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

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10
No exact matches found, but these alternatives could be just right

Recommended hotels in Sheffield

Exterior

1. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (66 reviews)
"Perfect little b&b."
United States
Mark
The price is CA $270
CA $301 total
includes taxes & fees
Sep 27 - Sep 28
Wilder House Berkshires
Exterior

2. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (44 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is CA $261
CA $619 total
includes taxes & fees
Oct 12 - Oct 13
Cheerful 3-bedroom cottage with woodstove
Exterior

3. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,001 reviews)
"It was perfect for our weekend away, clean, comfortable bed and a decent breakfast, definitely worth the value:)"
United States
Kimberly
The price is CA $142
CA $158 total
includes taxes & fees
Oct 18 - Oct 19
Quality Inn Great Barrington
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, (825 reviews)
"The location is very convenient. We have been going and staying at this hotel for the past 6 years every time we come to the Berkshire area."
United States
Maria Dulce
The price is CA $173
CA $194 total
includes taxes & fees
Oct 19 - Oct 20
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

5. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (912 reviews)
"very nice and comfortable"
United States
Analisia
The price is CA $108
CA $120 total
includes taxes & fees
Sep 20 - Sep 21
Monument Mountain Motel
Exterior

6. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (445 reviews)
"The whole vibe of the B&B was so simple and perfect. 10/10 will stay again."
United States
Nicholas
The price is CA $147
CA $169 total
includes taxes & fees
Sep 26 - Sep 27
Locust Tree Bed and Breakfast LLC
Exterior

7. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.4 out of 10, Good, (616 reviews)
"Front desk was very pleasant. Room was awful!"
United States
Kevin
The price is CA $105
CA $117 total
includes taxes & fees
Sep 20 - Sep 21
Travelodge by Wyndham Great Barrington Berkshires
Exterior

8. 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, (811 reviews)
"No extra amenities…just an average hotel"
United States
Bruce
The price is CA $272
CA $304 total
includes taxes & fees
Sep 22 - Sep 23
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Exterior

9. East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (54 reviews)
"great place!"
United States
ERIK
The price is CA $198
CA $221 total
includes taxes & fees
Oct 1 - Oct 2
East Rock Inn
Restaurant

10. Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.8 out of 10, Exceptional, (140 reviews)
"The staff did ann excellent job communicating before we got there, while we were there, and even after we checked out. Good room, easily accessible, and beautiful area."
United States
Kees
The price is CA $251
CA $281 total
includes taxes & fees
Sep 21 - Sep 22
Little Cat Lodge
Front of property

11. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (612 reviews)
"Great location. Functional and affordable. Pet friendly."
United States
Anne
The price is CA $145
CA $162 total
includes taxes & fees
Oct 18 - Oct 19
The Little Lion
Exterior

12. the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (269 reviews)
"Whenever I'm in Copake, I stay at the Alander!"
United States
Phil
The price is CA $202
CA $226 total
includes taxes & fees
Oct 12 - Oct 13
the Alander
Front of property

13. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (220 reviews)
"The Inn is lovely and charming - and the breakfast was especially great."
United States
Rachel
The price is CA $193
CA $222 total
includes taxes & fees
Oct 19 - Oct 20
Blackberry River Inn
Front of property - evening/night

14. Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (143 reviews)
"Beautiful location with a fantastic chef and meal options. Lee the bartender was great, too!"
United States
Terri
The price is CA $321
CA $352 total
includes taxes & fees
Sep 20 - Sep 21
Gedney Farm
Exterior

15. The Brooks Motel

The Brooks Motel
2.0 star property
Hillsdale
7.2 out of 10, Good, (154 reviews)
"Great value. Excellent location. Responsive staff."
United States
Nelson
The price is CA $188
CA $210 total
includes taxes & fees
Sep 21 - Sep 22
The Brooks Motel
Terrace/patio

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.6 out of 10, Exceptional, (4 reviews)
"Great location, great property, great host"
United States
Shelly B.
The price is CA $157
CA $230 total
includes taxes & fees
Oct 6 - Oct 7
Cozy 1-bedroom studio in serene Great Barrington with AC
Front of property

17. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (106 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
United States
Nicole
The price is CA $313
CA $350 total
includes taxes & fees
Sep 27 - Sep 28
Granville House
Desk, iron/ironing board, cribs (free), rollaway beds (surcharge)

18. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (698 reviews)
"Have stayed here several times and it is a basic, decent place. It is in a great location, relatively clean and comfortable. Would return again."
United States
Anna
The price is CA $97
CA $108 total
includes taxes & fees
Sep 27 - Sep 28
Econo Lodge Lee - Great Barrington
Exterior

19. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,001 reviews)
"Very nice stay"
United States
Christine
The price is CA $153
CA $171 total
includes taxes & fees
Oct 19 - Oct 20
Quality Inn Lee - Lenox South
Property grounds

20. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,001 reviews)
"this grand old hotel is warm and welcoming — a real hub of Bershires life and history"
United States
James
The price is CA $220
CA $315 total
includes taxes & fees
Sep 28 - Sep 29
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.
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Top Sheffield Hotel Reviews

Berkshires Untold

Berkshires Untold

8/10 Good
"Very well-designed "budget" (for the Berkshires) motel, but at almost $400/night, I'd expect a cleaner room at least. There was dog hair all over the shower floor, long human hair in the fridge?!, and I had to use a tissue to dust cobwebs off the TV and table lamps. Amenities were just ok - I was surprised that the TV had no streaming service, just very limited cable channels that kept cutting out to fuzz. No coffee in the room, just in the shared lobby and very minimal (no decaf option either days, no hot water for tea out on day 2). We had some apps at the bar before dinner that were basically inedible. Overall, I'd say a 3.5 star experience. The convenience of the location just outside of town and the great interior design are doing a lot of the heavy lifting here. Seems best suited for couples that need a pet-friendly crash pad for outdoor adventures and not much more."
Demelza 1-night trip
Posted less than an hour ago
Berkshires Untold

Find out more about Sheffield

Sheffield Cottages information

Number of reviews
5,452
Accommodation
110 Cottages
Lowest Price
CA $108
Highest Price
CA $619

Frequently asked questions

How much do cottages in Sheffield cost?
Cottages in Sheffield range between CA $108 and CA $619 per night. These stays offer a chance to touch base with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Sheffield?
There are 110 cottages in Sheffield. No matter if you're taking a trip with the kids or planning a getaway with your besties, Expedia can help you find the ideal space to get back to nature.
Why book your cottage in Sheffield with Expedia?
We think a getaway should be a walk in the park, so if you're in search of cottages in Sheffield at a nice price, Expedia has your back. Save money and check in to an economical option far from the downtown buzz, or book a 5-star cottage to pamper your loved ones.
How can I find cheap cottages in Sheffield?
With Expedia's handy filter tool, booking cheap cottages in Sheffield has never been simpler. To find accommodations that are very pocket friendly, tailor your search results by budget, amenities and star rating.
What is there to do in Sheffield near my cottage?
After you've checked in to your hotel, get out and discover the incredible things Sheffield has for you to experience. Magnolia Bluffs Casino is a great attraction to add to your itinerary.

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