Title: Book the Best Winchester LUXURY Hotels - Upscale Hotels in Winchester, MA | 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://a.travel-assets.com/travel-assets-manager/bex-affinities/luxury.jpeg?impolicy=fcrop&w=1200&h=500&q=medium) # Find luxury 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 Luxury Hotels Tonight [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-02&endDate=2025-10-03&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-03&endDate=2025-10-04&adults=2&propertyStyle=LUXURY&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&propertyStyle=LUXURY&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&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Luxury Hotels ## Top Winchester Hotel Reviews ![Seaport Hotel Boston](//images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "Loved the large harbor view king room. Easy and pleasant check in. Room ready early. Housekeeping staff were terrific- friendly and helpful. Everything immaculate. Only the shower tile floor shows wear. Enjoyed the harbor area- good dining options, walked to the port (a little long with luggage but doable)—-we were cruising so hotel is well situated for the port and airport. Boston traffic is pretty bad, so Ubers to the Back Bay or Cambridge take a while! Pick your hotel close to where you need or want to be!" [](https://expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![The Dagny Boston](//images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "Amazing hotel and location " [](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 "Historic aged hotel, so our expectations were more than served. Highly recommend for access to the city and all sites during traveling." [](https://expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.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 "All good" [](https://expedia.ca/Boston-Hotels-Sheraton-Boston.h22046.Hotel-Information) ![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) ![YOTEL Boston](//images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/245fc311_y.jpg) ### YOTEL Boston 10/10 Excellent "Moden design and clean. Will ask for mini coffee maker and fridge " [](https://expedia.ca/Boston-Hotels-YOTEL-Boston.h18090311.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) ## Frequently asked questions ### Are you looking for a luxury hotel for your Winchester vacation? > Let Expedia help you arrange your flight to Bedford, MA (BED-Laurence G. Hanscom Field) airport or Boston, MA (BNH-Boston Harbor Seaplane Base) airport, and then choose from some places to stay that will deliver the luxury you seek. Amenities are an important consideration when you plan a vacation, so we make it easy to get what you want to make your stay special. If you want a posh hotel that has fine dining, a spa, or several swimming pools, Expedia can help you find the best luxury hotel experience that Winchester offers. Winchester has some interesting things to see and do including Middlesex Fells Reservation and Winter Pond, so you might want to take in the local sights during your visit. ### When can I expect good weather in Winchester? > Planning for the weather is an important factor for making your trip to Winchester a success, especially when you're splurging. 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's there to see and do in Winchester? > Enjoy Winchester with a stop at Middlesex Fells Reservation, TD Garden, and Fenway Park. If you have a bit of extra time while you're in the area, you might want to check out New England Aquarium and Encore Boston Harbor. ### How can I get around Winchester? > It's easier to get around town in style when you know your options. 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