South Boston Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
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
Downtown Boston
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.
Back Bay
1 out of top 10 points of interest in this area
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.
Seaport District
1 out of top 10 points of interest in this area
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.
Beacon Hill
1 out of top 10 points of interest in this area
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.
North End
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.
South Boston Hotel Deals
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
CA $263
CA $354 total
Aug 30 - Aug 31
includes taxes & fees
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
CA $328
CA $438 total
Aug 20 - Aug 21
includes taxes & fees
9.2/10 Wonderful! (4,843 reviews)
"Check in was a little disorganized. It was my first time staying there and the staff didn’t properly explain how to use the elevators and how to access the pool. There was some miscommunication about the parking situation. The staff was very understanding and compensated us."
Reviewed on Aug 14, 2026
The Westin Boston Seaport District
425 Summer St Boston MA
CA $224
CA $326 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (2,430 reviews)
"The Westin had very friendly staff, a great room, and is in walking distance to most places that we wanted to go in Boston!"
Reviewed on Aug 13, 2026
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.
Frequently asked questions
How much does a South Boston vacation package cost?
We make it easy to travel somewhere new, with South Boston vacation packages starting from just CA $1,402. You'll have the flexibility to combine your preferred airlines, hotels and car rental. For the ultimate getaway, why not add some tours and activities to your travel itinerary?
How do I get a cheap travel package to South Boston?
Browse and book everything in the one place with our South Boston vacation packages. You'll find bargains on flights, hotels, tours and more that'll keep your pocketbook happy and your adventurous spirit alive. And, with more than 550 airlines and 1,000,000 hotel options all over the world to select from, you'll have the flexibility to mix and match your own way.
Where should I stay in South Boston?
Visitors come from near and far to see Fenway Park and TD Garden in South Boston. Book a room close to these must-see attractions to make sightseeing a breeze.
What are the top hotels in South Boston?
Book a stay at Hyatt Place Boston/seaport District. It's one of the area's most sought-after properties. Another top option in South Boston is Omni Boston Hotel at the Seaport.
How far in advance should I book my South Boston vacation?
Your safest bet is to book early. Airlines typically release flights nearly 12 months prior to departure, and this is when you can pick up some of the lowest prices. Boss just told you to use up some vacation time in a few weeks? No need to worry. Expedia are never short on fantastic bargains to help you have the getaway of your dreams, at an affordable price.
What does an Expedia South Boston travel package include?
Flights, rental cars and hotels — you'll discover them all here. With Expedia, you can shape your South Boston travel package just the way you want. All you have to do is work out exactly what you need. Once you've made your booking, you can add extras like activities and experiences. The more you bundle, the bigger the savings!
What should I know before booking a South Boston travel package?
When you book your hotels, flights and car rentals together, you'll score awesome discounts. Whether you're planning a mountain getaway in a cabin or want to stay in an upscale city hotel, Expedia will make it happen for less.
Can I choose my airline with a South Boston Expedia vacation package?
Expedia offers access to more than 550 partner airlines globally, so you definitely can. Simply choose the airline you want and craft your ideal South Boston trip.
If I'm not able to travel, can I cancel my South Boston vacation package?
Because we understand life is full of surprises, the answer is yes. To find out more, visit our Customer Service Portal. But generally speaking, if you've booked your South Boston vacation package in the last 24 hours, you may be able to change or cancel it without penalty. Your hotel, airline or car rental company may charge a fee if you made your booking a while ago.
Stay near popular South Boston attractions
Boston Convention and Exhibition Center
8.8/10 (2,207 reviews)
During your trip, find out what's happening at Boston Convention and Exhibition Center, a top convention center in Boston. Experience the acclaimed art scene or attend a sporting event in this vibrant area.
Photo by Vin Lane-Kieltyka
Boston Children's Museum
9.0/10 (269 reviews)
You can take time to visit Boston Children's Museum during your travels to Boston. Amble around this vibrant area's waterfront or attend a sporting event.
Boston Tea Party Ship
8.8/10 (505 reviews)
Come to this museum and the three historic ships in the Boston Harbor to relive the momentous events of the Boston Tea Party.
Leader Bank Pavilion
9.6/10 (8 reviews)
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.
Photo by Greater Boston Convention & Visitors Bureau
Castle Island
The ancient Fort Independence finds its home on this impressive harbor peninsula, a beautiful place to walk and relax along the waterfront.
Institute of Contemporary Art
8.8/10 (15 reviews)
Between its striking modern building and its vast collections of contemporary art, this museum on Boston’s waterfront provides delights to enjoy at every turn.
Harpoon Brewery
You can take time to visit Harpoon Brewery during your travels to Boston. Check out the shops and top-notch restaurants in this romantic area.
Liberty Wharf
9.0/10 (34 reviews)
Explore the waterfront in Boston with a trip to Liberty Wharf. Experience the fascinating museums or attend a sporting event in this vibrant area.
Things to do
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $72
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $118
per adult
92% of travellers recommend
View Boston Observation Deck Admission Tickets
CA $48
per adult
86% of travellers recommend
Explore a world of travel with Expedia
- B&B in Boston
- Hotels near Fenway Park
- Cambridge Hotels
- Hotels near TD Garden
- Marriott Hotels & Resorts in Boston
- Motels in Boston
- Back Bay Hotels
- Hotels with a Pool in Boston
- Cheap Hotels in Boston
- Hotels with Free Parking in Boston
- Seaport District Hotels
- Hotels with Free Breakfast in Boston
- Hotels near Boston Convention and Exhibition Center
- Cottages in Boston
- Hotels near Boston Common
- Hotels with Free Airport Shuttle in Boston
- Hotels near Boston Harbor
- Beacon Hill Hotels
- Hotels near Harvard University
- Hotels near Flynn Cruiseport Boston
- Hotels near Logan Intl.
- Boston Hotels
- Pet-Friendly Hotels in Boston
- Downtown Boston Hotels
- Salem Hotels
- Flights from Syracuse (SYR) to Boston (BOS)
- Flights from Toronto (YYZ) to Boston (BOS)
- Flights from Ottawa (YOW) to Boston (BOS)
- Flights from Regina (YQR) to Boston (BOS)
- Flights from Los Angeles (LAX) to Boston (BOS)
- Flights to Boston
- Flights from Vancouver (YVR) to Boston (BOS)
- Flights from Toronto (YTZ) to Boston (BOS)
- Flights from Minneapolis (MSP) to Boston (BOS)
- Flights from Victoria (YYJ) to Boston (BOS)
- Flights from Edmonton (YEG) to Boston (BOS)
- Flights from Detroit (DTW) to Boston (BOS)
- Air Canada Toronto (YYZ) to Boston (BOS) flights
- Flights from Logan Intl.
- Flights from Winnipeg (YWG) to Boston (BOS)
- Flights from Presque Isle (PQI) to Boston (BOS)
- Flights from Kitchener (YKF) to Boston (BOS)
- Flights from London (YXU) to Boston (BOS)
- Porter Airlines Toronto (YTZ) to Boston (BOS) flights
- Flights from Seattle (SEA) to Boston (BOS)
- Flights from Saint John (YSJ) to Boston (BOS)
- Flights from Hamilton (YHM) to Boston (BOS)
- Flights to Salem
- Flights from Saskatoon (YXE) to Boston (BOS)
- Flights from St. John's (YYT) to Boston (BOS)
- Flights from Miami (MIA) to Boston (BOS)
- Flights from Buffalo (BUF) to Boston (BOS)
- Flights from Moncton (YQM) to Boston (BOS)
- Flights from New York (NYC) to Boston (BOS)
- Flights from Halifax (YHZ) to Boston (BOS)
- Flights from Chicago (ORD) to Boston (BOS)
- Flights from Calgary (YYC) to Boston (BOS)
- Flights from Montreal (YUL) to Boston (BOS)
- Visit Boston
- Visit Seaport District
- Boston Harbor
- Td Garden
- Zakim Bunker Hill Bridge
- Newbury Street
- Salem Vacations
- Boston Common
- The Shops at Prudential Center
- Visit Manchester-by-the-Sea
- Isabella Stewart Gardner Museum
- Visit Downtown Boston
- Revere Beach
- Visit Massachusetts
- Faneuil Hall Marketplace
- Museum of Science
- Fenway Park
- Charles River Esplanade
- Massachusetts Institute of Technology
- All inclusive Vacation Packages Boston
- Massachusetts State House
- The Freedom Trail
- Boston Public Garden
- Waterfront Vacations
- Berklee College of Music
- New England Aquarium
- Prudential Tower
- Downtown Boston Vacations
- Boston Marathon Finish Line
- Boston Museum of Fine Arts
- Copley Square
- Boston Tea Party Ship
- Hynes Convention Center
- Harvard University
- Visit Beacon Hill
- Quincy Market
- Boston Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.