Title: Winchester Guest Houses from CA $142 | 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 [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) In two weeks [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-04-03&endDate=2026-04-05&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/ff84eaf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Economy Single Room, 1 Single Bed](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/f3a293b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 Queen Bed with Sofa bed, Kitchen](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/e742e199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/99ff7575.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 (1,981 reviews) "Great location, easy check in/out. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ricardo CA $136 CA $156 total includes taxes & fees Feb 8 - Feb 9 [](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) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/5fb2766c.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) ![Economy Double Room, Ensuite](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/fdbe5d3c.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 (1,412 reviews) "Friendly staff, great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Judith CA $148 CA $170 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Boston-Hotels-Oasis-Guest-House.h1145259.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145270/a55155e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145270/5234a55e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145270/baa5f11b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, Private Bathroom](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145270/44118475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clarendon Square [](https://www.expedia.ca/Boston-Hotels-Clarendon-Square-Bed-Breakfast.h1145270.Hotel-Information) South End 9.2/10 Wonderful (251 reviews) "Beautiful brownstone in a great area. Stephen was very accommodating and offered advice on nearby dining. Truly one our favorite stays. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Blake CA $252 CA $304 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Boston-Hotels-Clarendon-Square-Bed-Breakfast.h1145270.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/890000/889800/889743/c580a535.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) ![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) ### Beacon Inn 1087 [](https://www.expedia.ca/Boston-Hotels-Beacon-Inn-1087.h889743.Hotel-Information) Longwood 8.0/10 Very good (793 reviews) "Yes" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Walther CA $142 CA $159 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Boston-Hotels-Beacon-Inn-1087.h889743.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/6000000/5230000/5227600/5227514/16d44f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/6000000/5230000/5227600/5227514/1ed4afcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/6000000/5230000/5227600/5227514/c5614d58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/6000000/5230000/5227600/5227514/aa795184.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 (627 reviews) "Very pleasant, comfortable stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Valerie CA $157 CA $175 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Boston-Hotels-Coolidge-Corner-Guest-House.h5227514.Hotel-Information) ![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/1000000/900000/893000/892946/4b98a457.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) ![Room](https://images.trvl-media.com/lodging/1000000/900000/893000/892946/e123a03d.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 (760 reviews) "The room was clean and the staffs were nice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Xiaoyong CA $142 CA $159 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Boston-Hotels-Beacon-Inn-1750.h892946.Hotel-Information) ![Superior Room, 2 Bedrooms, Non Smoking, Connecting Rooms](https://images.trvl-media.com/lodging/22000000/21420000/21410900/21410883/4d5bc25a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21420000/21410900/21410883/3cdc69ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 2 Bedrooms, Non Smoking, Connecting Rooms | Living area](https://images.trvl-media.com/lodging/22000000/21420000/21410900/21410883/f2977ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21420000/21410900/21410883/2a04752e.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 (163 reviews) "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 Feb 24 - Feb 25 [](https://www.expedia.ca/Boston-Hotels-Kitty-House-Near-Harvard-Square.h21410883.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1180000/1170200/1170159/66e5a396.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/2000000/1180000/1170200/1170159/00b94875.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1180000/1170200/1170159/b69ea65c.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 (268 reviews) "This was a beautiful place! Great for relaxation, convenient to amenities. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melanie CA $127 CA $142 total includes taxes & fees Feb 24 - Feb 25 [](https://www.expedia.ca/Boston-Hotels-The-Inn-On-The-Horse-Farm.h1170159.Hotel-Information) ![Classic Room](https://images.trvl-media.com/lodging/109000000/108440000/108435200/108435179/acd5adfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Room](https://images.trvl-media.com/lodging/109000000/108440000/108435200/108435179/b86cf453.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 (28 reviews) "Thanks I liked my stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristina CA $80 CA $216 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Boston-Hotels-ESJACPE-GUEST-HOUSE.h108435179.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) ![Family Single Room](https://images.trvl-media.com/lodging/115000000/114180000/114173800/114173750/d2e2944d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Single Room](https://images.trvl-media.com/lodging/115000000/114180000/114173800/114173750/7afaca5e.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/b0c1d447.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 (45 reviews) "It was nice. The room has wi-fi and a kitchen near the living room. There's a pool table. The owner is very nice and respectable. The other guests are quiet and it felt pretty safe. The price was really good. Thank you." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shakari CA $96 CA $193 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Boston-Hotels-184-Heath-St.h114173750.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=2026-02-21&endDate=2026-02-22®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 "The staff was extremely friendly and accommodating. The decor was beautiful. The room was very clean and comfortable. " [](https://expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg) ### Harborside Inn Of Boston 10/10 Excellent "Best price for the location! Always clean and great staff!" [](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 "Wonderful service, gorgeous room" [](https://expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) ![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "Beautiful hotel, excellent staff and really nice location." [](https://expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![Hilton Boston Logan Airport](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/23c65d09_y.jpg) ### Hilton Boston Logan Airport 10/10 Excellent "Clean and comfortable, great view of the city and airplanes on approach to landing. " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.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 "Clean room. Great staff!" [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![Omni Boston Hotel at the Seaport](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/26d11bc3_y.jpg) ### Omni Boston Hotel at the Seaport 10/10 Excellent "The room looked amazing and the staff was very nice" [](https://expedia.ca/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information) ![Omni Parker House ](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/c414a1f3_y.jpg) ### Omni Parker House 10/10 Excellent "Clean room, classy service, valet and bellhops were awesome!" [](https://expedia.ca/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.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 "Location was great! Very clean and friendly staff!" [](https://expedia.ca/Boston-Hotels-Hyatt-Place-BostonSeaport-District.h46521349.Hotel-Information) ## Find out more about Winchester ## Winchester Guest Houses information | Number of reviews | 5,896 | | ----------------- | --------------- | | Accommodation | 16 Guest Houses | | Lowest Price | CA $142 | | Highest Price | CA $304 | ## 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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