Parkside Holidays

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  • Better together

    Save up to €900 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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

5 out of top 10 points of interest in this area
3.5/5(2 area reviews)

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

Top hotels in Parkside

Longfellow Hotel

Longfellow Hotel

4 out of 5
754 Congress St Portland ME
Fully refundableReserve now, pay when you stay
The price is €378 per night from 16 Jun to 17 Jun
€378
16 Jun - 17 Jun
includes taxes & fees
9.6/10 Exceptional! (169 reviews)
"This is an absolutely fabulous gem of a hotel. We were only there one night, but everything was superb. The room was lovely with a beautiful view (a bay view room). The shower was a highlight. The staff was very friendly and helpful. The best amenity was the town car available to shuttle us around ..."

Reviewed on 29 May 2026

Longfellow Hotel
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundable
The price is €108 per night from 14 Jun to 15 Jun
€108
14 Jun - 15 Jun
includes taxes & fees
8/10 Very Good! (1,488 reviews)
"This day was nice. We did have one issue with the lock on the room door. We had to wait for a maintenance man to come to repair the lock so we could re-enter our room but the other issue was at 3:30 AM in the morning, the batteries in the smoke alarm failed and the smoke alarm started chirping and ..."

Reviewed on 9 Jun 2026

Clarion Hotel Portland Airport ME
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is €304 per night from 14 Jun to 15 Jun
€304
14 Jun - 15 Jun
includes taxes & fees
9.4/10 Exceptional! (1,781 reviews)
"Great location!"

Reviewed on 9 Jun 2026

Portland Harbor Hotel
See all 2,445 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.

Things to do

Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

€13
per traveller
100% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

€15
per traveller
100% of travellers recommend
Ultimate Portland Self-Guided Driving GPS Audio Tour
Sunset Lighthouse Cruise Along Casco Bay

Sunset Lighthouse Cruise Along Casco Bay

€59
per adult
Sunset Lighthouse Cruise Along Casco Bay
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.