Title: Winchester Guest Houses from CA $150 | 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) ![Skyline of Boston](https://images.trvl-media.com/place/162713/d94e6534-0d00-46ec-b964-4dc54f45df9d.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Ana Lei # Search Guest Houses in Winchester from CA $150 - ![](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 [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester guest houses ![Property entrance](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/0af3b824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Studio, 1 King Bed with Sofa bed, Kitchen](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/67115820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/ac01edf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/5ebb4acf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Copley House [](https://www.expedia.ca/Boston-Hotels-Copley-House.h1482493.Hotel-Information) Back Bay 9.0/10 Wonderful (1935) "Fantastic place to stay and visit Boston." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Poorvajan [](https://www.expedia.ca/Boston-Hotels-Copley-House.h1482493.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/31868feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/4aea60d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/e425e9d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Economy Double Room, Ensuite](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/f81a74b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oasis Guest House [](https://www.expedia.ca/Boston-Hotels-Oasis-Guest-House.h1145259.Hotel-Information) Fenway–Kenmore 9.4/10 Exceptional (1393) "Lovely stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amelia CA $140 CA $161 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Boston-Hotels-Oasis-Guest-House.h1145259.Hotel-Information) ![King Room @ 1087 Beacon St. ](https://images.trvl-media.com/lodging/1000000/890000/889800/889743/ac883cf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/890000/889800/889743/c00ee678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room with Two Double Beds @ 1087 Beacon St. ](https://images.trvl-media.com/lodging/1000000/890000/889800/889743/585503aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room with One Double Bed and Private Detached Bath @ 1087 Beacon St. | Bathroom](https://images.trvl-media.com/lodging/1000000/890000/889800/889743/880d6c4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beacon Inn 1087 [](https://www.expedia.ca/Boston-Hotels-Beacon-Inn-1087.h889743.Hotel-Information) Longwood 8.0/10 Very good (780) "Staff was the best, led me directly to where to park and upgraded me to another room available. The room was extremely spacious with a nice tv and fireplace. The property appears to be a former home divided and has a very homely feel. Stayed one night to attend an event nearby, and was able to leave my car to take public transit to and from the event. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kyle CA $143 CA $160 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Boston-Hotels-Beacon-Inn-1087.h889743.Hotel-Information) ![Room](https://images.trvl-media.com/lodging/1000000/900000/893000/892946/4b98a457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/893000/892946/51517f14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/893000/892946/c04ca267.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/1000000/900000/893000/892946/011a3ac8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beacon Inn 1750 [](https://www.expedia.ca/Boston-Hotels-Beacon-Inn-1750.h892946.Hotel-Information) Brookline 7.4/10 Good (758) "A little older but great location and very nice staff. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Marc CA $143 CA $160 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Boston-Hotels-Beacon-Inn-1750.h892946.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/6000000/5230000/5227600/5227514/48469faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/6000000/5230000/5227600/5227514/2e412f68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/6000000/5230000/5227600/5227514/c8acdf30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/6000000/5230000/5227600/5227514/16d44f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coolidge Corner Guest House [](https://www.expedia.ca/Boston-Hotels-Coolidge-Corner-Guest-House.h5227514.Hotel-Information) Coolidge Corner South Side 8.2/10 Very good (625) "Very pleasant, comfortable stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Valerie CA $172 CA $193 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Boston-Hotels-Coolidge-Corner-Guest-House.h5227514.Hotel-Information) ![Standard Double Room, 1 Double Bed, Shared Bathroom | Private kitchen](https://images.trvl-media.com/lodging/22000000/21420000/21410900/21410883/be00b22a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21420000/21410900/21410883/f80ad6a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 1 Double Bed, Shared Bathroom](https://images.trvl-media.com/lodging/22000000/21420000/21410900/21410883/713d9857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/22000000/21420000/21410900/21410883/00fcaaee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tranquil House in Cambridge [](https://www.expedia.ca/Boston-Hotels-Kitty-House-Near-Harvard-Square.h21410883.Hotel-Information) Strawberry Hill 8.8/10 Excellent (162) "yes, nice and quiet kitchen was nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sean CA $131 CA $150 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Boston-Hotels-Kitty-House-Near-Harvard-Square.h21410883.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1180000/1170200/1170159/d574c037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1180000/1170200/1170159/60b0244b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, Tempur-Pedic beds, individually decorated](https://images.trvl-media.com/lodging/2000000/1180000/1170200/1170159/ce84b5b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1180000/1170200/1170159/9d20e578.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn on the Horse Farm [](https://www.expedia.ca/Boston-Hotels-The-Inn-On-The-Horse-Farm.h1170159.Hotel-Information) Sudbury 8.0/10 Very good (266) "Great area, historic. Near restaurants. Able to wander the property. Nice to relax before our journey home." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $188 CA $211 total includes taxes & fees Jan 17 - Jan 18, 2026 [](https://www.expedia.ca/Boston-Hotels-The-Inn-On-The-Horse-Farm.h1170159.Hotel-Information) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/115000000/114180000/114173800/114173750/a60c0158.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114180000/114173800/114173750/4d62b58c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114180000/114173800/114173750/35aa1738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, soap, toilet paper](https://images.trvl-media.com/lodging/115000000/114180000/114173800/114173750/4c7c5b5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 184 Heath St [](https://www.expedia.ca/Boston-Hotels-184-Heath-St.h114173750.Hotel-Information) Jamaica Plain 3.4/10 (41) "👍" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Musa CA $69 CA $163 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Boston-Hotels-184-Heath-St.h114173750.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/109000000/108440000/108435200/108435179/d763a41f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Room](https://images.trvl-media.com/lodging/109000000/108440000/108435200/108435179/59ef104a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Room | Private kitchen](https://images.trvl-media.com/lodging/109000000/108440000/108435200/108435179/f937a2cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108440000/108435200/108435179/e08c4325.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ESJACPE GUEST HOUSE [](https://www.expedia.ca/Boston-Hotels-ESJACPE-GUEST-HOUSE.h108435179.Hotel-Information) Jamaica Plain 2.8/10 (27) "Thanks I liked my stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristina CA $87 CA $225 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Boston-Hotels-ESJACPE-GUEST-HOUSE.h108435179.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=2025-12-31&endDate=2026-01-01®ionId=175481&adults=2&lodging=GUEST_HOUSE&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-Guest-Houses.d175481-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Guest-Houses.d175481-aaGuestHouses.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![The Godfrey Hotel Boston](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/e4d256d2_y.jpg) ### The Godfrey Hotel Boston 10/10 Excellent "We had a nice stay at this place, check in is a breeze, everyone is very nice. The bed is comfy, the room is nice and clean. The location is really good too, Macy’s is across the street, walking distance to Boston common and Faneuil Hall Market place, and North end. We will difinitely stay here again. " [](https://expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) ![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "Clean room and helpful staff. A lot of restaurant and pub n’est the Hotel. " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![Omni Parker House ](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/c414a1f3_y.jpg) ### Omni Parker House 10/10 Excellent "Class hotel with amazing history " [](https://expedia.ca/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.Hotel-Information) ![The Arcadian Hotel](https://images.trvl-media.com/lodging/32000000/31100000/31097800/31097754/f8ad7683_y.jpg) ### The Arcadian Hotel 10/10 Excellent "Very clean and the staff was friendly. Parking is a little tricky but that's to be expected. Would definitely go back. " [](https://expedia.ca/Boston-Hotels-Arcadian-Hotel-Brookline.h31097754.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 "Beautiful view! Clean. Convenient location " [](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 "Good" [](https://expedia.ca/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information) ![Hyatt Regency Boston](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/24991d94_y.jpg) ### Hyatt Regency Boston 10/10 Excellent "Excellent spa" [](https://expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information) ![Hilton Boston Back Bay](https://images.trvl-media.com/lodging/1000000/10000/6000/5928/f418fbdd_y.jpg) ### Hilton Boston Back Bay 10/10 Excellent "The hotel is undergoing renovations which will be an exciting improvement. Still a great staff and excellent location. Will return! " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Back-Bay.h5928.Hotel-Information) ![Boston Harbor Hotel](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b_y.jpg) ### Boston Harbor Hotel 10/10 Excellent "Yes" [](https://expedia.ca/Boston-Hotels-Boston-Harbor-Hotel.h26146.Hotel-Information) ## Find out more about Winchester ## Winchester Guest Houses information | Number of reviews | 5,686 | | ----------------- | --------------- | | Accommodation | 16 Guest Houses | | Lowest Price | CA $150 | | Highest Price | CA $225 | ## 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) - 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