A lakeside town with autumn foliage, a bridge, and a rocky shoreline.

Find hotels in Sheffield, MA from ļæ„9,887

  • 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

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Filter by

Property class

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Sheffield hotels

Interior detail

1. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (72 reviews)
"Clean, cozy, and charming. The breakfast is delicious and all went smoothly."
United States
Liliana
The price is ļæ„25,853
ļæ„28,877 total
includes taxes & fees
Nov 1 - Nov 2
Wilder House Berkshires
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

2. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Downtown Great Barrington
8.6 out of 10, Excellent, (1,000 reviews)
"Our room was spotless and the staff was helpful and welcoming!"
United States
Lynne
The price is ļæ„11,952
ļæ„13,350 total
includes taxes & fees
Nov 22 - Nov 23
Quality Inn Great Barrington
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

3. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (819 reviews)
"Nice view and location for fall color."
United States
Md
The price is ļæ„22,695
ļæ„25,349 total
includes taxes & fees
Nov 3 - Nov 4
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

4. 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, (846 reviews)
"Always a pleasurable stay. The rooms are clean, the amenities are appreciated, and the staff very attentive. Great location and as a single traveler I always feel safe staying here."
United States
Cynthia
The price is ļæ„14,199
ļæ„15,860 total
includes taxes & fees
Nov 12 - Nov 13
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

5. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (933 reviews)
"Super clean and cozy and safe"
United States
Andrea
The price is ļæ„9,443
ļæ„10,547 total
includes taxes & fees
Nov 2 - Nov 3
Monument Mountain Motel
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

6. East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (58 reviews)
"East Rock was a nice, clean, and comfortable place to stay. Everything was great, and I enjoyed my stay."
United States
Sharon
The price is ļæ„20,161
ļæ„22,520 total
includes taxes & fees
Nov 29 - Nov 30
East Rock Inn
A house with a stone patio and wooden stools.

7. Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (150 reviews)
"Beyond amazing, we loved it so much!"
United States
Stacy
The price is ļæ„23,997
ļæ„26,877 total
includes taxes & fees
Nov 12 - Nov 13
Little Cat Lodge
A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

8. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.4 out of 10, Good, (626 reviews)
"Stay was great. Staff very friendly and helpful. 1 guest was screaming at someone at 4am but other than that it was a great stay"
United States
Sherry
The price is ļæ„12,464
ļæ„13,923 total
includes taxes & fees
Oct 31 - Nov 1
Travelodge by Wyndham Great Barrington Berkshires
A wooden boat on calm water with a house in the background.

9. Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
10.0 out of 10, Exceptional, (48 reviews)
"Great stay!"
United States
Conor
The price is ļæ„43,833
ļæ„54,248 total
includes taxes & fees
Nov 29 - Nov 30
Prospect Berkshires
A bedroom with a large bed, a chair, and a window with curtains.

10. The White Hart

The White Hart
4.0 star property
Salisbury
9.8 out of 10, Exceptional, (156 reviews)
"Itā€™s an exceptional place in every aspect. "
United States
William
The price is ļæ„47,047
ļæ„54,104 total
includes taxes & fees
Nov 29 - Nov 30
The White Hart
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

11. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (251 reviews)
"Great Breakfast Bed was okay Room very quaint hotel was very nice inside"
United States
Melanie
The price is ļæ„27,917
ļæ„32,104 total
includes taxes & fees
Nov 1 - Nov 2
Blackberry River Inn
A white two-story house with a front door, windows, and a chimney.

12. The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (95 reviews)
"Lovely property.unique historic buildings and rooms with updated amenities! Quiet and peaceful beautiful dinner!"
United States
mary ellen
The price is ļæ„45,753
ļæ„55,210 total
includes taxes & fees
Nov 2 - Nov 3
The Old Inn On The Green
A large house with a balcony and a grassy yard.

13. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (636 reviews)
"A fine place for a quick overnight trip to the Berkshires."
United States
David
The price is ļæ„13,245
ļæ„14,795 total
includes taxes & fees
Nov 2 - Nov 3
The Little Lion
A straw hat, sunglasses, and two drinks on a striped towel by a body of water.

14. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,005 reviews)
"Enjoyed staying in the old hotel and loved the large porch with the bar to relax on."
United States
Mallory
The price is ļæ„24,852
ļæ„35,597 total
includes taxes & fees
Nov 8 - Nov 9
The Red Lion Inn
A covered porch with white railings and rocking chairs.

15. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (453 reviews)
"Wonderful stay, and wonderful breakfast."
United States
Daniel
The price is ļæ„16,566
ļæ„19,051 total
includes taxes & fees
Nov 10 - Nov 11
Locust Tree Bed and Breakfast LLC
A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

16. the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (289 reviews)
"Super cute, fairly clean and such a lovely breakfast!"
United States
Luis
The price is ļæ„26,032
ļæ„29,156 total
includes taxes & fees
Nov 20 - Nov 21
the Alander
A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

17. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
South Lee
9.2 out of 10, Wonderful, (1,001 reviews)
"Nice place to stay"
United States
Michael
The price is ļæ„19,737
ļæ„25,130 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

18. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,007 reviews)
"Perfect for a travel stop-over."
United States
James
The price is ļæ„14,617
ļæ„16,327 total
includes taxes & fees
Nov 18 - Nov 19
Quality Inn Lee - Lenox South
A dining area with a round table and four chairs, a radiator, and a window with a view of greenery.

19. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (110 reviews)
"We loved everything about Granville House, especially the innkeepers! Wonderful atmosphere and excellent food! It was definitely the highlight of our trip to New England."
United States
Cynthia
The price is ļæ„40,231
ļæ„44,939 total
includes taxes & fees
Nov 11 - Nov 12
Granville House
A lodge with a large building and a dock by a lake, surrounded by forest.

20. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,000 reviews)
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best itā€™s pet friendly !"
United States
Gustavo
The price is ļæ„17,299
ļæ„19,323 total
includes taxes & fees
Nov 22 - Nov 23
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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

Built in 1735, the Ashley House is where Elizabeth Freeman successfully sued for her freedom, helping end slavery in Massachusetts. Tour the historic rooms and learn about this pivotal chapter in American history.
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
A lakeside town with autumn foliage, a bridge, and a rocky shoreline.

Top Sheffield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"Very charming, particularly the main house. We were at another structure off the main place which was perfectly nice but perhaps less charming."
Diane 1-night trip
Posted 14 hours ago
The Red Lion Inn

More cheap stays in Sheffield

Quality Inn Great Barrington

Quality Inn Great Barrington

372 Main Street Great Barrington MA
The price is ļæ„11,952 per night from Nov 22 to Nov 23
ļæ„11,952
ļæ„13,350 total
Nov 22 - Nov 23
includes taxes & fees
8.6/10 Excellent! (1,000 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 traveler data. This B&B offers free breakfast and free parking. Other good choices for your trip to the area are Berkshire Mountain Lodge and Quality Inn Great Barrington. See all available top hotels, or vacation rentals in Sheffield.
What are some of the best vacation home rentals that Sheffield has to offer?
Antique Farmhouse Totally Restored: This highly rated vacation home rental in Sheffield is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. See all vacation rentals in Sheffield.
If I need to cancel my hotel reservation in Sheffield, will I receive a refund?
Yes! The majority of hotel room reservations are refundable provided that you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your check-in date. If you booked a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Sheffield.
Where can I learn more about changing or cancelling my trip to Sheffield?
To access more information about changing or cancelling your trip to Sheffield, go to https://www.expedia.com/service/.
What's the best place to stay near Ashley House?
Sheffield 1802 House is one of the top choices for your stay based on our traveler data, and this 3.5-star B&B offers free breakfast and free parking. It's located 3.2 mi (5.1 km) from Ashley House. Another good option is Locust Tree Bed and Breakfast, located 3.8 mi (6.2 km) away.
What about the best place to stay near Magnolia Bluffs Casino?
One of the top choices for your stay is Sheffield 1802 House, located 1.6 mi (2.6 km) from Magnolia Bluffs Casino, and this 3.5-star B&B offers free breakfast and free parking.
What are some accommodations with pools in Sheffield?
Berkshire Mountain Lodge: Provides free self parking, an indoor pool, and complimentary wireless internet access. The Yankee Inn and The Red Lion Inn are a couple of other choices that offer an onsite pool. View all hotels with pools in Sheffield.
What is the best accommodation for staying close to Albany International Airport (ALB)?
Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.
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 accommodations to choose from. Find out more about Sheffield.
What should I see while I'm in Sheffield?
Favorite places to visit include Housatonic River, Suter Farm, and Ashley House. A couple of additional sights to add to your agenda are Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary. Check out what more to see and do in Expedia's Sheffield guide.
What's the weather like in Sheffield?
The hottest months are usually July and August with an average temp of 66Ā°F, while the coldest months are January and February with an average of 28Ā°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

Explore a world of travel with Expedia