Title: Visit Chester: Best of Chester Tourism | Expedia Travel Guide - Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d89014.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d89014.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d89014.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d89014.Destination-Travel-Guides) # Chester ## Travel Guide ## Visit Chester Where to stay ### Where to stay in Chester ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Chester Depot If you're spending some time in Chester Depot, DaVallia Art & Accents and Bonnie's Bundles Dolls are top sights worth seeing. [](https://expedia.ca/Chester-Chester-Depot.dx553248635976384383) - Chester Hotel Deals - Vacation Rentals in Chester ![Woodstock Inn & Resort](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Woodstock Inn & Resort Fourteen The Green, Woodstock, VT CA $447 CA $553 total Nov 30 - Dec 1 includes taxes & fees Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ... 9.2/10 Wonderful! (545 reviews) The staff were so welcoming and friendly! When we got engaged they all cheered for us and were so sweet! Reviewed on Oct 31, 2025 [](https://expedia.ca/Hotel-Search?startDate=30%2F11%2F2025&endDate=01%2F12%2F2025&selected=25690&PinnedHotelID=25690&HadPinnedHotel=true®ionId=89014) ![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Shire Woodstock 46 Pleasant St., Woodstock, VT CA $163 CA $190 total Nov 11 - Nov 12 includes taxes & fees Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ... 8.6/10 Excellent! (870 reviews) Great location, walking distance to downtown Woodstock and there’s a grocery store across the street. Parking was easy and we loved the fire pits in the back at night. Room was spacious but felt a bit dated and dirty. Other than that it was great for a fall weekend in Woodstock. Reviewed on Nov 3, 2025 [](https://expedia.ca/Hotel-Search?startDate=11%2F11%2F2025&endDate=12%2F11%2F2025&selected=10453651&PinnedHotelID=10453651&HadPinnedHotel=true®ionId=89014) ![Jackson Gore Village](https://images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Jackson Gore Village 111 Jackson Gore Road, Ludlow, VT CA $261 CA $317 total Nov 6 - Nov 7 includes taxes & fees Stay at this 3-star spa hotel in Ludlow. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition ... 8.6/10 Excellent! (820 reviews) The room overall was nice. There were lots of marks on the walls and baseboards. However everything was pretty clean and the fireplace was a nice touch. Unfortunately due to the time of the year we were on our own for food. I wish they told us this ahead of hour stay. Otherwise it was a nice.stay. ... Reviewed on Oct 29, 2025 [](https://expedia.ca/Hotel-Search?startDate=06%2F11%2F2025&endDate=07%2F11%2F2025&selected=2417009&PinnedHotelID=2417009&HadPinnedHotel=true®ionId=89014) [See all 3,005 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=05%2F11%2F2025&endDate=06%2F11%2F2025®ionId=89014) 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. ![Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area](https://images.trvl-media.com/lodging/89000000/88940000/88933400/88933370/b26aecc3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area Chester Stay at this cabin in Chester. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial ... 9.8/10 Exceptional! (23 reviews) Hidden gem! This lovingly built off-grid glamping cabin is drenched with sun! It’s absolutely gorgeous! The kids enjoyed pumping their own water and sledding down the front hill. Paris is an excellent hostess- she answered all our questions very promptly & thoroughly. We cant wait to come back! Thank you!!! Reviewed on Feb 24, 2025 [](https://expedia.ca/Chester-Hotels-Luxury-Glamping-Cabin-Close-To-Hiking-And-15-Minutes-From-Ski-Area.h88933370.Hotel-Information) ![Ski in & out Spruce Glen Townhomes on Great Eastern Trail](https://images.trvl-media.com/lodging/22000000/21440000/21432600/21432554/6ca4befa_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Ski in & out Spruce Glen Townhomes on Great Eastern Trail 3387 East Mountain Road, Killington, VT Stay at this 3-star ski cabin in Killington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Killington Resort and Skyeship Express Gondola Stage ... 9/10 Wonderful! (53 reviews) Arrived after dark. Didn’t know where to park. Very secluded. Outside light would not stay lit. Upstairs needs attention. Reviewed on Oct 27, 2025 [](https://expedia.ca/Killington-Hotels-Ski-In-Out-Spruce-Glen-Townhomes-On-Great-Eastern-Trail.h21432554.Hotel-Information) ![Long Trail House at Stratton Mountain Resort](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/31db03a1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Long Trail House at Stratton Mountain Resort 761 Stratton Access Rd, Stratton, VT Stay at this 3-star ski aparthotel in Stratton. Enjoy free WiFi, free parking, and 10 restaurants. Popular attractions Stratton Mountain Resort and Villager ... 8.4/10 Very Good! (76 reviews) Nice lodge. Room needs updating Reviewed on Oct 19, 2025 [](https://expedia.ca/Stratton-Hotels-Long-Trail-House-At-Stratton-Mountain-Resort.h6602401.Hotel-Information) [See all properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=89014&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 Chester hotel availability [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-11-04&endDate=2025-11-05) [Tonight](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-11-04&endDate=2025-11-05) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-11-04&endDate=2025-11-05) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-11-04&endDate=2025-11-05)[Nov 4 - Nov 5](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-11-04&endDate=2025-11-05) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-11-05&endDate=2025-11-06) [Tomorrow night](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-11-05&endDate=2025-11-06) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-11-05&endDate=2025-11-06) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-11-05&endDate=2025-11-06)[Nov 5 - Nov 6](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-11-05&endDate=2025-11-06) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=07%2F11%2F2025&endDate=09%2F11%2F2025) [This weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=07%2F11%2F2025&endDate=09%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=07%2F11%2F2025&endDate=09%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=07%2F11%2F2025&endDate=09%2F11%2F2025)[Nov 7 - Nov 9](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=07%2F11%2F2025&endDate=09%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=14%2F11%2F2025&endDate=16%2F11%2F2025) [Next weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=14%2F11%2F2025&endDate=16%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=14%2F11%2F2025&endDate=16%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=14%2F11%2F2025&endDate=16%2F11%2F2025)[Nov 14 - Nov 16](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=14%2F11%2F2025&endDate=16%2F11%2F2025) ## Cities near Chester ![Ludlow showing street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94298-Ludlow.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Ludlow [](https://expedia.ca/Ludlow.dx8496) ![Weston](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94317-Weston.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Weston [](https://expedia.ca/Weston.dx177460) ![Photo by Ed Gaffny](https://mediaim.expedia.com/destination/2/13052aa4a5c8af2074b472b24fe19c69.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Perkinsville [](https://expedia.ca/Perkinsville.dx184065) - Cities near Chester - Places of interest [Ludlow](https://expedia.ca/Ludlow.dx8496)[Weston](https://expedia.ca/Weston.dx177460)[Perkinsville](https://expedia.ca/Perkinsville.dx184065)[Andover](https://expedia.ca/Andover.dx6023580) - [Killington Resort](https://expedia.ca/Killington-Resort-Killington.d6082887.Vacation-Attraction) - [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) - [Bromley Mountain Ski Resort](https://expedia.ca/Bromley-Mountain-Ski-Resort-Bromley-Mountain.d6115890.Vacation-Attraction) - [Golf Club at Equinox](https://expedia.ca/Golf-Club-At-Equinox-Manchester.d6179922.Vacation-Attraction) - [Vermont Country Store](https://expedia.ca/Vermont-Country-Store-Bellows-Falls.d553248621532666908.Vacation-Attraction) - [Mount Ascutney](https://expedia.ca/Mount-Ascutney-Brownsville.d553248621532666931.Vacation-Attraction) - [Billings Farm and Museum](https://expedia.ca/Billings-Farm-And-Museum-Woodstock.d6175222.Vacation-Attraction) - [Landmark College](https://expedia.ca/Landmark-College-Putney.d553248635937215663.Vacation-Attraction) - [Mt Ascutney State Park](https://expedia.ca/Mt-Ascutney-State-Park-Vermont.d6175264.Vacation-Attraction) - [American Express Ski Lift](https://expedia.ca/American-Express-Ski-Lift-Stratton.d6328793.Vacation-Attraction) - [Emerald Lake State Park](https://expedia.ca/Emerald-Lake-State-Park-East-Dorset.d6265781.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. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)