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 Docent's Collection at 121 Middle Street
Downtown Portland
CA $1,619
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
9.6/10 Exceptional! (400 reviews)
We loved staying at the Docent's Collection at 121 Middle Street. Great staff, great location and great studio. Bed was excellent and the bathroom was large with very nice shower. Loved staying there.
Reviewed on Oct 24, 2026
Inn By The Sea
CA $2,402
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
9.6/10 Exceptional! (342 reviews)
Great pet friendly resort that allowed the dog to remain in the room while dining in the restaurant. Pet was allowed in the lounge area where they offered the same dining room menu, if you wanted to bring you pet along
. Pet treats and food and water dishes already in place in the room.
Reviewed on Oct 22, 2026
Portland Regency Hotel & Spa
Downtown Portland
CA $1,839
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
9.4/10 Exceptional! (1,759 reviews)
The staff are helpful, friendly and approachable. the hotel location is extremely convenient to old port, as well as East and west neighborhoods.
Reviewed on Oct 25, 2026
Pond And Pine
CA $2,571
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
10/10 Exceptional! (5 reviews)
This glamping cabin was everything we hoped for and more! Cozy, romantic, and clean. The outdoor kitchen had all the essentials, the private hot tub was amazing, and watching the sunrise and sunset from the deck felt magical. We roasted marshmallows by the fire pit overlooking the water and felt totally tucked away from the world yet the grocery store and casino were just minutes away. The perfect mix of peace, fun, and luxury. Can’t wait to come back!
Reviewed on Oct 27, 2025
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
5 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.
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.
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.
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.
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
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
CA $151
CA $167 total
Nov 18 - Nov 19
includes taxes & fees
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
CA $117
CA $129 total
Nov 1 - Nov 2
includes taxes & fees
8.2/10 Very good! (1,814 reviews)
"Everything!"
Reviewed on Oct 25, 2026
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
CA $101
CA $110 total
Nov 11 - Nov 12
includes taxes & fees
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 $1,619. 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
Harbor Lights and Sights Cruise
CA $86
per adult
90% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
CA $109
per adult
92% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
CA $83
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.