South Boston Vacations from $324
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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.
The Cove at Yarmouth by Westgate Resorts
Save 100% on your flight
Price was $562, price is now $343 per person
$343
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.2/10 Wonderful! (243 reviews)
The unit on or suite units are on second floor with no elevator. In addition, the bedroom is on another level.
For those with physical issues only.insist on first floor
I found 1st floor bath dirty.
This is a time share rental which suits families with young kids.
Reviewed on Oct 6, 2025
Comfort Inn & Suites Logan International Airport
Save 100% on your flight
Price was $548, price is now $351 per person
$351
per person
Feb 18 - Feb 23
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9/10 Wonderful! (2,178 reviews)
Easy in and out to airport and prompt shuttle service.
Reviewed on Dec 22, 2025
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
4.5/5(2,415 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.
South Boston Hotel Deals
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$182 nightly
The price is $212 total per night from Dec 25 to Dec 26
$212 total
Dec 25 - Dec 26
Total with taxes and fees
9/10 Wonderful! (4,319 reviews)
Hotel was nice and clean environment? Last night we went the
Reviewed on Dec 22, 2025
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $202 total per night from Dec 25 to Dec 26
$202 total
Dec 25 - Dec 26
Total with taxes and fees
9.6/10 Exceptional! (3,823 reviews)
The grab and go breakfast option was perfect.
Reviewed on Dec 19, 2025
Hyatt Place Boston/Seaport District
295 NORTHERN AVENUE Boston MA
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $157 total per night from Dec 28 to Dec 29
$157 total
Dec 28 - Dec 29
Total with taxes and fees
9.4/10 Exceptional! (2,227 reviews)
Everything was great except valet. Each time I come, valet is not up to par.
Reviewed on Dec 22, 2025
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.
Discover the most popular places to visit in South Boston
Boston Convention and Exhibition Center
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.
Boston Children's Museum
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
Come to this museum and the three historic ships in the Boston Harbor to relive the momentous events of the Boston Tea Party.
Things to do
Boston CityPASS®: Admission to Top 4 Attractions
$79
per adult
92% of travellers recommend
Boston: Freedom Trail History Small Group Walking Tour
$35
per adult
100% of travellers recommend
Explore a world of travel with Expedia
- Boston Hotels
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- Cheap Hotels in Boston
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- Hotels near Boston Common
- Hotels near Boston Convention and Exhibition Center
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- Luxury Hotels in Seaport District
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- Flights to Boston
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- Boston Vacations
- Visit Boston
- Boston Museum of Fine Arts
- Columbus Park
- Our Lady of Czestochowa Roman Catholic Church
- Museum of Science
- New England Aquarium
- Boston Convention and Exhibition Center
- Boston Tea Party Ship
- Visit Seaport District
- Seaport District Vacations
- Bromfield Art Gallery
- Innovation District
- Boston Common
- Boston Design Center
- Flynn Cruiseport Boston
- Harpoon Brewery
- Cathedral of the Holy Cross
- Boston Medical Center
- Quincy Market
- Liberty Wharf
- Faneuil Hall Marketplace
- Leader Bank Pavilion
- Boston Children's Museum
- Institute of Contemporary Art
- Copley Square
- Shirley-Eustis House
- Isabella Stewart Gardner Museum
- Tufts Medical Center
- Blue Man Group
- Long Wharf
- John F. Kennedy Presidential Library and Museum
- Charles Playhouse
- Boston Public Garden
- Chinatown Vacations
- Zakim Bunker Hill Bridge
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.