East Bayside Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in East Bayside

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

Stage Neck Inn

4 out of 5
Price was CA $1,938, price is now CA $1,783 per person
CA $1,783
per person
Dec 2 - Dec 7
found 3 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
9.4/10 Exceptional! (551 reviews)
Great place to stay and relax!

Reviewed on Oct 17, 2026

Sauna Hot Tub Game Room Theater Firepit

Sauna Hot Tub Game Room Theater Firepit

2 out of 5
Price was CA $7,517, price is now CA $6,569 per person
CA $6,569
per person
Dec 20 - Dec 26
found 3 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
No reviews

River View Resort

River View Resort

2.5 out of 5
Price was CA $3,172, price is now CA $2,780 per person
CA $2,780
per person
Dec 20 - Dec 26
found 3 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
9/10 Wonderful! (337 reviews)

Close to Sunday River Hot Tub Sauna Cold Plunge

Close to Sunday River Hot Tub Sauna Cold Plunge

2 out of 5
Price was CA $7,306, price is now CA $6,403 per person
CA $6,403
per person
Dec 20 - Dec 26
found 3 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
No reviews

Admiral Peary Inn

Admiral Peary Inn

3 out of 5
Price was CA $2,430, price is now CA $2,242 per person
CA $2,242
per person
Dec 20 - Dec 26
found 3 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
8.8/10 Excellent! (65 reviews)
The host was quick in responding to texts - long day and I was confused iver simple things…. Breakfast is not to be missed - fruit cobbler bake was scrumptious!

Reviewed on Oct 25, 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

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.

Find hotels in Downtown Portland

East 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 $151 per night from Nov 18 to Nov 19
CA $151
CA $167 total
Nov 18 - Nov 19
includes taxes & fees
The Westin Portland Harborview
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundable
The price is CA $117 per night from Nov 2 to Nov 3
CA $117
CA $129 total
Nov 2 - Nov 3
includes taxes & fees
Clarion Hotel Portland Airport ME
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

2.5 out of 5
738 Main Street South Portland ME
Fully refundable
The price is CA $101 per night from Nov 11 to Nov 12
CA $101
CA $110 total
Nov 11 - Nov 12
includes taxes & fees
Quality Inn & Suites South Portland
See all 2,424 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $1,783. 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.
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Things to do

Harbor Lights and Sights Cruise

Harbor Lights and Sights Cruise

CA $86
per adult
90% of travellers recommend
Harbor Lights and Sights Cruise
Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

CA $109
per adult
92% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Portland: Casco Bay Morning Lighthouse Cruise

Portland: Casco Bay Morning Lighthouse Cruise

CA $83
per adult
80% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
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.