South Side Holidays

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Your South Side Holiday

Take all the hassle out of organising your next getaway with a South Side holiday package. Take in the sights and sounds of this unique neighbourhood and experience all it has to offer. Start your trip to South Side by heading to nearby attractions such as Bentley College, Brandeis University and Moody Street Historic District. Expedia is here to put your travel plans into action. Book your perfect South Side holiday now.

Our guide on where to stay in South Side

Find the best South Side areas and neighborhoods for the activities you enjoy most. Learn more about South Side
Downtown Boston showing a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(17 area reviews)

This is Boston’s business district, now and back when the city was just starting.

Find hotels in Downtown Boston

Our pick of the best South Side 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 AU$312 per night from 22 Mar to 23 Mar
AU$312
22 Mar - 23 Mar
includes taxes & fees
9.2/10 Wonderful! (4,510 reviews)
Nice

Reviewed on 11 Mar 2026

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is AU$280 per night from 23 Mar to 24 Mar
AU$280
23 Mar - 24 Mar
includes taxes & fees
8.4/10 Very Good! (3,116 reviews)
Second stay here. This is now our go to hotel in Boston. Excellent staff, location, and wonderful lobby/lounge. Can’t wait to return.

Reviewed on 13 Mar 2026

Hilton Boston Park Plaza
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is AU$457 per night from 17 Mar to 18 Mar
AU$457
17 Mar - 18 Mar
includes taxes & fees
9.2/10 Wonderful! (6,353 reviews)
Location was perfect! Blue line stop right outside hotel, easy and short walk to restaurants, historic sites, other shops. Hotel and staff were great. Would love to stay here again!

Reviewed on 13 Mar 2026

Harborside Inn Of Boston
See all 3,836 properties in South Side
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a South Side holiday package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in South Side from just . And the more you bundle, the more money you save. Your dream escape has never been so affordable.
How do I get a cheap travel package to South Side?
One of the easiest ways to save money (and time) is to bundle your bookings with Expedia. Flights, rental cars, hotels and activities — we've got them all. Pick and choose a combination that suits your style and see your savings stack up. We know a package deal is never a one-size-fits-all. That's why we offer more than 550 airlines and 1 000 000 properties around the globe, which lets you customize your South Side adventure.
Where should I stay in South Side?
Stay at a hotel near Bentley College. This impressive sight is in the thick of the action and on the to-do lists of most travellers.
What are the top hotels in South Side?
When it comes to comfortable places to stay in South Side, you can't go past Crescent Suites Hotel. Check out our deals and score a bargain.
How far in advance should I book my South Side holiday?
While prices change frequently, we generally recommend booking your holiday as early as possible. Most international airfares become available on Expedia up to 12 months in advance. If circumstances have left you booking late, you may still get lucky. Cheaper tickets to South Side occasionally appear in the weeks prior to departure.
What does an Expedia South Side travel package include?
Expedia has all you need to plan your South Side escape, but what goes into your package is your choice. Choose from a combination of hotels, flights and rental cars. Chasing some tours or experiences to keep you on the move? Once you've made your booking, you can add them too. No matter your style, there's a holiday package to meet your needs.
What should I know before booking a South Side travel package?
Discover deals that fit your budget with an Expedia package. Hotels, flights, rental cars — we're a one-stop shop for all of them. You'll save precious cash just by combining your bookings. Whether you're embarking on a skiing adventure or venturing someplace warm, your dream holiday is only a few clicks away.
Can I choose my airline with a South Side Expedia holiday package?
Yes, the choice is all yours. Expedia has access to more than 550 airlines around the world, so you can design your South Side trip according to your needs and budget.
If I'm not able to travel, can I cancel my South Side holiday package?
Whether it's your hotel or flight, you can cancel or change it. Locked in your South Side holiday package in the last 24 hours? You may be able to make changes for free. For older bookings, you may be charged a fee by your airline, hotel or car rental company. For more information, look up our Customer Service Portal. We're here to help you every step of the way.

Discover the most popular places to visit in South Side

Fenway Park which includes night scenes and a sporting event as well as a large group of people

Fenway Park

4.5/5(9 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Boston Common which includes landscape views, a skyscraper and a park

Boston Common

4.5/5(32 reviews)

The oldest public park in the United States, Boston Common is the ideal place to relax, unwind and soak up some history.

Boston Common
Harvard University which includes heritage architecture and a city

Harvard University

4.5/5(27 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University

Activities

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

AU$74
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
History and Hauntings of Salem Guided Walking Tour

History and Hauntings of Salem Guided Walking Tour

AU$51
per adult
98% of travellers recommend
History and Hauntings of Salem Guided Walking Tour
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

AU$33
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
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.