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.
Boston Lodge and Suites
Dorchester
CA $811
per person
Oct 21 - Oct 23
found 1 day 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
Fairmont Copley Plaza, Boston
Back Bay
CA $1,579
per person
Sep 30 - Oct 3
found 16 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9/10 Wonderful! (1,316 reviews)
Beautiful hotel excellent location very helpful staff Highly recommend for your next trip to Boston
Reviewed on Aug 27, 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
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
CA $263
CA $354 total
Sep 7 - Sep 8
includes taxes & fees
9.6/10 Exceptional! (4,873 reviews)
"Great location. Safe and clean. Perfect view of the harbor. Only complaint is they need to lose the automated phone call line when trying to reach the bellman or front desk. Called for bags using their robot and it never connected to a live human. Human touch is key in customer service. So lose the ..."
Reviewed on Aug 27, 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
CA $179
CA $208 total
Aug 30 - Aug 31
includes taxes & fees
9/10 Wonderful! (2,872 reviews)
"Polite staff, but unhelpful, when I booked, I am pretty sure I did so with an ensuite, when I checked in I was told the bathroom was down the hall (not what I booked), for the price bracket and star rating, this was a big no no. I was told I couldn't cancel, the staff polite but unhelpful. I lost ..."
Reviewed on Aug 28, 2026
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
CA $304
CA $410 total
Aug 30 - Aug 31
includes taxes & fees
9.2/10 Wonderful! (4,808 reviews)
"Great hotel!"
Reviewed on Aug 27, 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 $811. 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 $68
per adult
90% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
CA $64
per adult
80% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $116
per adult
92% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.