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

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Check availability on Bennington Historic Hotels

Tonight
Aug 30 - Aug 31
Tomorrow
Aug 31 - Sep 1
Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13

Our top choices for Bennington historic hotels

Private kitchen
Exterior detail
Exterior
Living area

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 $262
CA $548 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Dining
Interior
Outdoor dining
Private kitchen

2. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
United States
Jennifer O.
CA $318
CA $669 total
includes taxes & fees
Sep 9 - Sep 10
A roomy remodeled retreat close to MassMoCA
Pool
Property grounds
Exterior
Private kitchen

3. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
United States
Kristina L.
CA $134
CA $306 total
includes taxes & fees
Sep 1 - Sep 2
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Exterior
Room
Dining
Interior

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

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
United States
Eleanor D.
CA $236
CA $514 total
includes taxes & fees
Sep 1 - Sep 2
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Front of property
Living room
Condo Hotel Room
Lobby lounge

5. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Mirco
CA $303
CA $330 total
includes taxes & fees
Sep 3 - Sep 4
Castle Hill Resort And Spa
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Top Bennington Hotel Reviews

Hampton Inn Bennington

Hampton Inn Bennington

10/10 Excellent
"Going through an upgrade but the room we stayed in was brand new."
Justin 1-night trip
Posted 8 hours ago
Hampton Inn Bennington
Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

8/10 Good
"Nice staff. Dirty pool. Rooms were okay."
Taylor 1-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 13 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 3 weeks 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, Robert Frost Stone House Museum, and Old First Congregational Church. 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.

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