Parkside Vacation Packages

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  • Better together

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

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Top Holiday Package Deals in Parkside

Price found within the past 48 hours. Click for updated prices.
Saco Bay Hotel

Saco Bay Hotel

2.5 out of 5
Price was CA $1,303, price is now CA $1,093 per person
CA $1,093
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
7.6/10 Good! (1,051 reviews)
We just had a night stay there during a journey but it was comfortable and what we needed

Reviewed on May 7, 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was CA $2,283, price is now CA $1,858 per person
CA $1,858
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Lovely suite! Comfy king bed, everything spotless, Great location. Would stay here again

Reviewed on Apr 23, 2026

1802 House Bed and Breakfast

1802 House Bed and Breakfast

3.5 out of 5
Price was CA $1,622, price is now CA $1,347 per person
CA $1,347
per person
Jun 18 - Jun 20
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.6/10 Exceptional! (104 reviews)
Great place to stay for a getaway. Breakfast is outstanding, hostess and her husband prepare fresh ingredients with three tasty courses. Rooms are well decorated, clean, bright and comfortable. We stayed there in 2001 and again in 2025. Our favorite in Kennebunk Port.

Reviewed on Oct 28, 2025

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was CA $1,336, price is now CA $1,134 per person
CA $1,134
per person
Jun 18 - Jun 20
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9/10 Wonderful! (1,000 reviews)
The front desk was incredibly nice. They moved us closer to our family in another room without being asked. It was very appreciated, thank you.

Reviewed on May 3, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $1,700, price is now CA $1,453 per person
CA $1,453
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,753 reviews)
Really enjoyed our stay. Staff was great as well!

Reviewed on May 8, 2026

Where to stay in Parkside

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

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 $257 per night from May 17 to May 18
CA $257
CA $337 total
May 17 - May 18
includes taxes & fees
9.6/10 Exceptional! (158 reviews)
Clean, beautiful room with a vintage feel. Great staff, very attentive. If you have a show to go to they offer a car service to take you there. It’s a 5 minute walk to the theater though so that was nice. Tandem bakery is right next door. You have to get coffee and pastries. Make sure to get a loaded ...

Reviewed on Apr 14, 2026

Longfellow Hotel
The Francis

The Francis

3.5 out of 5
747 Congress Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $280 per night from May 12 to May 13
CA $280
CA $346 total
May 12 - May 13
includes taxes & fees
9.4/10 Exceptional! (387 reviews)
Great location, comfortable bed, charming property, friendly and helpful staff.

Reviewed on May 1, 2026

The Francis
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 $134 per night from May 10 to May 11
CA $134
CA $148 total
May 10 - May 11
includes taxes & fees
8.6/10 Excellent! (2,232 reviews)
It said free self parking but when I got there I was charged for parking

Reviewed on May 9, 2026

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
See all 2,397 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.
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Frequently asked questions

How much does a Parkside vacation package cost?
From as little as CA $1,093, 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.

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 $14
per traveller
Downtown Portland: Coastal Vibe and Old Mansions with In-Add 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
Self-Guided Driving & Walking Bundle of Portland Maine Tours

Portland Maine App-Based Driving & Walking Audio Tour Bundle

CA $31
per traveller
Portland Maine App-Based Driving & Walking Audio Tour Bundle
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.