Title: Book the Best Winter Hill FAMILY FRIENDLY Hotels from CA $184 - Kid-Friendly Hotels in Winter Hill, Boston | Expedia.ca [Winter Hill Travel Guide](https://expedia.ca/Boston-Winter-Hill.dx553248635976476697)[Vacation Rentals in Boston](https://expedia.ca/Boston-Vacation-Rentals.d178239.Travel-Guide-VacationRentals)[Flights to Boston](https://expedia.ca/Cheap-Flights-To-Boston.d178239.Travel-Guide-Flights)[Things to do in Boston](https://expedia.ca/Things-To-Do-In-Boston.d178239.Travel-Guide-Activities)[Winter Hill Car Rentals](https://expedia.ca/Car-Rentals-In-Winter-Hill.d553248635976476697.Car-Rental-Guide)[Winter Hill Vacations](https://expedia.ca/Winter-Hill.d553248635976476697.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Family Hotels in Winter Hill, Boston from CA $184 ![](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 availability on Winter Hill Family Hotels Tonight [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976476697&startDate=2025-10-29&endDate=2025-10-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=553248635976476697&startDate=2025-10-30&endDate=2025-10-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976476697&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976476697&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Top Winter Hill Family Hotels ![6 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/120000000/119390000/119388800/119388758/73668f5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/120000000/119390000/119388800/119388758/96a930c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119390000/119388800/119388758/842756f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/120000000/119390000/119388800/119388758/f31ce7be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 6BR4BATH Home in Somerville Prospect Hill CA $2,120 CA $3,171 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Boston-Hotels-6BR4BATH-Home-In-Somerville.h119388758.Hotel-Information) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/120000000/119390000/119380100/119380094/74883517.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119390000/119380100/119380094/1c1508f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/120000000/119390000/119380100/119380094/64c3c722.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119390000/119380100/119380094/4c12d6e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3BR2BATH Lux Home in Somerville Prospect Hill CA $1,192 CA $1,798 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Boston-Hotels-3BR2BATH-Lux-Home-In-Somerville.h119380094.Hotel-Information) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/120000000/119480000/119471100/119471085/33f62a5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119480000/119471100/119471085/1aafbc53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119480000/119471100/119471085/167ca508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119480000/119471100/119471085/c91616d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 3-bedroom 2bath apartment in Somerville Prospect Hill CA $1,259 CA $1,882 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Boston-Hotels-Spacious-3-Bedroom-2bath-Apartment-In-Somerville.h119471085.Hotel-Information) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/120000000/119390000/119384300/119384270/82659054.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119390000/119384300/119384270/ce4d9d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/120000000/119390000/119384300/119384270/37ce7a17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119390000/119384300/119384270/9654ca99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3BR2BATH 12G Home in Somerville Prospect Hill CA $1,325 CA $1,966 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Boston-Hotels-3BR2BATH-12G-Home-In-Somerville.h119384270.Hotel-Information) ![9 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/120000000/119390000/119382400/119382334/8250e982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/120000000/119390000/119382400/119382334/4c036237.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/120000000/119390000/119382400/119382334/21ee6670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119390000/119382400/119382334/ed7d23c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 9Bedroom 6Bath Home in Somerville Prospect Hill CA $2,981 CA $4,406 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Boston-Hotels-9Bedroom-6Bath-Home-In-Somerville.h119382334.Hotel-Information) ![Interior detail](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/w6102h4419x0y0-1bd063ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/f354ccdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/90056141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/f21696a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### citizenM Boston Back Bay Fenway–Kenmore 9.4/10 Exceptional (1958) "Really enjoyed our stay here" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin CA $194 CA $226 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![Standard Room, 1 Queen Bed](https://images.trvl-media.com/lodging/1000000/20000/15800/15746/5e10c317.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) ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/15800/15746/f7a78de2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Found Hotel Boston Common Bay Village 8.2/10 Very good (1239) "Staff was very helpful and friendly, the room was Tiny But had everything I needed and the stay was easy." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nenette CA $158 CA $184 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Boston-Hotels-Found-Hotel-Boston-Common.h15746.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/82ab675e.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/6dc716eb.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) ### Hilton Boston Park Plaza Bay Village 8.4/10 Very good (3152) "Nice hotel centrally located, friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deanna CA $175 CA $261 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/dbccf1fb.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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/c2b6fbff.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 Back Bay 8.6/10 Excellent (3854) "Amazing hotel! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $164 CA $191 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.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/1000000/80000/79900/79888/40a54799.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/f8efea04.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 Seaport District 9.6/10 Exceptional (3621) "Great location and stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Krithika CA $225 CA $268 total includes taxes & fees Nov 28 - Nov 29 [](https://www.expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.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=2025-11-13&endDate=2025-11-14®ionId=553248635976476697&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Winter Hill Hotel Reviews ![Seaport Hotel Boston](//images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "Excellent service, as always! Thank you!" [](https://expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![Hilton Boston Logan Airport](//images.trvl-media.com/lodging/1000000/290000/281600/281536/23c65d09_y.jpg) ### Hilton Boston Logan Airport 10/10 Excellent "Very friendly and competent staff. Excellent dinner at the restaurant. " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.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 staff was super friendly, clean rooms, very neat hotel, walkable to several things in the city, subway stop right outside. Neighborhood was safe and quiet. Will definitely stay again. " [](https://expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![Club Quarters Hotel Faneuil Hall, Boston](//images.trvl-media.com/lodging/1000000/70000/67000/66938/1b7afb42_y.jpg) ### Club Quarters Hotel Faneuil Hall, Boston 10/10 Excellent "Good" [](https://expedia.ca/Boston-Hotels-Club-Quarters-Hotel-In-Boston.h66938.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 "Yes" [](https://expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) ![The Dagny Boston](//images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "Great service id totally come again! I wish I got a little bit of a bigger room but everything else was 10/10 th valet guys are really great also! " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![YOTEL Boston](//images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/245fc311_y.jpg) ### YOTEL Boston 10/10 Excellent "Very aestheticly pleasing. " [](https://expedia.ca/Boston-Hotels-YOTEL-Boston.h18090311.Hotel-Information) ![The Godfrey Hotel Boston](//images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/e4d256d2_y.jpg) ### The Godfrey Hotel Boston 10/10 Excellent "Didn't have breakfast " [](https://expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) ![Hampton Inn Boston - Logan Airport](//images.trvl-media.com/lodging/1000000/580000/578500/578419/w3839h2488x0y0-d5429574_y.jpg) ### Hampton Inn Boston - Logan Airport 10/10 Excellent "didnt use shuttel l no kitchen in room " [](https://expedia.ca/Boston-Hotels-Hampton-Inn-Boston-Logan-Airport.h578419.Hotel-Information) ## Frequently asked questions ### What's Winter Hill like for family-friendly vacations? > The destination of Winter Hill is a great choice if you've been thinking about a vacation with your kids. There are some interesting activities the entire family might enjoy. Take to the air and fly into Boston, MA (BNH-Boston Harbor Seaplane Base), which is the closest airport, or Logan International Airport (BOS), which is located 4.4 mi (7 km) from the center of Winter Hill. ### What's there to see and do with your family in Winter Hill? > While you and your family are visiting Winter Hill, you might want to check out some kid-friendly attractions such as TD Garden and Fenway Park. Make sure you have plenty of time to take in activities in the area like New England Aquarium, Encore Boston Harbor, and Harvard Square. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [2 Star Hotels in Somerville](https://www.expedia.ca/2Star-Somerville-Hotels.s20-0-d55192.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Somerville](https://www.expedia.ca/3Star-Somerville-Hotels.s30-0-d55192.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Assembly Square](https://www.expedia.ca/Assembly-Square-Boston-Hotels-All-Inclusive-Hotel.0-n553248635976007391-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Assembly Square](https://www.expedia.ca/Assembly-Square-Boston-Hotels-Boutique-Hotel.0-n553248635976007391-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Assembly Square](https://www.expedia.ca/Assembly-Square-Boston-Hotels-Business-Hotel.0-n553248635976007391-0-tBusinessHotel.Travel-Guide-Filter-Hotels) - 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[Hotels with Free Airport Shuttle in South Medford](https://www.expedia.ca/South-Medford-Boston-Hotels-Hotels-With-Free-Airport-Shuttle.0-n553248635976476927-0-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in South Medford](https://www.expedia.ca/South-Medford-Boston-Hotels-Pet-Friendly-Hotel.0-n553248635976476927-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in South Medford](https://www.expedia.ca/South-Medford-Boston-Hotels-Waterpark-Hotels.0-n553248635976476927-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Spring Hill](https://www.expedia.ca/Spring-Hill-Boston-Hotels-Cheap-Hotels.0-n553248635976473569-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Spring Hill Hotels](https://www.expedia.ca/Spring-Hill-Boston-Hotels.0-n553248635976473569-0.Travel-Guide-Filter-Hotels) - [Hotels near TD Garden](https://www.expedia.ca/TD-Garden-Hotels.0-l6070137-0.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Ward Two](https://www.expedia.ca/Ward-Two-Boston-Hotels-Hotel-With-Early-Check-In.0-n553248635976480170-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - 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