Sheffield Condominium Resorts to Rent

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Recommended hotels in Sheffield

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
$182 nightly
The price is $203
Nov 10 - Nov 11
Total with taxes and fees
Wilder House Berkshires

2. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$366 nightly
The price is $409
Nov 18 - Nov 19
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove

3. 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
$76 nightly
The price is $85
Nov 29 - Nov 30
Total with taxes and fees
Quality Inn Great Barrington

4. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (939 reviews)
"Super clean and cozy and safe"
United States
Andrea
$67 nightly
The price is $74
Nov 8 - Nov 9
Total with taxes and fees
Monument Mountain Motel

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, (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."
United States
Cynthia
$90 nightly
The price is $101
Nov 30 - Dec 1
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG

6. 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
$79 nightly
The price is $88
Nov 6 - Nov 7
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires

7. 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, (820 reviews)
"Nice view and location for fall color."
United States
Md
$161 nightly
The price is $179
Nov 10 - Nov 11
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

8. 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
$116 nightly
The price is $129
Dec 6 - Dec 7
Total with taxes and fees
East Rock Inn

9. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (454 reviews)
"Wonderful stay, and wonderful breakfast."
United States
Daniel
$105 nightly
The price is $121
Nov 10 - Nov 11
Total with taxes and fees
Locust Tree Bed and Breakfast LLC

10. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (637 reviews)
"A fine place for a quick overnight trip to the Berkshires."
United States
David
$86 nightly
The price is $96
Nov 8 - Nov 9
Total with taxes and fees
The Little Lion

11. Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (155 reviews)
"Beyond amazing, we loved it so much!"
United States
Stacy
$147 nightly
The price is $165
Dec 6 - Dec 7
Total with taxes and fees
Little Cat Lodge

12. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great 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"
United States
Deborah S.
$96 nightly
The price is $107
Nov 12 - Nov 13
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC

13. the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (291 reviews)
"Super cute, fairly clean and such a lovely breakfast!"
United States
Luis
$165 nightly
The price is $185
Nov 20 - Nov 21
Total with taxes and fees
the Alander

14. 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
$173 nightly
The price is $199
Dec 3 - Dec 4
Total with taxes and fees
Blackberry River Inn

15. Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
10.0 out of 10, Exceptional, (51 reviews)
"Great experience!"
United States
Sunny
$295 nightly
The price is $330
Nov 30 - Dec 1
Total with taxes and fees
Prospect Berkshires

16. The Cozy Cat Motel

The Cozy Cat Motel
Copake Falls
$135 nightly
The price is $151
Nov 8 - Nov 9
Total with taxes and fees
The Cozy Cat Motel

17. The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (96 reviews)
"Lovely property.unique historic buildings and rooms with updated amenities! Quiet and peaceful beautiful dinner!"
United States
mary ellen
$319 nightly
The price is $350
Nov 6 - Nov 7
Total with taxes and fees
The Old Inn On The Green

18. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (713 reviews)
"It was super clean and safe"
United States
Fernando
$56 nightly
The price is $63
Dec 1 - Dec 2
Total with taxes and fees
Econo Lodge Lee - Great Barrington

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
$255 nightly
The price is $285
Nov 18 - Nov 19
Total with taxes and fees
Granville House

20. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,007 reviews)
"Enjoyed staying in the old hotel and loved the large porch with the bar to relax on."
United States
Mallory
$195 nightly
The price is $218
Nov 12 - Nov 13
Total with taxes and fees
The Red Lion Inn
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.

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

Top reviews in Sheffield

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