Parkside Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    deals illustration

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    stays illustration

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration

    Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Parkside

Price found within the past 48 hours. Click for updated prices.
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
per person
Aug 17 - Aug 22
found 15 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Portland (PWM)
7.8/10 Good! (1,032 reviews)
Quick check in. The staff has been very helpful. I am on a motorcycle, it has been raining, they offered towels to dry the bike and found some towels i could take with me, as my seat is very soggy.

Reviewed on Jul. 10, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Aug 17 - Aug 22
found 15 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Portland (PWM)
9.2/10 Wonderful! (1,533 reviews)
The staff were super friendly and helpful. The room was beautiful and the garden atmosphere was fantastic. I would recommend this hotel.

Reviewed on Jul. 10, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
per person
Aug 17 - Aug 22
found 15 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Portland (PWM)
9.6/10 Exceptional! (209 reviews)
We loved our stay at The Docent's Collection, would come here again.

Reviewed on Jul. 8, 2025

Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

3 out of 5
Downtown Portland
Save 100% on your flight
per person
Aug 17 - Aug 22
found 15 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Portland (PWM)
8.8/10 Excellent! (1,144 reviews)
Loved it's proximity to everything in Old Port!

Reviewed on Jun. 28, 2025

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Save 100% on your flight
per person
Aug 17 - Aug 22
found 15 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Portland (PWM)
9.8/10 Exceptional! (113 reviews)
Great location. Quiet street. Well maintained property. Warm and welcoming.

Reviewed on Jul. 5, 2025

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 Maine College of Art, you won't get bored spending a day wandering around this part of Portland.

Find hotels in Downtown Portland

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 CA $449 per night from Aug 11 to Aug 12
CA $449
CA $550 total
Aug 11 - Aug 12
includes taxes & fees
9.4/10 Exceptional! (93 reviews)
"Nice stay"

Reviewed on Jul. 10, 2025

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 CA $440 per night from Jul 14 to Jul 15
CA $440
CA $521 total
Jul 14 - Jul 15
includes taxes & fees
9.4/10 Exceptional! (332 reviews)
"Beautiful, renovations were excellent. Bed was extremely comfortable and clean. Bathrooms were prestige, clean and newly renovated the old character with the renovated amenities. Made this a very excellent day."

Reviewed on Jul. 10, 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 $190 per night from Jul 14 to Jul 15
CA $190
CA $207 total
Jul 14 - Jul 15
includes taxes & fees
7.8/10 Good! (1,012 reviews)
"Great for the price, clean rooms and good breakfast"

Reviewed on Jul. 10, 2025

Days Inn by Wyndham Airport/Maine Mall
See all 2,484 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 $744, 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

Portland Downtown Highlights: "The Golden Adventure" Exploration Game

Downtown Golden Adventure Quest Experience in Portland

CA $12
per adult
Downtown Golden Adventure Quest Experience in Portland
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
Sunset Lighthouse Cruise Tour from Casco Bay

Sunset Lighthouse Cruise Tour from Casco Bay

CA $77
per adult
90% of travellers recommend
Sunset Lighthouse Cruise Tour from Casco Bay
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.