Sheffield, MA
Travel Guide
Visit Sheffield
Wilder House Berkshires
48 S Main Street Sheffield MA
The price is AED 630 per night from Jul 1 to Jul 2
AED 630
AED 703 total
1 Jul - 2 Jul
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 ...
9.8/10 Exceptional! (56 reviews)
"Bed was super comfortable. Breakfast was great (love that homemade yogurt) and Laura, the innkeeper, was lovely. Thank you and we can’t wait to come back."
Reviewed on 20 June 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
The price is AED 526 per night from Jul 7 to Jul 8
AED 526
AED 588 total
7 Jul - 8 Jul
includes taxes & fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9.2/10 Wonderful! (1,005 reviews)
"I had an excellent experience with the Yankee Inn. The room was updated and the house keeping was excellent. The location was good and the staff was very nice. The breakfast was very good. I would definitely recommend staying here."
Reviewed on 23 June 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundable
The price is AED 516 per night from Jul 26 to Jul 27
AED 516
AED 658 total
26 Jul - 27 Jul
includes taxes & fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (999 reviews)
"We thoroughly enjoyed our stay. The rooms are spacious and beautifully furnished, and having a stove and refrigerator along with a separate living/dining room was a definite plus. The 24/7 coffee and hot chocolate machine in the lobby was another perk, as were the hot tub and large (albeit shallow) ..."
Reviewed on 24 June 2026
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.
Antique Farmhouse Totally Restored
Sheffield MA
Book a stay at this family-friendly vacation home in Sheffield. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Mount Riga State Park and ...
9.8/10 Exceptional! (98 reviews)
"This is our third visit to the farmhouse in Sheffield and we plan to be back again if it’s available. The house has everything you could possibly need or want with lots of space and an outstanding fully equipped kitchen Robin, our host makes it easy for us to wanna come back."
Reviewed on 2 June 2026
The Race Mountain House
Sheffield MA
Stay at this vacation home in Sheffield. Enjoy laundry facilities, patios, and in-room fireplaces. Popular attractions Mount Everett State Reservation and Drury ...
9.6/10 Exceptional! (7 reviews)
"We had a wonderful 2-day stay at this charming house! The location is perfect, nestled near the mountains with breathtaking views. The house itself is clean and cozy, with comfortable bedrooms stocked with extra blankets and pillows. The spacious bathrooms (both upstairs and downstairs!) had plenty ..."
Reviewed on 3 January 2026
Guesthouse Cabin vacation rentals in Berkshire County
Sheffield MA
Stay at this cabin in Sheffield. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Mount Everett State Reservation and Plaintain Pond ...
10/10 Exceptional! (10 reviews)
"We were a group of moms who snuck away for the night and this cabin was the perfect retreat. Well stocked and very cozy on a winter night. We had to leave very early the next morning to beat a snowstorm and the very long driveway was already sanded and we felt very safe. Lisette was great to work ..."
Reviewed on 29 January 2026
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.
