Bayside Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, 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.
The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

3 out of 5
Price was CA $913, price is now CA $647 per person
CA $647
per person
May 15 - May 18
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (254 reviews)
From the moment we arrived, we was welcomed with warm hospitality and genuine friendliness The room was spotless, comfortable, and beautifully maintained, and I especially appreciated the attention to detail throughout the property. The indoor pool a plus in these cold months - The location was perfect as well—close to everything I wanted to explore, yet peaceful and relaxing. Your staff went above and beyond to ensure a pleasant experience, and it did not go unnoticed. It’s clear that you take great pride in providing exceptional service, and it made my trip all the more memorable. Thank you for such a wonderful stay. I will absolutely be recommending your hotel to friends and family, and I look forward to returning in the future.

Reviewed on Mar 29, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $2,150, price is now CA $1,349 per person
CA $1,349
per person
Jun 22 - Jun 24
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
8.8/10 Excellent! (1,426 reviews)
Location, location, location! Breakfast is top notch. The entire staff was helpful and friendly.

Reviewed on Apr 3, 2026

The Westin Waltham-Boston

The Westin Waltham-Boston

4 out of 5
Price was CA $1,901, price is now CA $1,288 per person
CA $1,288
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.8/10 Excellent! (1,095 reviews)
No eating at the hotel

Reviewed on Apr 3, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $2,129, price is now CA $1,513 per person
CA $1,513
per person
May 19 - May 23
found 8 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (252 reviews)
Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was CA $2,240, price is now CA $1,596 per person
CA $1,596
per person
May 19 - May 23
found 8 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (1,196 reviews)
Absolutely amazing. Thank you so much

Reviewed on Apr 2, 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

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

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
The price is CA $255 per night from Apr 10 to Apr 11
CA $255
CA $354 total
Apr 10 - Apr 11
includes taxes & fees
9.2/10 Wonderful! (4,552 reviews)
Very nice outdoor pool. Plenty of towels. Had some pillows brought to My room apon request.

Reviewed on Apr 4, 2026

Omni Boston Hotel at the Seaport
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
The price is CA $211 per night from Apr 9 to Apr 10
CA $211
CA $293 total
Apr 9 - Apr 10
includes taxes & fees
9.6/10 Exceptional! (4,130 reviews)
Easy parking and nice room and staff

Reviewed on Apr 4, 2026

Seaport Hotel Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $255 per night from Apr 9 to Apr 10
CA $255
CA $354 total
Apr 9 - Apr 10
includes taxes & fees
8.4/10 Very Good! (3,130 reviews)
Great hotel, very clean and large! Windows were a bit difficult to open but overall I will stay here again. Easy to tourist attractions and trains

Reviewed on Apr 4, 2026

Hilton Boston Park Plaza
See all 4,009 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Bayside vacation package cost?
Custom build your Bayside vacation package from as low as CA $647. 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.

Discover the most popular places to visit in Bayside

Fenway Park

Fenway Park

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University

Harvard University

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common

Boston Common

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

CA $72
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 $115
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 $47
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.