Title: Winchester Inns from CA $216 | 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 [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=INN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=INN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=INN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-05-15&endDate=2026-05-17&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) ![Dining room](https://images.trvl-media.com/lodging/97000000/96350000/96341500/96341402/6a4af7a2.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 9.4/10 Exceptional (69 reviews) "Brilliant place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $214 CA $240 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Salem-Hotels-Silsbees-By-Daniels-House.h96341402.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1260000/1254500/1254427/414d0f0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Queen Fireplace Room ](https://images.trvl-media.com/lodging/2000000/1260000/1254500/1254427/1424a8f5.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1260000/1254500/1254427/c5c5b979.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 Historic District 9.8/10 Exceptional (319 reviews) "The Inn and the rooms are so cozy and charming. We loved our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $430 CA $480 total includes taxes & fees Apr 17 - Apr 18 [](https://www.expedia.ca/Boston-Hotels-Harbor-Light-Inn.h1254427.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/94000000/93680000/93677600/93677568/f21a960d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/94000000/93680000/93677600/93677568/22892a49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/94000000/93680000/93677600/93677568/0900f43f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/94000000/93680000/93677600/93677568/a2ac9f36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ginkgo House on Harvard [](https://www.expedia.ca/Cambridge-Hotels-Ginkgo-House-On-Harvard.h93677568.Hotel-Information) Central Square 9.8/10 Exceptional (77 reviews) "Room was very clean . When in that area I will choose to stay here again !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $188 CA $216 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Cambridge-Hotels-Ginkgo-House-On-Harvard.h93677568.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=2026-03-31&endDate=2026-04-01®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 ![Encore Boston Harbor](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/a1d3b824_y.jpg) ### Encore Boston Harbor 10/10 Excellent "Everything was perfect. From check in to checkout " [](https://expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) ![citizenM Boston Back Bay](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/57348ff5_y.jpg) ### citizenM Boston Back Bay 10/10 Excellent "Best hotel you could find in Boston from design to staff friendliness" [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/f403d96c_y.jpg) ### Harborside Inn Of Boston 10/10 Excellent "Had a great time as usual. The staff was very accommodating when I asked to check in early. Super friendly and professional. The location is amazing and centrally situated for any adventure you wanna take in the city" [](https://expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![Omni Parker House ](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/de788f3d_y.jpg) ### Omni Parker House 10/10 Excellent "Property is great, staff is super friendly and everything is a short walking distance. " [](https://expedia.ca/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.Hotel-Information) ![The Midtown Hotel MOD Collection by Sonesta](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/e1e25d35_y.jpg) ### The Midtown Hotel MOD Collection by Sonesta 10/10 Excellent "Very nice hotel! Staff was friendly and helpful! Great location and on a budget! Only complaint was the rooms HVAC was outdated and the room was warm and not able to control. Otherwise a fun trip and great stay! " [](https://expedia.ca/Boston-Hotels-Midtown-Hotel.h2898.Hotel-Information) ![Hilton Boston Logan Airport](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/7fd62fb9_y.jpg) ### Hilton Boston Logan Airport 8/10 Good "Extremely convenient when catching an early flight, and it is a Hilton - clean, well staffed, professional and courteous " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information) ![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "Loved the pool. " [](https://expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![Hampton Inn Boston - Logan Airport](https://images.trvl-media.com/lodging/1000000/580000/578500/578419/fa1c0549_y.jpg) ### Hampton Inn Boston - Logan Airport 4/10 Poor "Rude Staff, Dirty Room and Breakfast was terrible. " [](https://expedia.ca/Boston-Hotels-Hampton-Inn-Boston-Logan-Airport.h578419.Hotel-Information) ![Hilton Boston Park Plaza](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/6e9f8959_y.jpg) ### Hilton Boston Park Plaza 4/10 Poor "The bed and shower are terrible. Room ugly and small. Locations it’s great. I definitely not coming back" [](https://expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information) ## Find out more about Winchester ## Winchester Inns information | Number of reviews | 388 | | ----------------- | ------- | | Accommodation | 4 Inns | | Lowest Price | CA $216 | | Highest Price | CA $480 | ## 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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