Bayside Vacation Packages
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Top Holiday Package Deals in Bayside
Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
North End
CA $1,412
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
This hotel is one of, if not the, nicest hotels I have ever stayed at around the world. The level of service is second to none, and hotel itself, physically, is incredibly elegant. Being situated on Boston Harbor puts this hotel over the top and into a class of its own.
Reviewed on Oct 16, 2026
Four Seasons Hotel Boston
Bay Village
CA $1,802
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (487 reviews)
Your staff is Five star! Hotel needs updating badly. My far the worst Four Seasons we have stayed in.
On the day of check-in, our flight was delayed and we got in at 2:30 in the morning had room service and it was an edible. Your staff indicated they would remove the charges, but I see we were still charged for them as well.
Reviewed on Oct 6, 2026
Raffles Boston
Back Bay
CA $1,659
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (332 reviews)
A stunning hotel with super helpful staff. Would highly recommend the Raffles, from start to finish it was excellent and we’ll definitely be back.
Reviewed on Oct 14, 2026
Where to stay in Bayside
Find the best Bayside areas and neighborhoods for the activities you enjoy most. Learn more about Bayside
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.
Back Bay
1 out of top 10 points of interest in this area
Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower.
Seaport District
1 out of top 10 points of interest in this area
Experience a transformed industrial area with office towers, innovation labs, and 78 restaurants. Visit the Institute of Contemporary Art and easily access Downtown Boston via the Evelyn Moakley Bridge.
Beacon Hill
1 out of top 10 points of interest in this area
Historic Federal-style rowhouses, gaslit streets, and brick sidewalks create a charming atmosphere. Explore the Boston African American National Historic Site, shop on Charles Street, and easily access MBTA stations.
North End
Indulge in Italian cuisine at numerous restaurants and bakeries, explore historic sites like Old North Church and Paul Revere House, and enjoy performances at NEMPAC and Improv Asylum Theater. Easily accessible via MBTA lines, buses, and ferries.
Bayside Hotel Deals
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
CA $384
CA $504 total
Oct 30 - Oct 31
includes taxes & fees
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
CA $213
CA $248 total
Nov 12 - Nov 13
includes taxes & fees
9/10 Wonderful! (2,977 reviews)
"The bed was very comfortable. Staff responsive. The shared bathrooms were manageable. Just had to be organized."
Reviewed on Oct 17, 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
CA $241
CA $330 total
Nov 8 - Nov 9
includes taxes & fees
9.6/10 Exceptional! (5,114 reviews)
"The location of this hotel was ideal for our visit. We planned a 2-day pre-cruise stay on our own. It's easy to take an Uber, taxi or Silver Line bus to the Flynn cruise port from this hotel. The room was comfortable, nicely appointed and had great western views over a park. It was quiet. The food ..."
Reviewed on Oct 16, 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.
Frequently asked questions
How much does a Bayside vacation package cost?
Custom build your Bayside vacation package from as low as CA $923. Choose from any combination of flights, hotels and rental cars to craft the trip you've been dreaming about. Don't forget to add on some tours and experiences!
How do I get a cheap travel package to Bayside?
Bundle your hotels and flights with Expedia to save big bucks on your next exciting adventure. With more than 550 partner airlines and 1,000,000 hotels globally, your Bayside vacation package can be customized exactly to suit your budget. With all those extra dollars, why not add one or more exciting tours and activities? It's an easy way to unlock even more bargains. Your dream getaway to Bayside is closer than you thought!
Where should I stay in Bayside?
Stay where the action happens. Many travelers book hotels within easy reach of top sights, such as Nantasket Beach Reservation, Hull Lifesaving Museum and Fort Revere Park.
How far in advance should I book my Bayside vacation?
Reserving your flights early with Expedia means one less thing to have to worry about. Most carriers advertise prices up to 12 months prior to take off. Generally, this is the cheapest time to book. If circumstances have left you booking late, discount prices to Bayside occasionally appear just a few weeks before departure.
What does an Expedia Bayside travel package include?
Flights, hotels and a shiny set of wheels for all your fun road trip adventures. Simply mix and match your favorite bundle and get access to incredible deals. Once you've made your booking, add on a couple of sightseeing tours and watch your savings grow. When it comes to creating your Bayside escape, the choice is all yours!
What should I know before booking a Bayside travel package?
You'll pick up impressive savings when you combine your hotels, flights and rental cars into a travel package. Not only that, booking everything in one place will make your trip planning easier. So why waste money or time? Whether you're organizing a fancy romantic getaway or a budget family adventure, have a look at our vacation packages today.
Can I choose my airline with a Bayside Expedia vacation package?
Yes — that's one of the best things about an Expedia vacation package. You can pick and choose your flights, hotels and more. We have more than 550 partner airlines all over the world, so you have lots of choice when creating your Bayside trip.
If I'm not able to travel, can I cancel my Bayside vacation package?
It's impossible to predict what tomorrow might bring, so it's comforting to know that you can cancel or change your Bayside vacation package. If you booked in the last 24 hours, you may be entitled to a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal for further details.
Things to do
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $69
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $117
per adult
92% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
CA $65
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.