Title: Book the Best HISTORIC Hotels in Winchester in 2026 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d3000447144.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d3000447144.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d3000447144.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d3000447144.Destination-Travel-Guides) ![Winchester, New Hampshire in winter ](https://images.trvl-media.com/place/3000447144/3e6a6279-072b-4adb-98ce-884d4d6659f9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/3000447144/3e6a6279-072b-4adb-98ce-884d4d6659f9.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 Winchester Historic Hotels Tonight [Jan 25 - Jan 26](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-01-25&endDate=2026-01-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 26 - Jan 27](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-01-26&endDate=2026-01-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester 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) ![Shower, eco-friendly toiletries, hair dryer](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/17c13c0f.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) ### 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 Jan 26 - Jan 27 [](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 Jan 26 - Jan 27 [](https://www.expedia.ca/Walpole-Hotels-Your-Own-Private-Farmhouse-On-Spectacular-Farm.h33549240.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=2026-02-08&endDate=2026-02-09®ionId=3000447144&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![Holiday Inn Express Hotel & Suites Brattleboro by IHG](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/b5010c60_y.jpg) ### Holiday Inn Express Hotel & Suites Brattleboro by IHG 10/10 Excellent "Very clean room and super friendly staff!" [](https://expedia.ca/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information) ![Colonel Williams Inn](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/0d3a6bb4_y.jpg) ### Colonel Williams Inn 10/10 Excellent "The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious." [](https://expedia.ca/Brattleboro-Hotels-Colonel-Williams-Inn.h16817080.Hotel-Information) ![The Putney Inn](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg) ### The Putney Inn 10/10 Excellent "Clean, roomy, and has a mini fridge and microwave. Great for college kids going skiing! " [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg) ### Hampton Inn Brattleboro 10/10 Excellent "As always, Hampton Inn are great. I think I’m reliable, super comfortable, good breakfast. What makes this location stand out was the really outstanding customer service. Everyone was so helpful and engaging and funny! Which always helps. So, we’ll definitely be back." [](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![Best Western Plus Keene Hotel](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8_y.jpg) ### Best Western Plus Keene Hotel 10/10 Excellent "There was a college sports team staying there and were slamming doors until 1am. Send someone to walk the halls occasionally." [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![The Inn At Crumpin Fox](https://images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/b4ead30a_y.jpg) ### The Inn At Crumpin Fox 10/10 Excellent "Staff very accomodating when we needed to check in very early" [](https://expedia.ca/Bernardston-Hotels-The-Inn-At-Crumpin-Fox.h4570044.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 "Great staff" [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Latchis Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg) ### Latchis Hotel 10/10 Excellent "Comfy room!" [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ![Hampton Inn & Suites Greenfield](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/72e137d6_y.jpg) ### Hampton Inn & Suites Greenfield 10/10 Excellent "very quiet" [](https://expedia.ca/Greenfield-Hotels-Hampton-Inn-Suites-Greenfield.h1601018.Hotel-Information) ## Frequently asked questions ### What can a history buff expect from a stay in Winchester? ### How many historically relevant hotels will I find in Winchester? ### What are the top historical sites and other places to visit in Winchester? ### What is a historic hotel like in Winchester? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Winchester have modern facilities? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [4 Star Hotels in Keene ](https://www.expedia.ca/4Star-Keene-Hotels.s40-0-d6057413.Travel-Guide-Filter-Hotels) - 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