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

Find Historic Hotels in Sheffield, MA

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Check availability on Sheffield Historic Hotels

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

Our top choices for Sheffield historic hotels

Property grounds
Pub
Exterior
Outdoor pool, sun loungers

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
James
AED 577
AED 826 total
includes taxes & fees
28 Sep - 29 Sep
The Red Lion Inn
Interior
2 bedrooms, iron/ironing board, WiFi (free), bed sheets
Smart TV, fireplace, table tennis, books
Interior

2. rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
United States
BRIAN PATRICK M.
AED 1,055
AED 1,333 total
includes taxes & fees
8 Sep - 9 Sep
rural, serene + sophisticated space
Coffee/tea maker, fridge, microwave, oven
Exterior
TV, fireplace, books
Terrace/patio

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.
AED 3,269
AED 5,410 total
includes taxes & fees
9 Sep - 10 Sep
A Country Lodge Straight Out of the Pages of a Great Novel
View all properties

Top Sheffield Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"The room was clean and comfortable and the pool was well heated (though small). I liked the breakfast options. Good location too."
Bella 1-night trip
Posted 2 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

8/10 Good
"We only stayed for one night. The room was clean. Easy access for handicap needs we we required"
Deborah 1-night trip
Posted 4 hours ago
Quality Inn Lee - Lenox South
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 6 hours 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 7 hours ago
The Yankee Inn

Frequently asked questions

What should a history buff expect from a stay in Sheffield?
Those coming to Sheffield should consider one of the historical tours to learn more. While you're in town, why not also explore the many sights to visit such as casinos?
How many historical hotels are located in Sheffield?
In Sheffield, there are 32 hotels and other lodging options bookable on Expedia though not many historic hotels to choose from.
What are the most important historical sites and other places in Sheffield?
Sheffield is notable for landmarks like Ashley House. A couple of additional sights to add to your agenda are Housatonic River and Three Mile Pond Wildlife Management Area.
What is a historic hotel like in Sheffield?
Guests who choose a historic hotel can enjoy a vacation someplace that has an official historic designation. A palace, castle, grand home or even an old police station, pub, lodge, or skyscraper can be transformed into 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, bringing the history to life.
What is the difference between a historic hotel and a heritage hotel?
"Heritage hotel" is more common in Asia and Europe, while "historic hotel" is a term often used in the U.S. but overall the terms are quite similar. The building and architecture of historic hotels are generally the most significant aspect. For a heritage hotel, mainly, it's cultural value and how it influenced the community.
Do historic hotels in Sheffield have modern facilities?
Hotel interiors feature the modern conveniences and safety features you expect to find, but every effort is made to preserve the historic aspects and traditions. Private rooms with updated bathroom facilities, heating and air conditioning, free and fast Internet, and the amenities found in most hotels 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 or rundown.

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