South Boston Vacation Packages
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Top Holiday Package Deals in South Boston
Price found within the past 48 hours. Click for updated prices.
Battery Wharf Hotel, Boston Waterfront
North End
CA $764
per person
Jan 8 - Jan 10
found 18 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9/10 Wonderful! (2,071 reviews)
2nd time at Battery Wharf and love the rooms closest to the harbor and beautiful views!
But hate the crappy Sunday buffet for $48 per person which didn’t know until after getting the bill!!!
Also why $40 charge per day?????
Also asked for an extra hour for late check out but wanted to charge me $150 for the hour!!!
Reviewed on Oct 26, 2026
Boston Harbor Hotel
North End
CA $982
per person
Dec 11 - Dec 13
found 19 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
Great hotel for the weekend! My husband and I were celebrating our anniversary!
Reviewed on Oct 25, 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
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
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
CA $258
CA $357 total
Nov 22 - Nov 23
includes taxes & fees
9.2/10 Wonderful! (4,948 reviews)
"Beautiful hotel"
Reviewed on Oct 26, 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
CA $190
CA $269 total
Nov 24 - Nov 25
includes taxes & fees
9.6/10 Exceptional! (5,159 reviews)
"Clean rooms and lovely staff! I loved the location."
Reviewed on Oct 26, 2026
YOTEL Boston, Select by Hilton
65 Seaport Blvd Boston MA
Fully refundableReserve now, pay when you stay
CA $164
CA $264 total
Nov 22 - Nov 23
includes taxes & fees
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 $764. 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 fascinating museums or attend a sporting event in this vibrant area.
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 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.
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.
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.
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 vibrant area.
Seaport Common
After visiting Seaport Common, make a plan to see the other sights and activities in Boston. Stroll along the waterfront in this vibrant area, or check out its top-notch restaurants.
Things to do
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $69
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $119
per adult
92% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
CA $65
per adult
80% of travellers recommend
Explore a world of travel with Expedia
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- 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.