South Side Vacation Packages

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Top Holiday Package Deals in South Side

Price found within the past 48 hours. Click for updated prices.
The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was CA $1,214, price is now CA $796 per person
CA $796
per person
May 25 - May 28
found 23 hours ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.2/10 Wonderful! (2,268 reviews)
Nothing to complain about!

Reviewed on Mar 1, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,283, price is now CA $1,325 per person
CA $1,325
per person
May 25 - May 28
found 23 hours ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Friendly staff, clean room

Reviewed on Feb 20, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,183, price is now CA $1,910 per person
CA $1,910
per person
May 7 - May 10
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $1,390, price is now CA $870 per person
CA $870
per person
May 25 - May 28
found 23 hours ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
8.6/10 Excellent! (1,337 reviews)
Lovely room. Friendly staff

Reviewed on Mar 2, 2026

The Cove At Yarmouth

The Cove At Yarmouth

3 out of 5
Price was CA $1,279, price is now CA $835 per person
CA $835
per person
May 14 - May 19
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (243 reviews)
Room was not easy to get to and it was 0 degrees out …1st they put me out in a building where the property was a sheet of ice so I asked to be moved to the main building since I was by myself. Fortunately, they moved me, but the room was confusing to get to. :-( The pool was closed for maintenance, and I was planning to swim. :-( The room was great, clean and a comfortable bed, so I would stay again, but I would request staying closer to the lobby next time.

Reviewed on Jan 31, 2026

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 $173 per night from Mar 8 to Mar 9
CA $173
CA $248 total
Mar 8 - Mar 9
includes taxes & fees
9.6/10 Exceptional! (4,024 reviews)
Staff were exceptionally helpful and pleasant. Loved our stay

Reviewed on Mar 2, 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 CA $203 per night from Mar 8 to Mar 9
CA $203
CA $292 total
Mar 8 - Mar 9
includes taxes & fees
9.2/10 Wonderful! (4,479 reviews)
Difficulty turning Shower handle & was unable to turn on hot water on & had to take an ice cold shower on my last nite. Room as configuration was small but clean. Not sure if my military and/or AARP discount was applied on this 3 nite stay at Omni hotel as rate was 233.80 per nite. Not great on a ...

Reviewed on Mar 2, 2026

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Mar 22 to Mar 23
CA $167
CA $250 total
Mar 22 - Mar 23
includes taxes & fees
8.4/10 Very Good! (3,113 reviews)
Yes the room was very clean. And very comfortable for a small room. The shower's tight. I think that is the only Town side to the wicked small room. I stay here a lot. The staff is always top notch. Love the little sitting room with the fire it's. Very uncomfortable. Always enjoy staying here.

Reviewed on Mar 2, 2026

Hilton Boston Park Plaza
See all 3,853 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.
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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 $796. 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

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

Fenway Park
Gillette Stadium is also home to the New England Revolution, our pro soccer team. Tickets are easy to get and not crazy expensive. And there is always a section reserved for the hooligans, who keep the energy up for the whole stadium!

Gillette Stadium

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

Gillette Stadium
Boston Common which includes flowers, a garden and landscape views

Boston Common

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 Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

CA $72
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $108
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

CA $47
per adult
88% 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.