Parkside Holidays

Book a Hotel + Flight or Car together to unlock savings

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 Maine College of Art.

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 4.006.922 ₫ per night from 3 May to 4 May
4.006.922 ₫
5.452.154 ₫ total
3 May - 4 May
includes taxes & fees
9.6/10 Exceptional! (157 reviews)
Clean, beautiful room with a vintage feel. Great staff, very attentive. If you have a show to go to they offer a car service to take you there. It’s a 5 minute walk to the theater though so that was nice. Tandem bakery is right next door. You have to get coffee and pastries. Make sure to get a loaded ...

Reviewed on 14 Apr 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 2.943.152 ₫ per night from 29 Apr to 30 Apr
2.943.152 ₫
3.998.229 ₫ total
29 Apr - 30 Apr
includes taxes & fees
9.4/10 Exceptional! (385 reviews)
Excellent breakfast option for eggs or tasty fresh yogurt. One day out of four they strangely neglected to clean the room, even with a door sign requesting service, but the night front desk person took it upon herself to do so when we noted the problem after returning around dinner time. She’s a ...

Reviewed on 12 Apr 2026

The Francis
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 3.808.948 ₫ per night from 30 Apr to 1 May
3.808.948 ₫
5.219.244 ₫ total
30 Apr - 1 May
includes taxes & fees
9.2/10 Wonderful! (1,753 reviews)
Nice accommodations.

Reviewed on 28 Apr 2026

Portland Harbor Hotel
See all 2,397 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 1null000null000 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.

Popular places to visit

State Theatre

State Theatre

You can get tickets for a performance at State Theatre during your stay in Portland. Experience the area's great live music and acclaimed theatre scene.

State Theatre
Portland Museum of Art

Portland Museum of Art

You can spend time browsing the exhibits at Portland Museum of Art during your travels in Portland. Stroll along the area's waterfront or experience its entertainment choices.

Portland Museum of Art
Portland Observatory

Portland Observatory

After visiting Portland Observatory, make a plan to see the other sights and activities in Portland. Stroll along the area's waterfront or experience its great live music.

Portland Observatory