South Side Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
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- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Top Holiday Package Deals in South Side
Price found within the past 48 hours. Click for updated prices.
The Langham, Boston
Downtown Boston
CA $1,836
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,002 reviews)
Elegant surroundings. The service was very good, especially the valet, who was very busy but we did not have to wait at all for our car. Very nice restaurants at the hotel property.
Reviewed on Aug 12, 2026
Hyatus Luxury Residences Somerville
Assembly Square
CA $2,410
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
10/10 Exceptional! (1 review)
I have lived a long time, but I have never experienced a stay as warm and beautiful as this luxury furnished apartment. Every corner felt lovingly prepared, and I often caught myself smiling at how comfortable and peaceful the home was. The modern touches wowed me and the place wrapped me in the familiar coziness of being in a real home. I will remember this stay fondly and with great gratitude to the team at building and leasing team.
Reviewed on Dec 6, 2025
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
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 Side Hotel Deals
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
CA $263
CA $354 total
Aug 30 - Aug 31
includes taxes & fees
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
CA $189
CA $221 total
Aug 16 - Aug 17
includes taxes & fees
9/10 Wonderful! (2,812 reviews)
"A"
Reviewed on Aug 12, 2026
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
CA $327
CA $438 total
Aug 30 - Aug 31
includes taxes & fees
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 Side vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in South Side from just CA $1,558. 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 travelers.
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 vacation?
While prices change frequently, we generally recommend booking your vacation 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 vacation 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 vacation is only a few clicks away.
Can I choose my airline with a South Side Expedia vacation 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 vacation package?
Whether it's your hotel or flight, you can cancel or change it. Locked in your South Side vacation 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.
Things to do
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $72
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $118
per adult
92% of travellers recommend
View Boston Observation Deck Admission Tickets
CA $48
per adult
86% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.