Title: Book the Best BOUTIQUE Hotels in Chester in 2025 | 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) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/boutique.jpeg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Boutique Hotels in Chester, VT ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chester Boutique Hotels Tonight [Sep 28 - Sep 29](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-09-28&endDate=2025-09-29&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 29 - Sep 30](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-09-29&endDate=2025-09-30&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-03&endDate=2025-10-05&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-10&endDate=2025-10-12&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chester Boutique Hotels ## Top Chester Hotel Reviews ![Latchis Hotel](//images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg) ### Latchis Hotel 10/10 Excellent "Very cute vintage stay, prompt communicative staff. Walkable to a very cute bookstore, coffee, breakfast spots and a vegan restaurant (vegan AF) that was 10/10. Beautiful view and accessible parking. " [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ![Kimpton Taconic Hotel by IHG](//images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/72cb9377_y.jpg) ### Kimpton Taconic Hotel by IHG 10/10 Excellent "Great checkout. Friendliness." [](https://expedia.ca/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.Hotel-Information) ## Frequently asked questions ### What's there to see and do in Chester? > The shopping, coffeehouses, and skiing are just some of the things to enjoy while you're in the area. Activities and attractions to experience around Chester include DaVallia Art & Accents, Vermont Museum of Mining and Minerals, and Plummer's Sugar House. You might also want to consider exploring Vermont Country Store, Lowell Lake State Park, and Magic Mountain Ski Resort while you're here. ### What kind of weather should I plan for when I travel to Chester? > Having a good idea of the weather in Chester will help you enjoy your stay to the fullest. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall. ### What's the best way to get to my boutique hotel in Chester? > You have a few options for traveling to and around Chester. The closest major airport is Springfield, VT (VSF-Hartness State), which is located 6.6 mi (10.7 km) from the heart of the city, but Rutland, VT (RUT-Rutland Southern Vermont Regional) may also be an option. 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