A covered bridge with a sign reading "Silk Road Bridge" and a height restriction of 10 feet 6 inches.

Find Historic Hotels in Bennington, VT from CA $327

  • 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 Bennington Historic Hotels

Tonight
Aug 24 - Aug 25
Tomorrow
Aug 25 - Aug 26
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Bennington historic hotels

Private kitchen
Outdoor dining
Living area
Exterior

1. Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
United States
Anita T.
CA $288
CA $580 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Exterior
Interior
Room
Dining

2. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
United States
Eleanor D.
CA $234
CA $509 total
includes taxes & fees
Aug 25 - Aug 26
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Dining
Interior
Interior
Private kitchen

3. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
United States
Jennifer O.
CA $315
CA $666 total
includes taxes & fees
Sep 9 - Sep 10
A roomy remodeled retreat close to MassMoCA
Front of property
Standard Room, 1 Queen Bed
Living room
Lobby lounge

4. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Mirco
CA $300
CA $327 total
includes taxes & fees
Aug 30 - Aug 31
Castle Hill Resort And Spa
View all properties

Top Bennington Hotel Reviews

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

8/10 Good
"The staff was incredibly helpful and the breakfast was homemade not powdered eggs. Down side was the walls were a bit thin. Rooms were well appointed and it’s in a great location. I was there to volunteer for a RAm event and a lot of us stayed there. Next year I would stay there again. Maybe we can get all the RAM volunteers in one building as we have to get up at 4 am"
Beth 3-night trip
Posted 3 days ago
Hotel Vervana, Trademark Collection by Wyndham
Starlight Inn

Starlight Inn

8/10 Good
"They do accept pets; however, there is a 20 dollar per pet per night fee. Adds up fast!"
Lionel 3-night trip
Posted 7 days ago
Starlight Inn
Bennington Motor Inn

Bennington Motor Inn

8/10 Good
"It was handy to everywhere in Bennington (which, admittedly is a small town)and was a fine place to stay. Parking was a bit dicey, being on a steep side hill, and the main walkway out front ( a first floor balcony) was tilted a bit away from the building- a drink and I might have been over into the driveway. I would stay there again."
schuyler 1-night trip
Posted 13 days ago
Bennington Motor Inn
The Four Chimneys Inn

The Four Chimneys Inn

10/10 Excellent
"Room was clean. Staff helpful. Didn’t get a chance to have breakfast either days, the system of pre filled form for breakfast didn’t work for us. Didn’t get a chance to go to the bar"
diana 2-night trip
Posted 1 month ago
The Four Chimneys Inn

Frequently asked questions

What should I expect on my historical trip to Bennington?
Significant historical sites in Bennington are likely at the top of your travel itinerary. While you're here, you might want to visit the ski slopes and array of shops. You can also take some time enjoying the majestic mountain landscape.
What's the best place to stay in Bennington that's close to historical sites?
A Real Farm Vacation is one of the top choices for history buffs.
How many historically relevant hotels are there in Bennington?
In Bennington, you'll find 49 hotels and other lodging options bookable on Expedia but not many designated as historic hotels.
What are the top historical places and other sights to visit in Bennington?
Bennington is notable for landmarks like Bennington Potters Yard, Old First Congregational Church, and Robert Frost Stone House Museum. The mountain views and hiking trails highlight the natural beauty with places to discover including Green Mountain National Forest, Harmon Hill, and Harmen Hills Trail. A couple of additional sights to add to your agenda are Bennington Museum and Hemmings Motor News Car Lover's Convenience Store & Vehicle Display.
What is a historic hotel like in Bennington?
Guests who choose historic hotels have a chance to stay in a place recognized with an official historic designation. Historic hotels throughout the world have had many former lives and uses, such as castles, palaces, grand homes or even old police stations, pubs, lodges or skyscrapers. These types of hotels in Bennington typically retain authentic elements 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 "heritage hotel" is often used in Asia and Europe. Historic hotels tend to emphasize the building and architecture itself. A heritage hotel draws meaning mainly from the cultural value and how it shaped the community.
Do historic hotels in Bennington have modern facilities?
Yes, every effort is made to preserve historic facades and treasured traditions, but hotel interiors are fitted with modern conveniences and safety features. Visitors can expect the usual amenities you'd get from a hotel such as WiFi, heating and air conditioning, and updated bathroom facilities. When you book a historic hotel in Bennington, it doesn't mean you're picking a place that's rundown or uncomfortable for guests.

Explore a world of travel with Expedia