Search Resort Hotels in Sheffield from CA $105

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Check prices for these dates

Next weekend
May 29 - May 31
In two weeks
Jun 5 - Jun 7
In one month
Jun 19 - Jun 21
In two months
Jul 17 - Jul 19
No exact matches found, but these alternatives could be just right

Recommended hotels in Sheffield

Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (49 reviews)
"Very comfortable bed, that was mostly what I cared about. I got my beauty sleep)"
United States
Maria
The price is CA $226
CA $252 total
includes taxes & fees
May 20 - May 21
Wilder House Berkshires
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is CA $550
CA $965 total
includes taxes & fees
May 27 - May 28
Guesthouse Cabin vacation rentals in Berkshire County
Fridge, microwave, oven, stovetop

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 $326
CA $694 total
includes taxes & fees
May 25 - May 26
Cheerful 3-bedroom cottage with woodstove
Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is CA $146
CA $164 total
includes taxes & fees
May 26 - May 27
The Yankee Inn
Room, 2 Queen Beds, Non Smoking

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (855 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is CA $94
CA $105 total
includes taxes & fees
May 26 - May 27
Monument Mountain Motel
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (417 reviews)
"Clean, good breakfast, friendly staff"
United States
Debra
The price is CA $144
CA $166 total
includes taxes & fees
May 28 - May 29
Locust Tree Bed and Breakfast LLC
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (938 reviews)
"Clean and great job staffing "
United States
Pedro
The price is CA $121
CA $165 total
includes taxes & fees
May 24 - May 25
Berkshire Mountain Lodge
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,010 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
The price is CA $116
CA $130 total
includes taxes & fees
May 25 - May 26
Quality Inn Great Barrington
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (96 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
The price is CA $174
CA $195 total
includes taxes & fees
May 28 - May 29
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lobby sitting area

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.0 out of 10, Very good, (2 reviews)
"After a little snafu with check-in (we had completed the form in advance and never received the room number text), we were able to get checked in with the virtual front desk. The inn was clean and well appointed and centrally located. The common areas felt inviting and useful for both the adults and kids. We would stay again."
United States
Samantha
The price is CA $152
CA $170 total
includes taxes & fees
May 20 - May 21
Hideaway Inn Lenox
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (950 reviews)
"Great stay!"
United States
Aditya
The price is CA $172
CA $192 total
includes taxes & fees
May 25 - May 26
Berkshires Untold
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (853 reviews)
The price is CA $109
CA $121 total
includes taxes & fees
May 25 - May 26
Howard Johnson by Wyndham Lenox
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (180 reviews)
"Great staff. "
United States
wesley
The price is CA $193
CA $221 total
includes taxes & fees
Jun 2 - Jun 3
Blackberry River Inn
Exterior

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.8 out of 10, Exceptional, (6 reviews)
"The new owners have done a great job. The place is immaculate, the room was very comfortable and well appointed, the common areas charming. Highly recommended."
United States
Robert
The price is CA $340
CA $379 total
includes taxes & fees
Jun 1 - Jun 2
The Berkshire Mountain Inn
In-room safe, desk, free cribs/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (579 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
The price is CA $103
CA $115 total
includes taxes & fees
May 28 - May 29
Travelodge by Wyndham Great Barrington Berkshires
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (455 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is CA $164
CA $179 total
includes taxes & fees
May 27 - May 28
Shaker Mill Inn
Lobby lounge

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is CA $230
CA $256 total
includes taxes & fees
May 25 - May 26
Element by Marriott Lenox Berkshires
Lobby

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)
"Great location "
United States
Edith
The price is CA $155
CA $173 total
includes taxes & fees
Jun 14 - Jun 15
Quality Inn Lee - Lenox South
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (561 reviews)
"Avoid this place."
United States
Carole
The price is CA $131
CA $146 total
includes taxes & fees
Jun 11 - Jun 12
The Little Lion
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is CA $200
CA $517 total
includes taxes & fees
May 20 - May 21
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Very nice staff. Clean and comfortable rooms."
SHANNON 1-night trip
Posted 1 hour ago
Quality Inn Great Barrington

Find out more about Sheffield

Sheffield Resorts information

Number of reviews
8,090
Accommodation
7 Resorts
Lowest Price
CA $105
Highest Price
CA $965

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 resort near Sheffield: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 12.2 mi (19.6 km) from Sheffield. Enjoy the sauna, fitness center, and terrace.
What can I do in Sheffield?
Housatonic River, Magnolia Bluffs Casino, and Thom Reed UFO Monument Park are a few of the interesting sights to visit. Lime Kiln Farm Wildlife Sanctuary and Three Mile Pond Wildlife Management Area 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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