Title: Winchester Inns from CA $335 | 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) ![Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA. ](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-01-23&endDate=2026-01-25&adults=2&lodging=INN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=INN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=INN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=INN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester inns ![Romantic Room](https://images.trvl-media.com/lodging/97000000/96350000/96341500/96341402/16cad30b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/97000000/96350000/96341500/96341402/c6ea9c24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite | Private kitchen](https://images.trvl-media.com/lodging/97000000/96350000/96341500/96341402/12502bfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96350000/96341500/96341402/w1999h1512x17y0-924fe751.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silsbee's by Daniels House [](https://www.expedia.ca/Salem-Hotels-Silsbees-By-Daniels-House.h96341402.Hotel-Information) Salem 9.6/10 Exceptional (67 reviews) "Brilliant place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $300 CA $335 total includes taxes & fees Jan 24 - Jan 25 [](https://www.expedia.ca/Salem-Hotels-Silsbees-By-Daniels-House.h96341402.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1260000/1254500/1254427/4550789b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1260000/1254500/1254427/06a689d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1260000/1254500/1254427/c5c5b979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1260000/1254500/1254427/feddda7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbor Light Inn [](https://www.expedia.ca/Boston-Hotels-Harbor-Light-Inn.h1254427.Hotel-Information) Marblehead 9.8/10 Exceptional (316 reviews) "The Harbor Light Inn is a beautiful historic inn. The staff are very nice and accommodating. They have several sitting areas, a quaint tavern and a dining room with pretty views and a fireplace in just about every area. We loved everything about our stay and would definitely return. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diana [](https://www.expedia.ca/Boston-Hotels-Harbor-Light-Inn.h1254427.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=2026-01-31&endDate=2026-02-01®ionId=175481&adults=2&lodging=INN&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-Inns.d175481-aaInns.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Inns.d175481-aaInns.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg) ### Harborside Inn Of Boston 10/10 Excellent "The Harborside Inn is in a fantastic location! Quincy Market is a few minutes away. Parking is not on site, but a very sort walk to the parking garage which is discounted for staying at the hotel. The rooms are nicely done. They are updated, but still have a historic feel. The staff were friendly and accommodating! We will absolutely stay here again!" [](https://expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![Encore Boston Harbor](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5_y.jpg) ### Encore Boston Harbor 10/10 Excellent "Excellent service casino is amazing " [](https://expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) ![Omni Parker House ](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/c414a1f3_y.jpg) ### Omni Parker House 10/10 Excellent "Yes" [](https://expedia.ca/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.Hotel-Information) ![citizenM Boston North Station](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/0eda38d5_y.jpg) ### citizenM Boston North Station 10/10 Excellent "Very helpful and courteous staff" [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ![The Revolution Hotel](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/cce5d2b3_y.jpg) ### The Revolution Hotel 10/10 Excellent "Clean and smelled good" [](https://expedia.ca/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information) ![citizenM Boston Back Bay](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/90056141_y.jpg) ### citizenM Boston Back Bay 10/10 Excellent "Love this place. Funky in the best way. " [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![The Lenox Hotel Boston](https://images.trvl-media.com/lodging/1000000/10000/6500/6446/db068914_y.jpg) ### The Lenox Hotel Boston 10/10 Excellent "I loved the atmosphere, it was a lovely in a great location. " [](https://expedia.ca/Boston-Hotels-The-Lenox-Hotel-Boston.h6446.Hotel-Information) ![Hyatt Place Boston/Seaport District](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/5fe1e844_y.jpg) ### Hyatt Place Boston/Seaport District 10/10 Excellent "I really like staying here. Rooms were clean & upscale and very quiet. The hotel in convenient to harbor, conv center & great restaurants. Cocorico is an amazing coffee bar with pastries in lobby & the sports bar is large & lively. The staff is very friendly. " [](https://expedia.ca/Boston-Hotels-Hyatt-Place-BostonSeaport-District.h46521349.Hotel-Information) ![Hyatt Regency Boston](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/24991d94_y.jpg) ### Hyatt Regency Boston 10/10 Excellent "Great location!!!" [](https://expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information) ## Find out more about Winchester ## Winchester Inns information | Number of reviews | 383 | | ----------------- | ------- | | Accommodation | 4 Inns | | Lowest Price | CA $335 | | Highest Price | CA $335 | ## 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) - 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