Title: Book The Best Hotels in Winchester, MA for 2026 from CA $119 - Fully Refundable Options - Expedia.ca [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 ## Go beyond your typical stay in Winchester Pool [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-15&d2=2026-02-15&amenities=POOL) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-15&d2=2026-02-15&travelerType=family_friendly) Spa [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-15&d2=2026-02-15&amenities=SPA_ON_SITE) Apart hotel [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-15&d2=2026-02-15&lodging=APART_HOTEL) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-15&d2=2026-02-15&amenities=HOT_TUB) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-15&d2=2026-02-15&amenities=PETS) Ocean view [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-15&d2=2026-02-15&amenities=OCEAN_VIEW) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-15&d2=2026-02-15&lodging=APARTMENT) Condo [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-15&d2=2026-02-15&lodging=CONDO) Waterpark [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-15&d2=2026-02-15&amenities=WATER_PARK) House­boat [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-15&d2=2026-02-15&lodging=HOUSE_BOAT) ## Check prices for these dates Tonight [Jan 30 - Jan 31](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-01-30&endDate=2026-01-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 31 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-01-31&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester hotels ![International cuisine](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/57348ff5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/d17a08ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/98af3a24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/61974d0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### citizenM Boston Back Bay [](https://www.expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) Fenway–Kenmore 9.4/10 Exceptional (2,271 reviews) "An amazing hotel, clean, nice staff, great service " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tamar CA $156 CA $182 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/6e9f8959.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/3aa5107f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Boston Park Plaza [](https://www.expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information) Bay Village 8.4/10 Very good (3,104 reviews) "Clean and amenities were great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lauryn CA $128 CA $205 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/e8240d00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/328c763f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/80b97ccf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/b4f639c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Dagny Boston [](https://www.expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) Downtown Boston 9.4/10 Exceptional (7,019 reviews) "Beautiful hotel, great location, very friendly and helpful staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey CA $159 CA $233 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![In-room safe, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/72cd2881.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/e1a64100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/213feb43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/a1ab1c31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Copley Square Hotel, a FOUND Hotel [](https://www.expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) Back Bay 8.6/10 Excellent (3,917 reviews) "Great location, clean and comfy room, friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zachary CA $114 CA $133 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/1000000/10000/4100/4054/4ee2b5dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, desk](https://images.trvl-media.com/lodging/1000000/10000/4100/4054/99039e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/4100/4054/b57212de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/4100/4054/59f7788e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Staypineapple, A Delightful Hotel, South End [](https://www.expedia.ca/Boston-Hotels-Staypineapple.h4054.Hotel-Information) South End 9.0/10 Wonderful (1,001 reviews) "Super cute room staff was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aimee CA $76 CA $128 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Boston-Hotels-Staypineapple.h4054.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/fd67eab2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Private Bathroom](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/c7da4186.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee shop](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/8ac4fbcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/c80dc7a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Revolution Hotel [](https://www.expedia.ca/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information) South End 9.0/10 Wonderful (2,431 reviews) "Great stay! Clean room, kind staff, and excellent location. Would stay here again and would recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mia Lian CA $106 CA $123 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/b920b61e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/73cb3288.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/c874e48e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/65b5aa9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Boston Seaport District [](https://www.expedia.ca/Boston-Hotels-The-Westin-Boston-Seaport-District.h1450057.Hotel-Information) Seaport District 9.2/10 Wonderful (2,397 reviews) "Clean room, nice restaurant and quiet. The pool was busy but still enjoyable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Glendaly CA $153 CA $303 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Boston-Hotels-The-Westin-Boston-Seaport-District.h1450057.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/d6de0f74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/c50bac3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/116c5658.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/2d0dd8e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft by Marriott, Boston Seaport District [](https://www.expedia.ca/Boston-Hotels-Aloft-Boston-Seaport-District.h11263952.Hotel-Information) Seaport District 9.0/10 Wonderful (1,408 reviews) "Nice hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $142 CA $204 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Boston-Hotels-Aloft-Boston-Seaport-District.h11263952.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/e1e25d35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/416ad7d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/a8ad449d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/c1a7b53a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Midtown Hotel MOD Collection by Sonesta [](https://www.expedia.ca/Boston-Hotels-Midtown-Hotel.h2898.Hotel-Information) Back Bay 7.6/10 Good (1,004 reviews) "Very clean and nice rooms. The hotel staff is also very kind." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $132 CA $154 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Boston-Hotels-Midtown-Hotel.h2898.Hotel-Information) ![Presidential Suite](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/866dc285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/w4973h3840x4y0-87fd5a36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/84f4c8df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/6306f7e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Boston [](https://www.expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information) Downtown Boston 9.0/10 Wonderful (1,818 reviews) "Amazing place to stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yohlman CA $153 CA $226 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information) ![Peruvian cuisine](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/e4d256d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/db3fd34b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/3aefc22e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/3c267db5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Godfrey Hotel Boston [](https://www.expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) Downtown Boston 9.4/10 Exceptional (4,886 reviews) "Nice hotel in great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric CA $152 CA $240 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/f2f31351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/c37d2403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/0277dcdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed (View)](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/23e9f070.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### citizenM Boston North Station [](https://www.expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) West End 9.4/10 Exceptional (4,312 reviews) "Great stay and view! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shauna CA $156 CA $182 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ![Rooftop terrace](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/0ab5b9a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/245fc311.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/e67c2116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/8de2892c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### YOTEL Boston [](https://www.expedia.ca/Boston-Hotels-YOTEL-Boston.h18090311.Hotel-Information) Seaport District 8.6/10 Excellent (2,411 reviews) "Great stay overall! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lourdes CA $127 CA $210 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Boston-Hotels-YOTEL-Boston.h18090311.Hotel-Information) ![Serves breakfast, lunch, and dinner](https://images.trvl-media.com/lodging/39000000/38770000/38766200/38766175/b8807d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, free cribs/infant beds](https://images.trvl-media.com/lodging/39000000/38770000/38766200/38766175/8d14bce6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/39000000/38770000/38766200/38766175/49683728.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/39000000/38770000/38766200/38766175/cfaa2fff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Moxy Boston Downtown [](https://www.expedia.ca/Boston-Hotels-Moxy-Boston-Downtown.h38766175.Hotel-Information) Bay Village 8.8/10 Excellent (1,029 reviews) "Clean rooms, friendly staff, nice bar area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $121 CA $195 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Boston-Hotels-Moxy-Boston-Downtown.h38766175.Hotel-Information) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/d1e2c1a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/a41b9393.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 restaurants, breakfast served](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/bc3320d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/89bc4993.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Omni Boston Hotel at the Seaport [](https://www.expedia.ca/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information) Seaport District 9.2/10 Wonderful (4,439 reviews) "Beautiful hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Suzanne CA $165 CA $247 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/e07ab872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/dea35c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/3a90f50b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seaport Hotel Boston [](https://www.expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) Seaport District 9.6/10 Exceptional (3,940 reviews) "Great accommodations and friendly staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas CA $173 CA $248 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/26b9dda9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/b025cdc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/ee0d02d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/6f0677c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Boston/Seaport District [](https://www.expedia.ca/Boston-Hotels-Hyatt-Place-BostonSeaport-District.h46521349.Hotel-Information) Seaport District 9.4/10 Exceptional (2,279 reviews) "Absolutely spotless with great staff, comfortable beds, fun location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah CA $182 CA $212 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Boston-Hotels-Hyatt-Place-BostonSeaport-District.h46521349.Hotel-Information) ![Standard Room, 1 Queen Bed](https://images.trvl-media.com/lodging/1000000/20000/15800/15746/8f309a43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/20000/15800/15746/3da48020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/15800/15746/5e786b7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Building design](https://images.trvl-media.com/lodging/1000000/20000/15800/15746/7fdd8c83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Found Hotel Boston Common [](https://www.expedia.ca/Boston-Hotels-Found-Hotel-Boston-Common.h15746.Hotel-Information) Bay Village 8.4/10 Very good (1,312 reviews) "It was great stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $114 CA $133 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Boston-Hotels-Found-Hotel-Boston-Common.h15746.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/ef05180d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/e8e42358.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed with Sofa bed (Water View)](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/407ab4b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/c304377b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Boston Seaport District [](https://www.expedia.ca/Boston-Hotels-Hampton-Inn-Boston-Seaport.h55421972.Hotel-Information) Seaport District 9.2/10 Wonderful (2,812 reviews) "Breakfast was amazing, I really liked that place! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yasmin CA $178 CA $207 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Boston-Hotels-Hampton-Inn-Boston-Seaport.h55421972.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/30000000/29670000/29669200/29669123/4962c754.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/30000000/29670000/29669200/29669123/70b8223b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/30000000/29670000/29669200/29669123/8b031beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/30000000/29670000/29669200/29669123/000c36d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric Faneuil Hall Boston [](https://www.expedia.ca/Boston-Hotels-Hyatt-Centric-Faneuil-Hall-Boston.h29669123.Hotel-Information) Downtown Boston 9.2/10 Wonderful (1,291 reviews) "Courteous and helpful staff, clean rooms and great location for exploring on foot. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Jordan CA $147 CA $225 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Boston-Hotels-Hyatt-Centric-Faneuil-Hall-Boston.h29669123.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=2026-02-13&endDate=2026-02-14®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.d175481.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels.d175481.Travel-Guide-Hotels) ## Stay near popular Winchester attractions ### Winter Pond Enjoy an outing to Winter Pond during your stay in Winchester. Discover the top-notch restaurants and acclaimed art scene in this vibrant area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561930456) ## Learn more about Winchester Stroll along the shores of Mystic Lake, where locals gather for picnics and kayaking on sunny afternoons. History buffs can explore the Wright-Locke Farm, learning about sustainable agriculture while kids enjoy the farm animals and nature trails. [See all hotels in Winchester](https://www.expedia.ca/Hotel-Search?startDate=2026-02-13&endDate=2026-02-14&adults=2®ionId=175481) ![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=900&h=600&p=1&q=high) ## Top Winchester Hotel Reviews ![citizenM Boston Back Bay](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/90056141_y.jpg) ### citizenM Boston Back Bay 10/10 Excellent "very nice view and very easy quick check in" [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![Encore Boston Harbor](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5_y.jpg) ### Encore Boston Harbor 10/10 Excellent "GREAT LOCATION" [](https://expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) ![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "Very clean, friendly staff, awesome gym. " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.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 "My favorite hotel! So convenient! Great restaurant! " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.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 clean and well maintained. Staff was friendly and attentive. " [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "Wonderful staff and great experience! " [](https://expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.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 staff. Great location" [](https://expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.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 "Great staff, easy check in" [](https://expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.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 "The check in process was smooth and pleasant! Was given an upgrade which was very nice and much appreciated. Staff was amazing and very friendly, location is A++ " [](https://expedia.ca/Boston-Hotels-The-Lenox-Hotel-Boston.h6446.Hotel-Information) ## More cheap stays in Winchester ![enVision Hotel Boston Everett](https://images.trvl-media.com/lodging/18000000/17520000/17515300/17515205/09904e53_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### enVision Hotel Boston Everett 1834 Revere Beach Pkwy Everett MA CA $114 CA $127 total Feb 4 - Feb 5 includes taxes & fees 8.4/10 Very Good! (1,005 reviews) [](https://expedia.ca/Boston-Hotels-EnVision-Hotel-Boston-Everett.h17515205.Hotel-Information) ![Ramada by Wyndham Boston](https://images.trvl-media.com/lodging/1000000/10000/300/293/b875dc04_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Ramada by Wyndham Boston 800 Morrissey Blvd Boston MA CA $115 CA $134 total Feb 8 - Feb 9 includes taxes & fees 6.8/10 (1,610 reviews) [](https://expedia.ca/Boston-Hotels-Ramada-By-Wyndham-Boston.h293.Hotel-Information) ![Sonesta Simply Suites Boston Burlington](https://images.trvl-media.com/lodging/1000000/550000/544800/544728/a4844b99_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Sonesta Simply Suites Boston Burlington 130 Middlesex Tpke Burlington MA CA $125 CA $140 total Feb 20 - Feb 21 includes taxes & fees 8.8/10 Excellent! (171 reviews) [](https://expedia.ca/Boston-Hotels-Sonesta-Simply-Suites-Boston-Burlington.h544728.Hotel-Information) ![Hampton Inn Boston Logan Airport Chelsea](https://images.trvl-media.com/lodging/49000000/48880000/48879900/48879812/bfe287d7_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn Boston Logan Airport Chelsea 200 2nd Street Chelsea MA CA $130 CA $146 total Feb 2 - Feb 3 includes taxes & fees 9/10 Wonderful! (2,753 reviews) [](https://expedia.ca/Boston-Hotels-Hampton-Inn-Boston-Logan-Airport-Chelsea.h48879812.Hotel-Information) ![Hampton Inn & Suites Boston/Waltham](https://images.trvl-media.com/lodging/22000000/21910000/21904300/21904239/841c68d6_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn & Suites Boston/Waltham 135 2nd Ave Waltham MA CA $132 CA $147 total Feb 6 - Feb 7 includes taxes & fees 9.2/10 Wonderful! (1,627 reviews) [](https://expedia.ca/Boston-Hotels-Hampton-Inn-Suites-BostonWaltham.h21904239.Hotel-Information) ![Comfort Inn & Suites Logan International Airport](https://images.trvl-media.com/lodging/1000000/550000/543800/543784/fa5d7891_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Comfort Inn & Suites Logan International Airport 85 American Legion Hwy Revere MA CA $129 CA $152 total Feb 15 - Feb 16 includes taxes & fees 8.8/10 Excellent! (2,246 reviews) [](https://expedia.ca/Boston-Hotels-Comfort-Inn-Suites-Logan-International-Airport.h543784.Hotel-Information) ## Hotels in Winchester with star rating ![5 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_z.jpg) 5 Star Hotels 14 properties [](https://expedia.ca/5Star-Winchester-Hotels.s50-0-d175481.Travel-Guide-Filter-Hotels) ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 98 properties [](https://expedia.ca/4Star-Winchester-Hotels.s40-0-d175481.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 290 properties [](https://expedia.ca/3Star-Winchester-Hotels.s30-0-d175481.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 544 properties [](https://expedia.ca/2Star-Winchester-Hotels.s20-0-d175481.Travel-Guide-Filter-Hotels) ## Find out more about Winchester ### Top reasons to visit Winchester - **Outdoor Activities:** Winchester is perfect for outdoor enthusiasts, offering scenic parks and nearby ski fields for year-round fun. - **Historic Charm:** Explore the charming historic district filled with significant sites and rich local history. - **Cultural Experiences:** Enjoy educational attractions and visit historic colleges and universities in the area. - **Family-Friendly Adventures:** With a variety of activities, Winchester is ideal for families seeking leisure and excitement. - **Diverse Accommodations:** Choose from charming bed & breakfasts to well-equipped hotels tailored to various needs. ### Find great hotels near Winchester Winchester, Massachusetts, offers a delightful array of accommodation options, from charming bed & breakfasts to well-equipped hotels. Whether you're seeking a pet-friendly stay, a business-focused environment, or an LGBTQIA welcoming atmosphere, Winchester has something for everyone. Explore the best hotels in the area, ensuring a comfortable and memorable vacation experience while enjoying the rich history and vibrant community that this picturesque town has to offer. - **[citizenM Boston North Station: ](https://www.expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information)** A modern haven for business travellers, citizenM Boston North Station is a 4-star hotel that offers a unique blend of style and functionality. Located 11.3km from Winchester, this property prides itself on being LGBTQIA welcoming, making it a perfect choice for inclusive travel. The hotel features a 24-hour business centre, accessible meeting rooms, and a vibrant atmosphere that encourages creativity and collaboration. Guests appreciate the contemporary design and tech-savvy amenities, ensuring a seamless stay whether for work or leisure. - **[Hyatt Regency Boston/Cambridge: ](https://www.expedia.ca/Boston-Hotels-Hyatt-Regency-BostonCambridge.h16079.Hotel-Information)** Situated 11.3km from Winchester, Hyatt Regency Boston/Cambridge is an elegant 4-star retreat that caters to both business and leisure travellers. This LGBTQIA-friendly and pet-friendly hotel offers a wealth of amenities including conference spaces and business district access, making it ideal for corporate guests. For those travelling with furry friends, the hotel’s pet policy ensures a comfortable stay. Guests enjoy the sophisticated atmosphere, exceptional dining options, and breathtaking views of the Charles River, creating a memorable experience. - **[Four Points by Sheraton Boston Newton: ](https://www.expedia.ca/Boston-Hotels-Four-Points-By-Sheraton-Boston-Newton.h10301.Hotel-Information)** A charming 3.5-star hotel located 11.3km from Winchester, Four Points by Sheraton Boston Newton offers a family-friendly atmosphere alongside business amenities. This property is perfect for those seeking a nature-themed getaway with a touch of convenience for children, featuring video game consoles and complimentary cribs. The hotel’s business centre and meeting rooms cater to the needs of professional guests, while its warm and welcoming environment makes it an excellent choice for families looking to unwind and explore. ### Where to stay in Winchester Winchester, Massachusetts, offers an ideal blend of outdoor activities and cultural experiences for families and solo travellers alike. Explore the charming historic district, stroll through scenic parks, or enjoy a weekend getaway filled with friendly locals. Nearby, the vibrant atmosphere of urban life and rich history beckons, making it a convenient base for discovering the surrounding areas. Whether you're seeking family-friendly adventures or a taste of local business culture, Winchester has something for everyone. - **[Boston: ](https://www.expedia.ca/Boston-Hotels.d178239.Travel-Guide-Hotels)** As a vibrant metropolis, Boston offers a rich blend of history, culture, and modern attractions. Situated a short distance from Winchester, Boston is a must-visit for its educational institutions, lively music scene, and extensive shopping options. The city’s peak tourist seasons are in July to August and October, making these months ideal for experiencing its bustling atmosphere. Notable landmarks include historic sports stadiums and event venues, providing a perfect backdrop for both family outings and cultural explorations. - **[Woburn: ](https://www.expedia.ca/Woburn-Hotels.d10373.Travel-Guide-Hotels)** Located only 3.2km from Winchester, Woburn is a charming city that welcomes visitors with its family-friendly atmosphere and cultural experiences. With a consistent influx of travellers throughout the year, particularly in April, July, and September, Woburn is perfect for those looking to enjoy shopping at local centres and visiting nearby beaches. The city boasts attractions such as stadiums and event venues, making it a great spot for fun-filled days with family and friends. - **[West Medford: ](https://www.expedia.ca/West-Medford-Boston-Hotels.0-n173092-0.Travel-Guide-Filter-Hotels)** Just 3.2km from Winchester, West Medford is a quaint neighbourhood known for its seasonal charm. Visitors flock here in March to April and November to enjoy its cultural and outdoor experiences. The area features shopping areas and educational institutions, alongside historic buildings that tell the story of its past. West Medford is ideal for those who appreciate a mix of modern amenities and historical significance, making it an inviting stop on your journey. ### Things to do near Winchester Winchester, Massachusetts, is perfect for a family vacation with its outdoor activities and cultural experiences. Visitors can enjoy educational attractions, explore the local shopping mall, and even hit the nearby ski fields. Whether you're looking to unwind or engage in fun activities, a trip to Winchester offers a delightful mix of leisure and adventure for everyone. **Shopping** For a delightful shopping experience in Winchester, visit [Wine & Cheese Cask](https://www.expedia.ca/Wine-Cheese-Cask-Hotels.0-l553248621532667236-0.Travel-Guide-Filter-Hotels), just 8.0km away. [Harvard Square](https://www.expedia.ca/Harvard-Square-Hotels.0-l6070079-0.Travel-Guide-Filter-Hotels), 9.7km away, offers a vibrant mix of entertainment and shopping. If you're up for a drive, check out the [Boston Public Market](https://www.expedia.ca/Boston-Public-Market-Hotels.0-l553248621533117592-0.Travel-Guide-Filter-Hotels), located 11.3km away, for local goods and flavours. **Recreation** Experience the vibrant entertainment vibes at [MGM Music Hall at Fenway](https://www.expedia.ca/MGM-Music-Hall-At-Fenway-Hotels.0-l811179345399357440-0.Travel-Guide-Filter-Hotels), just 12.9km from Winchester, featuring captivating concerts. For sports enthusiasts, [Agganis Arena](https://www.expedia.ca/Agganis-Arena-Hotels.0-l6229782-0.Travel-Guide-Filter-Hotels), 11.3km away, offers thrilling events. Alternatively, enjoy ice skating at [Burlington Ice Palace](https://www.expedia.ca/Burlington-Ice-Palace-Hotels.0-l553248621532667274-0.Travel-Guide-Filter-Hotels), only 4.8km from Winchester, combining sports and adventure. **Adventure** Experience the beauty of [Horn Pond](https://www.expedia.ca/Horn-Pond-Hotels.0-l553248621561930457-0.Travel-Guide-Filter-Hotels), a serene outdoor haven 3.2km from Winchester, perfect for hiking and picnicking. For water sports enthusiasts, the [Courageous Sailing Center](https://www.expedia.ca/Courageous-Sailing-Center-Hotels.0-l6228826-0.Travel-Guide-Filter-Hotels), located 11.3km away, offers thrilling sailing adventures. Unleash your competitive spirit at [Boston Paintball](https://www.expedia.ca/Boston-Paintball-Hotels.0-l553248621532667271-0.Travel-Guide-Filter-Hotels), also 11.3km from Winchester. **Nightlife** Experience the adventure at [LEGOLAND® Discovery Center](https://www.expedia.ca/LEGOLAND-Discovery-Center-Hotels.0-l553248621561930613-0.Travel-Guide-Filter-Hotels), just 8.0km away, or catch a romantic film at [Somerville Theatre](https://www.expedia.ca/Somerville-Theatre-Hotels.0-l6262321-0.Travel-Guide-Filter-Hotels), 6.4km from Winchester. For a relaxed evening, enjoy drinks at [Cambridge Common](https://www.expedia.ca/Cambridge-Common-Hotels.0-l553248621532667235-0.Travel-Guide-Filter-Hotels), also 8.0km away, offering a charming atmosphere for entertainment and romance. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Winchester To save money during your visit to Winchester, consider travelling between December and February when hotel prices are lowest. Sundays are the most affordable days to book a stay, while Saturdays tend to be pricier. Use Expedia’s search tool to filter hotel options by budget and eco-friendly preferences, allowing you to find the best deals easily. Additionally, look for package deals that combine your hotel, flights, and activities for further savings. For getting around, take advantage of public transport options, which are typically more cost-effective. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Winchester are December to February, where the prices are slightly lower. This is in comparison to May and September to October, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Winchester is Sunday. The most expensive day to stay in Winchester is Saturday. - **Find cheap hotels on Expedia:** Expedia’s search tool enables you to specify your budget, desired location, and additional preferences. You can arrange your results to display prices from lowest to highest, making it easy to find the most affordable hotels first. Additionally, you have the option to refine your search by hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels available for booking. - **Consider bundling your trip:** You can save money by combining your hotel stay in Winchester with your flights and activities through an Expedia package. ### Find the best attractions near Winchester Winchester, Massachusetts, is an ideal destination for outdoor enthusiasts and culture-loving families. Visitors can explore a variety of attractions, including urban parks, historic colleges and universities, and significant historic sites. This charming town offers a perfect blend of culture, city experiences, and family-friendly activities, ensuring a memorable vacation for travellers of all interests. - **[Fenway Park: ](https://www.expedia.ca/Fenway-Park-Hotels.0-l6023384-0.Travel-Guide-Filter-Hotels)** Experience the iconic atmosphere of Fenway Park, one of the oldest baseball stadiums in the United States. Located 12.9km from Winchester, it offers a unique glimpse into sports history and a vibrant culture that resonates with both sports fans and casual visitors alike. - **[Harvard University: ](https://www.expedia.ca/Harvard-University-Hotels.0-l6034936-0.Travel-Guide-Filter-Hotels)** Immerse yourself in the rich heritage of Harvard University, just 9.7km away. This prestigious institution is renowned for its stunning architecture and cultural significance, providing a serene setting for exploration and inspiration. - **[TD Garden: ](https://www.expedia.ca/TD-Garden-Hotels.0-l6070137-0.Travel-Guide-Filter-Hotels)** Located 11.3km from Winchester, TD Garden is a bustling venue for events and conferences. Experience the lively business atmosphere while enjoying world-class entertainment, including sports and concerts. ### Best time to go to Winchester The best time to visit Winchester is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 28.6°F (-1.9°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | February | 29.8°F (-1.2°C) | Light Rain | Mostly Cloudy | Slightly Low | Slightly Low | | March | 36.9°F (2.7°C) | Light Rain | Mostly Sunny | Average | Average | | April | 47.7°F (8.7°C) | Light Rain | Mostly Sunny | Slightly High | Average | | May | 58.3°F (14.6°C) | Light Rain | Mostly Sunny | Average | Slightly High | | June | 66.4°F (19.1°C) | Light Rain | Mostly Sunny | Average | Average | | July | 73.6°F (23.1°C) | Light Rain | Mostly Sunny | Slightly High | Average | | August | 72.3°F (22.4°C) | Light Rain | Mostly Sunny | Average | Average | | September | 65.3°F (18.5°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | October | 54.9°F (12.7°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 43.3°F (6.3°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | December | 35.1°F (1.7°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | ### The nearest major airports for your trip to Winchester To reach Winchester, Massachusetts, you can fly into several nearby airports. Boston Logan International Airport ([BOS](https://www.expedia.ca/Logan-Intl-Airport-Hotels.0-aBOS-0.Travel-Guide-Filter-Hotels)) is located 14.5km away and offers excellent accommodations, including the 5-star [Encore Boston Harbor](https://www.expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information), [The Langham](https://www.expedia.ca/Boston-Hotels-The-Langham.h2558.Hotel-Information), Boston, and [The Liberty](https://www.expedia.ca/Boston-Hotels-The-Liberty.h1680030.Hotel-Information), a Marriott Luxury Collection Hotel, all within 4.8km of the airport. Providence's T.F. Green Airport ([PVD](https://www.expedia.ca/TF-Green-Airport-Hotels.0-aPVD-0.Travel-Guide-Filter-Hotels)) is 54.8km away, with nearby options like the [Omni Providence Hotel](https://www.expedia.ca/Providence-Hotels-Omni-Providence-Hotel.h24536.Hotel-Information) and [Graduate by Hilton Providence](https://www.expedia.ca/Providence-Hotels-Graduate-Providence.h20009389.Hotel-Information), both 11.3km from the airport. Lastly, Manchester-Boston Regional Airport ([MHT](https://www.expedia.ca/Manchester-Boston-Regional-Airport-Hotels.0-aMHT-0.Travel-Guide-Filter-Hotels)) is 57.9km from Winchester, with the 5-star Grand at Bedford Village Inn and [DoubleTree by Hilton Manchester Downtown](https://www.expedia.ca/Manchester-Hotels-DoubleTree-By-Hilton-Manchester-Downtown.h19860.Hotel-Information) located just 6.4km away. ## Frequently asked questions ### What is the best area to stay in Winchester? > Winchester Center is the town's main commercial and social hub. It's a compact and walkable area featuring a variety of local shops, cafes, and restaurants. The town common, a central green space, is a prominent landmark, often hosting community events. The area around Main Street and Thompson Street provides easy access to these amenities and the commuter rail station. > > > For couples looking for a relaxed and upscale experience, Winchester Center is an excellent choice. You'll find charming independent boutiques for a leisurely browse and a selection of quality restaurants for evening meals. The proximity to the commuter rail also offers convenient day trips into Boston without the need for a car. > > > Families will also find Winchester Center appealing due to its proximity to recreational facilities and open spaces. The town common is superb for children to play, and there are often family-friendly events happening. ### When is the best time to go to Winchester? > Spring in Winchester brings blooming flowers and trees, particularly noticeable around the Middlesex Fells Reservation, which offers walking trails and scenic views. Temperatures are mild, typically ranging from 10°C to 20°C, making it comfortable for outdoor activities like visiting the Wright-Locke Farm or enjoying a stroll along the Aberjona River. Couples often appreciate the picturesque scenery and the opportunity for relaxed outdoor experiences. > > > Autumn is another excellent time, with the New England foliage displaying spectacular colours. The weather remains mild, with temperatures generally between 10°C and 18°C, great for enjoying the town's parks and conservation lands. Families might particularly enjoy apple picking at local farms or participating in seasonal events. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Winchester hotel booking with Expedia? ### How much is the nightly rate at a Winchester hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Hotels near Alewife Station ](https://www.expedia.ca/Alewife-Station-Hotels.d6210670.Travel-Guide-Hotels) - [Hotels near Anderson/Woburn Station ](https://www.expedia.ca/AndersonWoburn-Station-Hotels.d6209689.Travel-Guide-Hotels) - [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) - [Hotels with a Pool in Arlington ](https://www.expedia.ca/Arlington-Hotels-Hotel-With-Pool.0-0-d74693-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Arlington ](https://www.expedia.ca/Arlington-Hotels-Hotels-With-Free-Parking.0-0-d74693-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Arlington ](https://www.expedia.ca/Arlington-Hotels-Hotels-With-Hot-Tubs.0-0-d74693-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Arlington ](https://www.expedia.ca/Arlington-Hotels-Hotels-With-Kitchenettes.0-0-d74693-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Arlington ](https://www.expedia.ca/Arlington-Hotels-Luxury-Hotel.0-0-d74693-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Arlington ](https://www.expedia.ca/Arlington-Hotels-Romantic-Hotel.0-0-d74693-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Taj Hotels in Arlington ](https://www.expedia.ca/Arlington-Hotels-Taj-Hotels.0-0-d74693--bTajHotels.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Arlington ](https://www.expedia.ca/Arlington-Hotels-Wedding-Hotels.0-0-d74693-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Arlington Hotels ](https://www.expedia.ca/Arlington-Hotels.d74693.Travel-Guide-Hotels) - [Inns in Arlington ](https://www.expedia.ca/Arlington-Inns.d74693-aaInns.Travel-Guide-Accommodation) - [Motels in Arlington ](https://www.expedia.ca/Arlington-Motels.d74693-aaMotels.Travel-Guide-Accommodation) - [Townhomes in Arlington ](https://www.expedia.ca/Arlington-Townhomes.d74693-aaTownhomes.Travel-Guide-Accommodation) - [Belmont Hotels ](https://www.expedia.ca/Belmont-Hotels.d78656.Travel-Guide-Hotels) - [Boston Hotels ](https://www.expedia.ca/Boston-Hotels.d178239.Travel-Guide-Hotels) - [Burlington Hotels ](https://www.expedia.ca/Burlington-Hotels.d6306.Travel-Guide-Hotels) - [Hotels near Burlington Mall ](https://www.expedia.ca/Burlington-Mall-Hotels.0-l6163632-0.Travel-Guide-Filter-Hotels) - [Davis Square Hotels ](https://www.expedia.ca/Davis-Square-Boston-Hotels.0-n6229794-0.Travel-Guide-Filter-Hotels) - [Downtown Boston Hotels ](https://www.expedia.ca/Downtown-Boston-Boston-Hotels.0-n6340396-0.Travel-Guide-Filter-Hotels) - [Hotels near Fenway Park ](https://www.expedia.ca/Fenway-Park-Hotels.0-l6023384-0.Travel-Guide-Filter-Hotels) - [Lexington Hotels ](https://www.expedia.ca/Lexington-Hotels.d8601.Travel-Guide-Hotels) - [Hotels near Logan Park ](https://www.expedia.ca/Logan-Park-Hotels.0-l6228854-0.Travel-Guide-Filter-Hotels) - [Hotels near Malden Center Station ](https://www.expedia.ca/Malden-Center-Station-Hotels.d6209582.Travel-Guide-Hotels) - [Malden Hotels ](https://www.expedia.ca/Malden-Hotels.d8444.Travel-Guide-Hotels) - [Cheap Hotels in Medford ](https://www.expedia.ca/Medford-Hotels-Cheap-Hotels.0-0-d8787-tCheapHotels.Travel-Guide-Filter-Hotels) - [Medford Hotels ](https://www.expedia.ca/Medford-Hotels.d8787.Travel-Guide-Hotels) - [Hotels near Medford Square ](https://www.expedia.ca/Medford-Square-Hotels.0-l6228850-0.Travel-Guide-Filter-Hotels) - [Melrose Hotels ](https://www.expedia.ca/Melrose-Hotels.d132285.Travel-Guide-Hotels) - [North Cambridge Hotels ](https://www.expedia.ca/North-Cambridge-Boston-Hotels.0-n553248635976389697-0.Travel-Guide-Filter-Hotels) - [Hotels near Oak Grove Station ](https://www.expedia.ca/Oak-Grove-Station-Hotels.d6210666.Travel-Guide-Hotels) - [Hotels near Old Ship Street Historic District ](https://www.expedia.ca/Old-Ship-Street-Historic-District-Hotels.0-l6228773-0.Travel-Guide-Filter-Hotels) - [Porter Square Hotels ](https://www.expedia.ca/Porter-Square-Boston-Hotels.0-n6229791-0.Travel-Guide-Filter-Hotels) - [Somerville Hotels ](https://www.expedia.ca/Somerville-Hotels.d55192.Travel-Guide-Hotels) - [Hotels near Somerville Theatre ](https://www.expedia.ca/Somerville-Theatre-Hotels.0-l6262321-0.Travel-Guide-Filter-Hotels) - [South Medford Hotels ](https://www.expedia.ca/South-Medford-Boston-Hotels.0-n553248635976476927-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Stoneham ](https://www.expedia.ca/Stoneham-Apart-Hotels.d162713-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Stoneham ](https://www.expedia.ca/Stoneham-Bed-And-Breakfast.d162713-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Stoneham ](https://www.expedia.ca/Stoneham-Guest-Houses.d162713-aaGuestHouses.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Stoneham ](https://www.expedia.ca/Stoneham-Hotels-Beach-Hotel.0-0-d162713-tBeachHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Stoneham ](https://www.expedia.ca/Stoneham-Hotels-Pet-Friendly-Hotel.0-0-d162713-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in Stoneham ](https://www.expedia.ca/Stoneham-Hotels-Ski-Hotel.0-0-d162713-tSkiHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Stoneham ](https://www.expedia.ca/Stoneham-Hotels-Spa-Hotel.0-0-d162713-tSpaHotel.Travel-Guide-Filter-Hotels) - [Stoneham Hotels ](https://www.expedia.ca/Stoneham-Hotels.d162713.Travel-Guide-Hotels) - [Lodges in Stoneham ](https://www.expedia.ca/Stoneham-Lodges.d162713-aaLodges.Travel-Guide-Accommodation) - [Motels in Stoneham ](https://www.expedia.ca/Stoneham-Motels.d162713-aaMotels.Travel-Guide-Accommodation) - [Resorts in Stoneham ](https://www.expedia.ca/Stoneham-Resort-Hotels.d162713-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in Stoneham ](https://www.expedia.ca/Stoneham-Townhomes.d162713-aaTownhomes.Travel-Guide-Accommodation) - [Hotels near Tufts University ](https://www.expedia.ca/Tufts-University-Hotels.0-l6092305-0.Travel-Guide-Filter-Hotels) - [West Medford Hotels ](https://www.expedia.ca/West-Medford-Boston-Hotels.0-n173092-0.Travel-Guide-Filter-Hotels) - [Winter Hill Hotels ](https://www.expedia.ca/Winter-Hill-Boston-Hotels.0-n553248635976476697-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Woburn ](https://www.expedia.ca/Woburn-Apart-Hotels.d10373-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Woburn ](https://www.expedia.ca/Woburn-Bed-And-Breakfast.d10373-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Woburn ](https://www.expedia.ca/Woburn-Guest-Houses.d10373-aaGuestHouses.Travel-Guide-Accommodation) - [Boutique Hotels in Woburn ](https://www.expedia.ca/Woburn-Hotels-Boutique-Hotel.0-0-d10373-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Woburn ](https://www.expedia.ca/Woburn-Hotels-Casino-Hotel.0-0-d10373-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Woburn ](https://www.expedia.ca/Woburn-Hotels-Cheap-Hotels.0-0-d10373-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Woburn ](https://www.expedia.ca/Woburn-Hotels-Couples-Resorts-Hotels.0-0-d10373-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Woburn ](https://www.expedia.ca/Woburn-Hotels-Family-Hotel.0-0-d10373-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Four Seasons Hotels in Woburn ](https://www.expedia.ca/Woburn-Hotels-Four-Seasons.0-0-d10373--bFourSeasons.Travel-Guide-Filter-Hotels) - [Historic Hotels in Woburn ](https://www.expedia.ca/Woburn-Hotels-Historic-Hotel.0-0-d10373-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Woburn ](https://www.expedia.ca/Woburn-Hotels-Hotel-With-Pool.0-0-d10373-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Woburn ](https://www.expedia.ca/Woburn-Hotels-Hotels-With-Balconies.0-0-d10373-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Woburn ](https://www.expedia.ca/Woburn-Hotels-Hotels-With-Free-Breakfast.0-0-d10373-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Woburn ](https://www.expedia.ca/Woburn-Hotels-Hotels-With-Indoor-Pool.0-0-d10373-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Woburn ](https://www.expedia.ca/Woburn-Hotels-Hotels-With-Kitchenettes.0-0-d10373-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Woburn ](https://www.expedia.ca/Woburn-Hotels-Luxury-Hotel.0-0-d10373-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Woburn ](https://www.expedia.ca/Woburn-Hotels-Pet-Friendly-Hotel.0-0-d10373-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Woburn ](https://www.expedia.ca/Woburn-Hotels-Romantic-Hotel.0-0-d10373-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Woburn ](https://www.expedia.ca/Woburn-Hotels-Shopping-Hotel.0-0-d10373-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Woburn ](https://www.expedia.ca/Woburn-Hotels-Spa-Hotel.0-0-d10373-tSpaHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Woburn ](https://www.expedia.ca/Woburn-Hotels-Waterpark-Hotels.0-0-d10373-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Wyndham Hotels in Woburn ](https://www.expedia.ca/Woburn-Hotels-Wyndham-Hotels.0-0-d10373--bWyndhamHotels.Travel-Guide-Filter-Hotels) - [Woburn Hotels ](https://www.expedia.ca/Woburn-Hotels.d10373.Travel-Guide-Hotels) - [Inns in Woburn ](https://www.expedia.ca/Woburn-Inns.d10373-aaInns.Travel-Guide-Accommodation) - [Lodges in Woburn ](https://www.expedia.ca/Woburn-Lodges.d10373-aaLodges.Travel-Guide-Accommodation) - [Hotels near Woburn Mishawum Station ](https://www.expedia.ca/Woburn-Mishawum-Station-Hotels.d6209686.Travel-Guide-Hotels) - [Motels in Woburn ](https://www.expedia.ca/Woburn-Motels.d10373-aaMotels.Travel-Guide-Accommodation) - [Townhomes in Woburn ](https://www.expedia.ca/Woburn-Townhomes.d10373-aaTownhomes.Travel-Guide-Accommodation) - [Flights to Arlington ](https://www.expedia.ca/Cheap-Flights-To-Arlington.d74693.Travel-Guide-Flights) - [Flights to Woburn ](https://www.expedia.ca/Cheap-Flights-To-Woburn.d10373.Travel-Guide-Flights) - [Flights from Toronto (YYZ) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yyz/bos/toronto-to-boston) - [Medford Square ](https://www.expedia.ca/Medford-Square-Boston.d6228850.Vacation-Attraction) - [Stoneham Vacations ](https://www.expedia.ca/Stoneham.d162713.Destination-Travel-Guides) - [Woburn Vacations ](https://www.expedia.ca/Woburn.d10373.Destination-Travel-Guides) - [Visit Woburn ](https://www.expedia.ca/Woburn.dx10373) - [Car rental Arlington ](https://www.expedia.ca/Car-Rentals-In-Arlington.d74693.Car-Rental-Guide) - [Car rental Medford ](https://www.expedia.ca/Car-Rentals-In-Medford.d8787.Car-Rental-Guide) - [Car rental Stoneham ](https://www.expedia.ca/Car-Rentals-In-Stoneham.d162713.Car-Rental-Guide) - [Car rental Woburn ](https://www.expedia.ca/Car-Rentals-In-Woburn.d10373.Car-Rental-Guide) - [Compact Car Rentals in Arlington ](https://www.expedia.ca/Compact-Car-Rentals-In-Arlington.d74693-tCompact.Car-Rental-Guide-Class) - [Stoneham Vacation Rentals ](https://www.expedia.ca/Stoneham-Vacation-Rentals.d162713.Travel-Guide-VacationRentals) - [Woburn Vacation Rentals ](https://www.expedia.ca/Woburn-Vacation-Rentals.d10373.Travel-Guide-VacationRentals) - [Things to do in Woburn ](https://www.expedia.ca/Things-To-Do-In-Woburn.d10373.Travel-Guide-Activities) - [Book Hotels in Winchester on Expedia.com ](https://www.expedia.com/Winchester-Hotels.d175481.Travel-Guide-Hotels) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app