Title: Hotels by Hilton Hotels in Winchester from CA $127 | 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 $127 - ![](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 [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-11-02&endDate=2025-11-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-11-03&endDate=2025-11-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-11-14&endDate=2025-11-16&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 (3538) "Will stay here again - very good accommodation " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $194 CA $226 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.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) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/6238869c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Boston Park Plaza Bay Village 8.4/10 Very good (3155) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $171 CA $256 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/10600/10575/857971b1.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) ### Hilton Boston/Woburn Woburn 8.4/10 Very good (1191) "The food was great, the service was great, it was a welcome change from the hotel we stayed at during our first night in Boston!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah CA $171 CA $191 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/Boston-Hotels-Hilton-BostonWoburn.h10575.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) ![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) ![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 (1232) "Very nice room great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sean CA $240 CA $321 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Boston-Hotels-Hilton-Boston-Back-Bay.h5928.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) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/10400/10391/fb5b70f5.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 (1023) "Excellent check in" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ali CA $114 CA $127 total includes taxes & fees Nov 28 - Nov 29 [](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=2025-11-16&endDate=2025-11-17®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 ![Omni Boston Hotel at the Seaport](//images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/26d11bc3_y.jpg) ### Omni Boston Hotel at the Seaport 10/10 Excellent "Amazing service, upgrades and the in-house dining is amazing! " [](https://expedia.ca/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information) ![Seaport Hotel Boston](//images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "Everything was sooo perrfect...." [](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 "Amazing stay!!! Made it better the front desk gals who work the late shift were so Amazing and welcoming! Found our go to Hotel! Have one in NY now this is my Boston one! " [](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 "We loved the breakfast" [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.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 "Nice hotel " [](https://expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) ![Hilton Boston Park Plaza](//images.trvl-media.com/lodging/1000000/10000/4300/4215/82ab675e_y.jpg) ### Hilton Boston Park Plaza 10/10 Excellent "Beautiful " [](https://expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information) ![Encore Boston Harbor](//images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5_y.jpg) ### Encore Boston Harbor 10/10 Excellent "Very nice rooms, free transportation to Bruins Games" [](https://expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.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 "Very friendly and competent staff. Excellent dinner at the restaurant. " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.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 staff was super friendly, clean rooms, very neat hotel, walkable to several things in the city, subway stop right outside. Neighborhood was safe and quiet. Will definitely stay again. " [](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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