Bayside Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Holiday Package Deals in Bayside

Price found within the past 48 hours. Click for updated prices.
Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Price was CA $1,643, price is now CA $1,045 per person
CA $1,045
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
8/10 Very good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was CA $2,326, price is now CA $1,339 per person
CA $1,339
per person
Aug 10 - Aug 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (1,254 reviews)
5 stars FAB Every thing!

Reviewed on Jul 10, 2026

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Price was CA $4,250, price is now CA $2,533 per person
CA $2,533
per person
Aug 10 - Aug 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (432 reviews)
This goes into one of the top hotels I've ever stayed at. I seriously can't think of a single complaint. They gave us the best view of the Boston fireworks on the top floor, and took care of us every step of the way. They even had a big TV set up in the lobby for the World Cup games. The front desk people were super nice, and Ivan was our favorite server!

Reviewed on Jul 7, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,349, price is now CA $1,410 per person
CA $1,410
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
From the moment I checked in with Natalie, our 4 days were superb! Natalie was so friendly and explained the property and amenities (our first time there). Even though I researched the property, and am originally from close to Boston, it was the 4th of July weekend, and there was Sooo much going on. Head concierge Nathan provided lots of tips about the best places to see certain events. So helpful. Our room was beautiful and well appointed. I miss the days of the shower cap, sewing kit, slippers, robes, etc. and they provided all that. The bed was extremely comfortable and the housekeeping staff wonderful. We go to Boston a few times a year and will be looking forward to returning here. Fabulous location!

Reviewed on Jul 8, 2026

Nantucket Inn

Nantucket Inn

3.5 out of 5
Price was CA $4,273, price is now CA $2,651 per person
CA $2,651
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (722 reviews)
Everything was amazing, my room the A/C wasn’t cooling properly but they fixed it quick,

Reviewed on Jul 10, 2026

Where to stay in Bayside

Find the best Bayside areas and neighborhoods for the activities you enjoy most. Learn more about Bayside
A nighttime street scene with illuminated trees, a market stall, and historic buildings.

Downtown Boston

4.5/5(197 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.

Find hotels in Downtown Boston

Bayside Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $268 per night from Aug 9 to Aug 10
CA $268
CA $360 total
Aug 9 - Aug 10
includes taxes & fees
9.6/10 Exceptional! (4,552 reviews)
"The staff was really nice and helpful! They had umbrellas ready as soon as the rain started picking up."

Reviewed on Jul 10, 2026

Seaport Hotel Boston
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
The price is CA $185 per night from Aug 9 to Aug 10
CA $185
CA $257 total
Aug 9 - Aug 10
includes taxes & fees
9/10 Wonderful! (2,436 reviews)
"The property was located in a nice quiet area for a city hotel. The view was nice by the water and the balcony was comfortable for outdoors dining. The rooms was not as big as we expected, especially traveling with teens. The room was designed with a lot of wasted space. The room AC unit was not ..."

Reviewed on Jul 10, 2026

Hyatt Regency Boston/Cambridge
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $226 per night from Aug 2 to Aug 3
CA $226
CA $263 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (2,732 reviews)
"The room was very clean. We didn’t know about the shared bathrooms but I have to say the staff kept them very clean. They were there several times a day. They gave us robes, towels, soap…. in a bag. Very convenient. It was a little far though from the downtown area. We didn’t have Uber."

Reviewed on Jul 10, 2026

The Revolution Hotel
See all 4,056 properties in Bayside
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.
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All Inclusive Vacations
Beach Vacations
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Frequently asked questions

How much does a Bayside vacation package cost?
Custom build your Bayside vacation package from as low as CA $1,045. 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 Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

CA $73
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $119
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

CA $39
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Boston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.