Title: Boston Vacation Packages & Trips 2026 from CA $738 | Expedia.ca [Hotels in Boston](https://expedia.ca/Boston-Hotels.d3000454369.Travel-Guide-Hotels)[Vacation Rentals in Boston](https://expedia.ca/Boston-Vacation-Rentals.d3000454369.Travel-Guide-VacationRentals)[Boston Car Rentals](https://expedia.ca/Car-Rentals-In-Boston.d3000454369.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) # Boston 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 Boston Vacation With plenty of highlights as well as some hidden gems, this city is best experienced with a Boston vacation package. Check out places to stay in Squirrel Hill South, which is great for cycling, golfing and dining. A trip to Boston is a superb opportunity to do a bit of sightseeing. Make sure you visit well-known attractions like [Kennywood](https://www.expedia.ca/Kennywood-West-Mifflin.d6193719.Vacation-Attraction), [McKeesport Little Theater](https://www.expedia.ca/McKeesport-Little-Theater-McKeesport.d553248621532660526.Vacation-Attraction) and [Round Hill Park](https://www.expedia.ca/Round-Hill-Park-Elizabeth.d553248621532660520.Vacation-Attraction). Don't put off your visit to this destination any longer. The ultimate Boston vacation is a few quick clicks away with Expedia. ## Top Boston Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Joinery Hotel Pittsburgh, Curio Collection by Hilton](https://images.trvl-media.com/lodging/18000000/17910000/17900800/17900777/6b099d23_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Joinery Hotel Pittsburgh, Curio Collection by Hilton Downtown Pittsburgh CA $738 per person Mar 4 - Mar 7 found 21 hours ago Roundtrip non-stop flight included Calgary (YYC) to Pittsburgh (PIT) 8.4/10 Very Good! (1,385 reviews) The room was super convenient for a quick trip to the city for my homecoming. Loved the hotel decor and the room was the perfect size for me. Reviewed on Dec 15, 2025 ![Kimpton Hotel Monaco Pittsburgh by IHG](https://images.trvl-media.com/lodging/9000000/8650000/8645100/8645076/2ee575df_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Hotel Monaco Pittsburgh by IHG Downtown Pittsburgh CA $973 per person Mar 4 - Mar 7 found 21 hours ago Roundtrip non-stop flight included Calgary (YYC) to Pittsburgh (PIT) 9.4/10 Exceptional! (1,253 reviews) Room was immaculately cleaned. Staff was friendly and helpful. Reviewed on Dec 9, 2025 ![Fairmont Pittsburgh](https://images.trvl-media.com/lodging/4000000/3060000/3056400/3056317/801aa0d0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Pittsburgh Downtown Pittsburgh CA $1,194 per person Mar 4 - Mar 7 found 21 hours ago Roundtrip non-stop flight included Calgary (YYC) to Pittsburgh (PIT) 8.8/10 Excellent! (1,002 reviews) Everyone was very friendly, we loved our first visit to Pittsburgh. I'm going to give our review 5 stars but the only thing I question was 2 out of the 3 nights we stayed our room wasn't cleaned. Not sure if that's normal because we had slept in and left around noon. But in any case it was a fun time. Reviewed on Dec 3, 2025 ![The Westin Pittsburgh, a Marriott Hotel](https://images.trvl-media.com/lodging/1000000/20000/14300/14295/17a40a56_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Pittsburgh, a Marriott Hotel Downtown Pittsburgh CA $953 per person Mar 4 - Mar 7 found 21 hours ago Roundtrip non-stop flight included Calgary (YYC) to Pittsburgh (PIT) 8.6/10 Excellent! (1,003 reviews) Nice hotel in downtown Pittsburgh. Room and common area were clean and well maintained. Reviewed on Dec 8, 2025 ![Placemakr Downtown Pittsburgh at The Pennsylvanian](https://images.trvl-media.com/lodging/115000000/114320000/114312800/114312743/0729901f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Placemakr Downtown Pittsburgh at The Pennsylvanian Downtown Pittsburgh CA $867 per person Mar 4 - Mar 7 found 21 hours ago Roundtrip non-stop flight included Calgary (YYC) to Pittsburgh (PIT) 7.6/10 Good! (37 reviews) Everyone I encountered was amazing through our experience related to our stay. There was an event occurring in the main entry way during our stay and the valet assisted us in locating parking, called the front desk and checked in from the door, they were very informative and helpful, even the building staff were very friendly and helpful helped us with the door on arrival. It would be nice to be able to use valet service, especially since it is paid parking anyways, and also enter through the nicer main lobby rather than a service entrance and padded frieght elevator... I did chose the Penn because of its prestige, location, amenities, and to view/enjoy craftsmanship of the architecture and chandilers specifically (as a former apprentice of the artist). Overall great stay. Reviewed on Dec 9, 2025 ## Ready to book your vacation to Boston? Choose your dates ## Boston Hotel Deals ![Wyndham Grand Pittsburgh Downtown](https://images.trvl-media.com/lodging/1000000/30000/25600/25509/14f19a0a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wyndham Grand Pittsburgh Downtown 600 Commonwealth Pl Pittsburgh PA Fully refundableReserve now, pay when you stay CA $166 CA $189 total Dec 30 - Dec 31 includes taxes & fees 8.2/10 Very Good! (3,235 reviews) Didn’t eat breakfast. The staff was friendly and wonderful overall. Reviewed on Dec 11, 2025 [](https://expedia.ca/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&selected=25509&PinnedHotelID=25509&HadPinnedHotel=true®ionId=3000454369) ![Omni William Penn Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2998/c923b3f2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Omni William Penn Hotel 530 William Penn Place Pittsburgh PA Fully refundableReserve now, pay when you stay CA $214 CA $244 total Dec 21 - Dec 22 includes taxes & fees 9/10 Wonderful! (1,829 reviews) Amazing, as always!! Reviewed on Dec 15, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F12%2F2025&endDate=22%2F12%2F2025&selected=2998&PinnedHotelID=2998&HadPinnedHotel=true®ionId=3000454369) ![Joinery Hotel Pittsburgh, Curio Collection by Hilton](https://images.trvl-media.com/lodging/18000000/17910000/17900800/17900777/6b099d23_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Joinery Hotel Pittsburgh, Curio Collection by Hilton 453 Boulevard of the Allies Pittsburgh PA Fully refundableReserve now, pay when you stay CA $146 CA $169 total Dec 27 - Dec 28 includes taxes & fees 8.4/10 Very Good! (1,406 reviews) Yes! Reviewed on Dec 13, 2025 [](https://expedia.ca/Hotel-Search?startDate=27%2F12%2F2025&endDate=28%2F12%2F2025&selected=17900777&PinnedHotelID=17900777&HadPinnedHotel=true®ionId=3000454369) [See all 1,774 properties in Boston](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F12%2F2025&endDate=18%2F12%2F2025®ionId=3000454369) 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) ### Discover the most popular places to visit in Boston #### Northeast Paddleboard Company Take the family on an outing to Northeast Paddleboard Company during your trip to Boston. Amble around the area's riverfront or attend a sporting event. [](https://expedia.ca/Northeast-Paddleboard-Company-Pennsylvania.d553248621532660522.Vacation-Attraction) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](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