Parkside Vacation Packages

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Top Holiday Package Deals in Parkside

Price found within the past 48 hours. Click for updated prices.
Microtel Inn & Suites by Wyndham York

Microtel Inn & Suites by Wyndham York

2 out of 5
Price was CA $798, price is now CA $715 per person
CA $715
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8/10 Very Good! (1,007 reviews)
Outdoor area could use some tidiness.

Reviewed on Sep. 3, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $2,059, price is now CA $1,892 per person
CA $1,892
per person
Oct 11 - Oct 13
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.2/10 Wonderful! (1,566 reviews)
Great hotel centralized great rooms nice breakfast station on each floor. Book w confidence.

Reviewed on Sep. 2, 2025

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
Downtown Portland
Price was CA $1,679, price is now CA $1,565 per person
CA $1,565
per person
Oct 11 - Oct 13
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
8.8/10 Excellent! (1,010 reviews)
Daniel who checked us in was extremely helpful and welcoming!

Reviewed on Sep. 2, 2025

Comfort Inn & Suites Scarborough - Portland

Comfort Inn & Suites Scarborough - Portland

2.5 out of 5
Price was CA $1,192, price is now CA $1,126 per person
CA $1,126
per person
Oct 11 - Oct 13
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
6.8/10 (668 reviews)
Rooms were clean and comfortable; however, the breakfast was substandard (including moldy mini bagels), and the parking lot was super sketchy with lots of people just hanging out and cars flying through.

Reviewed on Sep. 4, 2025

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Downtown Portland
Price was CA $1,819, price is now CA $1,733 per person
CA $1,733
per person
Oct 11 - Oct 13
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.4/10 Exceptional! (1,009 reviews)
Great experience, friendly staff and wonderful accommodations close to all.

Reviewed on Sep. 4, 2025

Where to stay in Parkside

Find the best Parkside areas and neighborhoods for the activities you enjoy most. Learn more about Parkside
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Downtown Portland

5 out of top 10 points of interest in this area
4.5/5(11 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

The Francis

The Francis

3.5 out of 5
747 Congress Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $325 per night from Sep 14 to Sep 15
CA $325
CA $395 total
Sep 14 - Sep 15
includes taxes & fees
The Francis
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
The price is CA $117 per night from Oct 5 to Oct 6
CA $117
CA $128 total
Oct 5 - Oct 6
includes taxes & fees
Germaine Inn South Portland
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Sep 7 to Sep 8
CA $186
CA $206 total
Sep 7 - Sep 8
includes taxes & fees
Clarion Hotel Portland
See all 2,418 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Parkside vacation package cost?
From as little as CA $715, 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

West End Bakery Crawl for Ladies only

West End Bakery Crawl for Ladies only

CA $89
per adult
West End Bakery Crawl for Ladies only
Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

CA $92
per adult
Afternoon Windjammer Cruise Along the Coast of Portland Maine
Portland: Sightseeing Cruise to Portland Head Light

Portland: Sightseeing Cruise to Portland Head Light

CA $56
per adult
98% of travellers recommend
Portland: Sightseeing Cruise to Portland Head Light
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.