Title: Book the Best Chester Hotels with FREE WIFI 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/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Wifi in Chester, VT from CA $187 ![](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 Hotels with Wifi Tonight [Oct 22 - Oct 23](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-22&endDate=2025-10-23&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 23 - Oct 24](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-23&endDate=2025-10-24&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chester Hotels with Wifi ![Garden](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/662925ab.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) ![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) ### Fullerton Inn Chester Depot 8.2/10 Very good (395) "Lovely stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine 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) ![Garden](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/327ad7fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 Queen Bed, Garden View](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/20cd6ab1.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) ### Stone Hearth Inn and Eatery Chester 9.2/10 Wonderful (102) "Good breakfast and dinner options. Great location for hiking." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $290 CA $317 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99880000/99874800/99874704/0b98ffc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99880000/99874800/99874704/4b878d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99880000/99874800/99874704/97fc21f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/100000000/99880000/99874800/99874704/8d67161d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic 150-year-old farmhouse, Jacuzzi included Chester Depot 9.8/10 Exceptional (8) "This was a lovely inviting piece of history to stay in! The amenities were wonderful, the host very engaged with being sure we had what we needed. It is (for those who may not know Vermont) SUPER close to all sorts of hiking, tours, cute stores and great food! Our family will absolutely stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy S. CA $164 CA $562 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chester-Hotels-Large-Farmhouse-W-Jacuzzi.h99874704.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938140/7656b8f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938140/d309381b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938140/6d1c5ec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938140/a93524b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### King & Queen Suite in Historic Inn Circa 1780 Chester Depot 9.8/10 Exceptional (16) "Central for our needs. easy check in process. Lovely large room with comfy beds. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) HIlary H. CA $195 CA $319 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Chester-Hotels-King-Queen-Suite-In-Historic-Inn-Circa-1780.h83938140.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/103000000/102120000/102120000/102119969/c51b349e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102120000/102120000/102119969/abe9b83f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102120000/102120000/102119969/223d62f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/103000000/102120000/102120000/102119969/2e170eb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! Chester Depot 9.0/10 Wonderful (2) "Property seemed well-maintained and cared for. We were only there a short time, but it was well put together. The check-in process was a little hectic, check in time was 3pm, but our room wasn't ready. The caretaker was very friendly. We only had to wait about 20 minutes. We weren't aware this property was a VRBO, and not a regular Inn. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacque CA $125 CA $226 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chester-Hotels-Historic-Chester-Inn-Circa.h102119969.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/4e6773ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/0d26f53b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/cf58af9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/dd9dbbe8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Whimsical Room & Private Bathroom in Historic Inn Chester Depot 8.8/10 Excellent (9) "After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul S. CA $139 CA $234 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chester-Hotels-Whimsical-Room-Private-Bathroom-In-Historic-Inn.h87135975.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/121000000/120820000/120819700/120819684/2d69a921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/121000000/120820000/120819700/120819684/42e5450e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120820000/120819700/120819684/bc89011e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/121000000/120820000/120819700/120819684/310e46a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quaint Queen room at the Chester Inn Chester Depot CA $97 CA $187 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chester-Hotels-Quaint-Queen-Room-At-The-Chester-Inn.h120819684.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/9fc41d82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/578d98e9.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/dffaa55c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/fb8c05d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chester Farmhouse Ski Retreat near Slopes Chester Depot 9.6/10 Exceptional (15) "Great cozy home for our trip to Vermont. Very comfortable. Recommend walking over to country girl dinner and the Scottish pub." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Benjamin M. CA $265 CA $559 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chester-Hotels-Charming-Chester-Farmhouse-Peaceful-And-Close-To-Everything.h101473310.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/e9669654.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/a0f7ed6b.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) ### Cozy Vermont Cabin · Mountain Views · Near Okemo Chester 10/10 Exceptional (3) "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 $756 CA $1,417 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chester-Hotels-WhiSki-Cabin-12-Acres-With-A-Mountain-View.h105335886.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/a1626ba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/1377c15b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/411cc5a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/3794da32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Room in Historic Inn! 20 Minutes to Okemo! Chester Depot 9.2/10 Wonderful (17) "The Chester Inn was beautiful and located in downtown Chester. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter C. CA $139 CA $234 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chester-Hotels-Room-In-Historic-Inn-20-Minutes-To-Okemo.h83938154.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=2025-11-05&endDate=2025-11-06®ionId=89014&adults=2&amenities=WIFI&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![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 "Beautiful property, wonderful views, loved our room, loved the huge indoor heated pool and the outdoor jacuzzi. Bar staff, food and drinks were fantastic at the on site bar/restaurant The Falcon, shout out to Maddie for being awesome. Bummer the steal house was closed the entirety of our stay (Sun-Weds), but what are ya gonna do. Would recommend, and would love to return next autumn. " [](https://expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ![Latchis Hotel](//images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg) ### Latchis Hotel 10/10 Excellent "Is a great historic building with great charm. Hope to stay there again soon." [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ![Woodstock Inn & Resort](//images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg) ### Woodstock Inn & Resort 10/10 Excellent "Beautiful hotel with excellent staff and room cleanliness. Red Rooster Inn had good breakfast options, however dinner was a little underwhelming and expensive. There are better options at the local fine dining restaurants. " [](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) ![Hampton Inn and Suites Manchester](//images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3_y.jpg) ### Hampton Inn and Suites Manchester 10/10 Excellent "We had a great time the hotel had everything we needed and more at a very reasonable price." [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.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 10/10 Excellent "Very nice & quiet. Close to downtown. Didn’t eat breakfast. " [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.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 "The on-site restaurant named Tempestas was excellent and a huge plus for our 3-night stay. We ate there every night and were pleased with the food, service, atmosphere and the prices were reasonable. On a broader note, the hotel was nice, staff very helpful and I should mention that the breakfast one of the best I've had on 3 continents, aided by a hostess who was friendly and took lots of pride in serving hot food and keeping the food and coffee fresh." [](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 10/10 Excellent "The staff truly made the experience stand out. From check-in to check-out, everyone I interacted with was professional, friendly, and genuinely welcoming. " [](https://expedia.ca/Ludlow-Hotels-Jackson-Gore-Village.h2417009.Hotel-Information) ![Mount Snow Grand Summit Resort](//images.trvl-media.com/lodging/1000000/670000/663200/663170/effe663b_y.jpg) ### Mount Snow Grand Summit Resort 10/10 Excellent "Amazing 2 big hot tubes and warm swim pool on the open air !!! A lot of restaurants around and Beautiful nature! But chairlifts was closed- so check availability " [](https://expedia.ca/West-Dover-Hotels-Mount-Snow-Grand-Summit-Resort.h663170.Hotel-Information) ![The Shire Woodstock](//images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Our room was clean and welcoming. 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[Luxury Hotels in Grafton](https://www.expedia.ca/Grafton-Hotels-Luxury-Hotel.0-0-d184049-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Grafton](https://www.expedia.ca/Grafton-Hotels-Spa-Hotel.0-0-d184049-tSpaHotel.Travel-Guide-Filter-Hotels) - [Winery Hotels in Grafton](https://www.expedia.ca/Grafton-Hotels-Winery-Hotel.0-0-d184049-tWineryHotel.Travel-Guide-Filter-Hotels) - [Grafton Hotels](https://www.expedia.ca/Grafton-Hotels.d184049.Travel-Guide-Hotels) - [Inns in Grafton](https://www.expedia.ca/Grafton-Inns.d184049-aaInns.Travel-Guide-Accommodation) - [Lodges in Grafton](https://www.expedia.ca/Grafton-Lodges.d184049-aaLodges.Travel-Guide-Accommodation) - [Motels in Grafton](https://www.expedia.ca/Grafton-Motels.d184049-aaMotels.Travel-Guide-Accommodation) - [Resorts in Grafton](https://www.expedia.ca/Grafton-Resort-Hotels.d184049-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near Magic Mountain Ski Resort](https://www.expedia.ca/Magic-Mountain-Ski-Resort-Hotels.0-l6115886-0.Travel-Guide-Filter-Hotels) - 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[Proctorsville Hotels](https://www.expedia.ca/Proctorsville-Hotels.d6023678.Travel-Guide-Hotels) - [B&B in Rockingham](https://www.expedia.ca/Rockingham-Bed-And-Breakfast.d3000008087-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Rockingham](https://www.expedia.ca/Rockingham-Chalets.d3000008087-aaChalets.Travel-Guide-Accommodation) - [Hostels in Rockingham](https://www.expedia.ca/Rockingham-Hostels.d3000008087-aaHostels.Travel-Guide-Accommodation) - [Cheap Hotels in Rockingham](https://www.expedia.ca/Rockingham-Hotels-Cheap-Hotels.0-0-d3000008087-tCheapHotels.Travel-Guide-Filter-Hotels) - [Rockingham Hotels](https://www.expedia.ca/Rockingham-Hotels.d3000008087.Travel-Guide-Hotels) - [Motels in Rockingham](https://www.expedia.ca/Rockingham-Motels.d3000008087-aaMotels.Travel-Guide-Accommodation) - [B&B in Saxtons River](https://www.expedia.ca/Saxtons-River-Bed-And-Breakfast.d6054130-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Saxtons River](https://www.expedia.ca/Saxtons-River-Chalets.d6054130-aaChalets.Travel-Guide-Accommodation) - 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