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) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Cheap Hotels in Winchester, MA ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Oct 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-01&endDate=2025-10-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-02&endDate=2025-10-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Cheap Hotels ## Top Winchester Hotel Reviews ![Harborside Inn Of Boston](//images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg) ### Harborside Inn Of Boston 10/10 Excellent "The girls at the front desk were super friendly and helpful. Room was simple but clean. Located close to places to eat and historic sites. " [](https://expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![Seaport Hotel Boston](//images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "Staff were very friendly and very informative. Roberto was the best! " [](https://expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![Hilton Boston Logan Airport](//images.trvl-media.com/lodging/1000000/290000/281600/281536/23c65d09_y.jpg) ### Hilton Boston Logan Airport 10/10 Excellent "The room was clean and well appointed." [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information) ![Hilton Boston Park Plaza](//images.trvl-media.com/lodging/1000000/10000/4300/4215/d4a5b47e_y.jpg) ### Hilton Boston Park Plaza 10/10 Excellent "Hotel staff were great. Unfortunately I booked through Expedia and they would not, give a refund. Hotel changed dates and camceled dates. Unfortunately hotel did not have the top tier room on the dates I needed, even after talking to them. I.checked expedia and they had room at same rate and the.dates.i needed. This was more than 30 days in advance. 1week later I needed to cancel first date. Expedia has already billed and would not give a refund...I talked to hotel and they approved the refund but Expedia will not refund . They even charged a a no show fees and canceled the rest of my trip. I had to pay for a new night this 3 bills for 1 night.. never use Expedia " [](https://expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information) ![Club Quarters Hotel Faneuil Hall, Boston](//images.trvl-media.com/lodging/1000000/70000/67000/66938/1b7afb42_y.jpg) ### Club Quarters Hotel Faneuil Hall, Boston 10/10 Excellent "Very comfortable bed and room, great workout room, very quiet and clean. The staff are very friendly and professional. I can’t wait to return again!! Thank you for a wonderful stay." [](https://expedia.ca/Boston-Hotels-Club-Quarters-Hotel-In-Boston.h66938.Hotel-Information) ![Sheraton Boston, a Marriott Hotel](//images.trvl-media.com/lodging/1000000/30000/22100/22046/dfa592c9_y.jpg) ### Sheraton Boston, a Marriott Hotel 10/10 Excellent "excellent hotel in great location. Only downside, the room was not ready until after 9pm" [](https://expedia.ca/Boston-Hotels-Sheraton-Boston.h22046.Hotel-Information) ![The Dagny Boston](//images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "A beautiful art deco age hotel, with a boutique hotel feel. Great staff very friendly and accommodating. A wonderful stay." [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![Copley Square Hotel, a FOUND Hotel](//images.trvl-media.com/lodging/1000000/20000/16100/16067/dbccf1fb_y.jpg) ### Copley Square Hotel, a FOUND Hotel 10/10 Excellent "The room was small but it was just what we needed. Everything was clean and comfortable. " [](https://expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) ![Midtown Hotel](//images.trvl-media.com/lodging/1000000/10000/2900/2898/e6722cab_y.jpg) ### Midtown Hotel 10/10 Excellent "The excellent location was only bested by the welcoming front desk staff!" [](https://expedia.ca/Boston-Hotels-Midtown-Hotel.h2898.Hotel-Information) ## Frequently asked questions ### What is Winchester like for travelers on a budget? > Check out cheap places to stay in Winchester on Expedia.com and plan a trip that matches your budget. You can scroll through a wide offering of accommodation choices with Member Prices to find great deals. With our site's handy page filters, you can search by price per night, or by top amenities like free breakfast and a swimming pool. If you're interested in affordable options near specific attractions, such as Middlesex Fells Reservation or Winter Pond, try filtering by location to refine your search. As you browse, click the heart button to keep track of your favorites so that you can return to them easily and make your final decision. Need a flight or a car for your trip? Take a look at the Bundle and Save vacation packages and discover more amazing deals when you reserve your transportation at the same time. ### When is the best time for a budget trip to Winchester? > Weather will likely play an important role when you plan your trip to Winchester, and keep in mind that cheaper options are usually available when the weather isn't as good. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 33°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 5 inches of snowfall. ### What is there to see and do in Winchester? > You don't need to spend big to find places to visit in Winchester. You can budget for the top local attractions that interest you most, such as TD Garden and Fenway Park, and then look for sights and activities that cost little or nothing at all. Check out the area's cultural spots like Somerville Theatre and Harvard Museum of Natural History, or get outdoors at Winter Pond. ### How can I get to Winchester and get around on a budget? > Scoping out the transportation options in Winchester can help keep you on budget. The closest airport is 7.7 mi (12.3 km) away from the center in Bedford, MA (BED-Laurence G. Hanscom Field). However, if that doesn't suit your budget, you can book a flight to Boston, MA (BNH-Boston Harbor Seaplane Base), located 8.4 mi (13.5 km) away. 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