Find Historic Hotels in Winchester, NH

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Historic Hotels

Our top choices for Winchester historic hotels

Free daily continental breakfast
The Carriage Barn Inn

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (165)
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
The price is AED 445
AED 482 total
includes taxes & fees
31 Dec - 1 January 2026
The Carriage Barn Inn
Exterior detail
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Peterborough
9.8 out of 10, Exceptional, (30)
"Fully equipped kitchen, comfortable open floor plan, easy walk to downtown and very hospitable—thank you—we’d like to stay here again next year!"
United States
Mark
The price is AED 231
AED 530 total
includes taxes & fees
17 Dec - 18 Dec
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
TV, books
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
10.0 out of 10, Exceptional, (8)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is AED 752
AED 895 total
includes taxes & fees
18 Dec - 19 Dec
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Property grounds
Entire Farmhouse with lots of open space 15 min north of Keene

Entire Farmhouse with lots of open space 15 min north of Keene

Entire Farmhouse with lots of open space 15 min north of Keene
Walpole
10.0 out of 10, Exceptional, (38)
"Lovely place would definitely book again"
United States
Sean M.
The price is AED 876
AED 1,075 total
includes taxes & fees
18 Dec - 19 Dec
Entire Farmhouse with lots of open space 15 min north of Keene
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.
View all properties

Top Winchester Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"Staff were very friendly. The pool was the perfect temperature. Would definitely stay again. "
Tiffany 1-night trip
Posted 3 days ago
Keene Elm City Hotel, an Ascend Collection Hotel

Explore a world of travel with Expedia

Frequently asked questions

What can a history buff expect from a stay in Winchester?
The historical sites in Winchester are probably a big part of your travel plans. Why not appreciate the lakeside during your visit?
How many historically relevant hotels will I find in Winchester?
In Winchester, you'll find 7 hotels and other lodging options bookable on Expedia though you won't find many designated historic hotels.
What are the top historical sites and other places to visit in Winchester?
Favorite places to visit include New England Sweetwater Farm & Distillery, Winchester Speedpark, and Bennett Gorge. A couple of additional sights to add to your agenda are Birch Point and Pisgah State Park.
What is a historic hotel like in Winchester?
Historic hotels give guests the opportunity to stay in a building that has been officially recognized with a national historic designation. Historic hotels throughout the world can take the form of stately homes, palaces or even lodges, old police stations or skyscrapers. These types of hotels in Winchester often preserve authentic characteristics like traditional architecture and period features in their public spaces or guestrooms.
What is the difference between a historic hotel and a heritage hotel?
The two are similar. "Historic hotel" is a term often used in the U.S., while you'll often hear "heritage hotel" in Asia and Europe. Historic hotels tend to place more significance on the architecture and building. A heritage hotel draws meaning mainly from the cultural value and how it influenced the community.
Do historic hotels in Winchester have modern facilities?
Yes, every effort is made to preserve the historic aspects and traditions, while interiors have safety features and modern conveniences. Visitors can expect the amenities from a contemporary hotel such as private rooms with updated bathroom facilities, heating and air conditioning, and free and fast Internet. When you book a historic hotel in Winchester, it doesn't mean you're choosing a place that's rundown or uncomfortable for guests.