South Side Holidays

Book a Hotel + Flight or Car together to unlock savings

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(95 area reviews)

Known for its must-see aquarium and captivating waterfront views, there's plenty to explore in Downtown Boston. Check out top attractions like Boston Harbor and Boston Massacre Site, and jump on the metro at State St. Station or Downtown Crossing Station to see more of the city.

Find hotels in Downtown Boston

Top hotels in South Side

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
The price is 4.529.806 ₫ per night from 7 May to 8 May
4.529.806 ₫
6.174.157 ₫ total
7 May - 8 May
includes taxes & fees
9.6/10 Exceptional! (4,267 reviews)
-

Reviewed on 3 May 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 6.299.348 ₫ per night from 10 May to 11 May
6.299.348 ₫
8.409.937 ₫ total
10 May - 11 May
includes taxes & fees
9.2/10 Wonderful! (4,617 reviews)
Clean room, helpful staff, pretty view, nice bar

Reviewed on 3 May 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 4.675.291 ₫ per night from 10 May to 11 May
4.675.291 ₫
6.518.910 ₫ total
10 May - 11 May
includes taxes & fees
9.4/10 Exceptional! (5,045 reviews)
Absolutely perfect in every way.

Reviewed on 3 May 2026

The Godfrey Hotel Boston
See all 3,843 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 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 1null000null000 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.

Popular places to visit

Fenway Park

Fenway Park

4.5/5(62 reviews)

Catch an event at Fenway Park during your trip to Boston. Attend a baseball game in this walkable area.

Fenway Park
Harvard University

Harvard University

4.5/5(104 reviews)

Take a campus tour or just explore the area around Harvard University, a top university in Boston. Amble around this vibrant area's riverfront or experience its acclaimed art galleries.

Harvard University
Gillette Stadium

Gillette Stadium

3/5(2 reviews)

Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theatre scene and great live music.

Gillette Stadium