Title: Winchester Houseboats from CA $554 | 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) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Houseboats in Winchester from CA $554 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=HOUSE_BOAT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=HOUSE_BOAT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=HOUSE_BOAT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=HOUSE_BOAT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Houseboats ![Marina](https://images.trvl-media.com/lodging/27000000/26470000/26461300/26461291/40c12f76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/27000000/26470000/26461300/26461291/d2dfb8c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/27000000/26470000/26461300/26461291/c62901de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/27000000/26470000/26461300/26461291/d7de5991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Boston Harbor Yacht, AC/Heat, Walk to North End WiFi Thompson Square - Bunker Hill 9.6/10 Exceptional (137) "We had an amazing trip to Boston. " [](https://www.expedia.ca/Boston-Hotels-Boston-Harbor-Yacht.h26461291.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102420000/102412600/102412573/0d783169.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/103000000/102420000/102412600/102412573/796b28bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102420000/102412600/102412573/598f4b52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102420000/102412600/102412573/05117bf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Capricornus: Oceanside Vacation Boston 9.2/10 Wonderful (36) "Great way to stay in Boston! It was clean and up to date and near everything North End. Parking was so easy. Keep in mind you are on a boat - I would suggest a pump out after each stay. I will book again the next time I’m in Boston. " CA $297 CA $603 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Boston-Hotels-Capricornus-Oceanside-Vacation.h102412573.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/103000000/102420000/102412200/102412109/821d4fe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102420000/102412200/102412109/79146103.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/103000000/102420000/102412200/102412109/aaff8012.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102420000/102412200/102412109/40f372e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Endless Summer: Oceanside Views Boston 10/10 Exceptional (35) "We had a wonderful time staying on the Endless Summer houseboat. It is beautiful, comfortable, and well-equipped. The location is great.Endless Summer is definitely on our list of best vacation rentals." CA $589 CA $947 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Boston-Hotels-Endless-Summer-Oceanside-Views.h102412109.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/38000000/37290000/37280700/37280691/63f2cb8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/38000000/37290000/37280700/37280691/31e3bef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/38000000/37290000/37280700/37280691/3bde57f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/38000000/37290000/37280700/37280691/8ad0a733.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charlestown Houseboat Walk to attractions Be rocked to sleep Thompson Square - Bunker Hill 9.6/10 Exceptional (92) "Great few days with the family at this location. We enjoyed long walks following the waterline and found several nice nearby playgrounds for the young kids." [](https://www.expedia.ca/Boston-Hotels-Charlestown-Houseboat-Walk-To-Attractions-Be-Rocked-To-Sleep.h37280691.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34010000/34008400/34008386/b4719409.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/35000000/34010000/34008400/34008386/0fb2b8d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34010000/34008400/34008386/4028f869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/35000000/34010000/34008400/34008386/09be33dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fun houseboat. Walk to Boston attractions WIFI Boston 9.8/10 Exceptional (82) "Great communication and location " CA $306 CA $819 total includes taxes & fees Oct 3 - Oct 4 [](https://www.expedia.ca/Boston-Hotels-Fun-Houseboat-Walk-To-Boston-Attractions-Wifi.h34008386.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/41000000/40200000/40191800/40191798/a782b2dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/41000000/40200000/40191800/40191798/11b15ad1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/41000000/40200000/40191800/40191798/96f81f73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/41000000/40200000/40191800/40191798/dc224d87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Your Floating Suite in Boston Harbor Thompson Square - Bunker Hill 9.6/10 Exceptional (59) "We had a great time in Boston and enjoyed our stay on the boat....." [](https://www.expedia.ca/Boston-Hotels-Your-Floating-Suite-In-Boston-Harbor.h40191798.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/42000000/41510000/41503600/41503536/53efafe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/42000000/41510000/41503600/41503536/27d9e327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/42000000/41510000/41503600/41503536/c4b6ba74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/42000000/41510000/41503600/41503536/48ff70c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Travelers Choice Award" Spacious 2 bedrm 45 ft yacht close to the Freedom Trail Boston 10/10 Exceptional (114) "The boat was very spacious and clean. We loved the outdoor spaces and views from the harbor. The location was great as well and easy commute to all the sites we wanted to see and activities while visiting. We very much enjoyed our stay. " CA $502 CA $934 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Boston-Hotels-Come-Float-In-Boston-Harbor-On-A-45-Foot-Yacht-Plenty-Of-Fresh-Air.h41503536.Hotel-Information) ![Fitness facility](https://images.trvl-media.com/lodging/73000000/72300000/72296700/72296648/0d8c59ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72300000/72296700/72296648/eb0b509a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/73000000/72300000/72296700/72296648/95e68b24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/73000000/72300000/72296700/72296648/63bd3c68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious & Comfy 2BR/2Bath Yacht - Heat & AC - On Freedom Trail-Walk to Downtown Thompson Square - Bunker Hill 9.8/10 Exceptional (69) "Marina was very peaceful. We felt safe and the facilities were great. The boat was clean and comfortable. We really enjoyed our stay and we would return. " CA $598 CA $959 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Boston-Hotels-2BR-Spacious-Comfy-43-Yacht-Heat-AC-Walk-To-North-End-Freedom-Trail.h72296648.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102420000/102413300/102413295/w639h426x1y1-bbc0f8e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102420000/102413300/102413295/7ceac6d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102420000/102413300/102413295/72af4012.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/103000000/102420000/102413300/102413295/428f2dc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Patriot: Three Story Vessel Boston 9.4/10 Exceptional (17) "Great spot, good communication. Would recommend " [](https://www.expedia.ca/Boston-Hotels-Patriot-A-Three-Story-Motor-Vessel-In-The-Heart-Of-Boston-Harbor.h102413295.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/104000000/103830000/103821400/103821326/75f4007c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/104000000/103830000/103821400/103821326/4585d856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/104000000/103830000/103821400/103821326/af9f1197.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/104000000/103830000/103821400/103821326/2e4229f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Poseidon's Escape: Ocean Retreat Boston 8.8/10 Excellent (8) "This place was so great! It was comfy and perfect for our little get away!" [](https://www.expedia.ca/Boston-Hotels-Poseidons-Escape-Ocean-Retreat.h103821326.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/23000000/22440000/22434600/22434545/7f48f825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/23000000/22440000/22434600/22434545/c3555a6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/23000000/22440000/22434600/22434545/59bde57b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/23000000/22440000/22434600/22434545/b6e4f3ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep Charlestown 9.8/10 Exceptional (197) "We were there for our daughter's graduation and the location was perfect - short uber from Logan and quick trips to Cambridge. would defintely do it again." CA $258 CA $821 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Boston-Hotels-Houseboat-In-Boston-Harbor-Wifi-AC-Heat-Be-Rocked-To-Sleep.h22434545.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/39000000/38260000/38256500/38256419/92238c71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers](https://images.trvl-media.com/lodging/39000000/38260000/38256500/38256419/88daa960.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/39000000/38260000/38256500/38256419/473172c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38260000/38256500/38256419/50e882f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelers Choice Best of Boston Houseboat Suite 1! Charlestown 10/10 Exceptional (232) "Loved staying in the marina on a houseboat!" CA $317 CA $554 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Boston-Hotels-Visit-Boston-On-Green-Turtle-Houseboat-In-Boston-Harbor-Plenty-Of-Fresh-Air.h38256419.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/77000000/76970000/76962200/76962167/491befcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76970000/76962200/76962167/91e1b7cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76970000/76962200/76962167/9b16bf06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76970000/76962200/76962167/e38265d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelers Choice Best of Boston Houseboat Suite 2! Thompson Square - Bunker Hill 9.8/10 Exceptional (48) "Wonderful little houseboat in a great area! Easy check in and out! Will refer friends! " CA $333 CA $575 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Boston-Hotels-Travelers-Choice-Award-Green-Turtle-Houseboat-Suite-2-Historic-Boston-Harbor.h76962167.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/45000000/44960000/44955600/44955544/d52f8209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/45000000/44960000/44955600/44955544/8a227c26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/45000000/44960000/44955600/44955544/9d0720aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/45000000/44960000/44955600/44955544/9d37417d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Romantic Getaway View the Boston Skyline, 10/15 minute drive to downtown. Marina Bay [](https://www.expedia.ca/Bouvet-Island-Hotels-Vrbo-Property.h44955544.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=2025-10-16&endDate=2025-10-17®ionId=175481&adults=2&lodging=HOUSE_BOAT&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-Houseboats.d175481-aaHouseboats.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Houseboats.d175481-aaHouseboats.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Seaport Hotel Boston](//images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "Loved the large harbor view king room. Easy and pleasant check in. Room ready early. Housekeeping staff were terrific- friendly and helpful. Everything immaculate. Only the shower tile floor shows wear. Enjoyed the harbor area- good dining options, walked to the port (a little long with luggage but doable)—-we were cruising so hotel is well situated for the port and airport. Boston traffic is pretty bad, so Ubers to the Back Bay or Cambridge take a while! Pick your hotel close to where you need or want to be!" [](https://expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![citizenM Boston North Station](//images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/0eda38d5_y.jpg) ### citizenM Boston North Station 10/10 Excellent "We loved our stay at CitizenM. " [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ![The Dagny Boston](//images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "Amazing hotel and location " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![Copley Square Hotel, a FOUND Hotel](//images.trvl-media.com/lodging/1000000/20000/16100/16067/dbccf1fb_y.jpg) ### Copley Square Hotel, a FOUND Hotel 10/10 Excellent "Historic aged hotel, so our expectations were more than served. Highly recommend for access to the city and all sites during traveling." [](https://expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) ![Sheraton Boston, a Marriott Hotel](//images.trvl-media.com/lodging/1000000/30000/22100/22046/dfa592c9_y.jpg) ### Sheraton Boston, a Marriott Hotel 10/10 Excellent "All good" [](https://expedia.ca/Boston-Hotels-Sheraton-Boston.h22046.Hotel-Information) ![Harborside Inn Of Boston](//images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg) ### Harborside Inn Of Boston 10/10 Excellent "The girls at the front desk were super friendly and helpful. Room was simple but clean. Located close to places to eat and historic sites. " [](https://expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![YOTEL Boston](//images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/245fc311_y.jpg) ### YOTEL Boston 10/10 Excellent "Moden design and clean. Will ask for mini coffee maker and fridge " [](https://expedia.ca/Boston-Hotels-YOTEL-Boston.h18090311.Hotel-Information) ![The Revolution Hotel](//images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/cce5d2b3_y.jpg) ### The Revolution Hotel 10/10 Excellent "Nothing, everything was fine. Thanks" [](https://expedia.ca/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information) ![Encore Boston Harbor](//images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5_y.jpg) ### Encore Boston Harbor 10/10 Excellent "Yes" [](https://expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) ## Find out more about Winchester ## Winchester Houseboats information | Number of reviews | 1,012 | | --- | --- | | Accommodation | 14 Houseboats | | Lowest Price | CA $554 | | Highest Price | CA $959 | ## 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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