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 Things to do ### 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 ![Fullerton Inn](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/662925ab_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Fullerton Inn 40 The Common, Chester, VT CA $219 CA $239 total Oct 19 - Oct 20 includes taxes & fees Stay at this inn in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ... 8/10 Very Good! (371 reviews) Great Inn in a quaint town. "A wonderful little Inn with such a pleasant owner and just a great vibe there. Would absolutely recommend for a summer or winter stay. Can imagine it is beautiful in the winter." Reviewed on Aug 3, 2025 [](https://expedia.ca/Hotel-Search?startDate=19%2F10%2F2025&endDate=20%2F10%2F2025&selected=15845368&PinnedHotelID=15845368&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 $351 CA $409 total Sep 24 - Sep 25 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! (822 reviews) "." Reviewed on Sep 17, 2025 [](https://expedia.ca/Hotel-Search?startDate=24%2F09%2F2025&endDate=25%2F09%2F2025&selected=10453651&PinnedHotelID=10453651&HadPinnedHotel=true®ionId=89014) ![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 $826 CA $969 total Sep 21 - Sep 22 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! (533 reviews) Old world charm "What a wonderful inn. Same class as The Greenbrier and The Homestead. Old world charm." Reviewed on Sep 12, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F09%2F2025&endDate=22%2F09%2F2025&selected=25690&PinnedHotelID=25690&HadPinnedHotel=true®ionId=89014) [See all 2,973 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=21%2F09%2F2025&endDate=22%2F09%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! (48 reviews) "Great value, comfortable space, responsive host!" Reviewed on Aug 13, 2025 [](https://expedia.ca/Killington-Hotels-Ski-In-Out-Spruce-Glen-Townhomes-On-Great-Eastern-Trail.h21432554.Hotel-Information) ![Treehouse lifted up over a stocked trout pond up in the beautiful birch trees! ](https://images.trvl-media.com/lodging/108000000/107560000/107553700/107553693/dc9c0b14_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Treehouse lifted up over a stocked trout pond up in the beautiful birch trees! Londonderry Stay at this cabin in Londonderry. Enjoy free WiFi, a sauna, and balconies. Popular attractions Magic Mountain Ski Resort and Stratton Mountain Golf Course are ... 10/10 Exceptional! (4 reviews) Beautiful property "Had a wonderful time - brought my 5 year old daughter for a weekend and we absolutely enjoyed it." Reviewed on Jun 3, 2025 [](https://expedia.ca/Londonderry-Hotels-Treehouse-Lifted-Up-Over-A-Stocked-Trout-Pond-Up-In-The-Beautiful-Birch-Trees.h107553693.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=2025-09-20&endDate=2025-09-21) [Tonight](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-09-20&endDate=2025-09-21) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-09-20&endDate=2025-09-21) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-09-20&endDate=2025-09-21)[Sep 20 - Sep 21](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-09-20&endDate=2025-09-21) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-09-21&endDate=2025-09-22) [Tomorrow night](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-09-21&endDate=2025-09-22) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-09-21&endDate=2025-09-22) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-09-21&endDate=2025-09-22)[Sep 21 - Sep 22](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-09-21&endDate=2025-09-22) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=26%2F09%2F2025&endDate=28%2F09%2F2025) [Next weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=26%2F09%2F2025&endDate=28%2F09%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=26%2F09%2F2025&endDate=28%2F09%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=26%2F09%2F2025&endDate=28%2F09%2F2025)[Sep 26 - Sep 28](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=26%2F09%2F2025&endDate=28%2F09%2F2025) ### Popular places to visit #### DaVallia Art & Accents Enjoy an outing to DaVallia Art & Accents during your stay in Chester. You can seek out the ski slopes while in the area. [](https://expedia.ca/DaVallia-Art-Accents-Chester-Depot.d553248621532666916.Vacation-Attraction) #### Bonnie's Bundles Dolls Enjoy an outing to Bonnie's Bundles Dolls during your stay in Chester. Discover the area's mountain views, or seek out its ski slopes. [](https://expedia.ca/Bonnies-Bundles-Dolls-Chester-Depot.d553248621561865050.Vacation-Attraction) ## 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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)