Title: Chester Guest Houses from CA $284 | 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) # Search Guest Houses in Chester from CA $284 - ![](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 prices for these dates Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chester Guest Houses ![Exterior](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/3cda440a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/99e3bb30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, 1 Queen Bed](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/c06df8ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/d7fa40cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Burrell House Keene 9.6/10 Exceptional (155) "Very helpful, kind staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paitris [](https://www.expedia.ca/Keene-Hotels-The-Burrell-House.h72611296.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1153600/1153540/3cc5cffc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/2000000/1160000/1153600/1153540/d594b2f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1153600/1153540/e8fee166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1160000/1153600/1153540/d878b297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn At Quail Run Wilmington 9.0/10 Wonderful (71) "Property was just as described, it was great staying there, outdoors was beautiful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tami CA $259 CA $284 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Wilmington-Hotels-The-Inn-At-Quail-Run.h1153540.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/101000000/100710000/100702800/100702715/5fa05705.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/101000000/100710000/100702800/100702715/b5317610.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room 4, Not Pet-friendly](https://images.trvl-media.com/lodging/101000000/100710000/100702800/100702715/8b3fdb1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/101000000/100710000/100702800/100702715/8f6b12a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Weston Weston 10/10 Exceptional (9) "Beautiful accommodations! You can't use enough flattering adjectives for this property and it's staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) LISA CA $555 CA $605 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Weston-Hotels-The-Weston.h100702715.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=2025-12-16&endDate=2025-12-17®ionId=89014&adults=2&lodging=GUEST_HOUSE&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-Guest-Houses.d89014-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Guest-Houses.d89014-aaGuestHouses.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![Jackson Gore Village](https://images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148_y.jpg) ### Jackson Gore Village 10/10 Excellent "Great location, pool, hot tub, game room, staff." [](https://expedia.ca/Ludlow-Hotels-Jackson-Gore-Village.h2417009.Hotel-Information) ![Mountaineer Inn](https://images.trvl-media.com/lodging/83000000/82910000/82906200/82906124/7d61f01d_y.jpg) ### Mountaineer Inn 10/10 Excellent "The room was very clean and the beds were comfortable. The location, at the base of Mt. Snow is great. The hotel had nice decor and a free coffee bar. No breakfast, but that was ok. We never saw anyone that worked there, but that was ok too as we were sent our room # and code on the day of check-in and never had any issues." [](https://expedia.ca/West-Dover-Hotels-Mountaineer-Inn.h82906124.Hotel-Information) ![The Jackson ](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg) ### The Jackson 10/10 Excellent "Fabulous " [](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![Aspen At Manchester](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/6f88107a_y.jpg) ### Aspen At Manchester 10/10 Excellent "Great location Everything updated Pleasant greeting in lobby" [](https://expedia.ca/Bennington-Hotels-Aspen-At-Manchester.h10254459.Hotel-Information) ![Comfort Inn & Suites Brattleboro I-91](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e_y.jpg) ### Comfort Inn & Suites Brattleboro I-91 10/10 Excellent "good" [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Hampton Inn and Suites Manchester](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3_y.jpg) ### Hampton Inn and Suites Manchester 10/10 Excellent "It was great. The room was wonderful and the staff great." [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information) ![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Clean good service and location " [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![The Equinox Golf Resort & Spa](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a_y.jpg) ### The Equinox Golf Resort & Spa 10/10 Excellent "Courteous staff Clean room" [](https://expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ![Keene Elm City Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg) ### Keene Elm City Hotel, an Ascend Collection Hotel 10/10 Excellent "Perfect spot for a quick overnight- clean and conveniently located! " [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ## Find out more about Chester ## Chester Guest Houses information | Number of reviews | 235 | | --- | --- | | Accommodation | 13 Guest Houses | | Lowest Price | CA $284 | | Highest Price | CA $605 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [B&B in Andover](https://www.expedia.ca/Andover-Bed-And-Breakfast.d6023580-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Andover](https://www.expedia.ca/Andover-Chalets.d6023580-aaChalets.Travel-Guide-Accommodation) - [Country Houses in Andover](https://www.expedia.ca/Andover-Country-House.d6023580-aaCountryHouse.Travel-Guide-Accommodation) - [Andover Hotels](https://www.expedia.ca/Andover-Hotels.d6023580.Travel-Guide-Hotels) - [Inns in Andover](https://www.expedia.ca/Andover-Inns.d6023580-aaInns.Travel-Guide-Accommodation) - [Motels in Andover](https://www.expedia.ca/Andover-Motels.d6023580-aaMotels.Travel-Guide-Accommodation) - 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