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Cheap Sheffield Hotels

Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street Sheffield MA
$162 nightly
The price is $181 total per night
$181 total
Dec 9 - Dec 10
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
0.31 mi from city center
With a stay at Wilder House Berkshires in Sheffield, you'll be within a 5-minute drive of Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary.
Breakfast included
Parking included
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Sheffield MA
4.75 mi from city center
Located in Sheffield, this vacation home is in a rural location, within a 5-minute drive of Mount Riga State Park and Mount Everett State Reservation.
Hot Tub
Kitchen
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$108 nightly
The price is $120 total per night
$120 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
21.4 mi from city center
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's Marketplace.
Pool
Hot Tub
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
$114 nightly
The price is $127 total per night
$127 total
Dec 7 - Dec 8
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
19.52 mi from city center
Located in Lenox, Berkshires Untold is within a 10-minute drive of Shakespeare and Company and The Mount.
Pet friendly
Parking included
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
$169 nightly
The price is $189 total per night
$189 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
12.1 mi from city center
With a stay at The Red Lion Inn in Stockbridge, you'll be in the historical district, within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Pool
Spa
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 out of 5
190 Meadow Street South Lee MA
$124 nightly
The price is $139 total per night
$139 total
Dec 8 - Dec 9
Total with taxes and fees
Free Cancellation
12.07 mi from city center
With a stay at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG in South Lee, you'll be near ski lifts, within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Pool
Air conditioning
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
$89 nightly
The price is $100 total per night
$100 total
Dec 11 - Dec 12
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
20.75 mi from city center
Located in Lenox, The Yankee, Trademark Collection by Wyndham is a 4-minute drive from Bousquet Ski Area and 8 minutes from The Mount.
Pool
Hot Tub
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St Lee MA
$101 nightly
The price is $113 total per night
$113 total
Dec 14 - Dec 15
Total with taxes and fees
Free Cancellation
15.4 mi from city center
With a stay at The Black Swan Lee - Lenox, an Ascend Collection Hotel in Lee, you'll be on the waterfront, within a 10-minute drive of Tanglewood Music Center and Berkshire Mountain Country Store.
Breakfast included
Pet friendly
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd Lenox MA
$103 nightly
The price is $115 total per night
$115 total
Dec 14 - Dec 15
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
20.59 mi from city center
Located in Lenox, Hampton Inn & Suites Berkshires-Lenox is in a rural location, within a 5-minute drive of Guido's Marketplace and Kennedy Park.
Pool
Breakfast included
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd Great Barrington MA
$107 nightly
The price is $120 total per night
$120 total
Dec 7 - Dec 8
Total with taxes and fees
Free Cancellation
7.14 mi from city center
With a stay at Holiday Inn Express Hotel & Suites Great Barrington by IHG in Great Barrington, you'll be on a river, just steps from Housatonic River and a 3-minute drive from Monument Mountain Reservation.
Pool
Breakfast included
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3 out of 5
70 Pittsfield Rd Lenox MA
$135 nightly
The price is $151 total per night
$151 total
Dec 14 - Dec 15
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
18.95 mi from city center
Located in Lenox, Courtyard by Marriott Lenox Berkshires is a 1-minute drive from Kennedy Park and 6 minutes from The Mount.
Pool
Parking included
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
$91 nightly
The price is $102 total per night
$102 total
Dec 14 - Dec 15
Total with taxes and fees
Free Cancellation
21.07 mi from city center
With a stay at Holiday Inn Express & Suites Pittsfield - Berkshires by IHG in Pittsfield, you'll be within a 10-minute drive of Tanglewood Music Center and Guido's Marketplace.
Pool
Hot Tub
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Sheffield hotels essential information

Accommodation
1,264 hotels
Lowest Price
$100
Highest Price
$189
Popular hotels
Wilder House Berkshires, Antique Farmhouse Totally Restored , Berkshire Mountain Lodge, Berkshires Untold, The Red Lion Inn, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Yankee, Trademark Collection by Wyndham, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Hampton Inn & Suites Berkshires-Lenox, Holiday Inn Express Hotel & Suites Great Barrington by IHG, Courtyard by Marriott Lenox Berkshires, Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Most Recent Sheffield Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

5 out of 5
Posted 20 hours ago
CheapTickets Verified Review
"I am a cross country traveling nurse. The Berkshire Mountain Lodge was perfect for my needs. A fully functioning well appointed kitchen. Spacious living quarters with excellent views. The best water pressure on a shower that I have ever known. Fantastic after a long day of work or out hiking the many nature trails here. And the bed was so perfectly firm and cozy that I drifted effortlessly to sleep. The grounds, the amenities and the coordinated activities to bring you together in community made me feel included. Definitely a place I will continue to return to for many years."
A verified traveler from tampa stayed at Berkshire Mountain Lodge
Berkshire Mountain Lodge