Plan, book, travel with confidence
Better together
Save up to CA $775 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
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.
Fairmont Copley Plaza, Boston
Back Bay
Save 100% on your flight
per person
Aug. 12 - Aug. 17
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.6/10 Excellent! (1,014 reviews)
The only negative i have, is the toilet bowl kept running all night and about 6 am it stopped.
Reviewed on Jun. 20, 2024
The Whitney Hotel
Beacon Hill
Save 100% on your flight
per person
Aug. 12 - Aug. 17
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (287 reviews)
This was one of the best hotel experiences I've had. The staff goes above and beyond to make you feel welcomed. From the Tates cookies and sparkling water available, to the water bottles at the end of the night, they really pay attention to small details, making it a great experience. The rooms were clean and roomy. We ended up walking the entire time in Boston since the hotel was at a great location, but if you plan on driving, keep in mind that you have to call ahead of time to access your car. Would definitely stay again!
Reviewed on May 28, 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
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.
South Side Hotel Deals
Omni Boston Hotel at the Seaport
450 Summer Street, Boston, MA
The price is CA $270 per night from Jul. 3 to Jul. 4
CA $270
CA $362 total
includes taxes & fees
Jul 3 - Jul 4
9/10 Wonderful! (2,220 reviews)
Great location
"Very comfortable, great location"
Reviewed on Jun. 19, 2024
Omni Parker House
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $248 per night from Jul. 1 to Jul. 2
CA $248
CA $337 total
includes taxes & fees
Jul 1 - Jul 2
8.8/10 Excellent! (2,692 reviews)
"Great location. I would stay there again and would highly recommend this property to family and friends"
Reviewed on Jun. 20, 2024
The Revolution Hotel
40 Berkeley Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from Jun. 30 to Jul. 1
CA $232
CA $270 total
includes taxes & fees
Jun 30 - Jul 1
8.6/10 Excellent! (1,564 reviews)
"This was such a classy hotel with a great balance of modern elegance and modesty, with a comfortable, convivial atmosphere! I will definitely be back!"
Reviewed on Jun. 20, 2024
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
Frequently asked questions
Discover the most popular places to visit in South Side
Fenway Park
4.5/5(305 reviews)
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
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.
Gillette Stadium
4.5/5(27 reviews)
Catch an event at Gillette Stadium during your trip to Foxboro. Experience the area's acclaimed theater scene and great live music.
Things to do
Boston CityPASS®: Admission to Top 4 Attractions
CA $100
Per adult
90% of travellers recommend
Bewitched Walking Tour of Salem
CA $41
Per adult
98% of travellers recommend
Odyssey Boston Premier Elegant Dinner Cruise
CA $186
Per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.