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Recommended hotels in Sheffield
1. Wilder House Berkshires
Wilder House BerkshiresSheffield
9.8 out of 10, Exceptional, (72 reviews)
"Clean, cozy, and charming. The breakfast is delicious and all went smoothly."
Liliana
The price is CA $229
CA $256 total
includes taxes & fees
Nov 10 - Nov 11
2. Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstoveSheffield
10.0 out of 10, Exceptional, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
Kelly R.
The price is CA $248
CA $572 total
includes taxes & fees
Nov 19 - Nov 20
3. Quality Inn Great Barrington
Quality Inn Great BarringtonDowntown Great Barrington
8.6 out of 10, Excellent, (1,000 reviews)
"Our room was spotless and the staff was helpful and welcoming!"
Lynne
The price is CA $106
CA $118 total
includes taxes & fees
Nov 29 - Nov 30
4. Monument Mountain Motel
Monument Mountain MotelGreat Barrington
9.0 out of 10, Wonderful, (939 reviews)
"Super clean and cozy and safe"
Andrea
The price is CA $84
CA $93 total
includes taxes & fees
Nov 8 - Nov 9
5. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
8.8 out of 10, Excellent, (854 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."
Cynthia
The price is CA $116
CA $130 total
includes taxes & fees
Dec 3 - Dec 4
6. Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington BerkshiresGreat 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"
Sherry
The price is CA $110
CA $123 total
includes taxes & fees
Nov 6 - Nov 7
7. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
9.4 out of 10, Exceptional, (820 reviews)
"Nice view and location for fall color."
Md
The price is CA $224
CA $251 total
includes taxes & fees
Nov 10 - Nov 11
8. East Rock Inn
East Rock InnGreat 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."
Sharon
The price is CA $172
CA $192 total
includes taxes & fees
Dec 6 - Dec 7
9. Locust Tree Bed and Breakfast LLC
Locust Tree Bed and Breakfast LLCEast Canaan
8.8 out of 10, Excellent, (454 reviews)
"Wonderful stay, and wonderful breakfast."
Daniel
The price is CA $147
CA $169 total
includes taxes & fees
Nov 6 - Nov 7
10. The Little Lion
The Little LionGreat Barrington
8.6 out of 10, Excellent, (637 reviews)
"A fine place for a quick overnight trip to the Berkshires."
David
The price is CA $116
CA $129 total
includes taxes & fees
Nov 9 - Nov 10
11. Little Cat Lodge
Little Cat LodgeCopake Falls
9.6 out of 10, Exceptional, (155 reviews)
"Beyond amazing, we loved it so much!"
Stacy
The price is CA $200
CA $224 total
includes taxes & fees
Dec 6 - Dec 7
12. Cozy 1-bedroom studio in serene Great Barrington with AC
Cozy 1-bedroom studio in serene Great Barrington with ACGreat Barrington
8.8 out of 10, Excellent, (10 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
Deborah S.
The price is CA $107
CA $149 total
includes taxes & fees
Nov 12 - Nov 13
13. the Alander
the AlanderCopake
9.0 out of 10, Wonderful, (291 reviews)
"Super cute, fairly clean and such a lovely breakfast!"
Luis
The price is CA $231
CA $258 total
includes taxes & fees
Nov 20 - Nov 21
14. Blackberry River Inn
Blackberry River InnNorfolk
9.4 out of 10, Exceptional, (251 reviews)
"Great Breakfast Bed was okay Room very quaint hotel was very nice inside"
Melanie
The price is CA $247
CA $284 total
includes taxes & fees
Nov 11 - Nov 12
15. Prospect Berkshires
Prospect BerkshiresEgremont
10.0 out of 10, Exceptional, (51 reviews)
"Great experience!"
Sunny
The price is CA $334
CA $420 total
includes taxes & fees
Nov 30 - Dec 1
16. The Cozy Cat Motel
The Cozy Cat MotelCopake Falls
The price is CA $208
CA $233 total
includes taxes & fees
Nov 8 - Nov 9
17. The Old Inn On The Green
The Old Inn On The GreenGreat Barrington
9.2 out of 10, Wonderful, (96 reviews)
"Lovely property.unique historic buildings and rooms with updated amenities! Quiet and peaceful beautiful dinner!"
mary ellen
The price is CA $405
CA $489 total
includes taxes & fees
Nov 6 - Nov 7
18. Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great BarringtonLee
6.4 out of 10, (713 reviews)
"It was super clean and safe"
Fernando
The price is CA $78
CA $88 total
includes taxes & fees
Dec 2 - Dec 3
19. Granville House
Granville HouseHousatonic
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."
Cynthia
The price is CA $356
CA $398 total
includes taxes & fees
Nov 19 - Nov 20
20. The Red Lion Inn
The Red Lion InnStockbridge
8.8 out of 10, Excellent, (1,006 reviews)
"Enjoyed staying in the old hotel and loved the large porch with the bar to relax on."
Mallory
The price is CA $220
CA $315 total
includes taxes & fees
Nov 12 - Nov 13
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.
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.
Top reviews in Sheffield
Monument Mountain Motel
Monument Mountain MotelGreat Barrington
10/10 Excellent
Perfect motel for an overnight stay.
The room and bathroom were fresh and clean.
The man and woman staff were friendly and polite.
Paul
