South Side Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in South Side

Price found within the past 48 hours. Click for updated prices.
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
Seaport District
Price was CA $868, price is now CA $577 per person
CA $577
per person
Oct 29 - Nov 1
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
9/10 Wonderful! (2,130 reviews)
Great hotel in a nice area. It’s not too far from the airport. They have a conference center so they do host events. Breakfast buffet was really good. There’s a Starbucks as well. They have a restaurant and laugh Boston on sight. Staff was great and accommodating. Just good experience overall. I recommend if you’re visiting Boston.

Reviewed on Sep. 2, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $3,617, price is now CA $2,080 per person
CA $2,080
per person
Oct 9 - Oct 13
found 8 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
9.6/10 Exceptional! (154 reviews)
Staff went above and beyond everyday! The dining options and location were amazing.

Reviewed on Sep. 2, 2025

Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End

3 out of 5
South End
Price was CA $987, price is now CA $637 per person
CA $637
per person
Oct 11 - Oct 13
found 20 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
8.8/10 Excellent! (1,001 reviews)
Rooms are very small, restaurant bar was just below our room and open til 1am-very loud, restaurant for breakfast has very limited menu and coffee is terrible.

Reviewed on Sep. 1, 2025

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St

2 out of 5
Back Bay
Price was CA $1,014, price is now CA $672 per person
CA $672
per person
Oct 29 - Nov 1
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
8.2/10 Very Good! (139 reviews)
Clean. Great location.

Reviewed on Jul. 31, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,804, price is now CA $1,204 per person
CA $1,204
per person
Oct 29 - Nov 1
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
9.6/10 Exceptional! (1,007 reviews)
First rate hotel. Definitely a Luxury hotel stay!

Reviewed on Sep. 1, 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 showing a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(193 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 CA $322 per night from Sep 4 to Sep 5
CA $322
CA $382 total
Sep 4 - Sep 5
includes taxes & fees
Seaport Hotel Boston
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 CA $379 per night from Sep 21 to Sep 22
CA $379
CA $498 total
Sep 21 - Sep 22
includes taxes & fees
Omni Boston Hotel at the Seaport
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $288 per night from Sep 21 to Sep 22
CA $288
CA $335 total
Sep 21 - Sep 22
includes taxes & fees
citizenM Boston North Station
See all 3,436 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family 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 CA $577. 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 featuring a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(305 reviews)

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

Fenway Park
Harvard University which includes a city and heritage architecture

Harvard University

4.5/5(279 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 Common which includes flowers, a garden and landscape views

Boston Common

4.5/5(518 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

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $109
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $75
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

CA $47
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.