Parkside Holidays

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Our guide on where to stay in Parkside

Find the best Parkside areas and neighborhoods for the activities you enjoy most. Learn more about Parkside
A tree-lined pathway leading to a brick building with a sign reading "Mercy Hospital Service Entrance".

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.

Find hotels in Downtown Portland

Our pick of the best 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 NZ$510 per night from 8 Nov to 9 Nov
NZ$510
8 Nov - 9 Nov
includes taxes & fees
9.4/10 Exceptional! (199 reviews)
"Very lovely boutique hotel in downtown Portland, Maine. Small rooms, and there is no storage, so you have to live out of your suitcase for a couple of days. And there is no table and only one chair so that’s a negative, if you want to work in your room or have room service, there’s nowhere to sit ..."

Reviewed on 26 Oct 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 NZ$298 per night from 7 Dec to 8 Dec
NZ$298
7 Dec - 8 Dec
includes taxes & fees
9.4/10 Exceptional! (418 reviews)
"This hotel was a mixed bag for me. Location was good, we could easily walk to the Old Port area and there were several good restaurants close to the property. The interior spaces were attractive and cozy. The room was cramped and short on shelves and storage so there wasn’t enough space to comfortably ..."

Reviewed on 31 Oct 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 NZ$199 per night from 6 Dec to 7 Dec
NZ$199
6 Dec - 7 Dec
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
"Very clean"

Reviewed on 6 Nov 2026

The Westin Portland Harborview
See all 2,395 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.

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.
See properties

Activities

Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

NZ$30
per traveller
100% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
Portland Maine Self-Guided Driving & Walking Audio Tour Bundle

Portland Maine Self-Guided Driving & Walking Audio Tour Bundle

NZ$44
per adult
90% of travellers recommend
Portland Maine Self-Guided Driving & Walking Audio Tour Bundle
Portland, Maine: Hidden Histories Guided Walking Tour

Portland, Maine: Hidden Histories Guided Walking Tour

NZ$95
per adult
Portland, Maine: Hidden Histories Guided Walking Tour
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.