Parkside Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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
A tree-lined pathway leading to a brick building with a sign reading "Mercy Hospital Service Entrance".

Downtown Portland

4 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
A marina with boats docked, a wooden pier, and a red brick building with balconies.

Old Port

Explore the cobblestone streets in Portland’s historic district, which combines a wealth of history with a thoroughly modern city experience.

Find hotels in Old Port
A lighthouse on a rocky shore with a sailboat in the distance.

West End

If you're spending some time in West End, Victoria Mansion and Portland Fire Museum are top sights worth seeing.

Find hotels in West End
A large, cream-colored building with white columns and a white picket fence in front.

Portland Arts District

The ample dining options and captivating waterfront views are top of the list for many visitors to Portland Arts District. A stop by Cross Insurance Arena or Portland Museum of Art might round out your trip.

Find hotels in Portland Arts District
A red brick building with Gothic architectural features, including pointed arches and a cross on top.

East Bayside

If you're spending some time in East Bayside, Maine Jewish Museum and Cathedral of the Immaculate Conception are top sights worth seeing.

Find hotels in East Bayside

Top hotels in Parkside

Longfellow Hotel

Longfellow Hotel

754 Congress St Portland ME
Fully refundableReserve now, pay when you stay
S$549
1 Sept - 2 Sept
includes taxes & fees
Longfellow Hotel
Clarion Pointe South Portland

Clarion Pointe South Portland

675 Main Street I-95 South Portland ME
Fully refundable
S$129
8 Sept - 9 Sept
includes taxes & fees
7.2/10 Good! (661 reviews)
"Poor management and lack of staff, fixtures falling off the wall, unable to get towels after asking for three days. We left early"

Reviewed on 10 Aug, 2026

Clarion Pointe South Portland
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

738 Main Street South Portland ME
Fully refundable
S$134
17 Aug - 18 Aug
includes taxes & fees
Quality Inn & Suites South Portland
See all 2,479 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

Fitzpatrick Stadium

Catch an event at Fitzpatrick Stadium during your trip to Portland. Amble around the area's waterfront or attend a sporting event.
See properties

Neal S. Dow House

You can spend an afternoon exploring the galleries in Neal S. Dow House in Portland. Stroll along the waterfront or attend a sporting event in the area.
See properties

Things to do

Portland Lighthouse Boat Cruise with Oysters & Prosecco

Portland Explorer: Boat Cruise with Oysters & Prosecco

S$177
per adult
Portland Explorer: Boat Cruise with Oysters & Prosecco
Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

S$99
per adult
90% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

S$22
per traveller
100% of travellers recommend
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.