Find Historic Hotels in Bennington, VT

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Check availability on Bennington Historic Hotels

Our top choices for Bennington historic hotels

Interior
6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT

6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT

6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT
Manchester Center
10.0 out of 10, Exceptional, (51)
"This was the most well-stocked house we've ever rented. It's like being in the comfort of your own home. Lots of herbs and spices in the kitchen and all sorts of pots and pans that make it possible to cook anything. Great location and clean."
United States
Anonymous traveler
The price is AED 3,289
AED 7,315 total
includes taxes & fees
18 Dec - 19 Dec
6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT
Lobby lounge
Castle Hill Resort And Spa

Castle Hill Resort And Spa

Castle Hill Resort And Spa
3.5 star property
Cavendish
9.0 out of 10, Wonderful, (104)
"Convenient that there is a restaurant is in the Castle, we also loved the outdoor hot tub and pool. "
United States
Jeff
The price is AED 890
AED 970 total
includes taxes & fees
11 Jan - 12 January 2026
Castle Hill Resort And Spa
Exterior
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (166)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
The price is AED 624
AED 1,312 total
includes taxes & fees
15 Dec - 16 Dec
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior detail
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!

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
9.8 out of 10, Exceptional, (99)
"Quiet and relaxing property "
United States
Michelle S.
The price is AED 426
AED 1,142 total
includes taxes & fees
14 Dec - 15 Dec
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Exterior
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

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
10.0 out of 10, Exceptional, (23)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
The price is AED 386
AED 866 total
includes taxes & fees
14 Dec - 15 Dec
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
TV, DVD player
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (25)
"Loved the location"
United States
Steven W.
The price is AED 364
AED 1,048 total
includes taxes & fees
16 Dec - 17 Dec
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Exterior
North Getaway Cottage

North Getaway Cottage

North Getaway Cottage
Williamstown
9.2 out of 10, Wonderful, (24)
"The cottage was the perfect accommodations for our overnight stay in town for a funeral. Thank you Claudia. "
United States
Mary Alice H.
The price is AED 859
AED 1,752 total
includes taxes & fees
12 Dec - 13 Dec
North Getaway Cottage
Microwave, oven, stovetop, dishwasher
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
10.0 out of 10, Exceptional, (102)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
The price is AED 544
AED 1,104 total
includes taxes & fees
15 Dec - 16 Dec
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
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.
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Top Bennington Hotel Reviews

Hampton Inn Bennington

Hampton Inn Bennington

10/10 Excellent
"Yes"
Mary 2-night trip
Posted 6 days ago
Hampton Inn Bennington

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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 54 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 Old First Congregational Church, Bennington Potters Yard, and Robert Frost Stone House Museum. The mountain views and hiking trails exemplify the natural beauty, and places to admire include Green Mountain National Forest and Harmen Hills Trail. Additionally, you'll find Mount Snow in the area.
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.