South Side Holidays

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    Better together
    Save up to €185 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Studio Allston Hotel
The Boxer
Fairmont Copley Plaza, Boston
Boston Harbor Hotel
Club Quarters Hotel Faneuil Hall, Boston

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

Top hotels in South Side

Seaport Hotel Boston
Seaport Hotel Boston
4 out of 5
1 Seaport Lane, Boston, MA
The price is €185 per night from 20 Dec to 21 Dec
€185
includes taxes & fees
20 Dec - 21 Dec
9.6/10 Exceptional! (2,591 reviews)
"Excellent property with friendly and welcoming staff. We would definitely stay again!"

Reviewed on 22 Nov 2024

Seaport Hotel Boston
Hilton Boston Park Plaza
Hilton Boston Park Plaza
4 out of 5
50 Park Plaza, Boston, MA
The price is €181 per night from 8 Dec to 9 Dec
€181
includes taxes & fees
8 Dec - 9 Dec
8.2/10 Very Good! (3,285 reviews)
"I’ll start with the bad- laying in bed getting ready for bed and a mouse goes running across the floor. I notified front desk and was moved to another room. The good- the staff was friendly, the breakfast buffet was well stocked, and is centrally located to a lot of amenities."

Reviewed on 21 Nov 2024

Hilton Boston Park Plaza
Omni Parker House
Omni Parker House
4 out of 5
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is €208 per night from 26 Nov to 27 Nov
€208
includes taxes & fees
26 Nov - 27 Nov
8.6/10 Excellent! (2,860 reviews)
"I couldn’t be more impressed with the level of service. From the moment I arrived the front desk staff went above and beyond to make me feel welcome. Check-in was smooth and efficient. Throughout my stay, the entire staff always responded and assisted promptly and kindly."

Reviewed on 20 Nov 2024

Omni Parker House
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 €855. 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.

Popular places to visit

Things to do

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