South Boston Vacations from ￥309,203

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The Latest South Boston Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was ￥413,422, price is now ￥309,203 per person
￥309,203
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.4/10 Exceptional! (1,005 reviews)
Clean and stylish room

Reviewed on Oct 13, 2025

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was ￥462,948, price is now ￥343,538 per person
￥343,538
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.4/10 Exceptional! (510 reviews)
Great location but they have no concierge , and for the price you will think they would. Rooms are small

Reviewed on Oct 8, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was ￥447,789, price is now ￥333,730 per person
￥333,730
per person
Nov 20 - Nov 23
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (160 reviews)
I wish the water was hotter, had to ask to have room cleaned after 1st day as housekeeping did not come. Very responsive though when inquiries made.

Reviewed on Oct 7, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was ￥504,422, price is now ￥382,912 per person
￥382,912
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
One of the best I’ve stayed at in a while

Reviewed on Oct 11, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was ￥420,812, price is now ￥338,568 per person
￥338,568
per person
Dec 27 - Jan 3
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.6/10 Exceptional! (457 reviews)
Love to the room, it was perfect for what we needed. Excellent service and excellent location. We will definitely stay here again.

Reviewed on Oct 13, 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 which includes night scenes and a city as well as a small group of people

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.

Find hotels in Downtown Boston

South Boston Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥27,298 per night from Nov 9 to Nov 10
￥27,298
￥37,999 total
Nov 9 - Nov 10
includes taxes & fees
9/10 Wonderful! (4,137 reviews)
"Clean room, great environment; staff was very accommodating."

Reviewed on Oct 13, 2025

Omni Boston Hotel at the Seaport
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥28,790 per night from Nov 9 to Nov 10
￥28,790
￥34,289 total
Nov 9 - Nov 10
includes taxes & fees
9.6/10 Exceptional! (3,499 reviews)
"AC is good. Legal Seafood restaurant excellent"

Reviewed on Oct 12, 2025

Seaport Hotel Boston
YOTEL Boston

YOTEL Boston

4 out of 5
65 Seaport Blvd, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥28,029 per night from Nov 9 to Nov 10
￥28,029
￥38,848 total
Nov 9 - Nov 10
includes taxes & fees
8.6/10 Excellent! (2,277 reviews)
"The focus on modern design, minimalism and eco friendly operations is different from traditional city hotels, but it very much worked for me. Well done - 👍"

Reviewed on Oct 8, 2025

YOTEL Boston
See all 1,332 properties in South Boston
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 ￥309,203. 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.

Discover the most popular places to visit in South Boston

Boston Convention and Exhibition Center

Boston Convention and Exhibition Center

4.5/5(732 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 Convention and Exhibition Center
Boston Tea Party Ship which includes a bay or harbor and boating

Boston Tea Party Ship

4.5/5(364 reviews)

Come to this museum and the three historic ships in the Boston Harbor to relive the momentous events of the Boston Tea Party.

Boston Tea Party Ship
Institute of Contemporary Art showing a bay or harbor, a city and modern architecture

Institute of Contemporary Art

4.5/5(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.

Institute of Contemporary Art

Things to do

The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

￥4,980
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
Hear the legendary true stories of Revolutionary Bostonians like Paul Revere, Midnight Rider at the Old North Church

Boston: Freedom Trail History Small Group Walking Tour

￥7,223
per adult
100% of travellers recommend
Boston: Freedom Trail History Small Group Walking Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

￥11,572
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
See all activities in Boston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.