Title: Holliston Vacation Packages & Trips 2025/2026 from CA $670 | Expedia.ca [Hotels in Holliston](https://expedia.ca/Holliston-Hotels.d3000441122.Travel-Guide-Hotels)[Vacation Rentals in Holliston](https://expedia.ca/Holliston-Vacation-Rentals.d3000441122.Travel-Guide-VacationRentals)[Holliston Car Rentals](https://expedia.ca/Car-Rentals-In-Holliston.d3000441122.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Holliston Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### Your Holliston Vacation Enjoy unforgettable adventures when you lock in a vacation package to Holliston. Whether you're a foodie, history buff or just a traveler who loves experiencing new places, there's something for everyone in this lively city. Make your trip to Holliston even more fulfilling by going sightseeing. [Ashland State Park](https://www.expedia.ca/Ashland-State-Park-Ashland.d553248633992331328.Vacation-Attraction), [Pinecrest Golf Club](https://www.expedia.ca/Pinecrest-Golf-Club-Holliston.d553248633992334149.Vacation-Attraction) and [Stoddard Park](https://www.expedia.ca/Stoddard-Park-Holliston.d553248635983992555.Vacation-Attraction) are among the popular attractions you'll want to explore. No matter your travel plans or the size of your budget, putting together a tailored Holliston vacation is a cinch with Expedia. ## Top Holliston Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Boston Lodge and Suites](https://images.trvl-media.com/lodging/22000000/21340000/21333100/21333029/d2b7feac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boston Lodge and Suites Dorchester CA $670 per person Jan 22 - Jan 25 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 8.4/10 Very Good! (186 reviews) Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available. Reviewed on Nov 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-22/2026-01-25/?FromAirport=YTO&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21333029&paandie=true&dealMarker=jZRBCG9fjcWQyFdS9NvAZAB6t4-KRrIWei2XqY5B9jVBUl6Ie8iWPM6K4gJHdGjM) ![The Inn at Hastings Park, Relais & Chateaux - Boston](https://images.trvl-media.com/lodging/8000000/7990000/7980700/7980601/8dcd0e80_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Inn at Hastings Park, Relais & Chateaux - Boston CA $1,563 per person Dec 29 - Jan 3 found 19 hours ago Roundtrip flight included Toronto (YYZ) to Boston (BOS) 9.6/10 Exceptional! (245 reviews) Beautiful property! Room was excellent. Great amenities and free continental breakfast brought to our room. Reviewed on Oct 21, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-03/?FromAirport=YYZ&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=7980601&paandie=true&dealMarker=etSLGuVR5_TAYwSnPo98wyhvbownr8b2WSRDkgG0uEROrx0g6qlDQgHKpznNI7yF) ![The Newbury Boston](https://images.trvl-media.com/lodging/1000000/10000/400/395/de8ba46e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Newbury Boston Back Bay CA $1,805 per person Dec 22 - Dec 29 found 1 hour ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 18.8/10 Exceptional! (536 reviews) This hotel has it all, best in class care and service. Reviewed on Oct 24, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-22/2025-12-29/?FromAirport=YTO&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=395&paandie=true&dealMarker=lKBDLkDaeBEAerKCsJfc15ndtst2dtFx9gV7kHqRPuGMB52cMiPBwCcw4J7a1Gn7) ![Mandarin Oriental, Boston](https://images.trvl-media.com/lodging/3000000/2180000/2175200/2175117/be69f75d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Mandarin Oriental, Boston Back Bay CA $2,250 per person Dec 25 - Dec 31 found 8 hours ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 18.8/10 Exceptional! (376 reviews) They should stop the issues with things breaking in the men’s spa Reviewed on Oct 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-25/2025-12-31/?FromAirport=YTO&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2175117&paandie=true&dealMarker=8Ygn8GpmWw41MyghC9upIfZxdDMcidtW7JfuaWNoGbr5Izr-qeKwfias4lwemOPT) ![XV Beacon](https://images.trvl-media.com/lodging/1000000/210000/201200/201184/0637e89e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### XV Beacon Beacon Hill CA $2,687 per person Dec 26 - Jan 2 found 5 hours ago Roundtrip flight included Toronto (YYZ) to Boston (BOS) 18.8/10 Exceptional! (383 reviews) I had a wonderful experience at the XV Beacon Hotel. The room and bathroom was modern and updated. I also thought the gym was clean. Reviewed on Nov 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2026-01-02/?FromAirport=YYZ&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=201184&paandie=true&dealMarker=jmX95pfHKMJC72zM73fkljG5LhxgdyctWWpaPW5gIZu3Nsxc-gxrmA5RizGSWfrg) ## Ready to book your vacation to Holliston? Choose your dates ## Holliston Hotel Deals ![citizenM Boston Back Bay](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/90056141_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### citizenM Boston Back Bay 408 Newbury street Boston MA Fully refundableReserve now, pay when you stay CA $199 CA $232 total Dec 15 - Dec 16 includes taxes & fees 9.2/10 Wonderful! (2,031 reviews) Excellent stay! Reviewed on Nov 17, 2025 [](https://expedia.ca/Hotel-Search?startDate=15%2F12%2F2025&endDate=16%2F12%2F2025&selected=96998829&PinnedHotelID=96998829&HadPinnedHotel=true®ionId=3000441122) ![Copley Square Hotel, a FOUND Hotel](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/72cd2881_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Copley Square Hotel, a FOUND Hotel 47 Huntington Ave Boston MA Fully refundableReserve now, pay when you stay CA $132 CA $154 total Nov 25 - Nov 26 includes taxes & fees 8.4/10 Very Good! (3,867 reviews) Clean room, nice staff and great location! Reviewed on Nov 12, 2025 [](https://expedia.ca/Hotel-Search?startDate=25%2F11%2F2025&endDate=26%2F11%2F2025&selected=16067&PinnedHotelID=16067&HadPinnedHotel=true®ionId=3000441122) ![The Charles Hotel](https://images.trvl-media.com/lodging/1000000/20000/15900/15861/66098bc6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Charles Hotel One Bennett Street Cambridge MA Fully refundableReserve now, pay when you stay CA $399 CA $462 total Dec 17 - Dec 18 includes taxes & fees 9.2/10 Wonderful! (1,003 reviews) Room was clean and tidy Reviewed on Nov 10, 2025 [](https://expedia.ca/Hotel-Search?startDate=17%2F12%2F2025&endDate=18%2F12%2F2025&selected=15861&PinnedHotelID=15861&HadPinnedHotel=true®ionId=3000441122) [See all 2,038 properties in Holliston](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=19%2F11%2F2025&endDate=20%2F11%2F2025®ionId=3000441122) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia - 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[Sudbury Vacations](https://www.expedia.ca/Sudbury.d9770.Destination-Travel-Guides) - [Sutton Vacations](https://www.expedia.ca/Sutton.d183346.Destination-Travel-Guides) - [Waban Vacations](https://www.expedia.ca/Waban.d170318.Destination-Travel-Guides) - [Walden Pond](https://www.expedia.ca/Walden-Pond-Boston.d6092271.Vacation-Attraction) - [Waltham Vacations](https://www.expedia.ca/Waltham.d10415.Destination-Travel-Guides) - [Westwood Vacations](https://www.expedia.ca/Westwood.d173770.Destination-Travel-Guides) - [Xfinity Center](https://www.expedia.ca/Xfinity-Center-Mansfield.d6034498.Vacation-Attraction) ### Cars - [Car rental Milford](https://www.expedia.ca/Car-Rentals-In-Milford.d8882.Car-Rental-Guide) - [Rent A Wreck Rental Cars in Framingham](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-Framingham.d7157-c33.Car-Rental-Guide-Suppliers) \* Savings based on package bookings compared to the price of the same components booked separately. 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