Parkside Vacation Packages

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Top Holiday Package Deals in Parkside

Price found within the past 48 hours. Click for updated prices.
Spinneys Guesthouse & Beach Cottages

Spinneys Guesthouse & Beach Cottages

3 out of 5
Price was CA $1,629, price is now CA $1,447 per person
CA $1,447
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) to Portland (PWM)
9.2/10 Wonderful! (42 reviews)
Beach beautiful. Encourage early morning walk at low tide. Can walk far out on sand bar. Only suggestion , better pillows.

Reviewed on Aug. 18, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Price was CA $1,964, price is now CA $1,662 per person
CA $1,662
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Québec (YQB) to Portland (PWM)
9.6/10 Exceptional! (226 reviews)
I had a wonderful stay! The place was clean, cozy, and exactly as described. The location was perfect, which made everything smooth and easy. I’d happily stay here again and recommend it to anyone visiting Portland.

Reviewed on Aug. 22, 2025

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
Downtown Portland
Price was CA $1,822, price is now CA $1,600 per person
CA $1,600
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Québec (YQB) to Portland (PWM)
8.8/10 Excellent! (1,004 reviews)
Great location and attentive staff service.

Reviewed on Aug. 23, 2025

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Downtown Portland
Price was CA $2,010, price is now CA $1,771 per person
CA $1,771
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Québec (YQB) to Portland (PWM)
9.4/10 Exceptional! (1,009 reviews)
Pretty stunning little spot. As close as you can get to the waterfront, amazing breakfast downstairs, walking distance to the ENTIRE old port, and the staff was sweet as heck. -t

Reviewed on Aug. 22, 2025

DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
Price was CA $1,781, price is now CA $1,581 per person
CA $1,581
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) to Portland (PWM)
8/10 Very Good! (1,217 reviews)
It just felt really obvious all the different ways the parent co of Double Tree has cut corners to make hotels worse for patrons and employees in favor or shareholder wallets (despite prices being astronomically higher with no additional benefits to the patrons or staff)

Reviewed on Aug. 18, 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 $361 per night from Aug 26 to Aug 27
CA $361
CA $434 total
Aug 26 - Aug 27
includes taxes & fees
9.4/10 Exceptional! (343 reviews)
"Everything was perfect except for the noise from the street. It was quite loud all night."

Reviewed on Aug. 21, 2025

The Francis
Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Aug 24 to Aug 25
CA $161
CA $175 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,214 reviews)
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Reviewed on Aug. 21, 2025

Days Inn by Wyndham Airport/Maine Mall
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 $210 per night from Aug 26 to Aug 27
CA $210
CA $233 total
Aug 26 - Aug 27
includes taxes & fees
7.8/10 Good! (1,018 reviews)
"The hotel definitely needs a facelift but it was fine for a brief one night stay. The bed was comfortable. When the elevator got stuck on the 5th floor while we waited in the lobby, the front desk clerk was quick to walk up the 5 flights to address the situation."

Reviewed on Aug. 17, 2025

Clarion Hotel Portland
See all 2,440 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
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Frequently asked questions

How much does a Parkside vacation package cost?
From as little as CA $1,447, 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.