Parkside Holidays
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- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Where to stay in Parkside
Find the best Parkside areas and neighborhoods for the activities you enjoy most. Learn more about Parkside
Downtown Portland
5 out of top 10 points of interest in this area
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.
Old Port
Explore the cobblestone streets in Portland’s historic district, which combines a wealth of history with a thoroughly modern city experience.
West End
If you're spending some time in West End, Victoria Mansion and Portland Fire Museum are top sights worth seeing.
Portland Arts District
The ample dining options and captivating waterfront views are top of the list for many visitors to Portland Arts District. A stop by Cross Insurance Arena or Portland Museum of Art might round out your trip.
West Bayside
When in West Bayside, you can plan a visit to Merrill Auditorium and Cross Insurance Arena, some noteworthy sights in the nearby area.
Top hotels in Parkside
Longfellow Hotel
754 Congress St Portland ME
Fully refundableReserve now, pay when you stay
€256
2 Nov - 3 Nov
includes taxes & fees
9.4/10 Exceptional! (198 reviews)
"Parking staff at night very unprofessional, Parking attendant didn’t appear after 10-15 min wait. Guy at front desk reluctant to call him to park our car. Didn’t want to bother him. Took much longer than expected and attitude opposite of service-oriented. At breakfast next day took 35 min to get ..."
Reviewed on 24 Oct 2026
The Francis
747 Congress Street Portland ME
Fully refundableReserve now, pay when you stay
€154
5 Nov - 6 Nov
includes taxes & fees
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
€107
18 Nov - 19 Nov
includes taxes & fees
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.
Stay near popular Parkside attractions
Deering Oaks Park
6.0/10 (2 reviews)
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.
Fitzpatrick Stadium
Catch an event at Fitzpatrick Stadium during your trip to Portland. Amble around the area's waterfront or attend a sporting event.
Neal S. Dow House
You can spend an afternoon exploring the galleries in Neal S. Dow House in Portland. Stroll along the waterfront or attend a sporting event in the area.
Things to do
Afternoon Windjammer Cruise Along the Coast of Portland Maine
€61
per adult
96% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
€69
per adult
92% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
€15
per traveller
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.