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 $508 CA $620 total Dec 17 - Dec 18 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! (555 reviews) I stay at Woodstock Inn every December and it never disappoints. The rooms are comfortable and well-appointed, but it's hard to decide whether to enjoy the comforts of the room or sitting in front if the fire in the lobby. I look forward to the next visit. Reviewed on Dec 13, 2025 [](https://expedia.ca/Hotel-Search?startDate=17%2F12%2F2025&endDate=18%2F12%2F2025&selected=25690&PinnedHotelID=25690&HadPinnedHotel=true®ionId=89014) ![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pointe at Castle Hill Resort 2940 State Route 103 Cavendish VT CA $198 CA $226 total Dec 17 - Dec 18 includes taxes & fees Book a stay at this spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ... 8.6/10 Excellent! (927 reviews) Yea Reviewed on Dec 12, 2025 [](https://expedia.ca/Hotel-Search?startDate=17%2F12%2F2025&endDate=18%2F12%2F2025&selected=1823093&PinnedHotelID=1823093&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 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! (887 reviews) After reading reviews I was pleasantly surprised of the high quality of our room. We had a premium king room in the river house. Was large and bathroom was also large with a jacuzzi tub, shared balcony overlooking the river. Walking distance to town, shops and restaurants. Only stayed one night for ... Reviewed on Dec 7, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&selected=10453651&PinnedHotelID=10453651&HadPinnedHotel=true®ionId=89014) [](https://expedia.ca/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&selected=10453651&PinnedHotelID=10453651&HadPinnedHotel=true®ionId=89014) [See all 3,066 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=17%2F12%2F2025&endDate=18%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=2025-12-16&endDate=2025-12-17)[Dec 16 - Dec 17](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-12-16&endDate=2025-12-17) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-12-17&endDate=2025-12-18)[Dec 17 - Dec 18](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=2025-12-17&endDate=2025-12-18) [This 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) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=26%2F12%2F2025&endDate=28%2F12%2F2025)[Dec 26 - Dec 28](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89014&startDate=26%2F12%2F2025&endDate=28%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) - [Vermont Country Store ](https://expedia.ca/Vermont-Country-Store-Bellows-Falls.d553248621532666908.Vacation-Attraction) - [Billings Farm and Museum ](https://expedia.ca/Billings-Farm-And-Museum-Woodstock.d6175222.Vacation-Attraction) - [Golf Club at Equinox ](https://expedia.ca/Golf-Club-At-Equinox-Manchester-Village-Historic-District.d6179922.Vacation-Attraction) - [American Express Ski Lift ](https://expedia.ca/American-Express-Ski-Lift-Stratton.d6328793.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) ![](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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