Parkside Vacations from $453

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • Better together

    Save up to $1,045 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

Your Parkside Vacation

Experience the beauty of this small neighborhood with a Parkside vacation package. From its festivals and markets to its walking, there's lots here for every traveler. Kick start your trip to Parkside by visiting nearby attractions such as Portland Museum of Art, University of Southern Maine and Victoria Mansion. Whatever your dream Parkside vacation may look like, you can make it a reality with Expedia.

The Latest Parkside Vacation Packages

Price found within the past 48 hours. Click for updated prices.
InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Price was $560, price is now $453 per person
$453
per person
Dec 15 - Dec 18
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (351 reviews)
Staff was great and room was exactly what we needed with lots of space!

Reviewed on Oct 19, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $658, price is now $524 per person
$524
per person
Dec 15 - Dec 18
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (283 reviews)
Absolutely 5 star. Best bed I’ve slept in at a hotel bar none.

Reviewed on Sep 10, 2025

Waldo Emerson Inn

Waldo Emerson Inn

3 out of 5
Price was $639, price is now $511 per person
$511
per person
Dec 3 - Dec 6
found 21 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
8.8/10 Excellent! (334 reviews)
This inn was so charming! Upon arrival, there were complimentary cookies and apple cider waiting for us. Amelia and Ron were so friendly and accommodating to ensure we had an amazing stay. Rooms were spotless and very comfortable.

Reviewed on Oct 28, 2025

Snowvillage Inn

Snowvillage Inn

4 out of 5
Price was $876, price is now $702 per person
$702
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
8.8/10 Excellent! (274 reviews)
Property was nice and quaint with a touch of serenity.

Reviewed on Oct 22, 2025

The Docent's Collection - New Opening

The Docent's Collection - New Opening

2 out of 5
Downtown Portland
Price was $777, price is now $643 per person
$643
per person
Dec 15 - Dec 18
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
No reviews
Really nice and clean new hotel!

Reviewed on Oct 27, 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(326 area reviews)

Known for its culinary delights, inspiring art and live music, the heart of Maine’s largest city is an exciting location.

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
$163 nightly
The price is $181 total per night from Nov 3 to Nov 4
$181 total
Nov 3 - Nov 4
Total with taxes and fees
9.4/10 Exceptional! (125 reviews)
This is a beautiful hotel built with many thoughtful features including French press coffee in the rooms. The staff was very friendly and helpful and we loved having a hotel car available for short trips to downtown/wharf area. The lobby/lounge is elegant yet cozy. Highly recommend.

Reviewed on Oct 27, 2025

Longfellow Hotel
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $92 total per night from Nov 5 to Nov 6
$92 total
Nov 5 - Nov 6
Total with taxes and fees
7.8/10 Good! (1,202 reviews)
The Clarion was excellent for my trip. Located close to airport and to downtown and priced reasonably.

Reviewed on Oct 27, 2025

Clarion Hotel Portland
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $183 total per night from Nov 30 to Dec 1
$183 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (1,656 reviews)
Amazing
Amazing location, unique hotel with beautiful decor and amenities

Reviewed on Oct 28, 2025

Portland Harbor Hotel
See all 2,326 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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Parkside

Deering Oaks Park

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.

Deering Oaks Park

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

Things to do

Portland: Maine Lighthouses Sightseeing Cruise with Drinks

Portland: Maine Lighthouses Sightseeing Cruise with Drinks

$69
per adult
Portland: Maine Lighthouses Sightseeing Cruise with Drinks
Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks

Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks

$69
per adult
Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks
Sunset Lighthouse Harbor Cruise from Portland's Old Port

Sunset Lighthouse Harbor Cruise from Portland's Old Port

$69
per adult
Sunset Lighthouse Harbor Cruise from Portland's Old Port
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.