West Bayside Vacation Packages

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Top Holiday Package Deals in West 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 9 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 5 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 9 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 9 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 West Bayside

Find the best West Bayside areas and neighborhoods for the activities you enjoy most. Learn more about West 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.

A red brick building with Gothic architectural features, including pointed arches and a cross on top.

East Bayside

Bordered by Franklin Street and Washington Avenue, East Bayside offers a community arts venue, Mayo Street Arts, and the relaxing green space of Kennedy Park. Explore nearby Old Port and Munjoy Hill.

West 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 2,473 properties in West 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 a West Bayside vacation package cost?
Live it up in West Bayside from as little as CA $1,031. We offer a wonderful selection of flights, rental cars and hotels to suit your budget. Land even better deals when you add some experiences or tours to your vacation package.
How do I get a cheap travel package to West Bayside?
Booking a West Bayside vacation package with Expedia is a simple way to save. We have over 550 partner airlines and 1,000,000 hotels worldwide. With such a huge range to choose from, you'll have no hassles creating your dream vacation.
Where should I stay in West Bayside?
Make sightseeing easier by staying in a hotel close to West Bayside's fantastic attractions. University of Southern Maine and Portland Museum of Art are two visitor favorites.
How far in advance should I book my West Bayside vacation?
It can be hard to know when the best time is to book your West Bayside trip. But generally the earlier you book, the lower the prices. Sometimes, you can reserve your flights and hotels nearly a year prior to departure. If you're eager to escape on a last-minute getaway, no need to panic! There are terrific deals posted on Expedia every day.
What does an Expedia West Bayside travel package include?
You can select from any combination of flights, hotels and rental cars. Once you've made your booking, you can add the fun stuff like activities and tours. Want to pick your airfare class? That's also possible. The choice is all yours when it comes to planning your perfect West Bayside trip.
What should I know before booking a West Bayside travel package?
So many places to wander around, so many things to experience. With a package, you'll be able to check more of them off your list. Combine your flights, hotels and rental cars and land big savings.
Can I choose my airline with a West Bayside Expedia vacation package?
Yes, and with over 550 airlines to choose from throughout the world, it's all about choice. Browse the available options and see which airline best suits your budget and needs.
If I'm not able to travel, can I cancel my West Bayside vacation package?
You sure can, and we'll help you every step of the way. You may be able to cancel and rebook your West Bayside vacation package at no cost within 24 hours of booking. However, you may be charged a fee by your hotel, airline or car rental company for older bookings. If your travel plans unexpectedly change, visit our Customer Service Portal for further information.

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.