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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17
No exact matches found, but these alternatives could be just right

Recommended hotels in Sheffield

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
$195 nightly
The price is $218
Sep 27 - Sep 28
Total with taxes and fees
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.
$393 nightly
The price is $439
Oct 12 - Oct 13
Total with taxes and fees
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
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
$101 nightly
The price is $113
Oct 18 - Oct 19
Total with taxes and fees
Quality Inn Great Barrington
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

4. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (915 reviews)
"Great place. Staff, property , parking, location"
United States
Victor
$76 nightly
The price is $85
Oct 25 - Oct 26
Total with taxes and fees
Monument Mountain Motel
A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

5. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (448 reviews)
"The whole vibe of the B&B was so simple and perfect. 10/10 will stay again."
United States
Nicholas
$105 nightly
The price is $121
Sep 27 - Sep 28
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
A modern hotel lobby with seating areas, tables, and a reception desk.

6. 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, (827 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
$129 nightly
The price is $144
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

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
$75 nightly
The price is $84
Sep 27 - Sep 28
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

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
$169 nightly
The price is $189
Sep 29 - Sep 30
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

9. East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (55 reviews)
"great place!"
United States
ERIK
$145 nightly
The price is $162
Oct 25 - Oct 26
Total with taxes and fees
East Rock Inn
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

10. Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.8 out of 10, Exceptional, (142 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
$199 nightly
The price is $223
Sep 27 - Sep 28
Total with taxes and fees
Little Cat Lodge
A large house with a balcony and a grassy yard.

11. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (613 reviews)
"Great location. Functional and affordable. Pet friendly."
United States
Anne
$115 nightly
The price is $128
Oct 18 - Oct 19
Total with taxes and fees
The Little Lion
A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

12. the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (271 reviews)
"Great on-site restaurant and bar. Fire pit and Adirondack chairs."
United States
Thomas
$145 nightly
The price is $162
Sep 28 - Sep 29
Total with taxes and fees
the Alander
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, (222 reviews)
"Great breakfast"
United States
Brian
$140 nightly
The price is $161
Oct 25 - Oct 26
Total with taxes and fees
Blackberry River Inn
A modern bedroom with a large bed, two bedside tables, and a textured wall behind the bed.

14. 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
$143 nightly
The price is $160
Oct 7 - Oct 8
Total with taxes and fees
The Brooks Motel
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

15. 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, (5 reviews)
$148 nightly
The price is $165
Oct 1 - Oct 2
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
A round wooden table with two wine glasses and a green bottle, set against a window with a view of a blue railing and trees.

16. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (699 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
$69 nightly
The price is $77
Oct 1 - Oct 2
Total with taxes and fees
Econo Lodge Lee - Great Barrington
A rustic wooden building labeled 'GEDNEY FARM' with a signboard indicating 'SERVING DINNER WED-FRI 5:00-9:00pm'.

17. 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
$270 nightly
The price is $296
Oct 1 - Oct 2
Total with taxes and fees
Gedney Farm
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

18. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,005 reviews)
"Great location for a trip to Tanglewood! Clean room, decent bedding, free breakfast, workout room, close to good restaurants. Would stay again"
United States
Wendy
$110 nightly
The price is $122
Oct 19 - Oct 20
Total with taxes and fees
Quality Inn Lee - Lenox South
A dining table with pastries, a coffee pot, and a vase of sunflowers.

19. 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
$224 nightly
The price is $250
Sep 27 - Sep 28
Total with taxes and fees
Granville House
A group of people performing yoga in an outdoor setting with grass and trees.

20. Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"The best aspect of this motel is the price. It is very close to the Tanglewood concert space and in West Stockbridge, a quaint town with galleries, a good bookstore, the excellent Turnpark Outdoor Sculpture Garden and "Amici" a nice Italian restaurant, etc."
United States
James
$69 nightly
The price is $76
Sep 27 - Sep 28
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
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 Yankee Inn

The Yankee Inn

10/10 Excellent
"Everything, delicious free breakfast, hot showers, plenty of room, outdoor patio w Adirondack chairs, pleasant staff, very clean place. Fabulous price! I would not hesitate to return to this place."
Joyce 2-night trip
Posted 15 hours ago
The Yankee Inn

Find out more about Sheffield

Sheffield Condo Rentals information

Number of reviews
5,438
Accommodation
4 Condo Rentals
Lowest Price
$76
Highest Price
$439

Frequently asked questions

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How can I find cheap condos in Sheffield?
With Expedia's helpful filter tool, comparing cheap condos in Sheffield is a breeze. To discover properties that'll make your hip pocket happy, narrow down your search by amenities, budget and star rating.
What is there to do in Sheffield near my condo?
After you've unpacked your bags, venture out and explore the awesome things Sheffield has for you to experience. Magnolia Bluffs Casino is a great attraction to add to your must-do list.

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