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 ![Old Bennington](https://images.trvl-media.com/place/6115862/c54b3750-17e2-410d-8469-3dda6fc27801.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Old Bennington](https://images.trvl-media.com/place/6057349/c2fb96a0-6411-4fe1-b288-d5ba2aaf3ada.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Old Bennington](https://images.trvl-media.com/place/6005393/7cbd9cb1-4263-4f4c-aca5-d9688c3a42f9.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Old Bennington](https://images.trvl-media.com/place/6115862/2be49982-b4c1-462e-82d0-d55b8a211643.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Old Bennington](https://images.trvl-media.com/place/6115862/1f7f8703-3956-45d5-b009-d10e981d0f35.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Old Bennington Things to do - 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 Fully refundable $222 nightly $242 total May 4 - May 5 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 ... [](https://expedia.com/Hotel-Search?startDate=5%2F4%2F2026&endDate=5%2F5%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/d239029a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Downstreet, an Ascend Collection Hotel 40 Main St North Adams MA $131 nightly $146 total May 3 - May 4 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! (1,001 reviews) Loud refrigerator overall 2.5 stars in terms of condition of the hotel Staff is friendly Reviewed on Apr 5, 2026 [](https://expedia.com/Hotel-Search?startDate=5%2F3%2F2026&endDate=5%2F4%2F2026&selected=2943&PinnedHotelID=2943&HadPinnedHotel=true®ionId=553248635976385350) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Williams Inn 101 Spring Street Williamstown MA $263 nightly $294 total Apr 7 - Apr 8 Total with taxes and fees Book a stay at this business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ... 9.6/10 Exceptional! (607 reviews) solid 4 stars, clean and comfy rooms Reviewed on Apr 5, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F7%2F2026&endDate=4%2F8%2F2026&selected=35658765&PinnedHotelID=35658765&HadPinnedHotel=true®ionId=553248635976385350) [See all 1,014 properties in Old Bennington](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=4%2F7%2F2026&endDate=4%2F8%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. ![Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake](https://images.trvl-media.com/lodging/110000000/109420000/109415600/109415543/0f4e686a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake Whitingham VT Stay at this apartment in Whitingham. Enjoy free breakfast, a sauna, and laundry facilities. Popular attractions Harriman Reservoir and Readsboro Community Library ... 10/10 Exceptional! (3 reviews) Gorgeous views even in March, ample heating/cooling, wonderful host experience, would just recommend bringing paper plates/utensils as we found ourselves running the dishwasher often. Reviewed on Mar 19, 2026 [](https://expedia.com/Whitingham-Hotels-Amazing-34-Foot-High-Shipping-Container-Home-In-Whitingham-On-Sadawga-Lake.h109415543.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! (32 reviews) Great place Reviewed on Feb 27, 2026 [](https://expedia.com/Shaftsbury-Hotels-Peaceful-Country-Getaway-Birds-Of-A-Feather-Farm.h89700465.Hotel-Information) ![Seasons On Mount Snow - Ski-in/Ski-out ](https://images.trvl-media.com/lodging/19000000/18980000/18978400/18978320/e86c9094_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Seasons On Mount Snow - Ski-in/Ski-out Dover VT Book a stay at this ski condo in West Dover. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Mount Snow and Seasons Ski Lift are ... 9.8/10 Exceptional! (187 reviews) Missing a few basic items which have always been included in the past. Tissues, napkins, and sugar. Also the fireplace was not cleaned and the doors very dirty. Reviewed on Mar 11, 2026 [](https://expedia.com/West-Dover-Hotels-Seasons-On-Mount-Snow-Ski-Inski-Out.h18978320.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=2026-04-06&endDate=2026-04-07)[Apr 6 - Apr 7](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=2026-04-06&endDate=2026-04-07) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=2026-04-07&endDate=2026-04-08)[Apr 7 - Apr 8](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=2026-04-07&endDate=2026-04-08) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=4%2F10%2F2026&endDate=4%2F12%2F2026)[Apr 10 - Apr 12](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=4%2F10%2F2026&endDate=4%2F12%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=4%2F17%2F2026&endDate=4%2F19%2F2026)[Apr 17 - Apr 19](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=4%2F17%2F2026&endDate=4%2F19%2F2026) ### Popular places to visit ![Bennington Battle Monument](https://images.trvl-media.com/place/6115862/63859824-3ecb-4453-aadc-662d0d0f2c45.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Bennington Battle Monument 4.5/5(72 reviews) 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 4.5/5(11 reviews) 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) #### Bennington Museum 4.5/5(11 reviews) 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) #### 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) #### Hemmings Motor News Car Lover's Convenience Store & Vehicle Display 4.5/5(2 reviews) You can spend an afternoon browsing the exhibits at Hemmings Motor News Car Lover's Convenience Store & Vehicle Display in Bennington. While you're here, you can savor the charming coffeehouses. [](https://expedia.com/Hemmings-Motor-News-Car-Lovers-Convenience-Store-Vehicle-Display-Bennington.d553248621533116692.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) ### Things to do ![Vermont RT 100 Self Guided Driving Audio Tour](https://mediaim.expedia.com/localexpert/48988132/fc006ec3-5e60-4c71-81f0-c520c3a7c8ec.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) - [Williamstown Theatre Festival ](https://expedia.com/Williamstown-Theatre-Festival-Williamstown.d553248621532665542.Vacation-Attraction) - [Mount Snow Golf Course ](https://expedia.com/Mount-Snow-Golf-Course-West-Dover.d553248621587242570.Vacation-Attraction) - [Grafton Lakes State Park ](https://expedia.com/Grafton-Lakes-State-Park-New-York.d6173181.Vacation-Attraction) - [Bennington College ](https://expedia.com/Bennington-College-North-Bennington.d6330089.Vacation-Attraction) - [Battenkill River ](https://expedia.com/Battenkill-River-United-States-of-America.d553248621532665333.Vacation-Attraction) - [Lake Shaftsbury State Park ](https://expedia.com/Lake-Shaftsbury-State-Park-Shaftsbury.d553248621551385179.Vacation-Attraction) - [Prospect Mountain Cross-Country Ski Center ](https://expedia.com/Prospect-Mountain-Cross-Country-Ski-Center-Bennington.d553248621533121047.Vacation-Attraction) - [Taconic Golf Club ](https://expedia.com/Taconic-Golf-Club-Williamstown.d553248621561173642.Vacation-Attraction) - [Harriman Reservoir ](https://expedia.com/Harriman-Reservoir-Vermont.d762079879267004416.Vacation-Attraction) - [Deerfield River ](https://expedia.com/Deerfield-River-United-States-of-America.d682156682122641408.Vacation-Attraction) - [The Hermitage Golf Club ](https://expedia.com/The-Hermitage-Golf-Club-Wilmington.d6225104.Vacation-Attraction) - [Natural Bridge State Park ](https://expedia.com/Natural-Bridge-State-Park-North-Adams.d553248621560926711.Vacation-Attraction) - [Sugar Shack ](https://expedia.com/Sugar-Shack-Arlington.d553248621532665335.Vacation-Attraction) - [Norman Rockwell Exhibition ](https://expedia.com/Norman-Rockwell-Exhibition-Arlington.d553248621532665334.Vacation-Attraction) - [Waubeeka Golf Links ](https://expedia.com/Waubeeka-Golf-Links-Williamstown.d553248621561173643.Vacation-Attraction) - [Western Gateway Heritage State Park ](https://expedia.com/Western-Gateway-Heritage-State-Park-North-Adams.d553248621532666699.Vacation-Attraction) - [Sterling and Francine Clark Art Institute ](https://expedia.com/Sterling-And-Francine-Clark-Art-Institute-Williamstown.d6091835.Vacation-Attraction) - [Windsor Lake Park ](https://expedia.com/Windsor-Lake-Park-North-Adams.d553248621560926712.Vacation-Attraction) - [Hemmings Motor News Car Lover's Convenience Store & Vehicle Display ](https://expedia.com/Hemmings-Motor-News-Car-Lovers-Convenience-Store-Vehicle-Display-Bennington.d553248621533116692.Vacation-Attraction) - [Bennington Battlefield Historic Site ](https://expedia.com/Bennington-Battlefield-Historic-Site-Hoosick-Falls.d553248621533116695.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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