Title: Book the Best South Side Ski Hotels in 2026 from CA $122 | Expedia.ca [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)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d553248635976471471.Car-Rental-Guide)[South Side Vacations](https://expedia.ca/South-Side.d553248635976471471.Destination-Travel-Guides) ![Charles River panorama aerial view in downtown Waltham, Massachusetts, MA, USA.](https://images.trvl-media.com/place/553248635976471471/4a46a752-15a5-4a18-8dfd-4426265bbe9d.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Ski Hotels in South Side, MA from CA $122 - ![](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 South Side Ski Hotels Tonight [Dec 6 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976471471&startDate=2025-12-06&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 7 - Dec 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976471471&startDate=2025-12-07&endDate=2025-12-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976471471&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976471471&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top South Side Ski Hotels ![Exterior](https://images.trvl-media.com/lodging/2000000/1780000/1778200/1778190/0e438e61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pub](https://images.trvl-media.com/lodging/2000000/1780000/1778200/1778190/a8d50009.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, minibar, in-room safe](https://images.trvl-media.com/lodging/2000000/1780000/1778200/1778190/981b2083.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1780000/1778200/1778190/caca53a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renaissance® Boston Seaport District Seaport District 9.0/10 Wonderful (1001) "Great location and hotel. Kids loved it!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) steven CA $175 CA $261 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Boston-Hotels-Renaissance-Boston-Waterfront-Hotel.h1778190.Hotel-Information) ![Blackout drapes, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1750000/1747300/1747236/33506893.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Blackout drapes, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1750000/1747300/1747236/2f672463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1750000/1747300/1747236/1be237d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1750000/1747300/1747236/5c7851f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Westford-Chelmsford Westford 8.8/10 Excellent (1004) "Clean room, friendly staff, convenient location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin CA $132 CA $147 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Westford-Hotels-Hampton-Inn-Suites-Westford-Chelmsford.h1747236.Hotel-Information) ![Ballroom](https://images.trvl-media.com/lodging/1000000/20000/18000/17910/4894a4f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/18000/17910/0c7f3522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/18000/17910/237b5220.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop beds, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/20000/18000/17910/f6deec07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Boston - Westborough Westborough 8.6/10 Excellent (1009) "Perfect stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rodrigo CA $140 CA $156 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Worcester-Hotels-DoubleTree-By-Hilton-Hotel-Boston-Westborough.h17910.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/660000/658900/658857/3e957c22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillowtop beds, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/660000/658900/658857/6fda3ca0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/660000/658900/658857/aaf3cd7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/660000/658900/658857/808752f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marriott Boston Quincy Quincy 8.8/10 Excellent (1291) "The room are nice, clean and modern. The staff are also very welcoming and accommodating." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anh CA $129 CA $144 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Boston-Hotels-Marriott-Boston-Quincy.h658857.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/1000000/20000/14700/14628/w3837h2557x3y3-f462cfa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/20000/14700/14628/w3836h2556x4y4-568b2d7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/14700/14628/b0032ae2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds, Refrigerator & Microwave, Courtyard View](https://images.trvl-media.com/lodging/1000000/20000/14700/14628/w3837h2560x3y0-d17a0820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Royal Plaza Hotel & Trade Center Marlborough 7.8/10 Good (1000) "Good place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexandra CA $109 CA $122 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Worcester-Hotels-Best-Western-Royal-Plaza-Hotel-Trade-Center.h14628.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/80000/77700/77662/623db6ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/80000/77700/77662/40dbd244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/80000/77700/77662/ea86c46b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, desk, free WiFi](https://images.trvl-media.com/lodging/1000000/80000/77700/77662/e4bf2c03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Boston Westborough Westborough 8.4/10 Very good (674) "It was a great stay. The room was clean and staff was friendly. The room also spacious. The location is a bit isolated but if you have a car then you should be fine. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yangjin CA $152 CA $170 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Worcester-Hotels-Courtyard-By-Marriott-Boston-Westborough.h77662.Hotel-Information) ![Ballroom](https://images.trvl-media.com/lodging/1000000/20000/10400/10391/fb23caba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/10400/10391/fb5b70f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10400/10391/41b6c1ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/20000/10400/10391/9d3c9c37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Boston/Dedham Dedham 7.8/10 Good (1041) "Awesome stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alonzo Shekila CA $129 CA $144 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Boston-Hotels-Hilton-BostonDedham.h10391.Hotel-Information) ![Snack bar](https://images.trvl-media.com/lodging/1000000/330000/327800/327794/7d5dbf92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/330000/327800/327794/3affbdaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/330000/327800/327794/5292cb68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/330000/327800/327794/eb9927de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Boston/Billerica Billerica 8.0/10 Very good (1002) "Front desk woman was so great, so friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Krystal CA $132 CA $147 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Boston-Hotels-Homewood-Suites-By-Hilton-BostonBillerica.h327794.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/10700/10639/853e94dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop beds, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/10700/10639/7bd5495f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop beds, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/10700/10639/664fdbf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/20000/10700/10639/5ece9344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Chelmsford Lowell Chelmsford 7.4/10 Good (542) "Lovely would come again! Room was enormous and front desk were friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $155 CA $164 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/Chelmsford-Hotels-Home2-Suites-By-Hilton-Chelmsford-Lowell.h10639.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/890900/890805/06eecf1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/1000000/900000/890900/890805/6d3a1a23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/900000/890900/890805/b54e487e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/900000/890900/890805/8517272d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Westford Regency Inn & Conference Center Westford 8.2/10 Very good (1000) "Staff was exceptional" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Martha [](https://www.expedia.ca/Westford-Hotels-Westford-Regency-Inn-Conference-Center.h890805.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-20&endDate=2025-12-21®ionId=553248635976471471&adults=2&location_highlights_explore=ski&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Cheap Hotels in Auburndale ](https://www.expedia.ca/Auburndale-Boston-Hotels-Cheap-Hotels.0-n75534-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Auburndale ](https://www.expedia.ca/Auburndale-Boston-Hotels-Hotels-With-Hot-Tubs.0-n75534-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Spa Hotels in Auburndale ](https://www.expedia.ca/Auburndale-Boston-Hotels-Spa-Hotel.0-n75534-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotels near Boston Children's at Waltham ](https://www.expedia.ca/Boston-Childrens-At-Waltham-Hotels.0-l667684610040918016-0.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Boston ](https://www.expedia.ca/Boston-Hotels-Adults-Only-Resorts.0-0-d178239-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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