Title: Dorchester Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,207 Expedia.ca [Dorchester Travel Guide](https://expedia.ca/Boston-Dorchester.dx97469)[Hotels in Dorchester](https://expedia.ca/Dorchester-Boston-Hotels.0-n97469-0.Travel-Guide-Filter-Hotels)[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)[Dorchester Car Rentals](https://expedia.ca/Car-Rentals-In-Dorchester.d97469.Car-Rental-Guide) ![](https://images.trvl-media.com/place/97469/339e3d2b-3377-4ef8-8d22-77ab1c757985.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Dorchester Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings ## Top Holiday Package Deals in Dorchester Price found within the past 48 hours. Click for updated prices. ![The Langham, Boston](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/54f3deb7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Boston Downtown Boston CA $1,207 per person May 22 - May 25 found 11 hours ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 9.6/10 Exceptional! (1,004 reviews) Great location within walking distance to many of Boston’s best spots including Faneuil Market, North End “little Italy,” and more! The hotel staff were welcoming and kind during our visit, and our room was well kept. No complaints. Reviewed on Mar 14, 2026 ![Boston Harbor Hotel](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boston Harbor Hotel North End CA $1,748 per person May 1 - May 4 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 9.8/10 Exceptional! (1,001 reviews) Excellent hotel- restaurants, room service, all of the staff, spacious room with view, bathroom amenities. Great location. Able to take a leisurely walk along the water, and close to many restaurants and theatre district. Also easy to catch a taxi or uber. Wonderful setting with water and city view. Will definitely return! Reviewed on Mar 14, 2026 ![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 $1,561 per person Jun 13 - Jun 17 found 1 day ago Roundtrip flight included Toronto (YYZ) to Boston (BOS) 9.6/10 Exceptional! (252 reviews) Excellent experience- clean and very helpful staff Reviewed on Mar 9, 2026 ![The Whitney Hotel](https://images.trvl-media.com/lodging/30000000/29870000/29866100/29866090/c39bbe4a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Whitney Hotel Beacon Hill CA $2,854 per person Jun 2 - Jun 8 found 1 day ago Roundtrip flight included Montreal (YUL) to Boston (BOS) 9.6/10 Exceptional! (526 reviews) Fantastic location, close to Mass Gen. Restaurant on property was also very good. Reviewed on Mar 19, 2026 ![Raffles Boston](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/f081d391_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Raffles Boston Back Bay CA $2,356 per person May 27 - May 30 just found Roundtrip flight included Toronto (YTZ) to Boston (BOS) 9.6/10 Exceptional! (238 reviews) I went to raffles Boston for fiancés birthday and I called a week ahead to get the room decorated for her special day and when I showed up the room was not decorated, I then called and said they didn’t decorate the room like I asked so they asked if they could come up during dinner and decorate so I agreed. When we returned from dinner the room was “decorated”, the sign was hanging off the ceiling and decorations taped poorly and just looked awful. Very disappointed considering this is a expensive 5 start hotel Reviewed on Mar 12, 2026 ## Where to stay in Dorchester Find the best Dorchester areas and neighborhoods for the activities you enjoy most. [Learn more about Dorchester](https://expedia.ca/Boston-Dorchester.dx97469) ![Downtown Boston showing a city and night scenes as well as a small group of people](https://images.trvl-media.com/place/6340396/147aba27-8694-4725-895d-0beb6077ab67.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Boston 4.5/5(193 area reviews) Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here. [Find hotel + flight trips in Downtown Boston](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Boston&DestID=6340396&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Back Bay featuring a city, heritage architecture and street scenes](https://images.trvl-media.com/place/800016/ecea0c09-2ade-4d56-b74d-09ed645f6ef5.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Back Bay 1 out of top 10 points of interest in this area 4.5/5(272 area reviews) Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower. [Find hotel + flight trips in Back Bay](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Back%20Bay&DestID=800016&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Seaport District featuring a high-rise building, a river or creek and a city](https://images.trvl-media.com/place/6146535/5487f5d9-6748-43ca-b7bd-e50e2e9d2a27.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Seaport District 4.5/5(64 area reviews) Experience a transformed industrial area with office towers, innovation labs, and 78 restaurants. Visit the Institute of Contemporary Art and easily access Downtown Boston via the Evelyn Moakley Bridge. [Find hotel + flight trips in Seaport District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Seaport%20District&DestID=6146535&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![East Boston showing sailing, a city and a river or creek](https://images.trvl-media.com/place/99089/ffb9946d-6df5-4058-a132-e180995361ac.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### East Boston 4/5(28 area reviews) First a shipbuilding hub and now home of Logan Airport, Boston’s easternmost neighborhood is a multicultural area with great ethnic restaurants and historic sites. [Find hotel + flight trips in East Boston](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=East%20Boston&DestID=99089&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Beacon Hill which includes landscape views](https://images.trvl-media.com/place/77649/9741c4ac-c840-46d1-b907-3b388935c98f.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Beacon Hill 1 out of top 10 points of interest in this area 5/5(1 area review) Historic Federal-style rowhouses, gaslit streets, and brick sidewalks create a charming atmosphere. Explore the Boston African American National Historic Site, shop on Charles Street, and easily access MBTA stations. [Find hotel + flight trips in Beacon Hill](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Beacon%20Hill&DestID=77649&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Dorchester Hotel Deals ![Ramada by Wyndham Boston](https://images.trvl-media.com/lodging/1000000/10000/300/293/0b01c717_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Ramada by Wyndham Boston 800 Morrissey Blvd Boston MA Fully refundableReserve now, pay when you stay CA $120 CA $139 total Mar 29 - Mar 30 includes taxes & fees 6.8/10 (1,652 reviews) It was excellent Reviewed on Mar 20, 2026 [](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=293&PinnedHotelID=293&HadPinnedHotel=true®ionId=97469) ![Holiday Inn Express Boston by IHG](https://images.trvl-media.com/lodging/1000000/120000/116800/116764/7cbe2bb2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Express Boston by IHG 69 Boston St Boston MA Fully refundable CA $204 CA $238 total Mar 22 - Mar 23 includes taxes & fees 8.8/10 Excellent! (1,003 reviews) We booked this hotel because it was a nice location to the St Patrick’s Day parade, shopping and the train station! The rooms were very clean. Reviewed on Mar 19, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=116764&PinnedHotelID=116764&HadPinnedHotel=true®ionId=97469) ![Omni Boston Hotel at the Seaport](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/d1e2c1a3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Omni Boston Hotel at the Seaport 450 Summer Street Boston MA Fully refundableReserve now, pay when you stay CA $186 CA $272 total Mar 22 - Mar 23 includes taxes & fees 9.2/10 Wonderful! (4,520 reviews) Clean room, great location and staff Reviewed on Mar 20, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=68014393&PinnedHotelID=68014393&HadPinnedHotel=true®ionId=97469) [See all 4,314 properties in Dorchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=22%2F03%2F2026&endDate=23%2F03%2F2026®ionId=97469) 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) ## Frequently asked questions ### How much does a Dorchester vacation package cost? ### How do I get a cheap travel package to Dorchester? ### Where should I stay in Dorchester? ### What are the top hotels in Dorchester? ### How far in advance should I book my Dorchester vacation? ### What does an Expedia Dorchester travel package include? ### What should I know before booking a Dorchester travel package? ### Can I choose my airline with a Dorchester Expedia vacation package? ### If I'm not able to travel, can I cancel my Dorchester vacation package? ### Discover the most popular places to visit in Dorchester ![John F. Kennedy Presidential Library and Museum which includes modern architecture and interior views](https://images.trvl-media.com/place/6070087/d2886c19-a0ee-42f0-b4a9-730253a26186.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### John F. Kennedy Presidential Library and Museum 4.5/5(2 reviews) You can study the exhibits at John F. Kennedy Presidential Library and Museum, a museum with a storied past, during your trip to Boston. Experience the fascinating museums or attend a sporting event in this vibrant area. [](https://expedia.ca/John-F-Kennedy-Presidential-Library-And-Museum-Dorchester.d6070087.Vacation-Attraction) ### Things to do ![Boston Hop-On Hop-Off Trolley Tour](https://mediaim.expedia.com/localexpert/172982/6f42f390-62da-409c-a976-5a931abb154f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Boston Old Town Trolley Hop-on Hop-Off City Tour CA $72 per adult **90%** of travellers recommend [](https://expedia.ca/things-to-do/boston-old-town-trolley-hop-on-hop-off-city-tour.a172982.activity-details) ![Boston CityPASS: Admission to Top 4 Boston Attractions](https://mediaim.expedia.com/localexpert/173116/5d73576c-38be-4337-8351-c85e937f9492.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Boston CityPASS®: Admission to Top 4 Attractions CA $108 per adult **92%** of travellers recommend [](https://expedia.ca/things-to-do/boston-citypass-admission-to-top-4-attractions.a173116.activity-details) ![Zac tells a story about the John Harvard statue](https://mediaim.expedia.com/localexpert/1349360/d8650b03-f74e-4c81-8957-837ce0090701.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Harvard University Campus Guided Walking Tour CA $32 per adult **92%** of travellers recommend [](https://expedia.ca/things-to-do/harvard-university-campus-guided-walking-tour.a1349360.activity-details) [See all activities in Boston](https://expedia.ca/things-to-do/search?rid=97469) \* 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