Parkside Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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 Parkside

Price found within the past 48 hours. Click for updated prices.
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
Price was CA $1,647, price is now CA $1,358 per person
CA $1,358
per person
Aug 3 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
8.8/10 Excellent! (196 reviews)
it was very unique having to take a ferry over, shuttle by golf cart and bikes. late in season only 1 restaurant available. looking for peace and quiet- this it the place. lots to walk around and look at with the old fort there.

Reviewed on Sep 25, 2025

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was CA $2,812, price is now CA $2,111 per person
CA $2,111
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Price was good for the amenities offered and location. Our room was just recently renovated.

Reviewed on Jun 22, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was CA $2,382, price is now CA $1,814 per person
CA $1,814
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9/10 Wonderful! (1,011 reviews)
The staff was excellent and the room immaculate. Our room had no balcony, which was disappointing. It would have been nice to have a small table and chairs in the room.

Reviewed on Jun 27, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $2,557, price is now CA $2,029 per person
CA $2,029
per person
Aug 24 - Aug 28
found 10 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Portland (PWM)
9.6/10 Exceptional! (185 reviews)
We were only there for 1 night, but the innkeeper made a great suggestion for dinner. Overall a great place and would stay again.

Reviewed on Jun 26, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $2,123, price is now CA $1,706 per person
CA $1,706
per person
Aug 24 - Aug 28
found 10 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Portland (PWM)
9.4/10 Exceptional! (1,786 reviews)
I was told I would get a text when my room was ready, I never did and while sitting in lobby hours later watched multiple guests get their rooms. I was told as an Expedia VIP, there would be a bottle of wine waiting for me in my room. There was none. The bed made a loud creaking noise every time I moved. Outlets next to the bed were very loose. While the location was great; not worth the money

Reviewed on Jun 26, 2026

Where to stay in Parkside

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

Parkside Hotel Deals

Longfellow Hotel

Longfellow Hotel

4 out of 5
754 Congress St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $436 per night from Jul 5 to Jul 6
CA $436
CA $537 total
Jul 5 - Jul 6
includes taxes & fees
9.6/10 Exceptional! (172 reviews)
"The staff was excellent. The rooms were a little tight. The area around the hotel seemed a little sketchy but it was safe."

Reviewed on Jun 22, 2026

Longfellow Hotel
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $226 per night from Jun 30 to Jul 1
CA $226
CA $250 total
Jun 30 - Jul 1
includes taxes & fees
8.6/10 Excellent! (2,194 reviews)
"The staff were very nice. I did find it odd that they charged a parking fee, given their location."

Reviewed on Jun 26, 2026

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
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 $395 per night from Jul 5 to Jul 6
CA $395
CA $491 total
Jul 5 - Jul 6
includes taxes & fees
9.4/10 Exceptional! (1,773 reviews)
"Iron broken. Construction outside."

Reviewed on Jun 26, 2026

Portland Harbor Hotel
See all 2,490 properties in Parkside
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 Parkside vacation package cost?
From as little as CA $1,358, you can customize your Parkside vacation package. Simply bundle flights, hotels and car rentals and we'll reward you with discounts.
How do I get a cheap travel package to Parkside?
Bundle, bundle, bundle. Flights, hotels and rental cars — combine whatever you need into a Parkside vacation package to save loads of cash. Score even more discounts when you include extras such as experiences or tours to your booking. But that's not the only good part. You have the freedom to customize your vacation your own way. We offer more than 550 air carriers and 1,000,000 hotels around the world, so that everyone has an opportunity to travel and fulfill those vacation dreams.
Where should I stay in Parkside?
Most people who visit Parkside put both University of Southern Maine and Portland Museum of Art on their bucket lists. Why not select a hotel right near these top attractions?
What are the top hotels in Parkside?
Book a room at Beautiful 1st Floor Apartment And Amazing Shower. It's one of the area's most sought-after properties. Another highly rated option in Parkside is 1st Floor Private Entrance Condo. Walk To Restaurants And Parks.
How far in advance should I book my Parkside vacation?
It can be hard to know when is the perfect time to book your Parkside trip. But usually the earlier you book, the lower the prices. Sometimes, you can book your flights and hotels nearly 12 months prior to departure. If you're considering a last-minute getaway, no need to panic! There are terrific bargains featured on Expedia every single day.
What does an Expedia Parkside travel package include?
It comes down to what you're looking for. If you're traveling by yourself, you might decide to combine hotels and flights. Taking the entire family to Parkside? A travel package including hotels, rental cars and flights might suit you better. Expedia gives you the flexibility and freedom to customize your travel package.
What should I know before booking a Parkside travel package?
Whether it's relaxation or adventure you're seeking, a Parkside vacation package lets you plan your escape your way. Plus, you'll get access to great discounts just for combining your hotel with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Parkside Expedia vacation package?
With a vacation package, you're in charge. Whether you're eager to fly to Parkside in coach or business class, simply choose from the available airline options. Expedia has access to more than 550 airline partners globally.
If I'm not able to travel, can I cancel my Parkside vacation package?
Certainly, and we'll help you every step of the way. You may be able to amend or cancel your Parkside vacation package at no cost if you booked in the last 24 hours. However, you may incur a fee from your hotel, airline or car rental company for older bookings. If your travel plans unexpectedly change, browse our Customer Service Portal for more information.

Stay near popular Parkside attractions

Fitzpatrick Stadium

Catch an event at Fitzpatrick Stadium during your trip to Portland. Amble around the area's waterfront or attend a sporting event.
See properties

Things to do

Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

CA $24
per traveller
100% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
Maine Whale Watching Tour in Portland

Maine Whale Watching Tour in Portland

CA $179
per adult
Maine Whale Watching Tour in Portland
Portland Tall Ship Cruise on Casco Bay

Portland Tall Ship Cruise on Casco Bay

CA $138
per adult
88% of travellers recommend
Portland Tall Ship Cruise on Casco Bay
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.