Title: Visit Old Bennington: Best of Old Bennington Tourism | Expedia Travel Guide - Expedia.ca [Hotels in Old Bennington](https://expedia.ca/Old-Bennington-Hotels.d553248635976385350.Travel-Guide-Hotels)[Vacation Rentals in Old Bennington](https://expedia.ca/Old-Bennington-Vacation-Rentals.d553248635976385350.Travel-Guide-VacationRentals)[Old Bennington Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Bennington.d553248635976385350.Car-Rental-Guide)[Old Bennington Vacation Packages](https://expedia.ca/Old-Bennington.d553248635976385350.Destination-Travel-Guides) # Old Bennington ## 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.ca/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/a1fa9bf1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Four Chimneys Inn 21 West Road Bennington VT 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 ... 9.6/10 Exceptional! (223 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 [Get rates](https://expedia.ca/Hotel-Search?startDate=04%2F03%2F2026&endDate=05%2F03%2F2026&selected=2394036&PinnedHotelID=2394036&HadPinnedHotel=true®ionId=553248635976385350) [](https://expedia.ca/Hotel-Search?startDate=04%2F03%2F2026&endDate=05%2F03%2F2026&selected=2394036&PinnedHotelID=2394036&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 CA $271 CA $303 total Mar 11 - Mar 12 includes taxes & 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! (573 reviews) A beautiful hotel to stay at while visiting the Williams campus. Our room had a nice view of the woods. Rooms were clean and with comfortable beds. The common areas of the hotel were beautiful and cozy with the fireplaces going. Easy check in and out with friendly staff. Reviewed on Feb 7, 2026 [](https://expedia.ca/Hotel-Search?startDate=11%2F03%2F2026&endDate=12%2F03%2F2026&selected=35658765&PinnedHotelID=35658765&HadPinnedHotel=true®ionId=553248635976385350) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Downstreet, an Ascend Collection Hotel 40 Main St North Adams MA CA $155 CA $173 total Mar 17 - Mar 18 includes taxes & 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) Spotless and front desk staff...friendly and accommodating Reviewed on Feb 11, 2026 [](https://expedia.ca/Hotel-Search?startDate=17%2F03%2F2026&endDate=18%2F03%2F2026&selected=2943&PinnedHotelID=2943&HadPinnedHotel=true®ionId=553248635976385350) [See all 1,010 properties in Old Bennington](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=19%2F02%2F2026&endDate=20%2F02%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. ![Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities](https://images.trvl-media.com/lodging/89000000/88640000/88639400/88639305/c941b5c2_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 ... 8.2/10 Very Good! (25 reviews) The local Vacasa team is very responsive.The accommodations are ok but the location can't be beat.There is an endless supply of firewood to have a fire, which was really nice. The ski locker outside makes it easy to get on and off the slopes.To get to the slopes, you walk out the front door to the ... Reviewed on Feb 13, 2026 [](https://expedia.ca/West-Dover-Hotels-Ski-Inski-Out-Condo-With-Deck.h88639305.Hotel-Information) ![Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym](https://images.trvl-media.com/lodging/101000000/100580000/100576200/100576128/4d4f4b44_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym Wilmington VT Stay at this cabin in Wilmington. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Mount Snow and The Hermitage Golf Club are located ... 6.4/10 (6 reviews) The house was clean and well set up We had everything we needed and moreIt was a wonderful place to stay! Reviewed on Oct 28, 2025 [](https://expedia.ca/Wilmington-Hotels-Classic-Vermont-Cabin-With-Forest-Views.h100576128.Hotel-Information) ![Elegant house w/ mountain views, trail to riverfront, balcony, dog-friendly, bbq](https://images.trvl-media.com/lodging/114000000/113820000/113818900/113818880/bb5dbe76_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Elegant house w/ mountain views, trail to riverfront, balcony, dog-friendly, bbq Readsboro VT Book a stay at this family-friendly vacation home in Readsboro. Enjoy a garden, laundry facilities, and patios. Popular attractions Readsboro Community Library ... 10/10 Exceptional! (4 reviews) The house was beautiful. So cozy and private. We enjoyed our stay Reviewed on Dec 29, 2025 [](https://expedia.ca/Readsboro-Hotels-Elegant-House-W-Mountain-Views.h113818880.Hotel-Information) [See all properties in Old Bennington](https://expedia.ca/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.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=2026-02-18&endDate=2026-02-19)[Feb 18 - Feb 19](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=2026-02-18&endDate=2026-02-19) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=2026-02-19&endDate=2026-02-20)[Feb 19 - Feb 20](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=2026-02-19&endDate=2026-02-20) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026)[Feb 20 - Feb 22](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=27%2F02%2F2026&endDate=01%2F03%2F2026)[Feb 27 - Mar 1](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976385350&startDate=27%2F02%2F2026&endDate=01%2F03%2F2026) ### Popular places to visit ![Bennington Battle Monument featuring 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.ca/Bennington-Battle-Monument-Bennington.d6115862.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.ca/Prospect-Mountain-Nordic-Ski-Center-Bennington.d553248621532649082.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.ca/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.ca/Woodford-State-Park-Bennington.d637214576238309376.Vacation-Attraction) #### Old First Congregational Church Find out about the history of Old Bennington with a stop at Old First Congregational Church. In the area, take in the art scene and mountain views. [](https://expedia.ca/Old-First-Congregational-Church-Bennington.d6329594.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.ca/Southern-Vermont-College-Bennington.d6329202.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 CA $23 per traveller [](https://expedia.ca/things-to-do/vermont-rt-100-self-guided-driving-audio-tour.a48988132.activity-details) [See all activities in Old Bennington](https://expedia.ca/Things-To-Do-In-Old-Bennington.d553248635976385350.Travel-Guide-Activities) - Cities near Old Bennington - Places of interest - [Mount Snow ](https://expedia.ca/Mount-Snow-West-Dover.d6115918.Vacation-Attraction) - [Green Mountain National Forest ](https://expedia.ca/Green-Mountain-National-Forest-Vermont.d6115904.Vacation-Attraction) - [Mount Equinox ](https://expedia.ca/Mount-Equinox-Arlington.d6330471.Vacation-Attraction) - [Lake Shaftsbury State Park ](https://expedia.ca/Lake-Shaftsbury-State-Park-Shaftsbury.d553248621551385179.Vacation-Attraction) - [Sugar Shack ](https://expedia.ca/Sugar-Shack-Arlington.d553248621532665335.Vacation-Attraction) - [Western Gateway Heritage State Park ](https://expedia.ca/Western-Gateway-Heritage-State-Park-North-Adams.d553248621532666699.Vacation-Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points 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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