Title: Book the Best HISTORIC 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)[Things to do in Chester](https://expedia.ca/Things-To-Do-In-Chester.d89014.Travel-Guide-Activities)[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 Historic Hotels Tonight [Mar 4 - Mar 5](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-03-04&endDate=2026-03-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 5 - Mar 6](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-03-05&endDate=2026-03-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-03-06&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-03-13&endDate=2026-03-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester historic hotels ![TV, books](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/8f769c56.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) ![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) ![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) ### Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro [](https://www.expedia.ca/Walpole-Hotels-Cozy-Farm-Cottage-On-Gorgeous-Landscape.h68711922.Hotel-Information) Walpole 10/10 Exceptional (8 reviews) "Beautiful cozy cottage. Very clean. Wonderful host." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gloria A. CA $280 CA $347 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Walpole-Hotels-Cozy-Farm-Cottage-On-Gorgeous-Landscape.h68711922.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33550000/33549300/33549240/c7719d69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/34000000/33550000/33549300/33549240/6fb4f927.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 [](https://www.expedia.ca/Walpole-Hotels-Your-Own-Private-Farmhouse-On-Spectacular-Farm.h33549240.Hotel-Information) Walpole 10/10 Exceptional (38 reviews) "Lovely place would definitely book again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sean M. CA $350 CA $433 total includes taxes & fees Mar 5 - Mar 6 [](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) ![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) ![Dining](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/c5d0a9bf.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) ### Charming Fully Renovated One-Room Schoolhouse on 22+ acres [](https://www.expedia.ca/Grafton-Hotels-Charming-Fully-Renovated-One-Room-Schoolhouse-On-22-Acres.h27117112.Hotel-Information) Grafton 9.6/10 Exceptional (167 reviews) "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 $232 CA $505 total includes taxes & fees Mar 19 - Mar 20 [](https://www.expedia.ca/Grafton-Hotels-Charming-Fully-Renovated-One-Room-Schoolhouse-On-22-Acres.h27117112.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1410000/1407200/1407156/c098bcf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/2000000/1410000/1407200/1407156/85e16c6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo Hotel Room](https://images.trvl-media.com/lodging/2000000/1410000/1407200/1407156/1d8473ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1410000/1407200/1407156/754a77bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castle Hill Resort And Spa [](https://www.expedia.ca/Cavendish-Hotels-Castle-Hill-Resort-And-Spa.h1407156.Hotel-Information) Cavendish 9.0/10 Wonderful (108 reviews) "Great place for a good price. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew CA $312 CA $341 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Cavendish-Hotels-Castle-Hill-Resort-And-Spa.h1407156.Hotel-Information) ![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) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/37889f48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/cb6b5625.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) ### 2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route [](https://www.expedia.ca/Central-Vermont-Killington-Hotels-Vrbo-Property.h45708952.Hotel-Information) Ludlow 9.8/10 Exceptional (105 reviews) "Great Condo. We had plenty of space. Wendi was very responsive and even accommodated us checking in an hour early when we arrived in town. We would definitely come back. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara M. CA $257 CA $484 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Central-Vermont-Killington-Hotels-Vrbo-Property.h45708952.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/455aec2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/146a8911.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) ![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) ### Ski-In/Out condo with patio, mountain views, washer/dryer, & cable [](https://www.expedia.ca/Ludlow-Hotels-Ski-InOut-Condo-With-Patio.h72131894.Hotel-Information) Clock Tower Base Area 9.2/10 Wonderful (28 reviews) "Overall very clean and nice. Needs some updating like more spoons, only 2, bigger coffee cups. And a new coffee table that is very worn. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David A. CA $156 CA $430 total includes taxes & fees Mar 11 - Mar 12 [](https://www.expedia.ca/Ludlow-Hotels-Ski-InOut-Condo-With-Patio.h72131894.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/fe1abb51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/ad47e382.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/1516e7fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/faf90773.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 [](https://www.expedia.ca/Ludlow-Hotels-Short-Walk-To-Shops.h22865847.Hotel-Information) Ludlow 9.8/10 Exceptional (107 reviews) "Had a wonderful stay. Clean,well kept and cozy." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edwin G. CA $345 CA $667 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Ludlow-Hotels-Short-Walk-To-Shops.h22865847.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72603600/72603570/w2000h1332x0y1-7eab51dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72610000/72603600/72603570/w1997h1332x0y1-5ccae90d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72610000/72603600/72603570/w1999h1332x1y1-792770fd.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/73000000/72610000/72603600/72603570/w1996h1332x1y1-302f86ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Two Double bed Hotel Room with outdoor heated pool 216 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Two-Double-Bed-Hotel-Room-With-Outdoor-Heated-Pool-216.h72603570.Hotel-Information) Killington CA $173 CA $252 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Two-Double-Bed-Hotel-Room-With-Outdoor-Heated-Pool-216.h72603570.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) ![Microwave, oven, coffee/tea maker, toaster](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/w1999h1332x1y1-198a7add.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 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-107-Deluxe-Studio-Queen.h38314377.Hotel-Information) Killington 8.0/10 Very good (7 reviews) "Efficient and affordable option for a short stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marnie O. CA $173 CA $252 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-107-Deluxe-Studio-Queen.h38314377.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413501/w2000h1332x0y1-0a9cdce6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413501/w1999h1332x1y1-4794ba40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413501/w1997h1332x0y1-df9edd8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413501/w1999h1332x1y1-4b045cbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Queen Studio on the 2nd floor with outdoor heated pool 207 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Queen-Studio-On-The-2nd-Floor-With-Outdoor-Heated-Pool-207.h38413501.Hotel-Information) Killington 8.0/10 Very good (6 reviews) "It was fine for our 1 night stay in the area. When I booked I did not realize that this is a motel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura D. CA $173 CA $252 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Queen-Studio-On-The-2nd-Floor-With-Outdoor-Heated-Pool-207.h38413501.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=2026-03-18&endDate=2026-03-19®ionId=89014&adults=2&specialized_stays_group_explore=historic_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 ![The Manchester View](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/738a0d56_y.jpg) ### The Manchester View 10/10 Excellent "This place worked out wonderfully. Clean, comfortable and a great value. Location around 5 min to downtown Manchester. 20 minnto Stratton. Highly recommend " [](https://expedia.ca/Bennington-Hotels-The-Manchester-View.h6846625.Hotel-Information) ![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/06298210_y.jpg) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG 10/10 Excellent "They allowed for early check-in, had a condo that slept 10 and my family was extremely comfortable" [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/b9b1ed95_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "Clean room, friendly staff, great pool and hot tub, and very conveniently located close to Okemo. " [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Aspen At Manchester](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/cbf700aa_y.jpg) ### Aspen At Manchester 10/10 Excellent "Very clean and comfortable " [](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 location for our needs and very comfortable" [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![The Equinox Golf Resort & Spa](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/c6f78187_y.jpg) ### The Equinox Golf Resort & Spa 10/10 Excellent "Beautiful hotel. Nice pool and gym. " [](https://expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ![The Palmer House Resort, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/7000000/6030000/6028500/6028480/4412313e_y.jpg) ### The Palmer House Resort, an Ascend Collection Hotel 10/10 Excellent "Our 2nd time staying here this season. We love it, perfect location to town and ski. Spotless rooms, microwave and fridge a bonus when kids are traveling. Rooms were so warm we turned off heat. Breakfast included. Check in and out very quick and friendly, we will absolutely stay again." [](https://expedia.ca/Bennington-Hotels-The-Palmer-House-Resort.h6028480.Hotel-Information) ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/8d6bfa64_y.jpg) ### On The River Inn 10/10 Excellent "Pool and sauna were wonderful after a day of skiing. Excellent breakfast. " [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ## Frequently asked questions ### What should I expect on my historical trip to Chester? ### What's the best place to stay in Chester that's close to historical sites? ### How many historical hotels are there in Chester? ### What are the must-see historical sites and other places to visit in Chester? ### What is a historic hotel like in Chester? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Chester have modern facilities? ## 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) - 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