Title: Book the Best CHEAP Hotels in Winchester, MA - Winchester Cheap Hotels | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d175481.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d175481.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d175481.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d175481.Destination-Travel-Guides) ![Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA. ](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Cheap Hotels in Winchester, MA - ![](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 Cheap Hotels Tonight [Dec 9 - Dec 10](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-09&endDate=2025-12-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget_property) Tomorrow [Dec 10 - Dec 11](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-10&endDate=2025-12-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget_property) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget_property) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget_property) ## Top Winchester Hotel Reviews ![Wyndham Boston Beacon Hill](https://images.trvl-media.com/lodging/1000000/30000/25700/25655/fa173b31_y.jpg) ### Wyndham Boston Beacon Hill 10/10 Excellent "Staff is very friendly and accommodating. Room was clean and the bed was comfortable. Breakfast was very good." [](https://expedia.ca/Boston-Hotels-Wyndham-Boston-Beacon-Hill.h25655.Hotel-Information) ![The Charles Hotel](https://images.trvl-media.com/lodging/1000000/20000/15900/15861/66098bc6_y.jpg) ### The Charles Hotel 10/10 Excellent "Every aspect was wonderful! The rooms was spotless and cozy, food in restaraunt was exceptional and staff could not have been more accommodating!! " [](https://expedia.ca/Boston-Hotels-The-Charles-Hotel.h15861.Hotel-Information) ![The Langham, Boston](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/9a3ebe8a_y.jpg) ### The Langham, Boston 10/10 Excellent "Lovely hotel, clean room, incredibly comfortable bed, great breakfast, kind staff. That's all I ask for. " [](https://expedia.ca/Boston-Hotels-The-Langham.h2558.Hotel-Information) ![Boston Harbor Hotel](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b_y.jpg) ### Boston Harbor Hotel 10/10 Excellent "Clean room, great staff, excellent food, great location " [](https://expedia.ca/Boston-Hotels-Boston-Harbor-Hotel.h26146.Hotel-Information) ![The Westin Copley Place, Boston, a Marriott Hotel](https://images.trvl-media.com/lodging/1000000/10000/4500/4443/ac4901eb_y.jpg) ### The Westin Copley Place, Boston, a Marriott Hotel 10/10 Excellent "Food and service were great as always. " [](https://expedia.ca/Boston-Hotels-The-Westin-Copley-Place.h4443.Hotel-Information) ![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "You have to start breakfast at 6am not 7am " [](https://expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg) ### Harborside Inn Of Boston 10/10 Excellent "The staff was very kind and helpful!!!" [](https://expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![Hilton Boston Logan Airport](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/23c65d09_y.jpg) ### Hilton Boston Logan Airport 10/10 Excellent "The property is well maintained and ideally situated within walking distance of terminal E. Staff are great and helpful. Only gripe would be very noisy plumbing heard in our room and prices have rocketed in the eateries." [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information) ![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "Amazing experience Amazing staff Ramy kept checking on us which was amazing " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ## Frequently asked questions ### How much does a budget hotel in Winchester cost? ### When is the most affordable time to visit Winchester? > Solo travellers looking for value might find these times particularly appealing. The cooler weather means fewer crowds at local attractions, allowing for a more relaxed exploration of the town's historical sites and beautiful natural spaces like the Middlesex Fells Reservation without the peak season price tag. Walking the scenic paths around Horn Pond or exploring the charming town centre becomes a more intimate experience. > > > Families can also benefit from visiting during these off-peak months. Many local events and school holidays in the area can drive up prices, so avoiding summer and major holiday weekends is a smart move. ### How can I save on a budget hotel in Winchester with Expedia? ### What free activities should we do in Winchester? > Families can spend a delightful afternoon at the Middlesex Fells Reservation, a vast natural park that borders Winchester. It features numerous walking and hiking trails suitable for all ages, offering opportunities for wildlife spotting and enjoying the fresh air. Another excellent option is a visit to the Winchester Public Library; beyond its extensive collection, it often hosts free community events, story times for children, and art exhibits. > > > For solo travellers, a stroll around the picturesque Winchester Town Common provides a relaxing experience. It's a lovely green space in the heart of town, great for people-watching or simply enjoying a quiet moment. Additionally, exploring the historic architecture of Winchester by foot offers a fascinating insight into the town's past, with many beautiful homes and public buildings to admire. ### Is it cheaper to book flights and a hotel in Winchester as a package? ### Can I cancel my budget hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Boutique Hotels in Arlington ](https://www.expedia.ca/Arlington-Hotels-Boutique-Hotel.0-0-d74693-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Arlington ](https://www.expedia.ca/Arlington-Hotels-Casino-Hotel.0-0-d74693-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Arlington ](https://www.expedia.ca/Arlington-Hotels-Cheap-Hotels.0-0-d74693-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Arlington ](https://www.expedia.ca/Arlington-Hotels-Hotel-With-Pool.0-0-d74693-tHotelwithPool.Travel-Guide-Filter-Hotels) - 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