A covered wooden structure with a sloped roof, surrounded by greenery and trees.

Historic Hotels & Resorts in Sheffield

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Check availability on Sheffield Historic Hotels

Tonight
7 Sept - 8 Sept
Tomorrow
8 Sept - 9 Sept
This weekend
11 Sept - 13 Sept
Next weekend
18 Sept - 20 Sept

Our top choices for Sheffield historic hotels

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A covered porch with wicker furniture and hanging flower baskets.
A backyard with a swimming pool, lounge chairs, and a hot tub.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
James
AU$314
includes taxes & fees
23 Sept - 24 Sept
The Red Lion Inn
A rustic interior with wooden beams, multiple windows, and a kitchen area with dishes and a coffee maker.
A spacious living area with a fireplace, a dining table, and a kitchen area with wooden cabinets and a stove.
A cozy interior with a fireplace, wooden walls, and a chandelier.
A rustic kitchen with wooden shelves, a gas stove, an oven, and a microwave.

2. rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
United States
BRIAN PATRICK M.
AU$501
includes taxes & fees
8 Sept - 9 Sept
rural, serene + sophisticated space
A modern kitchen with white cabinets, a large island, and a skylight.
A wooden cabin with a deck and stone steps, surrounded by a grassy area and trees.
A two-story house with a gravel driveway leading to a garage.
A bedroom with a large bed, built-in bookshelves, a bedside table, and a window with curtains.

3. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
United States
Hessie S.
AU$1,987
includes taxes & fees
8 Sept - 9 Sept
A Country Lodge Straight Out of the Pages of a Great Novel
View all properties

Top Sheffield Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"Black swann is great hotel with very helpful staff. They also have a Indian restaurant inside the hotel with lake view. It is a bit pricey but their fish curry is a must try!! I had it twice in a row and I am very picky eater."
Dheeraj 3-night trip
Posted less than an hour ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Yankee Inn

The Yankee Inn

10/10 Excellent
"On an overpriced holiday weekend in the Berkshires, Yankee Inn was a great balance of price and amenities. The indoor pool was nicer than most, and the hot tub was great. Outdoor pool was a bit oddly placed between the parking lot and the main road, but nice as well. Both very clean. Room was spacious and clean, beds were comfortable, though I think they were doubles rather than queens. The included breakfast was on the very good end of standard - the fruit was fresh and delicious, there were both eggs and waffles, plus cereal, yogurt, bacon/sausage. Meh on the pastries, and the coffee was terribly watery. My true only gripe is that there was truly not a single place to hang wet bathing suits that didn't result in them dripping all over the floor. Had we been on the 2nd floor, we would have had an outside railing, but on the first floor there was none. With 4 people using the pool and hot tub, it was an annoyance. Overall, great place for a quick stay."
Emily 2-night trip
Posted less than an hour ago
The Yankee Inn
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Clean spacious suite"
Joan 1-night trip
Posted less than an hour ago
Hampton Inn & Suites Berkshires-Lenox
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

8/10 Good
"Perfectly fine budget motel"
Thomas 2-night trip
Posted 2 hours ago
Quality Inn Lee - Lenox South
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

8/10 Good
"Only complaint was that the AC unit was somewhat loud in our room. Didn't get to use any of the amenities. Breakfast was typical of this type of hotel buffet. Front desk staff was very good."
Raymond 2-night trip
Posted 4 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Frequently asked questions

What should a history buff expect from a stay in Sheffield?
Those visiting Sheffield may want to seek out one of the historical tours to learn more. During your stay, why not also enjoy all there is to see and do such as the casinos?
How many historical hotels will I find in Sheffield?
In Sheffield, you'll find 32 lodging options bookable on Expedia but not many designated as historic hotels.
What are the top historical sites and other places in Sheffield?
Sheffield is notable for landmarks like Ashley House. A couple of additional sights to add to your itinerary are Housatonic River and Three Mile Pond Wildlife Management Area.
What is a historic hotel like in Sheffield?
By booking a historic hotel, guests can sleep someplace that has an official historic designation. A palace, castle, stately home or even a lodge, pub or skyscraper can be considered a historic hotel provided that it's of special interest. Traditional architecture and period features are typically preserved within the guestrooms or public spaces of historic hotels in Sheffield, giving a sense of history.
What is the difference between a historic hotel and a heritage hotel?
"Heritage hotel" is more common in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. overall though the terms are similar. The architecture and actual building of a historic hotel tends to be what's most important. For a heritage hotel, it's often the cultural value along with how it shaped the community.
Do historic hotels in Sheffield have modern facilities?
Hotels include modern conveniences and safety features you expect to find, though efforts have been made to preserve the historic aspects and traditions. Private rooms with updated bathroom facilities, heating and air conditioning, free and fast Internet, and the usual amenities found in a hotel will also be available in a historic hotel. When you choose a historic hotel in Sheffield, don't worry that you'll find yourself staying at a place that's uncomfortable for guests or simply rundown.

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