Union Square Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Union Square
Price found within the past 48 hours. Click for updated prices.
The Wylie Inn and Conference Center at Endicott College
Price was CA $904, price is now CA $617 per person
CA $617
per person
Aug 25 - Aug 28
found 16 hours ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
9.2/10 Wonderful! (1,170 reviews)
Great place to stay, very clean, and the staff was very friendly.
Reviewed on Jul 13, 2026
Boston Harbor Hotel
North End
Price was CA $2,988, price is now CA $1,829 per person
CA $1,829
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Love coming back to a refreshed clean room after a long hot day of sightseeing.
Reviewed on Jul 15, 2026
Boston Lodge and Suites
Dorchester
Price was CA $2,078, price is now CA $1,385 per person
CA $1,385
per person
Sep 10 - Sep 14
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
By the Sea Guests Bed & Breakfast & Suites
Price was CA $1,397, price is now CA $939 per person
CA $939
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (195 reviews)
The staff here was so kind and thoughtful. The breakfast was amazing all 3 days and the beach was very quiet and great waterfront. The section we stayed has not been updated like some of the other units but was fine and comfortable. The general location was good and easily walkable to food and drink places. Overall, we enjoyed it and would stay here again for sure.
Reviewed on Jul 12, 2026
Where to stay in Union Square
Find the best Union Square areas and neighborhoods for the activities you enjoy most. Learn more about Union Square
Downtown Boston
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.
Union Square Hotel Deals
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $266 per night from Jul 26 to Jul 27
CA $266
CA $357 total
Jul 26 - Jul 27
includes taxes & fees
9.6/10 Exceptional! (4,591 reviews)
"Loved the location and our top floor room with the view over the harbor! Great staff🙂 Really could have done without the smart ass who decided pulling the smoke alarm at 6am Sunday morning would be fun!😭 That is the only thing preventing a full 5 Star rating but not the hotels fault."
Reviewed on Jul 15, 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $247 per night from Aug 2 to Aug 3
CA $247
CA $287 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (2,733 reviews)
"The hotel was clean and the staff were super helpful. I was satisfied with the responsiveness. However, I didn’t like the room with the bathroom. It was very small but that was okay. The par I did not enjoy was the fact that the shower drain and the shower design was In away that a lot of water would ..."
Reviewed on Jul 15, 2026
Hyatt Regency Boston/Cambridge
575 Memorial Drive Cambridge MA
The price is CA $235 per night from Aug 2 to Aug 3
CA $235
CA $315 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (2,431 reviews)
"good view of the river and city"
Reviewed on Jul 15, 2026
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.
Stay near popular Union Square attractions
Things to do
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $73
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $119
per adult
92% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
CA $68
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.