Parkside Vacation Packages

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Top Holiday Package Deals in Parkside

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
per person
Aug. 22 - Aug. 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
7.8/10 Good! (1,003 reviews)
I made reservation sitting in car not familiar with area. After realizing I was already past Portland on my way home I tried to cancel. Called Hotel they refused because booked through Expedia, contacted Expedia and refused by them as well. Rather than lose my money I had to backtrack my travel. I was then awaken by people fighting in the hallway at 4:45 a.m. let's say this was not exactly a dream evening.

Reviewed on Jun. 18, 2024

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
Jul. 21 - Jul. 27
found 1 hour ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9/10 Wonderful! (1,194 reviews)
had a wonderful stay. hotel is lovely and we were upgraded to a beautiful comfortable room. breakfast was delicious. right in town -convenient.

Reviewed on Jun. 18, 2024

Hidden Pond

Hidden Pond

4 out of 5
Save 100% on your flight
per person
Jul. 28 - Aug. 3
found 1 hour ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
8/10 Very Good! (6 reviews)
The service was not top notch for the price. Family pool was too small. Spa lacked a sauna and steam and had a small waiting area. We liked the overall ambiance, charming main lobby and outdoor shower in the room. The room overall was good. But other than the person at checkout who was great, we did not feel the other service people were excited to have us there.

Reviewed on Jun. 17, 2024

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Downtown Portland
per person
Jul. 21 - Jul. 27
found 1 hour ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.4/10 Exceptional! (670 reviews)
We loved the people and the decor/layout of the hotel, and its rooms. The location was perfect for us. We enjoyed both the rooftop bar and downstairs restuarant/coffee area. The only negative for us was the $40 parking fee per night. Service by the valets was excellent, however.

Reviewed on Jun. 17, 2024

The Press Hotel, Marriott Autograph Collection

The Press Hotel, Marriott Autograph Collection

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Jul. 28 - Aug. 3
found 1 hour ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
9.6/10 Exceptional! (866 reviews)
Just spent a week here for our first trip to Maine. The location was amazing as there were dozens of shops and restaurants just outside the front door and within a two to three block radius. Many of the attractions we had planned on visiting were just blocks away and the Casco boat ferry shipyard was less than a ten minute walk. We felt safe in the area and the quality of the area was great. Our room was spacious and comfortable. We declined housekeeping service during our stay but the hallways, lobby and front desk areas were spotless. Having worked in hotels for 35 years I can say this property is exceptional and everyone from the hotel we encountered were friendly and welcoming. Highly recommend.

Reviewed on Jun. 7, 2024

Where to stay in Parkside

Find the best Parkside areas and neighborhoods for the activities you enjoy most. Learn more about Parkside
State Street Church

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 Wadsworth-Longfellow House, you won't get bored spending a day wandering around this part of Portland.

Find hotel + flight trips in Downtown Portland

Parkside Hotel Deals

The Francis
The Francis
3.5 out of 5
747 Congress Street, Portland, ME
The price is CA $379 per night from Jun. 24 to Jun. 25
CA $379
CA $454 total
includes taxes & fees
Jun 24 - Jun 25
9.4/10 Exceptional! (270 reviews)
"Parking was not the greatest. Nice and quiet, comfortable and convenient to walk around."

Reviewed on Jun. 15, 2024

The Francis
Casco Bay Hotel, Ascend Hotel Collection
Casco Bay Hotel, Ascend Hotel Collection
3.5 out of 5
80 John Roberts Rd., South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Jun. 23 to Jun. 24
CA $159
CA $174 total
includes taxes & fees
Jun 23 - Jun 24
8.4/10 Very Good! (1,620 reviews)
"Room was comfortable. It had a decent fitness room. Staff was very helpful. Breakfast was very lacking, to say the least. Other than the shopping mall, there's not much by this hotel. You pretty much are taking an Uber downtown for any food or drink options."

Reviewed on Jun. 17, 2024

Casco Bay Hotel, Ascend Hotel Collection
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 CA $348 per night from Jun. 23 to Jun. 24
CA $348
CA $396 total
includes taxes & fees
Jun 23 - Jun 24
8.4/10 Very Good! (1,050 reviews)
"All the staff were so helpful and kind."

Reviewed on Jun. 16, 2024

The Westin Portland Harborview
See all 2,182 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.

Explore other types of vacation packages

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 $1,006, 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.

Discover the most popular places to visit in Parkside

Image for Deering Oaks Park

Deering Oaks Park

Explore the great outdoors at Deering Oaks Park, a lovely green space in Portland. Experience the area's acclaimed theater scene or attend a sporting event.

Deering Oaks Park
Image for Fitzpatrick Stadium

Fitzpatrick Stadium

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

Fitzpatrick Stadium
Image for Neal S. Dow House

Neal S. Dow House

You can spend time exploring the galleries in Neal S. Dow House during your trip to Portland. Stroll along the waterfront or attend a sporting event in the area.

Neal S. Dow House

Things to do

Image for Portland: Old Port Seafood Lovers Tour

Portland: Old Port Seafood Lovers Tour

CA $198
Per adult
Portland: Old Port Seafood Lovers Tour
Image for Sunset Lighthouse Harbor Cruise from Portland's Old Port

Sunset Lighthouse Harbor Cruise from Portland's Old Port

CA $122
Per adult
Sunset Lighthouse Harbor Cruise from Portland's Old Port
Image for Portland, Maine: Old Port Brewery & Pub Walking Tour

Portland, Maine: Old Port Brewery & Pub Walking Tour

CA $121
Per adult
Portland, Maine: Old Port Brewery & Pub Walking Tour
See all activities in Portland

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.