Parkside Vacations

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    Save up to ￥45,448 when you book a flight and hotel together*

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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

5 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
Fully refundableReserve now, pay when you stay
The price is ￥18,537 per night from Apr 8 to Apr 9
￥18,537
￥26,600 total
Apr 8 - Apr 9
includes taxes & fees
9.6/10 Exceptional! (151 reviews)
I cannot say enough about how amazing the Longfellow Hotel is!! I almost don’t want to say how great it is so that I will be able to stay here whenever I like, and it won’t be booked!! so incredibly comfortable, hip, accommodating. Very simple yet every need is met just the way I like it.

Reviewed on Mar 18, 2026

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 ￥17,297 per night from Mar 29 to Mar 30
￥17,297
￥23,644 total
Mar 29 - Mar 30
includes taxes & fees
9.4/10 Exceptional! (380 reviews)
Hotel is amazing. Have stayed 4 times now.

Reviewed on Mar 26, 2026

The Francis
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is ￥20,597 per night from Apr 12 to Apr 13
￥20,597
￥22,789 total
Apr 12 - Apr 13
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
I frequently stay at this property. It is a very clean property with kind and helpful staff and an excellent restaurant and spa. I was locked out of the next door parking garage and Dan (door man?) helped me get my car out. He ran out there in the freezing cold, called the garage mgmt and got me ...

Reviewed on Mar 26, 2026

The Westin Portland Harborview
See all 2,376 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.

Things to do

Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

￥2,649
per traveler
100% of travellers recommend
Ultimate Portland Self-Guided Driving GPS Audio Tour
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

￥1,561
per traveler
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

￥2,649
per traveler
Portland Smartphone Audio Tour: Self-Guided Drive
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.