A covered wooden structure with a sloped roof, surrounded by greenery and trees.

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Jul 31 - Aug 2
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Aug 7 - Aug 9

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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, (59 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is ļæ„28,723
ļæ„32,084 total
includes taxes & fees
Aug 10 - Aug 11
Wilder House Berkshires
Lobby

2. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,002 reviews)
"Comfortable rooms within walking distance to Great Barrington."
United States
Lynn
The price is ļæ„21,636
ļæ„24,167 total
includes taxes & fees
Aug 2 - Aug 3
Quality Inn Great Barrington
Exterior

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, (798 reviews)
"Extremely friendly and helpful staff upon arrival. Provide great insights on local restaurant opportunities, and included a five star breakfast. Highly recommend!"
United States
Lisa
The price is ļæ„31,870
ļæ„35,599 total
includes taxes & fees
Aug 24 - Aug 25
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Exterior

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, (796 reviews)
"very responsive staff excellent check in and check out"
United States
Kathleen
The price is ļæ„22,939
ļæ„25,623 total
includes taxes & fees
Aug 23 - Aug 24
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

5. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (435 reviews)
"Below average B&B"
United States
Larry
The price is ļæ„17,192
ļæ„19,771 total
includes taxes & fees
Jul 31 - Aug 1
Locust Tree Bed and Breakfast LLC
Restaurant

6. Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (110 reviews)
"Absolutely loved our stay. The staff were warm and welcoming, the lodge is so cute & well put together, & the restaurant is delicious. We will definitely be back!"
United States
Jolie
The price is ļæ„36,103
ļæ„40,435 total
includes taxes & fees
Aug 19 - Aug 20
Little Cat Lodge
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, cribs (free), rollaway beds (surcharge), WiFi (free)

7. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (888 reviews)
"I was pleasantly surprised how clean,spacious,quiet and comfortable the room was ( two queens) Loved the place."
United States
Yekaterina
The price is ļæ„18,199
ļæ„20,329 total
includes taxes & fees
Aug 17 - Aug 18
Monument Mountain Motel
In-room safe, desk, cribs (free), rollaway beds (free)

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, (599 reviews)
"They had some kind of family party going on. The whole family would gather by the pool and have their meals, full tables with trays of food. My daughter was not able to use the pool and that was the main reason for us staying there. Otherwise fine. Oh the smoke alarm went off once too"
United States
Kerri
The price is ļæ„16,209
ļæ„18,106 total
includes taxes & fees
Aug 2 - Aug 3
Travelodge by Wyndham Great Barrington Berkshires
Library

9. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (199 reviews)
"Excellent breakfast, very nice staff."
United States
Leslie
The price is ļæ„31,109
ļæ„35,775 total
includes taxes & fees
Aug 2 - Aug 3
Blackberry River Inn
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

10. East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (51 reviews)
"Virtual check in. I prefer real staff."
United States
Eleanor
The price is ļæ„24,702
ļæ„27,592 total
includes taxes & fees
Aug 26 - Aug 27
East Rock Inn
Exterior

11. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (594 reviews)
"This place was a gem. Itā€™s small and surrounded by nature but close to restaurants, shopping, wildlife viewing areas, and historical sites. I loved that pets are free. The grounds were nice with a picnic bench and a large fire pit. If Iā€™m in the area again, I would definitely stay here."
United States
Linda
The price is ļæ„20,630
ļæ„23,044 total
includes taxes & fees
Aug 23 - Aug 24
The Little Lion
Exterior

12. the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (251 reviews)
"Very charming and well maintained"
United States
Jerry
The price is ļæ„27,834
ļæ„31,174 total
includes taxes & fees
Aug 20 - Aug 21
the Alander
Front of property

13. Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (140 reviews)
"Beautiful property, relaxing landscape."
United States
Jane
The price is ļæ„38,990
ļæ„42,772 total
includes taxes & fees
Aug 5 - Aug 6
Gedney Farm
John Harney Suite | Minibar, desk, iron/ironing board, WiFi (free)

14. The White Hart

The White Hart
4.0 star property
Salisbury
9.8 out of 10, Exceptional, (151 reviews)
"Itā€™s an exceptional place in every aspect. "
United States
William
The price is ļæ„56,217
ļæ„64,649 total
includes taxes & fees
Aug 10 - Aug 11
The White Hart
Porch

15. Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (305 reviews)
"Great staff and location!"
United States
Stacie
The price is ļæ„44,059
ļæ„50,668 total
includes taxes & fees
Aug 23 - Aug 24
Interlaken Inn & Resort
Exterior

16. The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.0 out of 10, Wonderful, (15 reviews)
"Friendly staff and attention to detail making our stay in a charming inn special"
United States
Kristen
The price is ļæ„47,072
ļæ„52,579 total
includes taxes & fees
Aug 5 - Aug 6
The Berkshire Mountain Inn
Lobby

17. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,010 reviews)
"great location very clean friendly staff"
United States
Jeanne
The price is ļæ„21,987
ļæ„24,559 total
includes taxes & fees
Aug 26 - Aug 27
Quality Inn Lee - Lenox South
In-room dining

18. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (679 reviews)
"Good location to towns in area"
United States
William
The price is ļæ„12,967
ļæ„14,484 total
includes taxes & fees
Aug 4 - Aug 5
Econo Lodge Lee - Great Barrington
Property grounds

19. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,011 reviews)
"Fantastic pool to top off the great location and fun historic hotel!"
United States
Antoinette G.
The price is ļæ„28,730
ļæ„39,407 total
includes taxes & fees
Aug 24 - Aug 25
The Red Lion Inn
Children's activities

20. Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"Very comfortable. Will stay there again"
United States
Peter
The price is ļæ„11,346
ļæ„12,446 total
includes taxes & fees
Aug 9 - Aug 10
Pleasant Valley Motel West Stockbridge
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

Magnolia Bluffs Casino

Why not roll the dice with a visit to Magnolia Bluffs Casino during your travels in Sheffield? Discover the area's breweries or seek out the hiking trails.
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 covered wooden structure with a sloped roof, surrounded by greenery and trees.

Top Sheffield Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"The hotel staffs were very friendly and super kind!!!"
Shigeyo 1-night trip
Posted 1 hour ago
Quality Inn Great Barrington

More cheap stays in Sheffield

Quality Inn Great Barrington

Quality Inn Great Barrington

372 Main Street Great Barrington MA
The price is ļæ„21,636 per night from Aug 2 to Aug 3
ļæ„21,636
ļæ„24,167 total
Aug 2 - Aug 3
includes taxes & fees
8.6/10 Excellent! (1,002 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 The Yankee Inn. See all available top hotels, or vacation rentals in Sheffield.
What are some of the best vacation home rentals that Sheffield has to offer?
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental outside of Sheffield is located near skiing 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. You can relax into your vacation with a garden and a selection of games. 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: Offers 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 28 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 Magnolia Bluffs Casino, Housatonic River, and Suter Farm. 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.

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