Title: South Boston Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,685 Expedia.ca [South Boston Travel Guide](https://expedia.ca/Boston-South-Boston.dx159768)[Hotels in South Boston](https://expedia.ca/South-Boston-Boston-Hotels.0-n159768-0.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)[South Boston Car Rentals](https://expedia.ca/Car-Rentals-In-South-Boston.d159768.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6146535/5487f5d9-6748-43ca-b7bd-e50e2e9d2a27.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South 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 ## Top Holiday Package Deals in South Boston Price found within the past 48 hours. Click for updated prices. ![Studio Allston Hotel](https://images.trvl-media.com/lodging/23000000/22760000/22757100/22757092/ab573c90_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Studio Allston Hotel Brighton CA $1,685 per person Jun 1 - Jun 8 found 1 day ago Roundtrip non-stop flight included Halifax (YHZ) to Boston (BOS) 8.6/10 Excellent! (1,247 reviews) It's a nice hotel. Quirky, but it's quiet and conveniently located. Reviewed on Mar 8, 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 $1,812 per person Apr 23 - Apr 26 found 8 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Boston (BOS) 9.8/10 Exceptional! (1,002 reviews) Best hotel ive ever stayed in. Reviewed on Mar 11, 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 $5,553 per person Apr 18 - Apr 25 found 15 hours ago Roundtrip non-stop flight included Halifax (YHZ) 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 ![Hyatt Regency Boston/Cambridge](https://images.trvl-media.com/lodging/1000000/20000/16100/16079/944dfde2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency Boston/Cambridge MIT CA $1,843 per person Jun 1 - Jun 8 found 1 day ago Roundtrip non-stop flight included Halifax (YHZ) to Boston (BOS) 9/10 Wonderful! (2,266 reviews) The valet parking is an additional $60.00 Reviewed on Mar 11, 2026 ![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 $2,104 per person May 15 - May 18 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 9.6/10 Exceptional! (1,004 reviews) Friendly staff, clean room Reviewed on Feb 20, 2026 ## Where to stay in South Boston Find the best South Boston areas and neighborhoods for the activities you enjoy most. [Learn more about South Boston](https://expedia.ca/Boston-South-Boston.dx159768) ![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(271 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) ![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) ![Boston Harbor which includes performance art, music and a bay or harbor](https://images.trvl-media.com/place/553248634340925170/190102c5-6ec7-4f3d-9631-9a7f002e9676.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### North End 1 out of top 10 points of interest in this area 4.5/5(18 area reviews) Indulge in Italian cuisine at numerous restaurants and bakeries, explore historic sites like Old North Church and Paul Revere House, and enjoy performances at NEMPAC and Improv Asylum Theater. Easily accessible via MBTA lines, buses, and ferries. [Find hotel + flight trips in North End](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=North%20End&DestID=6146485&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## South Boston Hotel Deals ![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 $208 CA $297 total Mar 22 - Mar 23 includes taxes & fees 9.2/10 Wonderful! (4,507 reviews) Nice Reviewed on Mar 11, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=68014393&PinnedHotelID=68014393&HadPinnedHotel=true®ionId=159768) ![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Seaport Hotel Boston 1 Seaport Lane Boston MA Fully refundableReserve now, pay when you stay CA $184 CA $260 total Apr 5 - Apr 6 includes taxes & fees 9.6/10 Exceptional! (4,039 reviews) Clean and in a great area Reviewed on Mar 12, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=79888&PinnedHotelID=79888&HadPinnedHotel=true®ionId=159768) ![YOTEL Boston](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/0ab5b9a8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### YOTEL Boston 65 Seaport Blvd Boston MA Fully refundableReserve now, pay when you stay CA $184 CA $286 total Mar 29 - Mar 30 includes taxes & fees 8.6/10 Excellent! (2,449 reviews) very good Reviewed on Mar 12, 2026 [](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=18090311&PinnedHotelID=18090311&HadPinnedHotel=true®ionId=159768) [See all 1,559 properties in South Boston](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=14%2F03%2F2026&endDate=15%2F03%2F2026®ionId=159768) 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 South Boston vacation package cost? ### How do I get a cheap travel package to South Boston? ### Where should I stay in South Boston? ### What are the top hotels in South Boston? ### How far in advance should I book my South Boston vacation? ### What does an Expedia South Boston travel package include? ### What should I know before booking a South Boston travel package? ### Can I choose my airline with a South Boston Expedia vacation package? ### If I'm not able to travel, can I cancel my South Boston vacation package? ### Discover the most popular places to visit in South Boston ![Boston Tea Party Ship featuring boating and a bay or harbour](https://images.trvl-media.com/place/6070037/6c2a2d2e-45d4-461e-8869-4ace089faceb.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Boston Tea Party Ship Come to this museum and the three historic ships in the Boston Harbor to relive the momentous events of the Boston Tea Party. [](https://expedia.ca/Boston-Tea-Party-Ship-South-Boston.d6070037.Vacation-Attraction) ![Boston_BlueHillsBankPavilion_6127112_03](https://images.trvl-media.com/place/6127112/f8d7fd0e-6fb0-48b8-859e-5b044c96d3a4.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Leader Bank Pavilion Enjoy a performance at Leader Bank Pavilion, a storied theater in Boston. Experience the fascinating museums or attend a sporting event in this vibrant area. [](https://expedia.ca/Leader-Bank-Pavilion-Seaport-District.d6127112.Vacation-Attraction) ![Castle Island showing a garden, a river or creek and a city](https://images.trvl-media.com/place/6229775/eb10f1ec-6f9c-4f59-8ae2-4fc438334d9c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Castle Island The ancient Fort Independence finds its home on this impressive harbor peninsula, a beautiful place to walk and relax along the waterfront. [](https://expedia.ca/Castle-Island-South-Boston.d6229775.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=159768) ## Explore a world of travel with Expedia - 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[Telegraph Hill Hotels ](https://www.expedia.ca/Telegraph-Hill-Boston-Hotels.0-n553248635976480455-0.Travel-Guide-Filter-Hotels) - [Flights to Boston ](https://www.expedia.ca/Cheap-Flights-To-Boston.d178239.Travel-Guide-Flights) - [Flights from Halifax (YHZ) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yhz/bos/halifax-to-boston) - [Flights from Ottawa (YOW) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yow/bos/ottawa-to-boston) - [Flights from Montreal (YUL) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yul/bos/montreal-to-boston) - [Flights from Vancouver (YVR) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yvr/bos/vancouver-to-boston) - [Flights from Calgary (YYC) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yyc/bos/calgary-to-boston) - [Flights from Toronto (YYZ) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yyz/bos/toronto-to-boston) - [Boston Common ](https://www.expedia.ca/Boston-Common-Beacon-Hill.d507377.Vacation-Attraction) - [Visit Downtown Boston ](https://www.expedia.ca/Boston-Downtown-Boston.dx6340396) - [Visit Fort Point ](https://www.expedia.ca/Boston-Fort-Point.dx553248635976477902) - [Boston Harbor ](https://www.expedia.ca/Boston-Harbor-Waterfront.d553248634340925170.Vacation-Attraction) - [Boston Marathon Finish Line ](https://www.expedia.ca/Boston-Marathon-Finish-Line-Back-Bay.d553248635975090955.Vacation-Attraction) - [Boston Medical Center ](https://www.expedia.ca/Boston-Medical-Center-South-End.d6161359.Vacation-Attraction) - [Boston Opera House ](https://www.expedia.ca/Boston-Opera-House-Downtown-Boston.d6070029.Vacation-Attraction) - [Boston Public Garden ](https://www.expedia.ca/Boston-Public-Garden-Beacon-Hill.d507376.Vacation-Attraction) - [Visit Seaport District ](https://www.expedia.ca/Boston-Seaport-District.dx6146535) - [Boston Tea Party Ship ](https://www.expedia.ca/Boston-Tea-Party-Ship-South-Boston.d6070037.Vacation-Attraction) - [Visit Telegraph Hill ](https://www.expedia.ca/Boston-Telegraph-Hill.dx553248635976480455) - [Boston Vacations ](https://www.expedia.ca/Boston.d178239.Destination-Travel-Guides) - [Visit Boston ](https://www.expedia.ca/Boston.dx178239) - [Castle Island ](https://www.expedia.ca/Castle-Island-South-Boston.d6229775.Vacation-Attraction) - [Chinatown Vacations ](https://www.expedia.ca/Chinatown.d6003519.Destination-Travel-Guides) - [Columbus Park ](https://www.expedia.ca/Columbus-Park-South-Boston.d507381.Vacation-Attraction) - [Copley Square ](https://www.expedia.ca/Copley-Square-Back-Bay.d6070057.Vacation-Attraction) - [Downtown Boston Vacations ](https://www.expedia.ca/Downtown-Boston.d6340396.Destination-Travel-Guides) - [Faneuil Hall Marketplace ](https://www.expedia.ca/Faneuil-Hall-Marketplace-Government-Center.d6070067.Vacation-Attraction) - [John F. Kennedy Presidential Library and Museum ](https://www.expedia.ca/John-F-Kennedy-Presidential-Library-And-Museum-Dorchester.d6070087.Vacation-Attraction) - [Leader Bank Pavilion ](https://www.expedia.ca/Leader-Bank-Pavilion-Seaport-District.d6127112.Vacation-Attraction) - [Long Wharf ](https://www.expedia.ca/Long-Wharf-North-End.d6123757.Vacation-Attraction) - [Massachusetts State House ](https://www.expedia.ca/Massachusetts-State-House-Beacon-Hill.d6070101.Vacation-Attraction) - [New England Aquarium ](https://www.expedia.ca/New-England-Aquarium-North-End.d6070109.Vacation-Attraction) - [Newbury Street ](https://www.expedia.ca/Newbury-Street-Back-Bay.d6160599.Vacation-Attraction) - [Old State House ](https://www.expedia.ca/Old-State-House-Downtown-Boston.d6070121.Vacation-Attraction) - [Parkman Bandstand ](https://www.expedia.ca/Parkman-Bandstand-Beacon-Hill.d553248621533117624.Vacation-Attraction) - [Prudential Tower ](https://www.expedia.ca/Prudential-Tower-Back-Bay.d6070133.Vacation-Attraction) - [Quincy Market ](https://www.expedia.ca/Quincy-Market-Government-Center.d553248621561096542.Vacation-Attraction) - [Robert Gould Shaw Memorial ](https://www.expedia.ca/Robert-Gould-Shaw-Memorial-Beacon-Hill.d553248621533117630.Vacation-Attraction) - [Rose Fitzgerald Kennedy Greenway ](https://www.expedia.ca/Rose-Fitzgerald-Kennedy-Greenway-North-End.d6341396.Vacation-Attraction) - [Spectacle Island ](https://www.expedia.ca/Spectacle-Island-Seaport-District.d553248621532667073.Vacation-Attraction) - [Suffolk University ](https://www.expedia.ca/Suffolk-University-East-Boston.d553248621562854462.Vacation-Attraction) - [Tufts Medical Center ](https://www.expedia.ca/Tufts-Medical-Center-Bay-Village.d6182998.Vacation-Attraction) - [Waterfront Vacations ](https://www.expedia.ca/Waterfront.d553248623992980699.Destination-Travel-Guides) - [Car rentals near Flynn Cruiseport Boston ](https://www.expedia.ca/Car-Rentals-In-Flynn-Cruiseport-Boston.d6182961.Car-Rental-Guide) - [Car rentals near Seaport District ](https://www.expedia.ca/Car-Rentals-In-Seaport-District.d6146535.Car-Rental-Guide) - [Things to do in Boston ](https://www.expedia.ca/Things-To-Do-In-Boston.d178239.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.