Title: Book The Best Hotels in Chester, VT for 2025 from CA $118 - Compare prices by date | Expedia.ca [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 hotels in Chester, VT from CA $118 ![](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 ## Go beyond your typical stay in Chester Spa [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2025-10-27&d1=2025-10-27&endDate=2025-10-29&d2=2025-10-29&amenities=SPA_ON_SITE) Resort [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2025-10-27&d1=2025-10-27&endDate=2025-10-29&d2=2025-10-29&lodging=HOTEL_RESORT) Cabin [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2025-10-27&d1=2025-10-27&endDate=2025-10-29&d2=2025-10-29&lodging=CABIN) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2025-10-27&d1=2025-10-27&endDate=2025-10-29&d2=2025-10-29&amenities=PETS) Pool [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2025-10-27&d1=2025-10-27&endDate=2025-10-29&d2=2025-10-29&amenities=POOL) Apart hotel [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2025-10-27&d1=2025-10-27&endDate=2025-10-29&d2=2025-10-29&lodging=APART_HOTEL) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2025-10-27&d1=2025-10-27&endDate=2025-10-29&d2=2025-10-29&amenities=HOT_TUB) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2025-10-27&d1=2025-10-27&endDate=2025-10-29&d2=2025-10-29&lodging=COTTAGE) Farm [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2025-10-27&d1=2025-10-27&endDate=2025-10-29&d2=2025-10-29&lodging=AGRITOURISM) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2025-10-27&d1=2025-10-27&endDate=2025-10-29&d2=2025-10-29&travelerType=family_friendly) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2025-10-27&d1=2025-10-27&endDate=2025-10-29&d2=2025-10-29&lodging=APARTMENT) Chalet [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2025-10-27&d1=2025-10-27&endDate=2025-10-29&d2=2025-10-29&lodging=CHALET) ## Check prices for these dates Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Compare 2,996 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable. ![Garden](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/662925ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/c887af2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/69a574aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/0b7fdcd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fullerton Inn Chester Depot 8.2/10 Very good (389) "Lovely stay" CA $181 CA $197 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Chester-Hotels-Fullerton-Inn.h15845368.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/f814b3d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/ae105a01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/0f0b56c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/327ad7fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stone Hearth Inn and Eatery Chester 9.2/10 Wonderful (100) "Good breakfast and dinner options. Great location for hiking." CA $391 CA $427 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/3e81c990.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/cd86c3e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/fd07d4fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodstock Inn & Resort Woodstock 9.2/10 Wonderful (537) "Beautiful hotel!! The staff, room, and spa were fantastic!!" CA $573 CA $692 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee and/or coffee maker](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/302c3d84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/9cdca5e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/a73c2787.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Shire Woodstock Woodstock 8.8/10 Excellent (848) "great location and the staff were great" CA $169 CA $197 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/7000000/6030000/6028500/6028480/b3cf5e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/7000000/6030000/6028500/6028480/01ec4a9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas](https://images.trvl-media.com/lodging/7000000/6030000/6028500/6028480/5c87ff8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/7000000/6030000/6028500/6028480/713c7c30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Palmer House Resort, an Ascend Collection Hotel Manchester Center 8.4/10 Very good (837) "Lovely property convenient to center of town " CA $177 CA $218 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bennington-Hotels-The-Palmer-House-Resort.h6028480.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/214f3dc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/548b84a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/d24f8b0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/acbfdae2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Covered Bridge Inn Brattleboro 7.8/10 Good (1015) "Good value for a two night stay for work " CA $138 CA $152 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/6f88107a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Two Queen Accessible](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/c243995a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Guesthouse A](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/102e0e1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Guesthouse C](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/309a4723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aspen At Manchester Manchester Center 8.8/10 Excellent (596) "Very relaxing environment. " CA $158 CA $189 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bennington-Hotels-Aspen-At-Manchester.h10254459.Hotel-Information) ![Deluxe Suite](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/7b3a7c11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/4dec58ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Accessible, Dog-Friendly Double](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/53cc1cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/32c31fca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Woodstock Motel Woodstock 9.6/10 Exceptional (529) "I come to area for medical visits often and Sleep Woodstock is my new favorite stay!" CA $145 CA $183 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Woodstock-Hotels-Sleep-Woodstock-Motel.h9658860.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 2 Queen Beds, Accessible, Bathtub (Mobility & Hearing)](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/b55c319b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/w3835h2559x0y0-b5950146.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/w3835h2559x0y0-24a9373a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn and Suites Manchester Manchester Center 9.6/10 Exceptional (1010) "This was the best Hampton Inn I’ve stayed at, and location is excellent. " CA $183 CA $201 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/96a629e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna, aromatherapy, hot stone massages, deep-tissue massages](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/a736e5ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/1d2c94d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pointe at Castle Hill Resort Cavendish 8.8/10 Excellent (901) "It was a beautiful place " CA $180 CA $206 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Premium bedding, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2557x3y3-db499e38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-4a5edcca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-baca4e54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Keene Hotel Keene 8.4/10 Very good (1014) "Hotel was great." CA $209 CA $226 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Sundeck](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/34b58580.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Select Comfort beds, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/601d670f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/e38be73f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Select Comfort beds, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/fab2ddfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverside Hotel, an Ascend Collection Hotel West Chesterfield 9.6/10 Exceptional (610) "Loved my stay" CA $213 CA $231 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Keene-Hotels-Riverside-Hotel.h2877372.Hotel-Information) ![Indoor spa tub](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/a75b732a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/4c29d0ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Yoga](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/3d6e59aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/7c69c2ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Bear Lodge at Stratton Mountain Resort Stratton 7.6/10 Good (924) "What a great, cozy place! Definitely would stay here again " CA $190 CA $231 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/52ec4e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/253542e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/d6e454fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jackson Gore Village Jackson Gore Base Area 8.6/10 Excellent (794) "Nice hotel and setting, wonderful customer service" CA $245 CA $298 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Ludlow-Hotels-Jackson-Gore-Village.h2417009.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/4b2f1194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/e0c2a7a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/c6f78187.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Equinox Golf Resort & Spa Manchester 7.4/10 Good (549) "Beautiful hotel! " CA $141 CA $230 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/06298210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/61c9c6e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/501f4323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG Brownsville 9.0/10 Wonderful (759) "It is Good place to stay. We enjoyed our stay here." CA $223 CA $262 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/72cb9377.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner served; American cuisine, alfresco dining ](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/a88566dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down comforters, minibar](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/55f5385b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/1702fe64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kimpton Taconic Hotel by IHG Manchester 9.4/10 Exceptional (808) "Very nice, beautiful inn" CA $220 CA $295 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/7000000/6610000/6602400/6602387/42aae2de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 2 Bedrooms | Balcony](https://images.trvl-media.com/lodging/7000000/6610000/6602400/6602387/aa5bf8b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 2 Bedrooms](https://images.trvl-media.com/lodging/7000000/6610000/6602400/6602387/2b9fdc82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Yoga](https://images.trvl-media.com/lodging/7000000/6610000/6602400/6602387/43a87c53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vantage Point Villas at Stratton Mountain Resort Stratton 8.4/10 Very good (67) "Amazing stay - The condo was cozy and perfect for our family! " CA $316 CA $393 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Stratton-Hotels-Vantage-Point-Villas-At-Stratton-Mountain-Resort.h6602387.Hotel-Information) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/f71e05d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/7bbf2ddc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/fa5ce310.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/b4de2547.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Keene NH Keene 7.0/10 Good (1011) "Would stay again" CA $146 CA $159 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Keene-Hotels-Days-Inn-By-Wyndham-Keene-NH.h50340.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/c6676368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Fireplace, Mountainside](https://images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/ca771bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 Queen Bed, Fireplace, Mountainside](https://images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/e3012ea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/8cc0d819.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deerfield Valley Inn West Dover 9.6/10 Exceptional (69) "We had a lovely time staying here. " CA $110 CA $160 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/West-Dover-Hotels-120-Vermont-Rte-100.h99792254.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-27&endDate=2025-10-28®ionId=89014&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Hotels.d89014.Travel-Guide-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Hotels.d89014.Travel-Guide-Hotels) ## Where to stay in Chester Chester, Vermont, offers a delightful blend of relaxation and adventure, making it a perfect getaway for Canadian travellers. Explore the charming city centre for unique shops and local eateries, or venture into nearby hidden gems that showcase the area's natural beauty. Whether you're seeking a romantic escape or a budget-friendly trip, Chester’s friendly atmosphere and proximity to ski resorts and outdoor activities will create lasting memories for every visitor. - Chester Depot [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=553248635976384383) ![Chester Depot map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:ooagGr%7DezLiAcAwAqGp%40iZKgJ%7DPc%40Ya%40%3Fs%40hAgB%7E%40cIe%40%7BCq%40cAJoFjA%7DEbBmDkA_%40iAp%40wA%3FqIoFiQbAsGuIoBqFgEuBrEqFbDcH%7C%40iDJ_FhCiCvOwXpPgJnDyCtLkKhQiSnDgB%7C%40%3FhAvBr%40NdGcIhA%60%40K%7CE%7C%40dHzD%7CEp%40vBbBp%40fE_%40zBrApIfI%60D%7CErG%7CDhAdBq%40%60GkHbPW%60OaFhJq%40xC%3FvBuAfC_A%3FwAgCiAq%40_Fc%40gGiDgEeA%7BBPyFzKaDhKYdIc%40vBsGbO%7D%40zDiC%7CSJnM%7D%40rHp%40hKWtAcD%7CE&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=6tE1A6bFmLDnspvwJI_lpxoGnCw=) ### Chester Depot Chester Depot, a charming neighbourhood in Vermont, offers a delightful blend of adventure and culture year-round. With peak visitor numbers in February, August, and October, it's an ideal destination for skiing and outdoor experiences. Explore the scenic Lowell Lake State Park for hiking and nature, immerse yourself in local culture at DaVallia Art & Accents, or discover the fascinating Vermont Museum of Mining and Minerals for a family-friendly outing. Whether you seek adventure or relaxation, Chester Depot promises a memorable vacation experience in the heart of New England. [See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976384383) ### Stay near popular Chester attractions Chester, Vermont, is perfect for ski and adventure vacations, offering a variety of outdoor and cultural experiences. Visitors can explore notable attractions such as Chester Castle and the charming Chester city. The area features stunning parks and national/state parks, making it an ideal destination for families and sports enthusiasts alike. Enjoy the blend of natural beauty and local culture that Chester has to offer! [](https://expedia.ca/DaVallia-Art-Accents-Hotels.0-l553248621532666916-0.Travel-Guide-Filter-Hotels) #### DaVallia Art & Accents Explore the vibrant atmosphere of DaVallia Art & Accents, where captivating art meets rich cultural vibes, offering a unique experience for every visitor. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532666916) [](https://expedia.ca/Bonnies-Bundles-Dolls-Hotels.0-l553248621561865050-0.Travel-Guide-Filter-Hotels) #### Bonnie's Bundles Dolls Bonnie's Bundles Dolls offers a charming experience with romantic vibes, showcasing an exquisite collection of dolls that evoke nostalgia and whimsy, perfect for a memorable visit. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561865050) ## More cheap stays in Chester ![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn Brattleboro 1378 Putney Road, Brattleboro, VT CA $139 CA $153 total Nov 5 - Nov 6 includes taxes & fees 8.2/10 Very Good! (897 reviews) [](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![Keene Elm City Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Keene Elm City Hotel, an Ascend Collection Hotel 175 Key Rd, Keene, NH CA $175 CA $190 total Oct 26 - Oct 27 includes taxes & fees 8.4/10 Very Good! (915 reviews) [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![The Covered Bridge Inn](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/214f3dc0_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Covered Bridge Inn 1043 Putney Road, Brattleboro, VT CA $138 CA $152 total Oct 14 - Oct 15 includes taxes & fees 7.6/10 Good! (1,005 reviews) [](https://expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information) ![Hampton Inn and Suites Manchester](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn and Suites Manchester 4519 Main St, Manchester Center, VT CA $183 CA $201 total Oct 26 - Oct 27 includes taxes & fees 9.6/10 Exceptional! (1,005 reviews) [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information) ![The Putney Inn](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Putney Inn 57 Putney Landing Rd, Putney, VT CA $107 CA $118 total Oct 26 - Oct 27 includes taxes & fees 8.4/10 Very Good! (1,003 reviews) [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Days Inn by Wyndham Keene NH](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/f71e05d0_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Days Inn by Wyndham Keene NH 3 Ash Brook Road, Keene, NH CA $146 CA $159 total Nov 11 - Nov 12 includes taxes & fees 7/10 Good! (1,004 reviews) [](https://expedia.ca/Keene-Hotels-Days-Inn-By-Wyndham-Keene-NH.h50340.Hotel-Information) ## Hotels in Chester with star-rating ![5 Star Hotels](https://images.trvl-media.com/lodging/101000000/100710000/100702800/100702715/5fa05705_w.jpg) 5 Star Hotels 1 properties [](https://expedia.ca/5Star-Chester-Hotels.s50-0-d89014.Travel-Guide-Filter-Hotels) ![4 Star Hotels](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a_w.jpg) 4 Star Hotels 20 properties [](https://expedia.ca/4Star-Chester-Hotels.s40-0-d89014.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_w.jpg) 3 Star Hotels 269 properties [](https://expedia.ca/3Star-Chester-Hotels.s30-0-d89014.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_z.jpg) 2 Star Hotels 190 properties [](https://expedia.ca/2Star-Chester-Hotels.s20-0-d89014.Travel-Guide-Filter-Hotels) ## Find out more about Chester ### Top reasons to visit Chester - **Outdoor Adventures:** Chester is perfect for skiing, hiking, and exploring local parks, catering to all adventure enthusiasts. - **Rich History:** History buffs can explore the area’s heritage at the local history museum, offering insights into the past. - **Charming Accommodations:** Enjoy a variety of cozy bed & breakfasts and agritourism properties for a unique stay. - **Scenic Beauty:** The picturesque surroundings provide stunning views and a tranquil atmosphere away from crowds. - **Family-Friendly Activities:** Chester offers various activities for families, ensuring a well-rounded vacation experience. ### Find great hotels near Chester Discover a charming selection of accommodations in Chester, Vermont, where agritourism properties and cozy bed & breakfasts cater to every type of traveler. Whether you're seeking family-friendly options, adventurous getaways, or pet-friendly stays, Chester offers a variety of hotels and inns to ensure a memorable experience. Explore the best hotels in the area, including the inviting Chester Inn, to enjoy a delightful stay in this picturesque New England town. - **[Best Western Springfield Hotel:](https://www.expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information)** Embrace a pet-friendly getaway at the Best Western Springfield Hotel, located 12.9km from Chester. This welcoming property is perfect for travellers looking to bring their furry friends along for the adventure. With amenities tailored for pets, including designated areas for dogs and a relaxed atmosphere, guests can enjoy a comfortable stay while exploring the surrounding beauty of Vermont. Convenience meets hospitality in this family-friendly hotel, making it an excellent choice for those seeking a home away from home. - **[Pointe at Castle Hill Resort:](https://www.expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information)** Experience the perfect blend of business and leisure at Pointe at Castle Hill Resort, just 14.5km from Chester. This 3.5-star hotel caters to business travellers with accessible meeting rooms and a fully equipped business centre. For those craving adventure, the resort offers a variety of outdoor activities, including fishing, skiing, and ziplining. After an exhilarating day, unwind at the full-service spa featuring massages and body treatments. Whether you're here for business or pleasure, this resort ensures an enriching stay. - **[Jackson Gore Village:](https://www.expedia.ca/Ludlow-Hotels-Jackson-Gore-Village.h2417009.Hotel-Information)** Ideal for families and golf enthusiasts, Jackson Gore Village is located 20.9km from Chester and offers a delightful blend of relaxation and recreation. With amenities designed for children, including a playground and arcade games, families can enjoy quality time together. Golfers will appreciate the on-site golfing experience, while the full-service spa provides rejuvenating treatments like hot stone and deep tissue massages. This 3-star hotel combines family fun with wellness, making it an excellent choice for a memorable vacation. ### Things to do near Chester Chester, Vermont, offers an exciting blend of skiing and outdoor adventures, making it an ideal destination for sports enthusiasts. Visitors can enjoy various activities at local ski resorts, explore scenic sightseeing opportunities, and unwind around cozy fire pits. Whether you're hitting the slopes or relaxing in the great outdoors, Chester promises a memorable vacation experience for all. **Shopping** In Chester, visit the [Vermont Country Store](https://www.expedia.ca/Vermont-Country-Store-Hotels.0-l553248621532666908-0.Travel-Guide-Filter-Hotels), a charming spot located 9.7km away, offering unique gifts and Vermont-made products. [My Minds Design](https://www.expedia.ca/My-Minds-Design-Hotels.0-l553248621532666897-0.Travel-Guide-Filter-Hotels), also 9.7km away, features eclectic home décor. If you're up for a drive, the [West River Farmers Market](https://www.expedia.ca/West-River-Farmers-Market-Hotels.0-l553248621532666878-0.Travel-Guide-Filter-Hotels), 17.7km away, showcases local produce and crafts. **Recreation** Experience the scenic [Fox Run Golf Course](https://www.expedia.ca/Fox-Run-Golf-Course-Hotels.0-l6115888-0.Travel-Guide-Filter-Hotels), just 19.3km from Chester, where you can enjoy outdoor sports in a vibrant atmosphere. Alternatively, indulge in wellness and relaxation at [The Ice House Ice Skating](https://www.expedia.ca/The-Ice-House-Ice-Skating-Hotels.0-l825491671559647232-0.Travel-Guide-Filter-Hotels), located 20.9km away, perfect for unwinding with friends and family. **Adventure** At [Okemo Mountain Resort](https://www.expedia.ca/Okemo-Mountain-Resort-Hotels.0-l6082889-0.Travel-Guide-Filter-Hotels), located 17.7km from Chester, experience thrilling skiing amidst stunning landscapes. [Morningside Flight Park](https://www.expedia.ca/Morningside-Flight-Park-Hotels.0-l553248621532666955-0.Travel-Guide-Filter-Hotels), 19.3km away, offers breathtaking scenic flights that will elevate your adventure. For more excitement, try the [Solitude Express Ski Lift](https://www.expedia.ca/Solitude-Express-Ski-Lift-Hotels.0-l750085676808343552-0.Travel-Guide-Filter-Hotels), also 19.3km from Chester, providing exhilarating access to the slopes. **Nightlife** In Chester, Vermont, the nightlife offers a mix of culture and entertainment. The [Weston Playhouse](https://www.expedia.ca/Weston-Playhouse-Hotels.0-l6330791-0.Travel-Guide-Filter-Hotels) and [Bellows Falls Opera House](https://www.expedia.ca/Bellows-Falls-Opera-House-Hotels.0-l6330782-0.Travel-Guide-Filter-Hotels) provide captivating theatrical experiences, while [Maple Lanes](https://www.expedia.ca/Maple-Lanes-Hotels.0-l553248621532666956-0.Travel-Guide-Filter-Hotels) ArcadeAdventureZone adds an adventurous twist with fun arcade games, perfect for families and friends seeking a lively night out. *\*Distances are measured in a straight line; actual driving distances may vary depending on the route.* ### Booking tips and Expedia advantages for Chester To save money on your trip to Chester, Vermont, consider visiting during the off-peak months of April to May and November for lower accommodation prices. Tuesdays are the most affordable days to stay, while Fridays tend to be pricier. Use Expedia’s search tool to find budget-friendly options, and consider eco-certified hotels for sustainable choices. Additionally, combining your hotel, flights, and activities into an Expedia package can lead to significant savings. Take advantage of free activities in the area, and explore on foot to save on transportation costs. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Chester are April to May and November, where the prices are slightly lower. This is in comparison to January to February and October, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Chester is Tuesday. The most expensive day to stay in Chester is Friday. - **Find cheap hotels on Expedia:** Utilize Expedia’s search tool to refine your preferences based on your budget, desired location, and preferred hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are currently available. To find the best prices and deals, simply sort the price filter from lowest to highest. - **Consider bundling your trip:** You can save money by combining your hotel stay in Chester with your flights and activities by choosing an Expedia package. ### Best time to go to Chester The best time to visit Chester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chester falls in January, visitor numbers are slightly low and weather is mostly cloudy with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | --- | --- | --- | --- | --- | --- | | January | 20.7°F (-6.3°C) | Light Rain | Mostly Cloudy | Slightly Low | Slightly High | | February | 22.6°F (-5.2°C) | Light Rain | Mostly Cloudy | Slightly Low | Slightly High | | March | 30.7°F (-0.7°C) | Light Rain | Mostly Cloudy | Slightly Low | Average | | April | 42.8°F (6.0°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | May | 55.8°F (13.2°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | June | 63.1°F (17.3°C) | Light Rain | Mostly Sunny | Average | Average | | July | 69.3°F (20.7°C) | Light Rain | Mostly Sunny | Slightly High | Average | | August | 67.3°F (19.6°C) | Light Rain | Mostly Sunny | Slightly High | Average | | September | 60.3°F (15.7°C) | Light Rain | Mostly Sunny | Slightly High | Average | | October | 48.6°F (9.2°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 36.1°F (2.3°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | December | 27.3°F (-2.6°C) | Light Rain | Mostly Cloudy | Average | Average | ### The nearest major airports for your trip to Chester To visit Chester, Vermont, you have several airport options. Lebanon Municipal Airport ([LEB](https://www.expedia.ca/Lebanon-Municipal-Airport-Hotels.0-aLEB-0.Travel-Guide-Filter-Hotels)) is situated 46.7km away, with nearby accommodations like the 4-star [Hanover Inn Dartmouth](https://www.expedia.ca/Lebanon-Hotels-Hanover-Inn-Dartmouth.h3974306.Hotel-Information), 8.0km from the airport, and the 3-star [Hotel Coolidge](https://www.expedia.ca/White-River-Junction-Hotels-Hotel-Coolidge.h1100199.Hotel-Information), 3.2km from LEB. Rutland Southern Vermont Regional Airport ([RUT](https://www.expedia.ca/Rutland-Southern-Vermont-Regional-Airport-Hotels.0-aRUT-0.Travel-Guide-Filter-Hotels)) is 28.0km away, with options such as the 3.5-star [Killington Grand Hotel](https://www.expedia.ca/Killington-Hotels-Killington-Grand-Hotel.h693673.Hotel-Information), 16.1km from RUT. Lastly, Hartness State Airport (VSF) is conveniently located just 11.3km from Chester, with nearby stays like the 4-star Inn at Weathersfield, 1.6km away. Each airport offers various transportation services to ensure a smooth arrival. ## Recent reviews of Chester hotels ![Claremont Motor Lodge](//images.trvl-media.com/lodging/39000000/38320000/38317200/38317142/64648cb7_y.jpg) ### Claremont Motor Lodge 5/5 Excellent "Quiet" A verified traveller stayed at Claremont Motor Lodge Posted 2 days ago [](https://expedia.ca/Mount-Sunapee-Hotels-Claremont-Motor-Lodge.h38317142.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 5/5 Excellent "Was" A verified traveller stayed at Best Western Plus Keene Hotel Posted 3 days ago [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Jackson Gore Village](//images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148_y.jpg) ### Jackson Gore Village 5/5 Excellent "It was a great hotel with a great view. " A verified traveller stayed at Jackson Gore Village Posted 4 days ago [](https://expedia.ca/Ludlow-Hotels-Jackson-Gore-Village.h2417009.Hotel-Information) ![The Equinox Golf Resort & Spa](//images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a_y.jpg) ### The Equinox Golf Resort & Spa 5/5 Excellent "Beautiful hotel! " A verified traveller stayed at The Equinox Golf Resort & Spa Posted 4 days ago [](https://expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ![Woodstock Inn & Resort](//images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg) ### Woodstock Inn & Resort 5/5 Excellent "Very nice property. Would love to visit again." A verified traveller stayed at Woodstock Inn & Resort Posted 6 days ago [](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) ![Pointe at Castle Hill Resort](//images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg) ### Pointe at Castle Hill Resort 5/5 Excellent "Gorgeous suite, staff was so nice and helpful. " A verified traveller stayed at Pointe at Castle Hill Resort Posted 6 days ago [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](//images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a_y.jpg) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG 5/5 Excellent "The staff was very helpful, the place was comfortable with home amenities, view and property was breathtaking. " A verified traveller stayed at Holiday Inn Club Vacations Mount Ascutney Resort by IHG Posted 6 days ago [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ![Keene Elm City Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg) ### Keene Elm City Hotel, an Ascend Collection Hotel 5/5 Excellent "The staff was helpful and friendly. The breakfast was good with many choices available. The room was good and the bed was comfortable. My wife would have liked to have a hair dryer available." A verified traveller stayed at Keene Elm City Hotel, an Ascend Collection Hotel Posted 6 days ago [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Colonial Motel And Spa](//images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a_y.jpg) ### Colonial Motel And Spa 5/5 Excellent "Excellent staff" A verified traveller stayed at Colonial Motel And Spa Posted 6 days ago [](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ## Frequently asked questions ### What is the best area to stay in Chester? > Chester Depot is the premier area to stay for travellers seeking both adventure and tranquillity in Vermont. This charming village combines picturesque landscapes with a welcoming community feel. Nestled between lush mountains and serene rivers, Chester Depot offers easy access to outdoor activities such as hiking and skiing in the nearby Green Mountains. The quaint downtown area features delightful shops, local eateries, and a rich history that beckons exploration. > > > > For couples planning a romantic escape, Chester Depot provides an idyllic backdrop. Stroll hand-in-hand along the scenic paths or enjoy a cosy meal at one of the charming bistros. The peaceful surroundings and stunning views create the great setting for memorable moments together. > > > > Families will also find Chester Depot appealing, as it offers a wealth of outdoor adventures suitable for all ages. From exploring the nearby state parks to enjoying family-friendly festivals, there's something for everyone. The community's warm hospitality ensures that families feel right at home while making lasting memories. ### What are the best hotels in Chester that travellers recommend? > [Stone Hearth Inn and Eatery](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) is a highly praised option in Chester, boasting an exceptional score of 9.2. This charming inn offers breathtaking mountain views and air-conditioned comfort, making it a relaxing retreat for couples seeking a romantic getaway or simply a peaceful escape from daily life. Guests rave about the cozy atmosphere and attentive service, ensuring a memorable stay. ### What are the best family hotels in Chester? > [Stone Hearth Inn and Eatery](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) in Chester, Vermont, is a delightful family-friendly retreat, boasting a traveller review score of 9.2, which reflects its warm hospitality and friendly setting. This charming inn offers a range of amenities designed to cater to families, including complimentary cribs and rollaway beds, ensuring that everyone has a comfortable stay. Find more [child-friendly accommodations in Chester](https://www.expedia.ca/Chester-Hotels-Family-Hotel.0-0-d89014-tFamilyHotel.Travel-Guide-Filter-Hotels). ### What hotels in Chester offer free breakfast? > [Stone Hearth Inn and Eatery](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) is a charming option in Chester, Vermont, known for its friendly space and excellent service, achieving an excellent review score of 9.2 from guests. This delightful inn offers a complimentary breakfast that features a buffet, allowing guests to start their day on a delicious note while enjoying breathtaking mountain views right from the property. Find more [hotels with free breakfast in Chester](https://www.expedia.ca/Chester-Hotels-Hotels-With-Free-Breakfast.0-0-d89014-tHotelsWithFreeBreakfast.Travel-Guide-Filter-Hotels). ### What are the best budget hotels in Chester? > [Stone Hearth Inn and Eatery](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) is a charming option for budget-conscious travellers seeking both comfort and convenience. With an impressive review score of 9.2, guests rave about the complimentary buffet breakfast and free in-room WiFi, making it easy to start your day and stay connected. Nestled in a picturesque mountain location, this inn offers easy access to outdoor adventures such as skiing, mountain biking, and cross-country skiing, ensuring that families and adventure-seekers alike will find their thrills nearby. > > > > For families, the Stone Hearth Inn is particularly accommodating, providing free cribs and highchairs, along with an assortment of books and games for children. This thoughtful attention to family needs creates a inviting space for those traveling with kids. > > > > Another budget-friendly property in Chester is the [Motel in the Meadow](https://www.expedia.ca/Chester-Hotels-Motel-In-The-Meadow.h14724639.Hotel-Information), which has a review score of 8.4. This cozy motel allows pets, making it an excellent choice for families who want to travel with their furry companions. Guests appreciate the included continental breakfast and the convenience of free self-parking. View all [budget hotels in Chester](https://www.expedia.ca/Chester-Hotels-Cheap-Hotels.0-0-d89014-tCheapHotels.Travel-Guide-Filter-Hotels). ### When is the best time to go to Chester? > The best time to visit Chester is during the late spring and early autumn months, particularly in May and September. In May, temperatures typically range from 10 to 17°C, creating a refreshing atmosphere great for exploring the city's historic sites and beautiful gardens. September, with similar mild conditions, offers the added charm of a vibrant community calendar filled with events and festivals. > > > > The peak tourist season runs from July to August when Chester sees the highest influx of visitors. During these months, you can enjoy a lively atmosphere, with numerous outdoor activities and cultural events taking place. The pleasant weather encourages leisurely strolls along the River Dee or through the picturesque rows of half-timbered buildings in the city centre. > > > > If you're someone who enjoys a good balance between pleasant weather and fewer crowds, May is particularly appealing. The blooming flowers in the city's parks and gardens create an enchanting backdrop for your adventures, while the overall atmosphere remains relaxed and welcoming. Plus, with lower accommodation prices compared to the peak summer months, you'll find excellent value for your stay. > > > > September is another wonderful option, especially for couples or those interested in cultural experiences. The city often hosts events celebrating local heritage, giving you a chance to engage with the community and discover Chester's rich history. Outdoor dining becomes a delightful experience as many restaurants offer al fresco seating, allowing you to enjoy local delicacies while soaking in the charming surroundings. ### Can I cancel my hotel reservation on Expedia? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Chester hotel for you. ### How can I save on a Chester hotel booking with Expedia? > With Expedia, you'll unlock our lowest prices by becoming a member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Chester hotels. Another way to save is by booking your hotel and flights together on Expedia, where bundling can lead to significant savings. ### How much is the nightly rate at a Chester hotel? > Prices for hotels in Chester often vary, but you can find a great deal from CA $118 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. 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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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)