Title: Book the Best HISTORIC Hotels in Bennington in 2025 | Expedia.ca [Hotels in Bennington](https://expedia.ca/Bennington-Hotels.d6057349.Travel-Guide-Hotels)[Vacation Rentals in Bennington](https://expedia.ca/Bennington-Vacation-Rentals.d6057349.Travel-Guide-VacationRentals)[Flights to Bennington](https://expedia.ca/Cheap-Flights-To-Bennington.d6057349.Travel-Guide-Flights)[Things to do in Bennington](https://expedia.ca/Things-To-Do-In-Bennington.d6057349.Travel-Guide-Activities)[Bennington Car Rentals](https://expedia.ca/Car-Rentals-In-Bennington.d6057349.Car-Rental-Guide)[Bennington Vacation Packages](https://expedia.ca/Bennington.d6057349.Destination-Travel-Guides) ![Bennington Battle Monument showing heritage elements and a monument](https://images.trvl-media.com/place/6115862/2e3e8ead-6a83-4024-b6a2-6587d8a27940.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Bennington, VT from CA $332 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Bennington Historic Hotels Tonight [Nov 20 - Nov 21](https://www.expedia.ca/Hotel-Search?regionId=6057349&startDate=2025-11-20&endDate=2025-11-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 21 - Nov 22](https://www.expedia.ca/Hotel-Search?regionId=6057349&startDate=2025-11-21&endDate=2025-11-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6057349&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6057349&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Bennington Historic Hotels ![Interior](https://images.trvl-media.com/lodging/63000000/62960000/62953900/62953803/94310558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/63000000/62960000/62953900/62953803/2cb10fb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/63000000/62960000/62953900/62953803/db211523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/63000000/62960000/62953900/62953803/b3486e4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT Manchester Center 10/10 Exceptional (51) "This is our second time renting the Greybourne house. The house is just as amazing as we remembered it - spacious, clean, well stocked and located within a short drive to Stratton, Okemo or Killington. Allison is a great host - very responsive and helpful. We can't wait to return again next year." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Masha S. CA $1,069 CA $2,559 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Manchester-Center-Hotels-6-Bed-7-Bath-VT-Retreat-Rent-A-Former-BB-Greybourne-House.h62953803.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/62670e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/becbfa0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/c5d0a9bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/306e8880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Fully Renovated One-Room Schoolhouse on 22+ acres Grafton 9.6/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Philip CA $238 CA $498 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Grafton-Hotels-Charming-Fully-Renovated-One-Room-Schoolhouse-On-22-Acres.h27117112.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/9c846f70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/w1008h683x16y0-72a8567d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/a110f773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/9abb62fb_edited_7b4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn Hancock 10/10 Exceptional (23) "This property is spacious, clean and well- appointed. I would stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda M. CA $157 CA $344 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Hancock-Hotels-SKI-ONOFF-1BR-SUITE-1ST-FLR-SLEEPS-4-JIMINY-PEAK.h69787457.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/41000000/40230000/40226600/40226569/fc1c3458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/41000000/40230000/40226600/40226569/c4a5d927.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/41000000/40230000/40226600/40226569/dd5fd351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/41000000/40230000/40226600/40226569/73c9709a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas! Hoosick Falls 9.8/10 Exceptional (99) "Quiet and relaxing property " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle S. CA $162 CA $432 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Hoosick-Falls-Hotels-Cozy-Ski-Retreat-With-New-Pet-Yard-And-Many-Upgrades-Close-To-3-Ski-Areas.h40226569.Hotel-Information) ![TV, DVD player](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/9a087dbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/0429cb18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/17514ada.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/77b10ad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski-In/Out condo with patio, mountain views, washer/dryer, & cable Clock Tower Base Area 9.2/10 Wonderful (25) "Loved the location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven W. CA $87 CA $332 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Ludlow-Hotels-Ski-InOut-Condo-With-Patio.h72131894.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w907h683x58y0-59aad182.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w507h683x259y0-1d5f8c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w905h683x60y0-b01f3b74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, printers](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w919h683x60y0-f3238385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Getaway Cottage Williamstown 9.4/10 Exceptional (23) "The cottage was the perfect accommodations for our overnight stay in town for a funeral. Thank you Claudia. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary Alice H. CA $284 CA $627 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Williamstown-Hotels-Vacation-Getaway-Or-Remote-Workschool-Location.h60763766.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/54a5f76c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/cc4de1c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/c6c8a740.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/b0da744f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route Ludlow 10/10 Exceptional (102) "Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew L. CA $206 CA $422 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Central-Vermont-Killington-Hotels-Vrbo-Property.h45708952.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/ba958cd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/20e76b9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/dd7457ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/c6fd9a81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle Ludlow 9.8/10 Exceptional (103) "A lovely time enjoying the off-season in a ski town. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ed C. CA $302 CA $617 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Ludlow-Hotels-Short-Walk-To-Shops.h22865847.Hotel-Information) 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](https://expedia.ca/Hotel-Search?startDate=2025-12-04&endDate=2025-12-05®ionId=6057349&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_6057349) ## Top Bennington Hotel Reviews ![Hotel Vervana, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/b33626c2_y.jpg) ### Hotel Vervana, Trademark Collection by Wyndham 10/10 Excellent "Great place for the price! Clean and comfortable. " [](https://expedia.ca/Bennington-Hotels-Paradise-Inn.h2577695.Hotel-Information) ![Best Western Bennington](https://images.trvl-media.com/lodging/1000000/20000/16400/16323/5ad1b90e_y.jpg) ### Best Western Bennington 8/10 Good "Room was clean and comfortable, but, there was an odor I didn’t like. We opened the windows to try and clear it, after that I think we just got used to it." [](https://expedia.ca/Bennington-Hotels-Best-Western-Bennington.h16323.Hotel-Information) ![Hampton Inn Bennington](https://images.trvl-media.com/lodging/2000000/1200000/1192000/1191981/aadd5504_y.jpg) ### Hampton Inn Bennington 10/10 Excellent "The breakfast was exceptional there was a lot of options to choose from the rooms are very clean we enjoyed our stay" [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-Bennington.h1191981.Hotel-Information) ![Bennington Motor Inn](https://images.trvl-media.com/lodging/2000000/1530000/1523000/1522906/0219b10e_y.jpg) ### Bennington Motor Inn 10/10 Excellent "Great hotel for the price and convenient to downtown area.." [](https://expedia.ca/Bennington-Hotels-Bennington-Motor-Inn.h1522906.Hotel-Information) ![The Autumn Inn](https://images.trvl-media.com/lodging/3000000/2390000/2381300/2381247/be4d3e05_y.jpg) ### The Autumn Inn 10/10 Excellent "Room was great for the price " [](https://expedia.ca/Bennington-Hotels-The-Autumn-Inn.h2381247.Hotel-Information) ![The Four Chimneys Inn](https://images.trvl-media.com/lodging/3000000/2400000/2394100/2394036/a1fa9bf1_y.jpg) ### The Four Chimneys Inn 10/10 Excellent "This is a beautiful, historic property and pretty consistent with the photos on the website. The room I had was just as pretty with some antique furnishings, but of course in person you notice that it is an old building. The room was a great size, and I loved the hardwood floors. The bathroom was also large and you are provided a sundry of items for convenience. The bed was comfortable, though it did seem to have a center depression. The only other issue I had was that though the the showerhead seemed to have a dial to adjust pressure, I was not able to. Overall the property is in great condition. The staff were welcoming, and the breakfast was outstanding, served in their traditional, historic, and charming restaurant space." [](https://expedia.ca/Bennington-Hotels-The-Four-Chimneys-Inn.h2394036.Hotel-Information) ![Starlight Inn](https://images.trvl-media.com/lodging/2000000/1510000/1507900/1507889/ae52b0fb_y.jpg) ### Starlight Inn 10/10 Excellent "Peaceful, quiet place to spend a night on the road." [](https://expedia.ca/Bennington-Hotels-Starlight-Inn.h1507889.Hotel-Information) ## 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](https://www.expedia.ca/Bennington-Hotels-5-Bedroom-Farmhouse-On-295-Acres-In-Historic-Bennington-VT.h53341313.Hotel-Information) 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. 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