South Boston Vacations from ￥189,464
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The Latest South Boston Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Cambridge Common House
West Cambridge
￥258,778
per person
Nov 23 - Nov 28
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Boston (BOS)
10/10 Exceptional! (34 reviews)
The cutest and most picturesque & cozy hotel, the staff were all very kind and the bed is so comfy!!! 1000% recommend!
Reviewed on Sep 3, 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
Seaport Hotel Boston
1 Seaport Lane Boston MA
￥29,541
￥39,731 total
Sep 20 - Sep 21
includes taxes & fees
9.6/10 Exceptional! (4,961 reviews)
"Very hospitable and kind."
Reviewed on Sep 6, 2026
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
￥36,393
￥48,748 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (4,859 reviews)
"Our stay was great. Easy to cruise port and airport"
Reviewed on Sep 6, 2026
The Westin Boston Seaport District
425 Summer St Boston MA
￥27,971
￥39,853 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (2,430 reviews)
"The hotel was fine, our biggest complaint involves billing. After pre-paying for the hotel on Expedia we were still billed an additional $296 by Westin. None of this was revealed to us prior to booking. That's dishonest."
Reviewed on Sep 6, 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 ￥189,464. 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.
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.
Liberty Wharf
9.0/10 (34 reviews)
Explore the waterfront in Boston with a trip to Liberty Wharf. Experience the acclaimed art scene or attend a sporting event in this vibrant area.
Things to do
Boston CityPASS®: Admission to Top 4 Attractions
￥13,448
per adult
92% of travellers recommend
Boston Red Sox Baseball Game at Fenway Park
￥10,781
per adult
Go City: Boston Explorer Pass - Choose 2 to 5 Attractions
￥8,213
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.