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

Search Resort Hotels in Sheffield from CA $101

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1
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, (62 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is CA $256
CA $286 total
includes taxes & fees
Sep 13 - Sep 14
Wilder House Berkshires
Property grounds

2. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is CA $342
CA $716 total
includes taxes & fees
Sep 22 - Sep 23
Cheerful 3-bedroom cottage with woodstove
Lobby

3. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,001 reviews)
"We only stayed a night but the rooms were clean enough and the staff was extremely kind. Would stay here again."
United States
Sisile
The price is CA $143
CA $160 total
includes taxes & fees
Sep 8 - Sep 9
Quality Inn Great Barrington
Lobby lounge

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, (817 reviews)
"The room was very clean and the staff were really nice."
United States
BJORN
The price is CA $183
CA $204 total
includes taxes & fees
Sep 15 - Sep 16
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

5. 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, (809 reviews)
"No extra amenities…just an average hotel"
United States
Bruce
The price is CA $222
CA $248 total
includes taxes & fees
Sep 10 - Sep 11
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Front of property

6. Manor House Inn

Manor House Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (140 reviews)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
The price is CA $423
CA $470 total
includes taxes & fees
Sep 22 - Sep 23
Manor House Inn
Exterior

7. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (443 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 $145
CA $167 total
includes taxes & fees
Sep 7 - Sep 8
Locust Tree Bed and Breakfast LLC
Room, 2 Queen Beds, Non Smoking

8. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (906 reviews)
"This motel is simple but has everything that you need for an inexpensive stay near Great Barrington."
United States
Charlie
The price is CA $118
CA $132 total
includes taxes & fees
Sep 7 - Sep 8
Monument Mountain Motel
In-room safe, desk, cribs (free), rollaway beds (free)

9. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.4 out of 10, Good, (612 reviews)
"Adequate but tired hotel. Not exceptionally clean."
United States
Nancy
The price is CA $116
CA $130 total
includes taxes & fees
Sep 7 - Sep 8
Travelodge by Wyndham Great Barrington Berkshires
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area

10. East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (53 reviews)
"great place!"
United States
ERIK
The price is CA $226
CA $252 total
includes taxes & fees
Sep 28 - Sep 29
East Rock Inn
Restaurant

11. Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.8 out of 10, Exceptional, (131 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 $248
CA $278 total
includes taxes & fees
Sep 7 - Sep 8
Little Cat Lodge
Library

12. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (215 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
Sep 13 - Sep 14
Blackberry River Inn
Exterior

13. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (607 reviews)
"Great location. Functional and affordable. Pet friendly."
United States
Anne
The price is CA $153
CA $171 total
includes taxes & fees
Sep 7 - Sep 8
The Little Lion
Front of property

14. Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (142 reviews)
"Beautiful property, relaxing landscape."
United States
Jane
The price is CA $311
CA $341 total
includes taxes & fees
Sep 7 - Sep 8
Gedney Farm
Exterior

15. the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (264 reviews)
"Whenever I'm in Copake, I stay at the Alander!"
United States
Phil
The price is CA $176
CA $198 total
includes taxes & fees
Sep 7 - Sep 8
the Alander
Coffee/tea maker, fridge, microwave, oven

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.4 out of 10, Exceptional, (3 reviews)
"Great location, great property, great host"
United States
Shelly B.
The price is CA $156
CA $228 total
includes taxes & fees
Sep 12 - Sep 13
Cozy 1-bedroom studio in serene Great Barrington with AC
Lobby

17. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,012 reviews)
"Very nice stay"
United States
Christine
The price is CA $140
CA $156 total
includes taxes & fees
Sep 27 - Sep 28
Quality Inn Lee - Lenox South
In-room dining

18. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (693 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 $91
CA $101 total
includes taxes & fees
Sep 27 - Sep 28
Econo Lodge Lee - Great Barrington
Property grounds

19. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,011 reviews)
"this grand old hotel is warm and welcoming — a real hub of Bershires life and history"
United States
James
The price is CA $206
CA $299 total
includes taxes & fees
Sep 30 - Oct 1
The Red Lion Inn
Egyptian cotton sheets, premium bedding, memory foam beds, desk

20. The Brooks Motel

The Brooks Motel
2.0 star property
Hillsdale
7.4 out of 10, Good, (152 reviews)
"Great value. Excellent location. Responsive staff."
United States
Nelson
The price is CA $170
CA $190 total
includes taxes & fees
Sep 7 - Sep 8
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sheffield Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"Excellent staff and excellent Indian restaurant!!! Hotel a little dated, but beds were comfortable and staff was great!"
Susan 1-night trip
Posted 3 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Sheffield

Sheffield Resorts information

Number of reviews
6,935
Accommodation
4 Resorts
Lowest Price
CA $101
Highest Price
CA $716

Frequently asked questions

What can I expect from a resort vacation in Sheffield?
Longing for a relaxing getaway? Indulge in all the comforts of a resort, where you can find everything you need for your stay from convenient food and drink options to activities and shopping. Browse the resort options in the area and discover the right one for you, whether you envision yourself sipping drinks by a sprawling pool or hitting the golf course for an afternoon game.
What's a top resort in Sheffield?
Our highest-rated resorts around Sheffield: Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA - 12.1 mi (19.5 km) from Sheffield. Has a fitness center. Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA - 12.1 mi (19.5 km) from Sheffield. Access to a fitness center.
What can I do in Sheffield?
Housatonic River, Three Mile Pond Wildlife Management Area, and Ashley House are a few of the interesting sights to visit. Mount Everett State Reservation and Thom Reed UFO Monument Park are a few additional attractions in the area that you might like.
What's the weather like in Sheffield?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to and around Sheffield?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 22 mi (35.4 km) from the city center. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 22.3 mi (35.9 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

Explore a world of travel with Expedia