Parkside Vacation Packages

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  • Better together

    Save up to CA $1,096 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.
84 Main

84 Main

4 out of 5
Price was CA $1,318, price is now CA $1,144 per person
CA $1,144
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
10/10 Exceptional! (52 reviews)
Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities.

Reviewed on Dec 29, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $1,319, price is now CA $1,168 per person
CA $1,168
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Really nice room. Tub, separate shower, nice linens.

Reviewed on Feb 7, 2026

The McKernan Inn

The McKernan Inn

3 out of 5
Price was CA $1,342, price is now CA $1,193 per person
CA $1,193
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
9/10 Wonderful! (83 reviews)
Gorgeous grounds and venue with a beautiful oceanfront view. Plenty of parking as part of SMCC campus. Short drive to downtown Portland and lots of stores around in South Portland. Very unique experience, would stay again without hesitation!

Reviewed on Dec 27, 2025

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was CA $1,347, price is now CA $1,201 per person
CA $1,201
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
9.4/10 Exceptional! (1,512 reviews)
The front desk and valet are always amazing.

Reviewed on Feb 9, 2026

Inn By The Sea

Inn By The Sea

4 out of 5
Price was CA $1,714, price is now CA $1,558 per person
CA $1,558
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (288 reviews)
Room was ready early friendly staff and room is better than expected

Reviewed on Nov 16, 2025

Where to stay in Parkside

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

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 Wadsworth-Longfellow House, 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
9.4/10 Exceptional! (143 reviews)
We loved our stay. Great staff, room was nice, cafe very good and the Town Car service for rides, so convenient!

Reviewed on Jan 5, 2026

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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 $147 per night from Feb 19 to Feb 20
CA $147
CA $201 total
Feb 19 - Feb 20
includes taxes & fees
9.4/10 Exceptional! (374 reviews)
Clean and great location

Reviewed on Jan 11, 2026

The Francis
Knock on Wood | Airy Charm in Heart of Downtown

Knock on Wood | Airy Charm in Heart of Downtown

Portland ME
The price is CA $204 per night from Mar 4 to Mar 5
CA $204
CA $467 total
Mar 4 - Mar 5
includes taxes & fees
8.8/10 Excellent! (25 reviews)
Easy in and out. Beds were super comfortable

Reviewed on Oct 25, 2025

Knock on Wood | Airy Charm in Heart of Downtown
See all 2,299 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 $1,144, 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 $23
per traveller
Portland Smartphone Audio Tour: Self-Guided Drive
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
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.