Title: Hotels by Hilton Hotels in Winchester from CA $190 | Expedia.ca [Winchester Travel Guide](https://expedia.ca/Winchester.dx175481)[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)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d175481.Travel-Guide-Flights)[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 Hotels by Hilton Hotels in Winchester from CA $190 ![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 prices for these dates Tonight [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-03&endDate=2025-10-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-04&endDate=2025-10-05&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 Hilton Hotels Hotels ![View from room](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/23c65d09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast served](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/eedce326.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/04f5c7a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/926f338a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Boston Logan Airport East Boston 9.0/10 Wonderful (3487) "Excellent hotel" CA $354 CA $412 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6000/5928/f418fbdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/10000/6000/5928/08c2b375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6000/5928/3e2a1fbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Serves lunch and dinner](https://images.trvl-media.com/lodging/1000000/10000/6000/5928/a128fc29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Boston Back Bay Fenway–Kenmore 8.4/10 Very good (1197) "Great hotel " CA $368 CA $470 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Boston-Hotels-Hilton-Boston-Back-Bay.h5928.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/10600/10575/645b1b52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/10600/10575/4b7c21ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/10600/10575/857971b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![55-inch LCD TV with satellite channels, TV](https://images.trvl-media.com/lodging/1000000/20000/10600/10575/fb88e6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Boston/Woburn Woburn 8.4/10 Very good (1179) "Beautiful hotel" CA $207 CA $232 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Boston-Hotels-Hilton-BostonWoburn.h10575.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/82ab675e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/6238869c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/abed7446.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/d4a5b47e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Boston Park Plaza Bay Village 8.4/10 Very good (3142) "Great place to stay" CA $319 CA $429 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information) ![Ballroom](https://images.trvl-media.com/lodging/1000000/20000/10400/10391/fb23caba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/10400/10391/w3839h2557x0y0-c9cf5ee6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/20000/10400/10391/9d3c9c37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10400/10391/41b6c1ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Boston/Dedham Dedham 7.8/10 Good (1039) "Great bar" CA $170 CA $190 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Boston-Hotels-Hilton-BostonDedham.h10391.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=2025-10-18&endDate=2025-10-19®ionId=175481&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels-Hilton-Hotels.0-0-d175481--bHiltonHotels.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels-Hilton-Hotels.0-0-d175481--bHiltonHotels.Travel-Guide-Filter-Hotels) ## Top Winchester Hotel Reviews ![citizenM Boston Back Bay](//images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/90056141_y.jpg) ### citizenM Boston Back Bay 10/10 Excellent "Great location and great vibes" [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![The Arcadian Hotel](//images.trvl-media.com/lodging/32000000/31100000/31097800/31097754/f8ad7683_y.jpg) ### The Arcadian Hotel 10/10 Excellent "Great service" [](https://expedia.ca/Boston-Hotels-Arcadian-Hotel-Brookline.h31097754.Hotel-Information) ![Midtown Hotel](//images.trvl-media.com/lodging/1000000/10000/2900/2898/e6722cab_y.jpg) ### Midtown Hotel 10/10 Excellent "The staff, from an original phone call, with a question, until check out could not have been more amazing. Personable, professional, friendly, and enthusiastic are just of the few ways I would describe them. From the moment we arrived until we left we were engaged in an amazing way. We loved Betsy Lynn at the desk and her colleague, Vereema. Next time I am Boston we will choose to stay at the Midtown for the staff alone, although the beds and room were extremely comfortable. I cannot wait to see the finished renovation." [](https://expedia.ca/Boston-Hotels-Midtown-Hotel.h2898.Hotel-Information) ![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) ![citizenM Boston North Station](//images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/0eda38d5_y.jpg) ### citizenM Boston North Station 10/10 Excellent "We loved our stay at CitizenM. " [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.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) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Aparthotels in Arlington](https://www.expedia.ca/Arlington-Apart-Hotels.d74693-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Arlington](https://www.expedia.ca/Arlington-Bed-And-Breakfast.d74693-aaBedAndBreakfast.Travel-Guide-Accommodation) - [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) - [Hersha Hospitality Hotels in Arlington](https://www.expedia.ca/Arlington-Hotels-Hersha-Hospitality.0-0-d74693--bHershaHospitality.Travel-Guide-Filter-Hotels) - 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