Title: Book the Best HISTORIC Hotels in Chester 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) ![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 Historic Hotels in Chester, VT from CA $250 - ![](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 Historic Hotels Tonight [Nov 17 - Nov 18](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-11-17&endDate=2025-11-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 18 - Nov 19](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-11-18&endDate=2025-11-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chester Historic Hotels ![Free daily continental breakfast](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/df603ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/d8604c97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Blue Room](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/a33464ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/ca21030b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Carriage Barn Inn Keene 9.6/10 Exceptional (165) "Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) natalia CA $231 CA $250 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Keene-Hotels-The-Elm-City-Carriage-Barn.h38505466.Hotel-Information) ![TV, books](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/8f769c56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/8d64a97b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/4c6a2082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/d16d9700.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro Walpole 10/10 Exceptional (8) "Easy hand's off check in and great communication with the host. The cottage itself was lovely - my friends and I were in town for a wedding and it was the perfect accommodations! Would definitely stay here again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frances D. CA $287 CA $354 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Walpole-Hotels-Cozy-Farm-Cottage-On-Gorgeous-Landscape.h68711922.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/34000000/33550000/33549300/33549240/d61c57d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/34000000/33550000/33549300/33549240/8ef13f68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33550000/33549300/33549240/3a6c32b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/34000000/33550000/33549300/33549240/8238a1ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Entire Farmhouse with lots of open space 15 min north of Keene Walpole 10/10 Exceptional (38) "Lovely place would definitely book again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sean M. CA $335 CA $413 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Walpole-Hotels-Your-Own-Private-Farmhouse-On-Spectacular-Farm.h33549240.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/62670e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Books, stereo](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/04dd28e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/becbfa0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/306e8880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Fully Renovated One-Room Schoolhouse on 22+ acres Grafton 9.6/10 Exceptional (166) "Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Philip CA $238 CA $514 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Grafton-Hotels-Charming-Fully-Renovated-One-Room-Schoolhouse-On-22-Acres.h27117112.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/64000000/63950000/63942500/63942414/815e1d11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/64000000/63950000/63942500/63942414/5ad0db17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/64000000/63950000/63942500/63942414/450d67d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/64000000/63950000/63942500/63942414/af77614e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful home offering privacy on 7 acres with private pond West Windsor 10/10 Exceptional (30) "Very relaxing house, we all enjoyed the fireplaces and pellet stove and the well-equipped kitchen allowed us to cook beautiful meals. The property is gorgeous and neighbors are far away. This was the perfect place for a friends reunion/ski trip!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roy S. CA $285 CA $682 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Windsor-Hotels-Beautiful-Home-Offering-Privacy-On-7-Acres-With-Private-Pond.h63942414.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/54a5f76c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/1662100f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/b0da744f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/cc4de1c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route Ludlow 10/10 Exceptional (102) "Wonderful two bedroom condo, fantastic communication from the manager, easy everything, parking, accessing the beautiful unit, checking out, just perfect!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charlie D. CA $182 CA $388 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Central-Vermont-Killington-Hotels-Vrbo-Property.h45708952.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/ba958cd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/dd7457ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/c6fd9a81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/20e76b9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle Ludlow 9.8/10 Exceptional (103) "A lovely time enjoying the off-season in a ski town. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ed C. CA $276 CA $581 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Ludlow-Hotels-Short-Walk-To-Shops.h22865847.Hotel-Information) ![TV, DVD player](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/9a087dbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/0429cb18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/77b10ad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/d0731b53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski-In/Out condo with patio, mountain views, washer/dryer, & cable Clock Tower Base Area 9.2/10 Wonderful (25) "Loved the location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven W. CA $97 CA $345 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Ludlow-Hotels-Ski-InOut-Condo-With-Patio.h72131894.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38320000/38314400/38314377/w2000h1332x0y1-82915084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/39000000/38320000/38314400/38314377/w1996h1332x1y1-12511705.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/39000000/38320000/38314400/38314377/w1999h1332x1y1-8d3faf6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/39000000/38320000/38314400/38314377/w1996h1332x1y1-71f4d760.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool Killington 8.0/10 Very good (6) "Efficient and affordable option for a short stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marnie O. CA $177 CA $260 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-107-Deluxe-Studio-Queen.h38314377.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/39000000/38420000/38412300/38412250/w1999h1332x1y1-b64fa2b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38420000/38412300/38412250/6774d1bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38420000/38412300/38412250/w1997h1332x0y1-9064c6b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/39000000/38420000/38412300/38412250/w1996h1332x1y1-7c898894.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Two Queen Bed Standard Hotel Room w/outdoor heated pool 204 Killington 8.4/10 Very good (18) "Great property that is very easy to get to and super comfortable.The room was farther away from check in, with the small patio overlooking a wooded area. Was nice & relaxing and it was great to hear the birds singing.The room itself was roomy, especially for one and bed was comfy.I'd stay there again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joey F. CA $177 CA $261 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Killington-Hotels-Two-Queen-Bed-Standard-Hotel-Room-Woutdoor-Heated-Pool-204.h38412250.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=2025-12-01&endDate=2025-12-02®ionId=89014&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ### Latchis Hotel 10/10 Excellent "Staff was outstanding! Informative, kind, engaging, helpful...facility is a wonderful, old building whose history has been respected. Convenient parking lot, and a very walkable area with great restaurants in the area. Looking forward to another stay!" [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ### The Putney Inn 10/10 Excellent "Nice rooms and quite " [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ### Pointe at Castle Hill Resort 10/10 Excellent "Loved our room. Very clean and enjoyed fireplace. Only thing we were bothered by was noise outside our room probably connected to pool heater or filter." [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ### On The River Inn 10/10 Excellent "Homey, cozy, clean, and accommodating. The continental breakfast each morning was so nice. A full buffet of hot foods plus cereals, muffins, yogurt, and fruit. Coffee available all day in multiple locations. The pool, hot tub, and sauna were great to have on cold days. The bedding was very comfortable as well. " [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG 10/10 Excellent "Clean room Front desk Miles was great Plenty of fresh towels and paper products " [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ### Best Western Plus Keene Hotel 10/10 Excellent "The hotel was very busy, so it was noisy. Can't be helped but the wall thermostats work better our rooms did not so I did struggle with the room temp. Too hot or too cold didn't seem to matter what temp it was on. The fan on high speed made a popping sound. No one caught the cobwebs over the headboard. And the lamp didn't work. It was not plugged in but doing so did not make it work. That being said I will stay there again in the future. All of the staff were extremely nice. Just little things, busy, time of year, and things that can be addressed." [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ### Comfort Inn & Suites Brattleboro I-91 10/10 Excellent "Great convenient spot just off the highway. The room was clean and the amenities were just right. " [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ### The Jackson 10/10 Excellent "Loved the casual, comfortable, easy atmosphere. Homey and welcoming but never overbearing. Staff were all wonderful and personable. " [](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ### The Equinox Golf Resort & Spa 10/10 Excellent "Nice old Inn!" [](https://expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ## Frequently asked questions ### What should I expect on my historical trip to Chester? > A trip to the sights with historical relevance in Chester is probably at the top of your sightseeing list. Visit the ski slopes and shops while you're in town. During your stay in this quaint area, you can also relish a trip to the coffeehouses. ### What's the best place to stay in Chester that's close to historical sites? > Based on our travel expertise, [1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!](https://www.expedia.ca/Chester-Hotels-1868-Carriage-House-Quaint-Cozy-Perfect-Escape-20-MIN-TO-Okemo.h22120284.Hotel-Information) is a top guesthouse for history seekers booking on Expedia, and it features free WiFi and laundry facilities. Baltimore Covered Bridge is a short 17-minute drive away. ### How many historical hotels are there in Chester? > In Chester, there are 68 hotels and other lodging options bookable on Expedia but not many designated as historic hotels. ### What are the must-see historical sites and other places to visit in Chester? > A couple of favorite places to visit are Bonnie's Bundles Dolls and DaVallia Art & Accents. Additionally, you'll find Stratton Mountain Resort in the area. ### What is a historic hotel like in Chester? > By choosing a historic hotel, you can spend a night or two in a building that has an officially recognized historic designation. A palace, castle, stately home or even a lodge, pub, or skyscraper can be turned into a historic hotel as long as it's a place of special interest. Traditional architecture and period features are typically found in the guestrooms or communal spaces of such hotels in Chester, giving a real sense of character. ### What is the difference between a historic hotel and a heritage hotel? > "Heritage hotel" is more common in Asia and Europe, while "historic hotel" is more common in the U.S. overall though the terms are similar. The architecture and actual building of a historic hotel is generally what's most important. For a heritage hotel, often it's the cultural value along with how it influenced the community. ### Do historic hotels in Chester have modern facilities? > Hotel interiors feature the modern conveniences and safety features you expect to find, while every effort is made to preserve historic facades and treasured traditions. WiFi, heating and air conditioning, updated bathroom facilities, and the amenities found in any hotel should be available at a historic hotel. Rest assured that when you choose a historic hotel in Chester, you won't find yourself staying at a place that is rundown or uncomfortable. ## 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) - [Resorts in Andover](https://www.expedia.ca/Andover-Resort-Hotels.d6023580-aaResortHotels.Travel-Guide-Accommodation) - 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