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

Best Resorts in Sheffield

Check prices for these dates

Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27
In one month
Oct 9 - Oct 11
In two months
Nov 6 - Nov 8
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, (64 reviews)
"Perfect little b&b."
United States
Mark
$191 nightly
The price is $213
Sep 15 - Sep 16
Total with taxes and fees
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.
$365 nightly
The price is $408
Sep 28 - Sep 29
Total with taxes and fees
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, (1,004 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
$104 nightly
The price is $116
Sep 14 - Sep 15
Total with taxes and fees
Quality Inn Great Barrington
Exterior

4. 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
$105 nightly
The price is $121
Sep 13 - Sep 14
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
Lobby lounge

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, (822 reviews)
"The room was very clean and the staff were really nice."
United States
BJORN
$134 nightly
The price is $150
Sep 20 - Sep 21
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Room, 2 Queen Beds, Non Smoking

6. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (911 reviews)
"very nice and comfortable"
United States
Analisia
$95 nightly
The price is $106
Sep 13 - Sep 14
Total with taxes and fees
Monument Mountain Motel
Room

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, (615 reviews)
"Front desk was very pleasant. Room was awful!"
United States
Kevin
$75 nightly
The price is $84
Sep 13 - Sep 14
Total with taxes and fees
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, (809 reviews)
"No extra amenities…just an average hotel"
United States
Bruce
$186 nightly
The price is $208
Sep 17 - Sep 18
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area

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
$155 nightly
The price is $173
Sep 13 - Sep 14
Total with taxes and fees
East Rock Inn
Restaurant

10. Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.8 out of 10, Exceptional, (137 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 13 - Sep 14
Total with taxes and fees
Little Cat Lodge
Exterior

11. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (609 reviews)
"Great location. Functional and affordable. Pet friendly."
United States
Anne
$111 nightly
The price is $124
Sep 16 - Sep 17
Total with taxes and fees
The Little Lion
Library

12. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (219 reviews)
"The Inn is lovely and charming - and the breakfast was especially great."
United States
Rachel
$140 nightly
The price is $161
Oct 13 - Oct 14
Total with taxes and fees
Blackberry River Inn
Exterior

13. the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (266 reviews)
"Whenever I'm in Copake, I stay at the Alander!"
United States
Phil
$145 nightly
The price is $162
Sep 14 - Sep 15
Total with taxes and fees
the Alander
In-room dining

14. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (696 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
Sep 20 - Sep 21
Total with taxes and fees
Econo Lodge Lee - Great Barrington
Property grounds

15. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,000 reviews)
"this grand old hotel is warm and welcoming — a real hub of Bershires life and history"
United States
James
$212 nightly
The price is $237
Sep 23 - Sep 24
Total with taxes and fees
The Red Lion Inn
Lobby

16. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,001 reviews)
"Very nice stay"
United States
Christine
$107 nightly
The price is $120
Sep 27 - Sep 28
Total with taxes and fees
Quality Inn Lee - Lenox South
Front of property

17. 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
$267 nightly
The price is $292
Oct 12 - Oct 13
Total with taxes and fees
Gedney Farm
Private kitchen

18. 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.
$148 nightly
The price is $165
Sep 27 - Sep 28
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
Room

19. 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
$148 nightly
The price is $165
Sep 20 - Sep 21
Total with taxes and fees
The Brooks Motel
Room

20. 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 13 - Sep 14
Total with taxes and fees
Granville House
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

10/10 Excellent
"excellent hotel… Excellent staff… Great price. Highly recommended."
Carrie 2-night trip
Posted less than an hour ago
Berkshires Untold

Find out more about Sheffield

Sheffield Resorts information

Number of reviews
5,946
Accommodation
4 Resorts
Lowest Price
$77
Highest Price
$408

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.

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