South Side Vacations

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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

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 Side Hotel Deals

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 ₩249,416 per night from May 3 to May 4
₩249,416
₩340,742 total
May 3 - May 4
includes taxes & fees
9.6/10 Exceptional! (4,236 reviews)
yes

Reviewed on Apr 28, 2026

Seaport Hotel Boston
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 ₩315,549 per night from May 1 to May 2
₩315,549
₩427,569 total
May 1 - May 2
includes taxes & fees
9.2/10 Wonderful! (4,606 reviews)
Great hotel

Reviewed on Apr 27, 2026

Omni Boston Hotel at the Seaport
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
505 Washington Street Boston MA
Fully refundableReserve now, pay when you stay
The price is ₩417,324 per night from May 21 to May 22
₩417,324
₩546,162 total
May 21 - May 22
includes taxes & fees
9.4/10 Exceptional! (5,016 reviews)
My second stay here and I loved it. It's close to everything, great bar, restaurant and cafe right on the property. I loved the room, perfect for my needs. And the staff is all very kind and attentive. Will be staying again in the future!

Reviewed on Apr 28, 2026

The Godfrey Hotel Boston
See all 3,866 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.

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 . 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.

Discover the most popular places to visit in South Side

Fenway Park

Fenway Park

4.5/5(2,543 reviews)

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

Fenway Park
Harvard University

Harvard University

4.5/5(1,983 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
Boston's Zakim Bridge

TD Garden

4.5/5(1,818 reviews)

Catch an event at TD Garden during your trip to Boston. Attend a sporting event or visit the notable monuments in this vibrant area.

TD Garden
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.