Title: Visit Old Bennington: 2026 Travel Guide for Old Bennington, Bennington | Expedia.com [Hotels in Old Bennington](https://expedia.com/Old-Bennington-Hotels.d553248635976385350.Travel-Guide-Hotels)[Vacation Rentals in Old Bennington](https://expedia.com/Old-Bennington-Vacation-Rentals.d553248635976385350.Travel-Guide-VacationRentals)[Flights to Old Bennington](https://expedia.com/Cheap-Flights-To-Old-Bennington.d553248635976385350.Travel-Guide-Flights)[Car Rentals in Old Bennington](https://expedia.com/Car-Rentals-In-Old-Bennington.d553248635976385350.Car-Rental-Guide)[Old Bennington Vacation Packages](https://expedia.com/Old-Bennington.d553248635976385350.Destination-Travel-Guides) # Old Bennington, VT ## Travel Guide ![2017](https://images.trvl-media.com/place/6115862/c54b3750-17e2-410d-8469-3dda6fc27801.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![2017](https://images.trvl-media.com/place/6115862/c54b3750-17e2-410d-8469-3dda6fc27801.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![2017](https://images.trvl-media.com/place/6057349/c2fb96a0-6411-4fe1-b288-d5ba2aaf3ada.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Shot from the top of the Bennington Monument ](https://images.trvl-media.com/place/6005393/7cbd9cb1-4263-4f4c-aca5-d9688c3a42f9.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![#history #monument](https://images.trvl-media.com/place/6115862/2be49982-b4c1-462e-82d0-d55b8a211643.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Old Bennington Things to do ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=DX_SPRING_PROMO_553248635976385350) - Old Bennington Hotel Deals - Vacation Rentals in Old Bennington ![The Four Chimneys Inn](https://images.trvl-media.com/lodging/3000000/2400000/2394100/2394036/e72452e8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Four Chimneys Inn 21 West Road Bennington VT $225 nightly $246 total Mar 16 - Mar 17 Total with taxes and fees Book a stay at this golf B&B in Bennington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ... 9.4/10 Exceptional! (281 reviews) This is a quintessential Vermont inn in beautiful historic Bennington. The inn was lovingly cared for by the owner who was very attentive to his guests. We will stay again. Reviewed on Jan 12, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F16%2F2026&endDate=3%2F17%2F2026&selected=2394036&PinnedHotelID=2394036&HadPinnedHotel=true®ionId=553248635976385350) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/9903b094_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Downstreet, an Ascend Collection Hotel 40 Main St North Adams MA $118 nightly $132 total Mar 31 - Apr 1 Total with taxes and fees Book a stay at this business-friendly hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ... 8.8/10 Excellent! (1,005 reviews) For the price, is a good property. Convenient for our purposes. While not up to more modern standards, it is reasonably furnished. Location is a bit noisy due to traffic and trains. Limited decent food options. Reviewed on Mar 5, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F31%2F2026&endDate=4%2F1%2F2026&selected=2943&PinnedHotelID=2943&HadPinnedHotel=true®ionId=553248635976385350) ![Hideaway Inn Mt. Snow](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/c5bdc83b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hideaway Inn Mt. Snow 270 Handle Rd West Dover VT $135 nightly $149 total Mar 24 - Mar 25 Total with taxes and fees Book a stay at this ski hotel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and Heavy Metal Ski Lift are ... 8.8/10 Excellent! (68 reviews) The hot tub was broken. Other than that. Nice place Reviewed on Mar 8, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F24%2F2026&endDate=3%2F25%2F2026&selected=122978111&PinnedHotelID=122978111&HadPinnedHotel=true®ionId=553248635976385350) [See all 1,006 properties in Old Bennington](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F10%2F2026&endDate=3%2F11%2F2026®ionId=553248635976385350) 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. ![Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating ](https://images.trvl-media.com/lodging/64000000/63080000/63074800/63074743/13b5f58a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating Whitingham VT Stay at this vacation home in Whitingham. Enjoy a garden, laundry facilities, and patios. Popular attractions Harriman Reservoir and The Ledge are located ... 9.8/10 Exceptional! (47 reviews) Wonderful property - bedrooms were great and heat worked well for a very cold weekend stay! Great house for a large group - appreciate the large spaces to hang out as a group - from the huge dining room table to the large living room on the third floor. Plenty of space to be together as well as be ... Reviewed on Jan 3, 2026 [](https://expedia.com/Whitingham-Hotels-Lakeside-Victorian-Mansion-WHot-Tub.h63074743.Hotel-Information) ![Peaceful Stay at Birds of a Feather Farm & Spa ](https://images.trvl-media.com/lodging/90000000/89710000/89700500/89700465/w906h683x59y0-81ea00c0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Peaceful Stay at Birds of a Feather Farm & Spa Shaftsbury VT Stay at this vacation home in Shaftsbury. Enjoy free WiFi, a garden, and patios. Popular attractions Howard Park and Robert Frost Stone House Museum are located ... 9.8/10 Exceptional! (33 reviews) Host was helpful via VRBO app. The location was inconvenient for me as it was too far from the event I was attending. Entrance to apartment was a-bit confusing and could be helped with signage. Very clean, pillows and mattress extremely firm(too hard and uncomfortable for me) touches of decor were ... Reviewed on Mar 5, 2026 [](https://expedia.com/Shaftsbury-Hotels-Peaceful-Country-Getaway-Birds-Of-A-Feather-Farm.h89700465.Hotel-Information) ![Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities](https://images.trvl-media.com/lodging/89000000/88640000/88639400/88639305/fce63aae_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities Dover VT Book a stay at this ski condo in West Dover. Enjoy a fitness center, tennis courts, and ski-in/ski-out access. Popular attractions Mount Snow and Seasons Ski ... 8.8/10 Excellent! (36 reviews) Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it. Reviewed on Feb 22, 2026 [](https://expedia.com/West-Dover-Hotels-Ski-Inski-Out-Condo-With-Deck.h88639305.Hotel-Information) [See all properties in Old Bennington](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=553248635976385350&sort=VACATION_RENTAL) 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. ## Check Old Bennington hotel availability [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=2026-03-09&endDate=2026-03-10)[Mar 9 - Mar 10](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=2026-03-09&endDate=2026-03-10) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=2026-03-10&endDate=2026-03-11)[Mar 10 - Mar 11](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=2026-03-10&endDate=2026-03-11) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=3%2F13%2F2026&endDate=3%2F15%2F2026)[Mar 13 - Mar 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=3%2F13%2F2026&endDate=3%2F15%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=3%2F20%2F2026&endDate=3%2F22%2F2026)[Mar 20 - Mar 22](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=3%2F20%2F2026&endDate=3%2F22%2F2026) ### Popular places to visit ![Bennington Battle Monument showing landscape views](https://images.trvl-media.com/place/6115862/63859824-3ecb-4453-aadc-662d0d0f2c45.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Bennington Battle Monument Learn about the local history of Old Bennington when you spend time at Bennington Battle Monument. In the area, take in the art scene and mountain views. [](https://expedia.com/Bennington-Battle-Monument-Bennington.d6115862.Vacation-Attraction) #### Prospect Mountain Cross-Country Ski Center Hit the slopes in Woodford with a visit to Prospect Mountain Cross-Country Ski Center. In the area, take in the festivals and mountain views. [](https://expedia.com/Prospect-Mountain-Cross-Country-Ski-Center-Bennington.d553248621533121047.Vacation-Attraction) #### Woodford State Park You can take time to visit Woodford State Park during your travels to Woodford. [](https://expedia.com/Woodford-State-Park-Bennington.d637214576238309376.Vacation-Attraction) #### Prospect Mountain Nordic Ski Center Hit the slopes in Woodford with a visit to Prospect Mountain Nordic Ski Center. Discover the area's mountain views and coffeehouses. [](https://expedia.com/Prospect-Mountain-Nordic-Ski-Center-Bennington.d553248621532649082.Vacation-Attraction) #### Southern Vermont College Explore the campus of Southern Vermont College, during your travels in Bennington. While you're here, you can savor the charming coffeehouses. [](https://expedia.com/Southern-Vermont-College-Bennington.d6329202.Vacation-Attraction) #### Bennington Museum You can spend an afternoon studying the exhibits at Bennington Museum during your travels in Old Bennington. Discover the area's mountain views and coffeehouses. [](https://expedia.com/Bennington-Museum-Bennington.d6115864.Vacation-Attraction) ### Things to do ![Vermont RT 100 Self Guided Driving Audio Tour](https://mediaim.expedia.com/localexpert/48988132/e3d55161-4da6-4678-970d-7686d5f338fa.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Vermont RT 100 Self Guided Driving Audio Tour $17 per traveler [](https://expedia.com/things-to-do/vermont-rt-100-self-guided-driving-audio-tour.a48988132.activity-details) [See all activities in Old Bennington](https://expedia.com/Things-To-Do-In-Old-Bennington.d553248635976385350.Travel-Guide-Activities) ## Cities near Old Bennington ![Silk Road covered bridge with trees showing fall colors near Paper Mill Village, Vermont.](https://images.trvl-media.com/place/6057349/050d26ec-80e0-46da-960f-412404f2cf24.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Bennington - Cities near Old Bennington - Places of interest [Bennington](https://expedia.com/Bennington.dx6057349) - [Bennington Battle Monument ](https://expedia.com/Bennington-Battle-Monument-Bennington.d6115862.Vacation-Attraction) - [Bennington Museum ](https://expedia.com/Bennington-Museum-Bennington.d6115864.Vacation-Attraction) - [Old First Congregational Church ](https://expedia.com/Old-First-Congregational-Church-Bennington.d6329594.Vacation-Attraction) - [Mount Snow ](https://expedia.com/Mount-Snow-West-Dover.d6115918.Vacation-Attraction) - [Williams College ](https://expedia.com/Williams-College-Williamstown.d6091833.Vacation-Attraction) - [Green Mountain National Forest ](https://expedia.com/Green-Mountain-National-Forest-Vermont.d6115904.Vacation-Attraction) - [Massachusetts Museum of Contemporary Art ](https://expedia.com/Massachusetts-Museum-Of-Contemporary-Art-North-Adams.d6091827.Vacation-Attraction) - [The Clark Art Institute ](https://expedia.com/The-Clark-Art-Institute-Williamstown.d553248621533116688.Vacation-Attraction) - [Mount Greylock ](https://expedia.com/Mount-Greylock-Adams.d6091829.Vacation-Attraction) - [Mount Equinox ](https://expedia.com/Mount-Equinox-Arlington.d6330471.Vacation-Attraction) - [Mount Snow Golf Course ](https://expedia.com/Mount-Snow-Golf-Course-West-Dover.d553248621587242570.Vacation-Attraction) - [Bennington College ](https://expedia.com/Bennington-College-North-Bennington.d6330089.Vacation-Attraction) - [Williamstown Theatre Festival ](https://expedia.com/Williamstown-Theatre-Festival-Williamstown.d553248621532665542.Vacation-Attraction) - [Lake Shaftsbury State Park ](https://expedia.com/Lake-Shaftsbury-State-Park-Shaftsbury.d553248621551385179.Vacation-Attraction) - [The Hermitage Golf Club ](https://expedia.com/The-Hermitage-Golf-Club-Wilmington.d6225104.Vacation-Attraction) - [Prospect Mountain Cross-Country Ski Center ](https://expedia.com/Prospect-Mountain-Cross-Country-Ski-Center-Bennington.d553248621533121047.Vacation-Attraction) - [Battenkill River ](https://expedia.com/Battenkill-River-United-States-of-America.d553248621532665333.Vacation-Attraction) - [Willard Mountain ](https://expedia.com/Willard-Mountain-Greenwich.d553248621532665323.Vacation-Attraction) - [Deerfield River ](https://expedia.com/Deerfield-River-United-States-of-America.d682156682122641408.Vacation-Attraction) - [Natural Bridge State Park ](https://expedia.com/Natural-Bridge-State-Park-North-Adams.d553248621560926711.Vacation-Attraction) - [Taconic Golf Club ](https://expedia.com/Taconic-Golf-Club-Williamstown.d553248621561173642.Vacation-Attraction) - [Grafton Lakes State Park ](https://expedia.com/Grafton-Lakes-State-Park-New-York.d6173181.Vacation-Attraction) - [Western Gateway Heritage State Park ](https://expedia.com/Western-Gateway-Heritage-State-Park-North-Adams.d553248621532666699.Vacation-Attraction) - [Harriman Reservoir ](https://expedia.com/Harriman-Reservoir-Vermont.d762079879267004416.Vacation-Attraction) - [Sugar Shack ](https://expedia.com/Sugar-Shack-Arlington.d553248621532665335.Vacation-Attraction) - [Bennington Battlefield Historic Site ](https://expedia.com/Bennington-Battlefield-Historic-Site-Hoosick-Falls.d553248621533116695.Vacation-Attraction) - [Prospect Mountain Nordic Ski Center ](https://expedia.com/Prospect-Mountain-Nordic-Ski-Center-Bennington.d553248621532649082.Vacation-Attraction) - [Southern Vermont College ](https://expedia.com/Southern-Vermont-College-Bennington.d6329202.Vacation-Attraction) - [Grand Summit Express Ski Lift ](https://expedia.com/Grand-Summit-Express-Ski-Lift-West-Dover.d750248025374998528.Vacation-Attraction) - [Taconic Lake ](https://expedia.com/Taconic-Lake-New-York.d3000449664.Vacation-Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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