Bayside 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 Bayside
Price found within the past 48 hours. Click for updated prices.
Battery Wharf Hotel, Boston Waterfront
North End
CA $1,356
per person
Nov 28 - Dec 2
found 13 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9/10 Wonderful! (2,041 reviews)
Staff was friendly. Had to ask for a microwave but it was brought quickly. Bathroom sliding door wasn’t on the track and didn’t really close, shower tile wasn’t the cleanest… a few times staff just came into our room without announcing themselves. Breakfast buffet was decent but not worth $38 dollars for adults. Hotel food was way overpriced… overall I feel the hotel itself was overpriced for what it is.
Reviewed on Oct 12, 2026
Boston Harbor Hotel
North End
CA $2,056
per person
Nov 28 - Dec 2
found 13 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
Great hotel. Loved the health club and pool. Great location. Easy walk to the North End. Comfortable bed. Great service and hospitality.
Reviewed on Oct 13, 2026
Four Seasons Hotel Boston
Bay Village
CA $1,950
per person
Dec 19 - Dec 22
found 18 hours 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
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
Fully refundableReserve now, pay when you stay
CA $376
CA $496 total
Nov 11 - Nov 12
includes taxes & fees
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
CA $184
CA $214 total
Nov 8 - Nov 9
includes taxes & fees
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
CA $270
CA $363 total
Nov 1 - Nov 2
includes taxes & fees
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 $1,356. 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.