions.
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is 1.967.764 ₫
2.197.993 ₫ total
includes taxes & fees
24 Dec - 25 Dec
The Yankee, Trademark Collection by Wyndham
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (437)
Tucked in West Stockbridge, this charming B&B offers complimentary morning meals and convenient self parking. Outdoor enthusiasts can explore nearby hiking trails, kayaking spots, and mountain biking routes. Ebenezer II Gifts and Hotchkiss Mobile Studio await just minutes away.
"Nice place, easy check in"
United States
Robert
The price is 2.867.463 ₫
3.145.607 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Shaker Mill Inn
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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, (707)
Experience comfort in Great Barrington at this welcoming hotel with clean rooms and attentive service. Visit nearby Lake Mansfield Park or explore the Housatonic River after enjoying the indoor pool, fitness centre, and complimentary WiFi.
"Great hospitality "
United States
regina maria
The price is 2.814.849 ₫
3.144.186 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (1000)
Enjoy panoramic lake vistas at this peaceful Lenox hotel, just 10 minutes from Tanglewood Music Centre. After working out in the 24-hour fitness centre, savour Indian cuisine at Mint restaurant while watching spectacular sunsets over the water.
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is 2.638.592 ₫
2.947.307 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
Located minutes from Tanglewood Music Centre, this Lenox hotel offers an indoor pool, bar, and free parking. Grab coffee at the café before exploring nearby Kennedy Park. Business travellers will appreciate the free WiFi and convenient amenities.
"New hotel very nice"
United States
joel
The price is 3.446.217 ₫
3.849.424 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Element Lenox Berkshires
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (805)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
Lobby
Quality Inn Great Barrington

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1002)
Set in a serene location near Housatonic River Walk, this hotel offers free breakfast, WiFi, and parking. Enjoy the fitness centre or explore nearby trails for hiking and skiing. Guests praise the helpful staff and quiet atmosphere in this convenient Great Barrington retreat.
"Clean room, nice location "
United States
Devron
The price is 1.990.125 ₫
2.222.970 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn Great Barrington
Exterior
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1002)
Surrounded by the beauty of West Stockbridge, this welcoming motel offers clean, comfortable rooms with complimentary WiFi and parking. Just 15 minutes from Tanglewood Music Centre and near local attractions like Hoffman's Pottery.
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is 1.396.902 ₫
1.532.401 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Pleasant Valley Motel West Stockbridge
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
This centrally located motel has an inviting outdoor pool where you can cool off after exploring nearby attractions. Free WiFi and self parking add extra value while the helpful staff ensures a pleasant stay in clean, comfortable rooms.
"Staff was very friendly and helpful."
United States
Pamela
The price is 2.078.253 ₫
2.321.330 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Howard Johnson by Wyndham Lenox
In-room safe, desk, free cots/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (562)
"The staff were very friendly and accommodating "
United States
Tom
The price is 1.973.025 ₫
2.204.000 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Travelodge by Wyndham Great Barrington Berkshires
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (788)
Set in Pittsfield near Guido's Marketplace and Herman Melville's Arrowhead, this lodge offers an indoor pool and hot tub for relaxation. Enjoy free WiFi and parking while staying in clean rooms. The helpful staff ensures a pleasant mountain getaway.
"This place is so peaceful and the staff is always helpful "
United States
Leona
The price is 2.596.107 ₫
3.487.549 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
Berkshire Mountain Lodge
Terrace/patio
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413)
Set in serene East Canaan, this welcoming B&B offers complimentary full breakfast daily and free self parking. Nearby Land of Nod Vineyard and Beckley Furnace Industrial Park provide local exploration opportunities. Guests consistently praise the helpful staff.
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is 2.762.235 ₫
3.176.570 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Locust Tree Bed and Breakfast LLC
Exterior
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1001)
Explore the Berkshires from this welcoming hotel with free breakfast and parking. Just a 10-minute drive to Tanglewood Music Centre, the indoor pool offers year-round relaxation. Nearby attractions include Guido's Marketplace and Bousquet Ski Area.
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is 2.714.882 ₫
3.032.523 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn & Suites Berkshires-Lenox
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (657)
Explore Berkshire County from this Pittsfield hotel featuring an indoor pool and fitness centre. Enjoy meals at Jae's Asian Fusion restaurant and bar, plus in-room refrigerators and microwaves. Nearby attractions include Herman Melville's Arrowhead and Guido's Marketplace.
"Clean and convenient to Mt. Greylock. Kind staff. "
United States
Kristen
The price is 2.714.882 ₫
3.032.522 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Lenox Pittsfield
Egyptian cotton sheets, premium bedding, down duvets, minibar
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
Discover a tranquil Great Barrington escape with an outdoor pool and rejuvenating sauna. Enjoy dinner at The Cliff House featuring local cuisine, then unwind at the bar. Near Catamount Aerial Adventure Park with free WiFi and parking for easy exploration.
"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 5.577.084 ₫
7.111.045 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Prospect Berkshires
Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"The room was very clean. The bed, linens & towels were exceptional. All of the staff were wonderful. "
United States
Joyce
The price is 3.946.050 ₫
5.583.134 ₫ total
includes taxes & fees
14 Jan - 15 Jan 2026
The Red Lion Inn
Lobby
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1002)
Experience tranquility at this welcoming hotel, just 15 minutes from Tanglewood Music Centre. Guests praise the quiet atmosphere, helpful staff, and complimentary continental breakfast. Conveniently located near Lee Library and local restaurants with easy access to shopping.
"Room was clean and comfortable; location was good with a breakfast restaurant next door. The in-house breakfast was OK, but we preferred an upgrade. Receptionist staff member was professional and pleasant. "
United States
Patrick
The price is 2.330.011 ₫
2.602.623 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn Lee - Lenox South
Seasonal outdoor pool
Sunset Inn

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (410)
Discover this charming motel in Lee with free WiFi and parking. The helpful staff ensures a welcoming stay while the seasonal outdoor pool provides refreshment. Nearby attractions include Lee Library and Tanglewood Music Centre, with hiking trails waiting for exploration.
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is 2.367.630 ₫
2.644.643 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Sunset Inn
Interior
Berkshires Untold

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (816)
This Lenox lodge combines comfort with convenience, just a short drive from Tanglewood Music Centre. The Club Room serves delicious American cuisine, while a welcoming bar and outdoor terrace enhance your stay. Kennedy Park and Pleasant Valley Wilderness Sanctuary await nearby.
"Easiest check in and out. Great food in dining room. "
United States
William
The price is 2.884.484 ₫
3.221.968 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Berkshires Untold
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

Bartholomews Cobble

Explore the great outdoors at Bartholomews Cobble, a lovely green space in 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 Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

10/10 Excellent
"Comfortable, quiet, clean, great breakfast "
Elizabeth 3-night trip
Posted 7 days ago
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Prospect Berkshires

Prospect Berkshires

10/10 Excellent
"Wow, just wow! My high school friend and I met up at Prospect Berkshires for a girls weekend. We had an incredible time relaxing by using all the amenities. The staff are so helpful and profession. "
Kate 2-night trip
Posted 2 weeks ago
Prospect Berkshires

More cheap stays in Sheffield

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA
The price is 1.967.764 ₫ per night from 24 Dec to 25 Dec
1.967.764 ₫
2.197.993 ₫ total
24 Dec - 25 Dec
includes taxes & fees
9/10 Wonderful! (1,002 reviews)

Hotels in Sheffield with star rating

Frequently asked questions

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