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

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Check prices for these dates

Next weekend
Nov 6 - Nov 8
In two weeks
Nov 13 - Nov 15
In one month
Nov 27 - Nov 29
In two months
Dec 25 - Dec 27
No exact matches found, but these alternatives could be just right

Recommended hotels in Sheffield

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 CA $229
CA $256 total
includes taxes & fees
Nov 1 - Nov 2
Wilder House Berkshires
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

2. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is CA $248
CA $602 total
includes taxes & fees
Nov 2 - Nov 3
Cheerful 3-bedroom cottage with woodstove
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

3. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Downtown Great Barrington
8.6 out of 10, Excellent, (1,001 reviews)
"Our room was spotless and the staff was helpful and welcoming!"
United States
Lynne
The price is CA $106
CA $119 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.

4. 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 CA $201
CA $225 total
includes taxes & fees
Nov 3 - Nov 4
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

5. 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, (847 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 CA $126
CA $141 total
includes taxes & fees
Nov 12 - Nov 13
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 CA $173
CA $194 total
includes taxes & fees
Nov 28 - Nov 29
East Rock Inn
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

7. 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 CA $84
CA $94 total
includes taxes & fees
Nov 1 - Nov 2
Monument Mountain Motel
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

8. 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 CA $213
CA $238 total
includes taxes & fees
Nov 2 - Nov 3
Little Cat Lodge
A dining area with round tables set for two, a fireplace, and a mural on the wall.

9. 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 CA $406
CA $490 total
includes taxes & fees
Nov 1 - Nov 2
The Old Inn On The Green
A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.

10. 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 CA $397
CA $490 total
includes taxes & fees
Nov 17 - Nov 18
Prospect Berkshires
A bedroom with a large bed, a chair, and a window with curtains.

11. The White Hart

The White Hart
4.0 star property
Salisbury
9.8 out of 10, Exceptional, (156 reviews)
"It’s an exceptional place in every aspect. "
United States
William
The price is CA $417
CA $480 total
includes taxes & fees
Nov 23 - Nov 24
The White Hart
A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

12. 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 CA $111
CA $123 total
includes taxes & fees
Oct 30 - Oct 31
Travelodge by Wyndham Great Barrington Berkshires
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

13. 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 CA $243
CA $279 total
includes taxes & fees
Nov 15 - Nov 16
Blackberry River Inn
A large house with a balcony and a grassy yard.

14. 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 CA $117
CA $131 total
includes taxes & fees
Nov 1 - Nov 2
The Little Lion
A dining table with pastries, a coffee pot, and a vase of sunflowers.

15. 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 CA $357
CA $399 total
includes taxes & fees
Nov 1 - Nov 2
Granville House
A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

16. 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 CA $147
CA $169 total
includes taxes & fees
Oct 30 - Oct 31
Locust Tree Bed and Breakfast LLC
A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

17. 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 CA $231
CA $259 total
includes taxes & fees
Nov 20 - Nov 21
the Alander
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

18. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,000 reviews)
"Enjoyed staying in the old hotel and loved the large porch with the bar to relax on."
United States
Mallory
The price is CA $220
CA $316 total
includes taxes & fees
Nov 8 - Nov 9
The Red Lion Inn
A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

19. 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 CA $175
CA $223 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A modern bedroom with a large bed, two bedside tables, and a textured wall behind the bed.

20. The Brooks Motel

The Brooks Motel
2.0 star property
Hillsdale
7.4 out of 10, Good, (156 reviews)
"Great value. Excellent location. Responsive staff."
United States
Nelson
The price is CA $204
CA $228 total
includes taxes & fees
Oct 30 - Oct 31
The Brooks Motel
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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Top Sheffield Hotel Reviews

The Whitlock

The Whitlock

10/10 Excellent
"My son and I stayed one night at The Whitlock Inn. We booked a living area which gave my teen his privacy and extra space mine as well. It’s centrally located in the cute town of Lenox. We dined in town at a wonderful restaurant down from our Inn. The Inn had a bon fire lit to enjoy. We would stay again. Great for families or traveling with your partner.."
Maryeliza 1-night trip
Posted 2 hours ago
The Whitlock

Find out more about Sheffield

Sheffield Townhomes information

Number of reviews
5,331
Accommodation
0 Townhomes
Lowest Price
CA $94
Highest Price
CA $602

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