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Cheap Sheffield Hotels
Wilder House Berkshires
48 S Main Street Sheffield MA
$162 nightly
The price is $181 total per night
$181 total
Dec 16 - Dec 17
Total with taxes and fees
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
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
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
$79 nightly
The price is $88 total per night
$88 total
Dec 24 - Dec 25
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
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$108 nightly
The price is $120 total per night
$120 total
Jan 13 - Jan 14, 2026
Total with taxes and fees
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
The Red Lion Inn
30 Main Street Stockbridge MA
$190 nightly
The price is $212 total per night
$212 total
Jan 14 - Jan 15, 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
Berkshires Untold
194 Pittsfield Rd Lenox MA
$114 nightly
The price is $127 total per night
$127 total
Dec 16 - Dec 17
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
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street South Lee MA
$138 nightly
The price is $154 total per night
$154 total
Dec 17 - Dec 18
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
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
Hampton Inn & Suites Berkshires-Lenox
445 Pittsfield Rd Lenox MA
$108 nightly
The price is $121 total per night
$121 total
Jan 4 - Jan 5, 2026
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
Quality Inn
372 Main Street Great Barrington MA
$76 nightly
The price is $85 total per night
$85 total
Dec 28 - Dec 29
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
5.7 mi from city center
With a stay at Quality Inn Great Barrington in Great Barrington, you'll be near ski lifts, just a 4-minute walk from Mahaiwe Performing Arts Center and 8 minutes by foot from Housatonic River.
Breakfast included
Parking included
Holiday Inn Express Hotel & Suites Great Barrington by IHG
415 Stockbridge Rd Great Barrington MA
$107 nightly
The price is $120 total per night
$120 total
Dec 18 - Dec 19
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
The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St Lee MA
$100 nightly
The price is $112 total per night
$112 total
Jan 5 - Jan 6, 2026
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
Courtyard by Marriott Lenox Berkshires
70 Pittsfield Rd Lenox MA
$135 nightly
The price is $151 total per night
$151 total
Dec 18 - Dec 19
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
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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Sheffield hotels essential information
Accommodation | 1,266 hotels |
|---|---|
Lowest Price | $85 |
Highest Price | $212 |
Popular hotels | Wilder House Berkshires, Antique Farmhouse Totally Restored , The Yankee, Trademark Collection by Wyndham, Berkshire Mountain Lodge, The Red Lion Inn, Berkshires Untold, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Hampton Inn & Suites Berkshires-Lenox, Quality Inn, Holiday Inn Express Hotel & Suites Great Barrington by IHG, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Courtyard by Marriott Lenox Berkshires |
Most Recent Sheffield Hotel Reviews
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
5 out of 5
Posted 4 days ago
CheapTickets Verified Review
"The rooms were clean and very spacious. The staff went on and above to make our stay a great memory. "
A verified traveler stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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