East Bayside Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Ana Lei
  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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 East Bayside

Price found within the past 48 hours. Click for updated prices.
The Kennebunk Inn

The Kennebunk Inn

CA $1,031
per person
Oct 9 - Oct 14
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8/10 Very good! (788 reviews)
Very friendly and helpful staff in a very nice location.

Reviewed on Aug 31, 2026

Nautical Mile

Nautical Mile

CA $1,283
per person
Oct 14 - Oct 21
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.6/10 Excellent! (24 reviews)
Bel endroit où séjourner! Tout près de Well’s Beach.

Reviewed on Jul 27, 2026

The Meadowmere Resort

The Meadowmere Resort

CA $1,575
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Portland (PWM)
8.6/10 Excellent! (1,010 reviews)
Clean room

Reviewed on Sep 1, 2026

The Lodge at Turbat's Creek

The Lodge at Turbat's Creek

CA $1,047
per person
Oct 9 - Oct 14
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (894 reviews)
Kings Port Inn

Kings Port Inn

CA $1,301
per person
Oct 9 - Oct 14
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,021 reviews)
We had a very nice stay at the King’s Port Inn. The location was perfect. The room was very clean. However, it was nothing that really wowed us. The bathroom was small and there wasn’t anywhere to hang things. We asked for 2 queen beds and got a pull out sofa instead. We constantly heard the people above us. The staff were super friendly and helpful. More outdoor seating areas would be nice. Maybe bikes…….We maybe would stay here again but honestly would look into other places.

Reviewed on Aug 31, 2026

Where to stay in East Bayside

Find the best East Bayside areas and neighborhoods for the activities you enjoy most. Learn more about East Bayside
A tree-lined pathway leading to a brick building with a sign reading "Mercy Hospital Service Entrance".

Downtown Portland

4 out of top 10 points of interest in this area

Downtown Portland is known for its captivating waterfront views, and with sights like Cross Insurance Arena and Merrill Auditorium, you won't get bored spending a day wandering around this part of Portland.

A marina with boats docked, a wooden pier, and a red brick building with balconies.

Old Port

Cobblestone streets, 19th-century brick buildings, and fishing piers define this district, offering boutiques, restaurants, and bars. Explore Post Office Park, Tommy's Park with its large mural, and stroll the Eastern Promenade Trail to East End Beach.

A lighthouse on a rocky shore with a sailboat in the distance.

West End

Distinguished by its well-preserved Victorian architecture, this downtown Portland neighborhood boasts the scenic Western Promenade park, offering views of the White Mountains, and several historic structures, such as the Gothic House and Morrill Mansion.

A large, cream-colored building with white columns and a white picket fence in front.

Portland Arts District

The ample dining options and captivating waterfront views are top of the list for many visitors to Portland Arts District. A stop by Cross Insurance Arena or Portland Museum of Art might round out your trip.

An aerial view of a coastal city with a harbor, marina, and residential area.

Parkside

While visiting Parkside, you might make a stop by sights like Fitzpatrick Stadium and Neal S. Dow House.

East Bayside Hotel Deals

Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

738 Main Street South Portland ME
Fully refundable
CA $105
CA $114 total
Sep 10 - Sep 11
includes taxes & fees
6.4/10 (1,106 reviews)
"Great location, but the property is old and run down. The gentleman working night shift was kind and helpful / the woman. Working yesterday morning was the opposite. Just know it is an okay price when in a pinch and simply needing to sleep. For. Expect anything more than that."

Reviewed on Sep 2, 2026

Quality Inn & Suites South Portland
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

80 John Roberts Rd. South Portland ME
Fully refundable
CA $161
CA $175 total
Sep 10 - Sep 11
includes taxes & fees
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
Clarion Pointe South Portland

Clarion Pointe South Portland

675 Main Street I-95 South Portland ME
Fully refundable
CA $94
CA $103 total
Oct 1 - Oct 2
includes taxes & fees
Clarion Pointe South Portland
See all 2,483 properties in East 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.

Frequently asked questions

How much does an East Bayside vacation package cost?
Say yes to new adventures with our East Bayside vacation packages, which start from only CA $1,031. Handpick the flights and hotels that suit your style. Then, add on a few sightseeing tours for a memorable getaway.
How do I get a cheap travel package to East Bayside?
Combine your bookings with Expedia to save big bucks on your next exciting adventure. With more than 550 air carriers and 1,000,000 hotels across the world, your East Bayside vacation package can be customized exactly to suit your travel style. With all those extra dollars, why not include a few interesting tours and activities? It's an easy way to unlock even more savings. Your dream getaway to East Bayside is much closer than you thought!
Where should I stay in East Bayside?
A journey to East Bayside isn't over until you've seen University of Southern Maine and Portland Museum of Art. Stay at a hotel nearby for quick access to these famous attractions.
What are the top hotels in East Bayside?
If it's your first visit to East Bayside, lock in a room at Portland Peninsula - Spacious Walkable East End Spot or Spacious And Contemporary Condo In The Heart Of Portland. Both hotels offer friendly service and are favorites among many travelers.
How far in advance should I book my East Bayside vacation?
It all depends on the airline, but you can usually compare international airfares on Expedia up to a year in advance. While it's generally a good idea to book ahead of time, lucky customers will sometimes nab a cheaper flight just weeks prior to the date of departure.
What does an Expedia East Bayside travel package include?
It comes down to what you want. If you're traveling solo, you might decide to combine flights and hotels. Bringing the whole crew to East Bayside? A travel package including rental cars, flights and hotels might be a better fit. Expedia gives you the flexibility and freedom to build your own travel package.
What should I know before booking an East Bayside travel package?
Tailor deals to suit your budget with an Expedia package. Flights, hotels, rental cars — we have everything you need to plan your escape. You'll save loads just by combining your bookings. Whether you're embarking on an adventure in the snow or sipping cocktails on a beach, your dream vacation is just a few clicks away.
Can I choose my airline with an East Bayside Expedia vacation package?
Yes, the choice is all yours. We have access to over 550 partner airlines worldwide, so you can design your East Bayside adventure according to your needs and budget.
If I'm not able to travel, can I cancel my East Bayside vacation package?
Don't worry if you're rethinking your East Bayside vacation package — you can cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your airline, hotel or car rental company. We realize your circumstances can change suddenly, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we'll be here to help.

Stay near popular East Bayside attractions

Maine Jewish Museum

Located in the immigrant-era Etz Chaim Synagogue, this museum tells the stories of Maine’s Jewish families and showcases Jewish artists from the area.
See properties

Cathedral of the Immaculate Conception

Find out about the history of Portland with a stop at Cathedral of the Immaculate Conception. Stroll along the area's waterfront or experience its entertainment choices.
See properties

Things to do

Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

CA $107
per adult
90% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Morning Lighthouse Cruise Along the Coast of Portland Maine

Morning Lighthouse Cruise Along the Coast of Portland Maine

CA $83
per adult
Morning Lighthouse Cruise Along the Coast of Portland Maine
See all activities in Portland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.