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Choose from 1285 Sheffield Hotel Deals
Wilder House Berkshires
"Just a beautiful home with clean, comfortable rooms and an amazing Innkeeper. Breakfasts are elegant and delicious. We stayed here in 2025 and returned in 2026 for Labor Day weekend. Will hopefully repeat in 2027."
Reviewed on Sep 8, 2026
Berkshire Mountain Lodge
The Yankee Inn
"Was very recently renovated and done quite well."
Reviewed on Sep 8, 2026
Berkshires Untold
"Unfortunately this was not a boutique hotel. It was a renovated motel. Our room was smallish & dark. We felt the website was a bit misleading! On positive note the staff was extremely friendly & professional."
Reviewed on Sep 8, 2026
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
"Convenient location"
Reviewed on Sep 9, 2026
The Red Lion Inn
Quality Inn Great Barrington
"It was a 60's vintage motel. The bathroom fixtures were dirty. There was a recent plaster patch in the bathroom. The TV remote barely worked. This is a very basic motel, not worth $200/night."
Reviewed on Sep 8, 2026
Holiday Inn Club Vacations Oak 'n Spruce Resort
"The temp was 67 degrees in our unit. I called the front desk and they sent someone immediately however who couldn’t get the heat to turn on. The thermostat was not set to turn on until later in the month. The owner must likely to blame for a lack of heat."
Reviewed on Sep 9, 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
"I was put in room 20 or 120 that shared a wall with the breakfast room, was woken up by them setting up and opening and closing refrigerators and then people eating breakfast starting at 6!!! I should have been notified of this when booking. I all my years of travel I have never seen something like ..."
Reviewed on Sep 8, 2026
The Whitlock
"Great quiet and peaceful walkable to all local places."
Reviewed on Sep 8, 2026
Quality Inn Lee - Lenox South
"Very clean property with kind staff. Nice room, decent complimentary coffee, breakfast offerings not for me."
Reviewed on Sep 8, 2026
The Cornell Inn, Lenox & The Berkshires
Find cheap hotels in Sheffield
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Frequently Asked Questions About Sheffield hotels
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