Title: Hotels by Hilton Hotels in Winchester from CA $187 | 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://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels by Hilton Hotels in Winchester from CA $187 ![](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 prices for these dates Tonight [Oct 10 - Oct 11](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-10&endDate=2025-10-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-11&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This 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) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-17&endDate=2025-10-19&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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/926f338a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/7fd62fb9.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) ### Hilton Boston Logan Airport East Boston 9.0/10 Wonderful (3513) "Excellent hotel" CA $302 CA $351 total includes taxes & fees Nov 10 - Nov 11 [](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) ![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) ![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) ### Hilton Boston Back Bay Fenway–Kenmore 8.4/10 Very good (1210) "Great hotel " CA $350 CA $450 total includes taxes & fees Oct 19 - Oct 20 [](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) ![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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/10600/10575/4b7c21ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/10600/10575/c7bfd2af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Boston/Woburn Woburn 8.4/10 Very good (1178) "Beautiful hotel" CA $208 CA $232 total includes taxes & fees Nov 3 - Nov 4 [](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) ![Presidential Suite, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/573419fc.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/abed7446.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Boston Park Plaza Bay Village 8.4/10 Very good (3154) "Great place to stay" CA $229 CA $324 total includes taxes & fees Nov 9 - Nov 10 [](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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10400/10391/41b6c1ff.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) ### Hilton Boston/Dedham Dedham 7.8/10 Good (1033) "Great." CA $168 CA $187 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=2025-10-25&endDate=2025-10-26®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 ![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 "Friendly hotel staff outside and in the lobby. All check in desks available for a quick check in. Nice and cozy lobby. " [](https://expedia.ca/Boston-Hotels-Sheraton-Boston.h22046.Hotel-Information) ![Seaport Hotel Boston](//images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "Our 3 days in Boston with 4 other couples was excellent mainly due to the Seaport Hotel’s concierge named Daniel Vargas. He arranged for all of our tickets and every recommendation about restaurants , shopping, and sites was excellent! He had that special touch of caring that made our trip wonderful! We will return Thank you Daniel! " [](https://expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![The Revolution Hotel](//images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/cce5d2b3_y.jpg) ### The Revolution Hotel 10/10 Excellent "Clean and quiet room. " [](https://expedia.ca/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information) ![citizenM Boston Back Bay](//images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/90056141_y.jpg) ### citizenM Boston Back Bay 10/10 Excellent "Great, helpful staff. Clean and quiet room. Location was perfect. " [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.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 "Great location when flying out of Boston. If ever back in Boston, I’d definitely stay again " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information) ![The Arcadian Hotel](//images.trvl-media.com/lodging/32000000/31100000/31097800/31097754/f8ad7683_y.jpg) ### The Arcadian Hotel 10/10 Excellent "GREAT FRONT DESK STAFF" [](https://expedia.ca/Boston-Hotels-Arcadian-Hotel-Brookline.h31097754.Hotel-Information) ![The Newbury Boston](//images.trvl-media.com/lodging/1000000/10000/400/395/de8ba46e_y.jpg) ### The Newbury Boston 10/10 Excellent "." [](https://expedia.ca/Boston-Hotels-The-Newbury-Boston.h395.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 "safe" [](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 "Clean room and staff were awesome." [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.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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