South Boston Vacations

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Price found within the past 48 hours. Click for updated prices.
  • Front of property
    Aug 24 - Aug 28

    Eurostars The Boxer + Flight

    West End
    4 nights
    4.0 star property
    8.8/10 - Excellent (1,507 reviews)
    "Amazing staff!"
    Reviewed June 2, 2026
    Roundtrip • Tokyo (HND) - Boston (BOS)
    HND - BOS • 1 stop BOS - HND • 1 stop
    ￥419,613
    ￥356,251
    per traveler
    found 1 day ago
    Eurostars The Boxer
  • Suite, Multiple Beds (John Adams Presidential Suite) | Frette Italian sheets, premium bedding, pillowtop beds, minibar
    Aug 24 - Aug 28

    Boston Harbor Hotel + Flight

    North End
    4 nights
    5.0 star property
    9.8/10 - Exceptional (1,001 reviews)
    "Wonderful classic harbor front hotel. Very nice front desk. Would stay again"
    Reviewed May 25, 2026
    Roundtrip • Tokyo (HND) - Boston (BOS)
    HND - BOS • 1 stop BOS - HND • 1 stop
    ￥657,291
    ￥456,585
    per traveler
    found 1 day ago
    Boston Harbor Hotel
  • Breakfast, lunch and brunch served
    Aug 24 - Aug 28

    The Langham, Boston + Flight

    Downtown Boston
    4 nights
    5.0 star property
    9.8/10 - Exceptional (1,006 reviews)
    "The rooms were clean, and friendly staff"
    Reviewed May 31, 2026
    Roundtrip • Tokyo (HND) - Boston (BOS)
    HND - BOS • 1 stop BOS - HND • 1 stop
    ￥545,104
    ￥431,372
    per traveler
    found 1 day ago
    The Langham, Boston
  • Game room
    Aug 6 - Aug 10

    Meco Hotel - Hostel + Flight

    West End
    4 nights
    2.0 star property
    8.6/10 - Excellent (436 reviews)
    "Desk clerk did not mention the birth I had contained a powered couch which I found out later was the easiet way to get into the under bed storage bin"
    Reviewed June 1, 2026
    Roundtrip • Osaka (KIX) - Boston (BOS)
    KIX - BOS • 2 stops BOS - KIX • 2 stops
    ￥485,348
    ￥397,804
    per traveler
    found 0 hours ago
    Meco Hotel - Hostel
  • Deluxe Single Room, 1 King Bed | Bathroom | Shower, hair dryer, towels, soap
    Aug 6 - Aug 10

    The Inn at Fireside Tavern Sherborn + Flight

    Sherborn
    4 nights
    2.0 star property
    10/10 - Exceptional (2 reviews)
    "Very cool place to stay outside of the city. Beautiful property with well maintained grounds. Short drive to the Natick mall which has so many places to shop and eat. Would recommend! 5/5⭐️"
    Reviewed May 26, 2026
    Roundtrip • Osaka (KIX) - Boston (BOS)
    KIX - BOS • 1 stop BOS - KIX • 1 stop
    ￥969,386
    ￥823,601
    per traveler
    found 1 hour ago
    The Inn at Fireside Tavern Sherborn

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

Downtown Boston

4.5/5(2,438 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

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is ￥34,421 per night from Jun 6 to Jun 7
￥34,421
￥46,605 total
Jun 6 - Jun 7
includes taxes & fees
9.2/10 Wonderful! (4,681 reviews)
"Great location, clean"

Reviewed on Jun 3, 2026

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 ￥41,200 per night from Jun 28 to Jun 29
￥41,200
￥53,434 total
Jun 28 - Jun 29
includes taxes & fees
9.6/10 Exceptional! (4,404 reviews)
"This property is perfect! My only complaint is that when I booked it stated that we would have free breakfast and upon arrival they stated that we did not have breakfast included in our stay. Pretty disappointed but it did not take away from the beauty and cleanliness at this hotel"

Reviewed on Jun 1, 2026

Seaport Hotel Boston
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
425 Summer St Boston MA
The price is ￥39,828 per night from Jul 3 to Jul 4
￥39,828
￥53,831 total
Jul 3 - Jul 4
includes taxes & fees
9.2/10 Wonderful! (2,378 reviews)
"Excellent service and facilities. However, for the rate paid I wish the hotel had included at least a continental breakfast."

Reviewed on Jun 2, 2026

The Westin Boston Seaport District
See all 1,480 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 . 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 and South Boston as viewed from the air

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 Convention and Exhibition Center
Boston Tea Party Ship

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.

Boston Tea Party Ship
Castle Island

Castle Island

The ancient Fort Independence finds its home on this impressive harbor peninsula, a beautiful place to walk and relax along the waterfront.

Castle Island

Things to do

View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

￥5,335
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
Tour of Historic Fenway Park, America's Most Beloved Ballpark

Tour of Historic Fenway Park, America's Most Beloved Ballpark

￥7,086
per adult
98% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

￥13,180
per adult
92% 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.