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, Bonnie's Bundles Dolls and DaVallia Art & Accents 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 $468 CA $576 total Dec 16 - Dec 17 includes taxes & fees Book a stay at this 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! (553 reviews) Top notch service. Great property and beautiful room. Went for anniversary and it did not disappoint. Romantic hotel and town Reviewed on Nov 26, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F12%2F2025&endDate=17%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 $155 CA $180 total Dec 10 - Dec 11 includes taxes & fees Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. ... 8.6/10 Excellent! (885 reviews) Wonderful place to stay! Reviewed on Dec 3, 2025 [](https://expedia.ca/Hotel-Search?startDate=10%2F12%2F2025&endDate=11%2F12%2F2025&selected=10453651&PinnedHotelID=10453651&HadPinnedHotel=true®ionId=89014) ![The Equinox Golf Resort & Spa](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Equinox Golf Resort & Spa 3567 Main Street Route 7A Manchester VT CA $227 CA $326 total Dec 11 - Dec 12 includes taxes & fees Book a stay at this luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Popular attractions Golf Club at Equinox and American ... 7.4/10 Good! (572 reviews) Courteous staff Clean room Reviewed on Nov 22, 2025 [](https://expedia.ca/Hotel-Search?startDate=11%2F12%2F2025&endDate=12%2F12%2F2025&selected=2759006&PinnedHotelID=2759006&HadPinnedHotel=true®ionId=89014) [See all 3,050 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=10%2F12%2F2025&endDate=11%2F12%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 VT 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) ![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 Book a stay at this ski aparthotel in Stratton. Enjoy free WiFi, free parking, and 10 restaurants. Popular attractions Stratton Mountain Resort and Villager ... 8.4/10 Very Good! (77 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) ![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 Book a stay at this ski cabin in Killington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Killington Resort and Pico Mountain at Killington ... 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) [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 [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-12-09&endDate=2025-12-10)[Dec 9 - Dec 10](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-12-09&endDate=2025-12-10) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-12-10&endDate=2025-12-11)[Dec 10 - Dec 11](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-12-10&endDate=2025-12-11) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=12%2F12%2F2025&endDate=14%2F12%2F2025)[Dec 12 - Dec 14](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=12%2F12%2F2025&endDate=14%2F12%2F2025) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=19%2F12%2F2025&endDate=21%2F12%2F2025)[Dec 19 - Dec 21](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=19%2F12%2F2025&endDate=21%2F12%2F2025) ### Popular places to visit #### 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) #### 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) ## 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 ![Weston](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94317-Weston.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Weston ![Photo by Ed Gaffny](https://mediaim.expedia.com/destination/2/13052aa4a5c8af2074b472b24fe19c69.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Perkinsville - 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) - [Mount Snow ](https://expedia.ca/Mount-Snow-West-Dover.d6115918.Vacation-Attraction) - [Killington Resort ](https://expedia.ca/Killington-Resort-Killington.d6082887.Vacation-Attraction) - [Bromley Mountain Ski Resort ](https://expedia.ca/Bromley-Mountain-Ski-Resort-Bromley-Mountain.d6115890.Vacation-Attraction) - [Green Mountain National Forest ](https://expedia.ca/Green-Mountain-National-Forest-Vermont.d6115904.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) - [Vermont Country Store ](https://expedia.ca/Vermont-Country-Store-Bellows-Falls.d553248621532666908.Vacation-Attraction) - [American Express Ski Lift ](https://expedia.ca/American-Express-Ski-Lift-Stratton.d6328793.Vacation-Attraction) - [Golf Club at Equinox ](https://expedia.ca/Golf-Club-At-Equinox-Manchester.d6179922.Vacation-Attraction) - [Landmark College ](https://expedia.ca/Landmark-College-Putney.d553248635937215663.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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