Title: Book the Best BOUTIQUE Hotels in Chester in 2026 | 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) ![](https://images.trvl-media.com/place/89014/92c0e546-2b37-46d6-9961-c387fdf435b7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Boutique Hotels Tonight [Feb 16 - Feb 17](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-02-16&endDate=2026-02-17&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 17 - Feb 18](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-02-17&endDate=2026-02-18&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-02-20&endDate=2026-02-22&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-02-27&endDate=2026-03-01&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) No exact matches found, but these alternatives could be just right ## Recommended hotels in Chester ![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) ![Dining](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/0b7fdcd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/78c81c21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fullerton Inn [](https://www.expedia.ca/Chester-Hotels-Fullerton-Inn.h15845368.Hotel-Information) Chester Depot 8.2/10 Very good (416 reviews) "Great staff and service. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris CA $176 CA $191 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Chester-Hotels-Fullerton-Inn.h15845368.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/52ce2be1.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) ![Porch](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/450d23d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/7060d495.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stone Hearth Inn and Eatery [](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) Chester 9.2/10 Wonderful (112 reviews) "So great all around!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janet CA $273 CA $298 total includes taxes & fees Mar 19 - Mar 20 [](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/4ae7b7c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/d409cd42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/35c5b21d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/df792487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chester Farmhouse Ski Retreat near Slopes [](https://www.expedia.ca/Chester-Hotels-Charming-Chester-Farmhouse-Peaceful-And-Close-To-Everything.h101473310.Hotel-Information) Chester Depot 9.6/10 Exceptional (18 reviews) "House was in a perfect location. The town was adorable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle A. CA $298 CA $593 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Chester-Hotels-Charming-Chester-Farmhouse-Peaceful-And-Close-To-Everything.h101473310.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/d906295e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/8f3740a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/98b36931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/0b80abe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Vermont Cabin · Mountain Views · Near Okemo [](https://www.expedia.ca/Chester-Hotels-WhiSki-Cabin-12-Acres-With-A-Mountain-View.h105335886.Hotel-Information) Chester 10/10 Exceptional (3 reviews) "We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donald M. CA $857 CA $1,531 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Chester-Hotels-WhiSki-Cabin-12-Acres-With-A-Mountain-View.h105335886.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99880000/99874800/99874704/6a78e813.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99880000/99874800/99874704/f51deb64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/100000000/99880000/99874800/99874704/fca309d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99880000/99874800/99874704/5f7adde2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic 150-year-old farmhouse, Jacuzzi included [](https://www.expedia.ca/Chester-Hotels-Historic-150-Year-Old-Farmhouse.h99874704.Hotel-Information) Chester Depot 9.8/10 Exceptional (14 reviews) "Brought my mom here for leaf peeping. The Farmhouse was clean, comfortable and very inviting. Plenty to do in the surrounding area. Soaking in the hot tub & stargazing in the evening was wonderful! Owner was easy to communicate with. Would highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michele B. CA $293 CA $718 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Chester-Hotels-Historic-150-Year-Old-Farmhouse.h99874704.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/d8a154ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/67ba1eb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Jetted Tub](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/8582bd1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/46351656.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Springfield Hotel [](https://www.expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) Springfield 8.8/10 Excellent (825 reviews) "Very friendly staff. The room and all surroundings were clean and fresh smelling." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alison CA $184 CA $203 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/59abbcdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/f8844d39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/f0fdbfec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/017470f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Keene Elm City Hotel, an Ascend Collection Hotel [](https://www.expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) Keene 8.4/10 Very good (983 reviews) "Staff were great place was clean and nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alex CA $162 CA $176 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Breakfast area](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/10a69b41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 2 Double Beds, Refrigerator & Microwave](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/a5ea8fc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Concierge desk](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/c5f36674.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/214f3dc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Covered Bridge Inn [](https://www.expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information) Brattleboro 7.6/10 Good (1,004 reviews) "Easy check in and good parking" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) nicholas CA $110 CA $121 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information) ![Deluxe Suite | Private kitchen](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/9d3fcb33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/3536a275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/7b3a7c11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Electric vehicle charging station](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/083f3b70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Woodstock Motel [](https://www.expedia.ca/Woodstock-Hotels-Sleep-Woodstock-Motel.h9658860.Hotel-Information) Woodstock 9.6/10 Exceptional (557 reviews) "So much love and thoughtfulness was put into our room and common area. Comfy beds, little touches like free snacks and goodies and super clean room. It's also super dog friendly! There's also a fantastic little coffee stand walking distance. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JILL [](https://www.expedia.ca/Woodstock-Hotels-Sleep-Woodstock-Motel.h9658860.Hotel-Information) ![Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave](https://images.trvl-media.com/lodging/39000000/38320000/38317200/38317142/4df4a560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/39000000/38320000/38317200/38317142/71a0fd3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/39000000/38320000/38317200/38317142/8f5011d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/39000000/38320000/38317200/38317142/61492abb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Claremont Motor Lodge [](https://www.expedia.ca/Mount-Sunapee-Hotels-Claremont-Motor-Lodge.h38317142.Hotel-Information) Claremont 8.8/10 Excellent (471 reviews) "Only 35 min from Okemo. Had what we needed and plenty of hot water " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marissa CA $127 CA $138 total includes taxes & fees Feb 24 - Feb 25 [](https://www.expedia.ca/Mount-Sunapee-Hotels-Claremont-Motor-Lodge.h38317142.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=2026-03-02&endDate=2026-03-03®ionId=89014&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_89014) ## Top Chester Hotel Reviews ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg) ### On The River Inn 10/10 Excellent "The accommodations, amenities and staff were wonderful. Perfect location for our planned, and unplanned, activities." [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Kimpton Taconic Hotel by IHG](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/72cb9377_y.jpg) ### Kimpton Taconic Hotel by IHG 10/10 Excellent "Best atmosphere and family stay ever. Kids friendly." [](https://expedia.ca/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.Hotel-Information) ## Frequently asked questions ### What's there to see and do in Chester? ### What kind of weather should I plan for when I travel to Chester? ### What's the best way to get to my boutique hotel in Chester? ## 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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