Sheffield Travel Guide
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Wilder House Berkshires
48 S Main Street Sheffield MA
Fully refundableReserve now, pay when you stay
The price is £165 per night from 27 Aug to 28 Aug
£165
27 Aug - 28 Aug
includes taxes & fees
Stay at this B&B in Sheffield. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife ...
9.8/10 Exceptional! (61 reviews)
"The Wilder House Berkshires is a lovely inn with helpful, friendly staff and delicious food! My well-appointed room (#1) was spacious, the bedding was luxurious and the king-sized bed was very comfortable. The bathroom was large with a roomy shower. All amenities in the room seemed to be recently ..."
Reviewed on 10 Aug 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
The price is £130 per night from 14 Sept to 15 Sept
£130
14 Sept - 15 Sept
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (1,003 reviews)
"It was very convenient for an overnight with pool and close to downtown. Affordable. I stayed in the annex so no noise from other guests!"
Reviewed on 14 Aug 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is £95 per night from 31 Aug to 1 Sept
£95
31 Aug - 1 Sept
includes taxes & fees
Stay at this golf aparthotel in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,074 reviews)
"A real gem. Wonderfully situated. Spacious rooms. Friendly service. I forgot a camera battery charger in the room and the hotel staff kept it for my son to pick up. So very efficient and honest staff. We will definitely consider staying here again."
Reviewed on 15 Aug 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
Stay at this family-friendly holiday home in Sheffield. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Mount Riga State Park and Taconic ...
The Race Mountain House
Sheffield MA
Stay at this holiday 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 Jan 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Stay at this golf aparthotel in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,074 reviews)
"A real gem. Wonderfully situated. Spacious rooms. Friendly service. I forgot a camera battery charger in the room and the hotel staff kept it for my son to pick up. So very efficient and honest staff. We will definitely consider staying here again."
Reviewed on 15 Aug 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.
