Parkside Holidays

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Our guide on where to stay in Parkside

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

4 out of top 10 points of interest in this area
4/5(1 area review)

A noteworthy feature of Downtown Portland is its captivating waterfront views. While you're in town, be sure to stop and check out Cross Insurance Arena and Merrill Auditorium.

Find hotels in Downtown Portland

Our pick of the best 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! (139 reviews)
Very stylish, clean, and comfortable hotel. We typically stay in the Oldport section of Portland but it was really nice to explore other areas. Lots of restaurants, bars, and coffee shops in the area. The hotel bar and coffee shop are great and very convenient. Look for those week day deals. Very ...

Reviewed on 12 Dec 2025

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Longfellow Hotel
The Francis

The Francis

3.5 out of 5
747 Congress Street Portland ME
9.4/10 Exceptional! (372 reviews)
Best hotel in Portland!

Reviewed on 11 Dec 2025

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The Francis
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

2.5 out of 5
369 Maine Mall Road South Portland ME
Fully refundableReserve now, pay when you stay
The price is NZ$125 per night from 11 Jan to 12 Jan
NZ$125
11 Jan - 12 Jan 2026
includes taxes & fees
8.8/10 Excellent! (1,651 reviews)
Clean room

Reviewed on 13 Dec 2025

Tru by Hilton Portland Airport Area
See all 2,317 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.

Frequently asked questions

How much does a Parkside holiday package cost?
From as little as , you can customize your Parkside holiday 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 holiday 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 holiday 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 fulfil those holiday 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 holiday?
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 travelling 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 holiday 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 holiday package?
With a holiday 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 holiday package?
Certainly, and we'll help you every step of the way. You may be able to amend or cancel your Parkside holiday 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

Deering Oaks Park

After visiting Deering Oaks Park, make a plan to see the other sights and activities in Portland. Amble around the area's waterfront or attend a sporting event.

Deering Oaks Park

Fitzpatrick Stadium

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

Fitzpatrick Stadium

Activities

Self-Guided Driving & Walking Bundle of Portland Maine Tours

Portland Maine Self-Guided Driving & Walking Audio Tour Bundle

NZ$45
per adult
100% of travellers recommend
Portland Maine Self-Guided Driving & Walking Audio Tour Bundle
Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

NZ$30
per traveller
74% of travellers recommend
Ultimate Portland Self-Guided Driving GPS Audio Tour
Tour of Palace & Monument of Marrakech

Tour of Palace & Monument of Marrakech

NZ$70
per adult
Tour of Palace & Monument of Marrakech
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.