South Side Vacations

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Your South Side Vacation

Your next big adventure is calling your name with a vacation package to South Side. Relaxation, entertainment and nothing but good times — you're sure to find it in this neighborhood. When it's time to get out and explore, you'll find loads of big-name attractions nearby including Bentley College, Brandeis University and Moody Street Historic District. Visit one, two (or even all!) during your trip to South Side. Stop dreaming and start doing. When you're ready to book your dream vacation to South Side, Expedia is here to help.

The Latest South Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
Excellent service, location, and amenities.

Reviewed on May 30, 2024

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
per person
Aug 7 - Aug 13
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Boston (BOS)
10/10 Exceptional! (3 reviews)
Everything was perfect

Reviewed on May 28, 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Jul 1 - Jul 4
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
This is an upscale hotel with excellent amenities and wonderfully helpful and friendly people who kindly made our stay a joy.

Reviewed on May 27, 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jul 1 - Jul 4
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (274 reviews)
Awesome, awesome, awesome. I could not find another word to describe my stay! Awesome.

Reviewed on May 22, 2024

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jul 3 - Jul 8
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (32 reviews)
Beautiful hotel, flowers in All areas. Staff was superb. Two very minor issue - no fan for toilet area, hot water in shower takes a bit. Doesn’t distract from my overall rating. Easily a come back recommendation

Reviewed on May 29, 2024

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 night scenes and a city as well as a small group of people

Downtown Boston

4.5/5(2,415 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 hotel + flight trips in Downtown Boston

South Side Hotel Deals

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4.5 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is $220 per night from Jun 16 to Jun 17
$220
$285 total
includes taxes & fees
Jun 16 - Jun 17
9/10 Wonderful! (2,122 reviews)
"Room was very clean overall hotel was clean front desk staff was meh not the friendliest but the room was soooooo tiny it was a shoe box and for what I spent the room wasn’t worth the money at all"

Reviewed on May 30, 2024

Omni Boston Hotel at the Seaport
Seaport Hotel Boston
Seaport Hotel Boston
4 out of 5
1 Seaport Lane, Boston, MA
The price is $269 per night from Jun 16 to Jun 17
$269
$318 total
includes taxes & fees
Jun 16 - Jun 17
9.6/10 Exceptional! (2,191 reviews)
"Did not need a car, convenient airport drop-off at hotel. Safe & easy access to Boston"

Reviewed on May 31, 2024

Seaport Hotel Boston
Omni Parker House
Omni Parker House
4 out of 5
60 School St, Boston, MA
The price is $207 per night from Jun 16 to Jun 17
$207
$276 total
includes taxes & fees
Jun 16 - Jun 17
8.8/10 Excellent! (2,580 reviews)
"Great location in the middle of all the historic sites"

Reviewed on May 30, 2024

Omni Parker House
See all 3,046 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

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 $717. 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

Image for Fenway Park

Fenway Park

4.5/5(2,499 reviews)

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

Fenway Park
Image for Harvard University

Harvard University

4.5/5(1,966 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
Image for Boston Common

Boston Common

4.5/5(4,786 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

Things to do

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$79
Per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Image for Bewitched Walking Tour of Salem

Bewitched Walking Tour of Salem

$30
Per adult
98% of travellers recommend
Bewitched Walking Tour of Salem
Image for Freedom Trail: Small Group Tour of Revolutionary Boston

Freedom Trail: Small Group Tour of Revolutionary Boston

$39
Per adult
100% of travellers recommend
Freedom Trail: Small Group Tour of Revolutionary Boston
See all activities in Boston

Other vacations you might like

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