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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    Rest easy
    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
per person
5 Sept - 10 Sept
found 17 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8/10 Very Good! (2,056 reviews)
Was actually too nice for us

Reviewed on 1 Jul 2025

The Cove At Salem

The Cove At Salem

3 out of 5
Save 100% on your flight
per person
5 Sept - 10 Sept
found 17 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (576 reviews)
Stay was great, only complaint was the cleaners banging on the door an hour before check out

Reviewed on 4 Jul 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
8 Aug - 12 Aug
found 22 hours ago
Return direct flight included
Shannon (SNN) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Beautiful Hotel and Great Location! Staff were so friendly and the waitress at The Dark Hour was so educational about the history of Boston! Love it!

Reviewed on 5 Jul 2025

The Beverly

The Beverly

3 out of 5
Save 100% on your flight
per person
5 Sept - 10 Sept
found 17 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8.4/10 Very Good! (305 reviews)
This was a first for me. They give you your room code through a welcome email. Id never done that and had trouble with it. To add insult to injury, when i arrived there was no one in the front office either. Once i managed to get someone on teh phone they were very helpful and we managed to figure it out. It's just something to be aware of going in.

Reviewed on 29 Jun 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
8 Aug - 12 Aug
found 22 hours ago
Return direct flight included
Shannon (SNN) to Boston (BOS)
9.6/10 Exceptional! (118 reviews)
Beautiful interior design

Reviewed on 3 Jul 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 which includes a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(94 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

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is €263 per night from 19 Jul to 20 Jul
€263
19 Jul - 20 Jul
includes taxes & fees
9/10 Wonderful! (3,613 reviews)
"Wonderful stay!"

Reviewed on 3 Jul 2025

Omni Boston Hotel at the Seaport
citizenM Boston Back Bay
citizenM Boston Back Bay
4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is €162 per night from 6 Jul to 7 Jul
€162
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (1,347 reviews)
"Great location."

Reviewed on 2 Jul 2025

citizenM Boston Back Bay
Seaport Hotel Boston
Seaport Hotel Boston
4 out of 5
1 Seaport Lane, Boston, MA
The price is €234 per night from 13 Jul to 14 Jul
€234
13 Jul - 14 Jul
includes taxes & fees
9.6/10 Exceptional! (3,010 reviews)
Great Stay!!!
"Great stay!!! I would HIGHLY recommend this hotel for the location and amenities!"

Reviewed on 2 Jul 2025

Seaport Hotel Boston
See all 3,417 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 €626. 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

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

Fenway Park

4.5/5(61 reviews)

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

Fenway Park
Harvard University which includes heritage architecture and a city

Harvard University

4.5/5(102 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
Copley Square

Copley Square

4/5(16 reviews)

Explore some of Boston’s finest buildings, educational and arts institutions, and shopping, or simply find a patch of grass and relax.

Copley Square

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

€69
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

€61
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

€30
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
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.