Parkside 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 Parkside

Price found within the past 48 hours. Click for updated prices.
Chebeague Island Inn

Chebeague Island Inn

4 out of 5
Price was CA $1,102, price is now CA $973 per person
CA $973
per person
Jun 20 - Jun 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (77 reviews)
Charming and easy access to the Golf Course

Reviewed on Sep 21, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $1,752, price is now CA $1,505 per person
CA $1,505
per person
Jul 20 - Jul 23
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.4/10 Exceptional! (1,753 reviews)
Great hotel with great staff!

Reviewed on May 12, 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was CA $2,989, price is now CA $2,660 per person
CA $2,660
per person
Jun 17 - Jun 21
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

InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Price was CA $1,210, price is now CA $1,089 per person
CA $1,089
per person
Jun 20 - Jun 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (385 reviews)
We loved our stay! Everyone was efficient and helpful, very friendly. The room was beautiful and huge, we loved the jacuzzi tub since it was a cold, rainy weekend. Absolutely fantastic!

Reviewed on May 9, 2026

Longfellow Hotel

Longfellow Hotel

4 out of 5
Parkside
Price was CA $2,756, price is now CA $2,486 per person
CA $2,486
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (158 reviews)
Lovely property. Upscale without being stuffy. Great food and drinks and lovely ambiance at the bar. Beautiful room if a little small. Great amenities and amazing location. Totally recommend

Reviewed on May 12, 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
The price is CA $257 per night from May 17 to May 18
CA $257
CA $338 total
May 17 - May 18
includes taxes & fees
9.6/10 Exceptional! (161 reviews)
Lovely property. Upscale without being stuffy. Great food and drinks and lovely ambiance at the bar. Beautiful room if a little small. Great amenities and amazing location. Totally recommend

Reviewed on May 12, 2026

Longfellow Hotel
The Francis

The Francis

3.5 out of 5
747 Congress Street Portland ME
The price is CA $256 per night from May 14 to May 15
CA $256
CA $320 total
May 14 - May 15
includes taxes & fees
9.4/10 Exceptional! (388 reviews)
Great location, comfortable bed, charming property, friendly and helpful staff.

Reviewed on May 1, 2026

The Francis
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
The price is CA $254 per night from May 26 to May 27
CA $254
CA $333 total
May 26 - May 27
includes taxes & fees
9.4/10 Exceptional! (1,767 reviews)
Great hotel with great staff!

Reviewed on May 12, 2026

Portland Harbor Hotel
See all 2,407 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 $973, 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.

Discover the most popular places to visit in Parkside

State Theatre

State Theatre

4.5/5(5 reviews)

The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.

State Theatre
Portland Museum of Art

Portland Museum of Art

5/5(5 reviews)

Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.

Portland Museum of Art
East End Beach

East End Beach

Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.

East End Beach

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
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.