South Boston Vacations from $451
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Your South Boston Vacation
Pick one of our vacation packages to South Boston and immerse yourself in the wonders of this neighborhood. Especially renowned for its festivals, your next great adventure starts right here. Begin your trip to South Boston with a visit to nearby attractions such as Fenway Park, Boston Common and Faneuil Hall Marketplace. Stop daydreaming and start doing. When you're ready to lock in your next vacation to South Boston, Expedia will help you get there.
The Latest South Boston Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Battery Wharf Hotel, Boston Waterfront
North End
$451
per person
Dec 3 - Dec 5
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9/10 Wonderful! (2,041 reviews)
The restaurant is just okay. We expected a better menu and better food. The coffee in the rooms were about the worst I ever had and wasn't worth making a second cup.
The staff were all very nice and friendly. Why doesn't the hotel provide a few little perks of convenience for the guest.
Reviewed on Oct 11, 2026
Four Seasons Hotel Boston
Bay Village
$1,305
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.4/10 Exceptional! (487 reviews)
Your staff is Five star! Hotel needs updating badly. My far the worst Four Seasons we have stayed in.
On the day of check-in, our flight was delayed and we got in at 2:30 in the morning had room service and it was an edible. Your staff indicated they would remove the charges, but I see we were still charged for them as well.
Reviewed on Oct 6, 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
$298 nightly
$347 total
Nov 1 - Nov 2
Total with taxes and fees
9.2/10 Wonderful! (4,891 reviews)
"Beautiful rooms and lobby. Excellent area surroundings. A lot of areas within the hotel to be hang with friends. Many restaurants. Good gym. Near the convention center (2 min walk) Close to the airport. Good places at walking distance to go."
Reviewed on Oct 11, 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$219 nightly
$254 total
Nov 1 - Nov 2
Total with taxes and fees
The Westin Boston Seaport District
425 Summer St Boston MA
$209 nightly
$244 total
Nov 1 - Nov 2
Total with taxes and fees
9.2/10 Wonderful! (2,452 reviews)
"Proximité au centre des congrès"
Reviewed on Oct 12, 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.
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 CityPASS®: Admission to Top 4 Attractions
$84
per adult
92% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
$46
per adult
80% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
$37
per adult
92% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.