Title: Book the Best Chester LUXURY Hotels - Upscale Hotels in Chester, VT | 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) ![aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont](https://images.trvl-media.com/place/89014/92c0e546-2b37-46d6-9961-c387fdf435b7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find luxury hotels in Chester, VT - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](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) - ![](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 Luxury Hotels Tonight [Nov 8 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-11-08&endDate=2025-11-09&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Nov 9 - Nov 10](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-11-09&endDate=2025-11-10&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-11-14&endDate=2025-11-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-11-21&endDate=2025-11-23&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Chester Luxury Hotels ## Top Chester Hotel Reviews ![Woodstock Inn & Resort](//images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg) ### Woodstock Inn & Resort 10/10 Excellent "I’ve traveled a lot around the world and this hotel has to be in my top 3 ever. Especially beautiful in autumn" [](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) ![The Black Bear Lodge at Stratton Mountain Resort](//images.trvl-media.com/lodging/1000000/810000/800800/800765/a75b732a_y.jpg) ### The Black Bear Lodge at Stratton Mountain Resort 10/10 Excellent "Wonderful Staff!" [](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) ![Best Western Plus Keene Hotel](//images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8_y.jpg) ### Best Western Plus Keene Hotel 10/10 Excellent "Front desk woman excellent " [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Latchis Hotel](//images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg) ### Latchis Hotel 10/10 Excellent "Friendly staff. Unique stay. " [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ![Pointe at Castle Hill Resort](//images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "We had a great experience at Resort and the room was clean and very nice. " [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![The Equinox Golf Resort & Spa](//images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a_y.jpg) ### The Equinox Golf Resort & Spa 10/10 Excellent "Nice room, comfortable bed. This is an old grand hotel in tip top shape. We often stay in this type of hotel in NH and VT and found the Equinox to be the best maintained of them all. All the architectural class of its age in virtually new condition. Nice, reasonably priced onsite dining. We didn’t use the large indoor pool but it looked first class. Pleasant staff. We hope to return. Recommend “Ok for breakfast”, a 2nd floor breakfast & lunch restaurant downtown. " [](https://expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ![Days Inn by Wyndham Keene NH](//images.trvl-media.com/lodging/1000000/60000/50400/50340/f71e05d0_y.jpg) ### Days Inn by Wyndham Keene NH 10/10 Excellent "A group of us come here every year and we never hesitate to come back. Not the Ritz, but perfectly fine and very reasonably priced to have access to a pretty nice part of NH." [](https://expedia.ca/Keene-Hotels-Days-Inn-By-Wyndham-Keene-NH.h50340.Hotel-Information) ## Frequently asked questions ### Are you looking for a luxury hotel for your stay in Chester? > Expedia can help you arrange a flight to Springfield, VT (VSF-Hartness State) airport or Rutland, VT (RUT-Rutland Southern Vermont Regional) airport, and then you can select from various places to stay that will deliver the luxury you'd like to find. Amenities are an important consideration when you plan a vacation, so we make it easy to find what you need to make your stay special. If you want a posh hotel that has a spa, an indoor pool, or luxury bedding, Expedia can help you find the best luxury hotel experience that Chester has to offer. During your visit, you might want to enjoy the restaurants and coffee shops which Chester is known for. ### When can I expect good weather in Chester? > Planning for the weather is a good way to make your trip to Chester relaxing and enjoyable, especially when you're splurging. 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 there to see and do in Chester? > Enjoy Chester with a stop at DaVallia Art & Accents, Grafton Historical Society, and Vermont Country Store. 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