Parkside Vacations

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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

Downtown Portland

4 out of top 10 points of interest in this area
4.5/5(328 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 ₩276,876 per night from May 25 to May 26
₩276,876
₩363,265 total
May 25 - May 26
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 ₩372,429 per night from May 18 to May 19
₩372,429
₩450,769 total
May 18 - May 19
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 ₩277,104 per night from May 25 to May 26
₩277,104
₩363,579 total
May 25 - May 26
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.

Frequently asked questions

How much does a Parkside vacation package cost?
From as little as , 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

Merrill Auditorium

You can enjoy a show at Merrill Auditorium during your trip to Portland. Stroll along the area's seaside or experience its acclaimed theater scene.

Merrill Auditorium

Maine Narrow Gauge Railroad

You can spend an afternoon studying the exhibits at Maine Narrow Gauge Railroad in Portland. Experience the area's great live music and entertainment choices.

Maine Narrow Gauge Railroad
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.