West 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 West Bayside

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

USA Inn

2.5 out of 5
Price was CA $1,318, price is now CA $1,043 per person
CA $1,043
per person
Jun 28 - Jul 4
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8/10 Very Good! (767 reviews)
Parking was convenient. Staff was goo

Reviewed on Nov 1, 2025

River View Resort

River View Resort

2.5 out of 5
Price was CA $1,655, price is now CA $1,119 per person
CA $1,119
per person
Jun 28 - Jul 4
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9/10 Wonderful! (323 reviews)
Clean room. Space for everyone, pool was nice, staff was friendly. Perfect for our last minute ski trip.

Reviewed on Apr 12, 2026

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was CA $2,888, price is now CA $2,140 per person
CA $2,140
per person
Jun 28 - Jul 4
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (692 reviews)
Historic, cozy, and charming mansions and rooms...our stay was amazing.

Reviewed on Mar 15, 2026

The Kennebunk Inn

The Kennebunk Inn

2.5 out of 5
Price was CA $1,532, price is now CA $1,219 per person
CA $1,219
per person
Jun 28 - Jul 4
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
7.8/10 Good! (753 reviews)
I would visit again

Reviewed on Dec 4, 2025

Port Inn & Suites Kennebunk, an Ascend Collection Hotel

Port Inn & Suites Kennebunk, an Ascend Collection Hotel

2.5 out of 5
Price was CA $1,662, price is now CA $1,332 per person
CA $1,332
per person
Jun 28 - Jul 4
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (1,003 reviews)
Was a bad continental breakfast as cheap as you can get, bedding was thin and bed not that comfortable. Shower was meh. Staff was very nice and still a cute cozy place to stay. Very simple

Reviewed on Apr 17, 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
Downtown Portland

Downtown Portland

5 out of top 10 points of interest in this area
4.5/5(11 area reviews)

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

Find hotels in Downtown Portland

West Bayside Hotel Deals

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Apr 29 to Apr 30
CA $167
CA $184 total
Apr 29 - Apr 30
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Desk staff was very friendly and helpful, and we were pleasantly surprised to get a corner room with stunning views. Will definitely be back!

Reviewed on Apr 21, 2026

The Westin Portland Harborview
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
The price is CA $166 per night from Apr 26 to Apr 27
CA $166
CA $236 total
Apr 26 - Apr 27
includes taxes & fees
9.2/10 Wonderful! (1,760 reviews)
Close to Becky’s Diner !

Reviewed on Apr 19, 2026

Portland Harbor Hotel
HomeAwhile

HomeAwhile

4 out of 5
205 Southborough Drive Scarborough ME
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Apr 28 to Apr 29
CA $162
CA $177 total
Apr 28 - Apr 29
includes taxes & fees
9.6/10 Exceptional! (24 reviews)
Super nice place!!

Reviewed on Apr 19, 2026

HomeAwhile
See all 2,377 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a West Bayside vacation package cost?
Live it up in West Bayside from as little as CA $1,043. 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.

Discover the most popular places to visit in West Bayside

State Theatre

State Theatre

4.5/5(5 reviews)

The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.

State Theatre
Portland Museum of Art

Portland Museum of Art

5/5(5 reviews)

Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.

Portland Museum of Art
East End Beach

East End Beach

Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.

East End Beach

Things to do

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

CA $13
per traveller
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

CA $23
per traveller
100% of travellers recommend
Ultimate Portland Self-Guided Driving GPS Audio Tour
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

CA $21
per traveller
Portland Smartphone Audio Tour: Self-Guided Drive
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.