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
16 Sep - 17 Sep
Tomorrow
17 Sep - 18 Sep
This weekend
18 Sep - 20 Sep
Next weekend
25 Sep - 27 Sep

Our top choices for Sheffield historic hotels

Property grounds
Pub
Exterior
Exterior

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
James
AED 592
AED 843 total
includes taxes & fees
23 Sep - 24 Sep
The Red Lion Inn
Exterior
Dining
Interior
Coffee/tea maker, fridge, microwave, oven

2. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
AED 1,102
AED 1,958 total
includes taxes & fees
1 Oct - 2 Oct
Gorgeous Mountain Views Retreat: Family & Nature
Coffee/tea maker, fridge, microwave, oven
Exterior
Terrace/patio
TV, fireplace, books

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 2,920
AED 4,737 total
includes taxes & fees
16 Oct - 17 Oct
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

10/10 Excellent
"Beautiful view. Clean and comfortable. Great breakfast choices"
toan 3-night trip
Posted less than an hour ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Bedding and bed were lovely. excellent to have good lighting at sink as well as a magnified mirror! Often lacking in places we have stayed. AC had trouble cooling the room down until we turned it on full blast. too much ambient light from floodlight on property next door and from hall (I finally turned off hallway light which helped. ) Common areas and halls need some brightening up with fresh, lighter paint--seemed dingy. Was terribly frustrating trying to make the Nespresso machine work. We do not own one and there were NO INSTRUCTIONS. You should assume people do not know how to operate any appliances like that and should have a card with directions. We gave up and went to the Tavern where we had lovely coffee and breakfast. Also had a great dinner in Tavern after our arrival. The patch burrata salad was superb. As was our waitress."
Judith 1-night trip
Posted 11 hours ago
The Red Lion Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Beds were comfortable but the pillows not so great but clean and quiet."
Sue 1-night trip
Posted 1 day ago
Quality Inn Great Barrington

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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