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Our top choices for Sheffield hotels

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Wilder House Berkshires

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (41 reviews)
"The place is lovely, room is cozy, and the bed is comfy"
United States
Mark
Wilder House Berkshires
Library
Blackberry River Inn

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (166 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is ₩238,891
₩274,725 total
includes taxes & fees
Jan 13 - Jan 14
Blackberry River Inn
Front of property
Gedney Farm

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (134 reviews)
"We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return."
United States
Lynda
The price is ₩269,619
₩295,773 total
includes taxes & fees
Jan 11 - Jan 12
Gedney Farm
Breakfast, lunch, dinner served; American cuisine
The Old Inn On The Green

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is ₩443,333
₩534,979 total
includes taxes & fees
Jan 11 - Jan 12
The Old Inn On The Green
Exterior
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 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is ₩152,623
₩175,516 total
includes taxes & fees
Jan 13 - Jan 14
Locust Tree Bed and Breakfast LLC
Free WiFi, bed sheets
Hitching Post Country Motel

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.6 out of 10, (81 reviews)
"Basic accommodation that was clean and easy."
United States
Elizabeth
The price is ₩188,962
₩217,306 total
includes taxes & fees
Jan 11 - Jan 12
Hitching Post Country Motel
Individually decorated, individually furnished, desk, laptop workspace
Pilgrim Inn

Pilgrim Inn

Pilgrim Inn
2.5 star property
Lee
5.8 out of 10, (332 reviews)
"Was horrible. Unsafe and scarey"
United States
Sharon
The price is ₩64,102
₩71,602 total
includes taxes & fees
Feb 3 - Feb 4
Pilgrim 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, (1,000 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is ₩119,618
₩133,613 total
includes taxes & fees
Feb 1 - Feb 2
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, (411 reviews)
"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 ₩130,820
₩146,125 total
includes taxes & fees
Jan 11 - Jan 12
Sunset Inn
Front of property
Chambery Inn

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (374 reviews)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
In-room dining
Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (653 reviews)
"The room was clean and the service adequate"
United States
David
The price is ₩103,347
₩115,439 total
includes taxes & fees
Jan 17 - Jan 18
Econo Lodge Lee - Great Barrington
Free daily continental breakfast
Cornwall Inn and Lodge

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (155 reviews)
"This inn was very quaint and welcoming. It was a nice inn for the value. "
United States
Jacqueline
The price is ₩307,571
₩353,707 total
includes taxes & fees
Jan 13 - Jan 14
Cornwall Inn and Lodge
Front of property - evening/night
Devonfield Inn B&B

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (134 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Miscellaneous
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, (1,003 reviews)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is ₩142,628
₩159,315 total
includes taxes & fees
Feb 1 - Feb 2
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Property amenity
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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (818 reviews)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is ₩154,440
₩200,927 total
includes taxes & fees
Jan 11 - Jan 12
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Porch
Lakehouse Inn

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is ₩209,311
₩245,491 total
includes taxes & fees
Jan 16 - Jan 17
Lakehouse Inn
Front of property
The Inn at Stockbridge

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is ₩347,108
₩407,110 total
includes taxes & fees
Jan 29 - Jan 30
The Inn at Stockbridge
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (73 reviews)
"Very clean and friendly staff that go above and beyond for their guests even in a snow storm! "
United States
Kira
The price is ₩178,133
₩198,975 total
includes taxes & fees
Feb 8 - Feb 9
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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, (661 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is ₩185,880
₩207,625 total
includes taxes & fees
Jan 23 - Jan 24
Hilton Garden Inn Lenox Pittsfield
In-room safe, desk, laptop workspace, iron/ironing board
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 reviews)
"Staff was very friendly and helpful."
United States
Pamela
The price is ₩114,830
₩128,261 total
includes taxes & fees
Jan 14 - Jan 15
Howard Johnson by Wyndham Lenox
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

Ashley House

You can learn about the history of Sheffield with a trip to Ashley House. Discover the area's breweries or seek out the hiking trails.
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Drury Preserve

You can take time to visit Drury Preserve during your travels to Sheffield. Make some time to visit the casinos while you're in the area.
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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
"Extraordinary"
Lee 2-night trip
Posted 3 days ago
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

More cheap stays in Sheffield

Quality Inn

Quality Inn

372 Main Street Great Barrington MA
The price is ₩109,961 per night from Jan 29 to Jan 30
₩109,961
₩122,827 total
Jan 29 - Jan 30
includes taxes & fees
8.4/10 Very Good! (1,006 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 The Yankee, Trademark Collection by Wyndham 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 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?
The Yankee, Trademark Collection by Wyndham: Provides a seasonal outdoor pool, an indoor pool, and buffet. Berkshire Mountain Lodge 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 33 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, Magnolia Bluffs Casino, and Drury Preserve. A couple of additional sights to add to your agenda are Ashley House and Mount Everett State Reservation. 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 66°F, while the coldest months are January and February with an average of 28°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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