Book Cheap Hotels in Sheffield
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Most frequently booked Sheffield hotels

Wilder House Berkshires
48 S Main Street, Sheffield, MA
Free cancellation
Reserve now, pay when you stay
0.5 km from city centre
The price is CA $203 per night
CA $203
CA $227 total
Oct 27 - Oct 28
includes taxes & fees
Stay at this B&B in Sheffield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary are located nearby.
Breakfast included
Parking included

Guesthouse Cabin vacation rentals in Berkshire County
7.53 km from city centre
The price is CA $576 per night
CA $576
CA $1,004 total
Oct 26 - Oct 27
includes taxes & fees
Stay at this cabin in Sheffield. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Mount Everett State Reservation and Plaintain Pond are located nearby.
Kitchen
Pet-friendly

Antique Farmhouse Totally Restored
7.66 km from city centre
Book a stay at this family-friendly vacation home in Sheffield. Enjoy free WiFi, a water park, and a fitness center. Popular attractions Mount Riga State Park and Taconic Chapel Park are located nearby.
Hot tub
Kitchen

Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Free cancellation
Reserve now, pay when you stay
34.46 km from city centre
The price is CA $131 per night
CA $131
CA $178 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.

Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
31.44 km from city centre
The price is CA $123 per night
CA $123
CA $137 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.

The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St, Lee, MA
Free cancellation
Reserve now, pay when you stay
24.8 km from city centre
The price is CA $149 per night
CA $149
CA $167 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Tanglewood Music Center and Berkshire Mountain Country Store are located nearby.
Breakfast included
Pet-friendly

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Free cancellation
Reserve now, pay when you stay
19.43 km from city centre
The price is CA $163 per night
CA $163
CA $202 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.

The Red Lion Inn
30 Main Street, Stockbridge, MA
Free cancellation
Reserve now, pay when you stay
19.48 km from city centre
The price is CA $186 per night
CA $186
CA $271 total
Nov 16 - Nov 17
includes taxes & fees
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Tanglewood Music Center and Schantz Galleries are located nearby.

Quality Inn
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Free cancellation
Reserve now, pay when you stay
9.19 km from city centre
The price is CA $118 per night
CA $118
CA $132 total
Nov 2 - Nov 3
includes taxes & fees
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mahaiwe Performing Arts Center and Housatonic River Walk are located nearby.
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.
Top hotels in Sheffield for Extended Stay

Suite 4 - Quiet and private accommodations in a country setting.
Spencertown
10/10 Exceptional! (2 reviews)
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.
Sheffield hotels essential information
Accommodation | 1,256 hotels |
---|---|
Lowest Price | CA $132 |
Highest Price | CA $1,004 |
Popular hotels | Wilder House Berkshires, Guesthouse Cabin vacation rentals in Berkshire County, Antique Farmhouse Totally Restored , Berkshire Mountain Lodge, Berkshires Untold, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Red Lion Inn, Quality Inn |
Frequently asked questions
Recent Sheffield hotel reviews by fellow wanderers

Berkshire Mountain Lodge
5 out of 5
Posted 16 hours ago
Travelocity Verified Review
"Great for family"
A verified traveller from Trenton stayed at Berkshire Mountain Lodge
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