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 $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 East Bayside

Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $1,851, price is now CA $1,322 per person
CA $1,322
per person
May 31 - Jun 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.2/10 Wonderful! (1,776 reviews)
Very nice room, hotel was clean, staff kind and attentive. The location of thos hotel is great.

Reviewed on Mar 24, 2026

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Price was CA $4,313, price is now CA $2,919 per person
CA $2,919
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
9.4/10 Exceptional! (1,007 reviews)
Gorgeous room in a gorgeous setting. Norman the lead bartender is a treasure. Hector was great as well. Everything was outstanding.

Reviewed on Mar 25, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $3,261, price is now CA $2,455 per person
CA $2,455
per person
May 31 - Jun 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (175 reviews)
The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend!

Reviewed on Mar 10, 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was CA $1,941, price is now CA $1,519 per person
CA $1,519
per person
May 31 - Jun 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (275 reviews)
Property is in an excellent location with so much to see and do (and eat) in walking distance. My room was clean, quiet, and well maintained. Staff interaction was minimal (by design) but the few times I spoke with the concierge on site she was pleasant and accommodating. My only negative comment is regarding the toiletry products. I’m a toilet paper snob and that angel soft just doesn’t cut it. Overall I am beyond satisfied with my stay and would absolutely stay here again.

Reviewed on Mar 22, 2026

Inn By The Sea

Inn By The Sea

4 out of 5
Price was CA $3,117, price is now CA $2,440 per person
CA $2,440
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
9.4/10 Exceptional! (304 reviews)
Such a beautiful place, great to walk on beach, nice view, staff great.. cozy place.. so well decorated.. highly recommend for a nice quiet get away

Reviewed on Mar 4, 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
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 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 $179 per night from Apr 12 to Apr 13
CA $179
CA $198 total
Apr 12 - Apr 13
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
I frequently stay at this property. It is a very clean property with kind and helpful staff and an excellent restaurant and spa. I was locked out of the next door parking garage and Dan (door man?) helped me get my car out. He ran out there in the freezing cold, called the garage mgmt and got me ...

Reviewed on Mar 26, 2026

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 $119 per night from Apr 13 to Apr 14
CA $119
CA $132 total
Apr 13 - Apr 14
includes taxes & fees
8/10 Very Good! (1,402 reviews)
Great rooms and nice staff

Reviewed on Mar 26, 2026

Clarion Hotel Portland Airport ME
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Apr 5 to Apr 6
CA $157
CA $227 total
Apr 5 - Apr 6
includes taxes & fees
9.2/10 Wonderful! (1,774 reviews)
Very nice room, hotel was clean, staff kind and attentive. The location of thos hotel is great.

Reviewed on Mar 24, 2026

Portland Harbor Hotel
See all 2,372 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 $1,322. 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.

Discover the most popular places to visit in East Bayside

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 great live music.

Cathedral of the Immaculate Conception

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.