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Check prices for these dates

Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan
In one month
6 Feb - 8 Feb
In two months
6 Mar - 8 Mar
No exact matches found, but these alternatives could be just right

Recommended hotels in Sheffield

Interior detail
Wilder House Berkshires

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (41)
"The place is lovely, room is cozy, and the bed is comfy"
United States
Mark
Wilder House Berkshires
Interior
Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (9)
"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 AED 1,443
AED 2,548 total
includes taxes & fees
11 Jan - 12 Jan
Guesthouse Cabin vacation rentals in Berkshire County
Lobby lounge
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (15)
"The room we stayed in was extremely clean and comfy. The whole hotel was very nice and had an awesome breakfast. Will be staying here again for sure. "
United States
Keith
The price is AED 511
AED 570 total
includes taxes & fees
19 Jan - 20 Jan
Element Lenox Berkshires
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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, (716)
"Nice warm pool and hot tub. Good little fitness center. "
United States
Fawn
The price is AED 360
AED 402 total
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (440)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is AED 392
AED 430 total
includes taxes & fees
13 Jan - 14 Jan
Shaker Mill Inn
Lobby
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1000)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is AED 302
AED 337 total
includes taxes & fees
1 Feb - 2 Feb
Quality Inn Lee - Lenox South
In-room safe, desk, laptop workspace, iron/ironing board
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
The price is AED 290
AED 324 total
includes taxes & fees
9 Jan - 10 Jan
Howard Johnson by Wyndham Lenox
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is AED 372
AED 415 total
includes taxes & fees
15 Jan - 16 Jan
The Yankee, Trademark Collection by Wyndham
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1002)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is AED 359
AED 401 total
includes taxes & fees
28 Jan - 29 Jan
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (814)
"Room was very well designed and clean. The woman who worked at the desk was wonderful!"
United States
Cynthia
Monument Mountain Motel
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (566)
"Excellent location!!"
United States
Abdul Samad
The price is AED 275
AED 308 total
includes taxes & fees
11 Jan - 12 Jan
Travelodge by Wyndham Great Barrington Berkshires
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (660)
" Nice staff - beautiful hotel!"
United States
MARY
The price is AED 470
AED 525 total
includes taxes & fees
23 Jan - 24 Jan
Hilton Garden Inn Lenox Pittsfield
Exterior
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (18)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is AED 779
AED 993 total
includes taxes & fees
26 Jan - 27 Jan
Prospect Berkshires
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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, (73)
"Very clean and friendly staff that go above and beyond for their guests even in a snow storm! "
United States
Kira
The price is AED 450
AED 503 total
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Exterior
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is AED 386
AED 444 total
includes taxes & fees
11 Jan - 12 Jan
Locust Tree Bed and Breakfast LLC
Lobby
Quality Inn Great Barrington

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1001)
"My go to place for my ski weekends"
United States
Ryan
The price is AED 278
AED 310 total
includes taxes & fees
21 Jan - 22 Jan
Quality Inn Great Barrington
Exterior
the Alander

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (194)
"Nice room and reasonable prices! Will recommend."
United States
Jianyang
The price is AED 514
AED 576 total
includes taxes & fees
9 Jan - 10 Jan
the Alander
Lobby lounge
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Very comfortable beds! "
United States
Gerald
The price is AED 408
AED 456 total
includes taxes & fees
25 Jan - 26 Jan
Hampton Inn & Suites Berkshires-Lenox
Exterior
The Little Lion

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (548)
"Perfect for pets "
United States
Maria
The price is AED 404
AED 451 total
includes taxes & fees
11 Jan - 12 Jan
The Little Lion
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (818)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is AED 344
AED 456 total
includes taxes & fees
11 Jan - 12 Jan
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

10/10 Excellent
"Extraordinary"
Lee 2-night trip
Posted 2 days ago
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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. Has a sauna, a fitness center, and a terrace.
What can I do in Sheffield?
Housatonic River, Magnolia Bluffs Casino, and Drury Preserve are a few of the interesting sights to visit. Ashley House and Mount Everett State Reservation 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.