Parkside Vacations from $605
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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.
The McKernan Inn
Price was $782, price is now $605 per person
$605
per person
Mar 27 - Mar 30
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9/10 Wonderful! (83 reviews)
Gorgeous grounds and venue with a beautiful oceanfront view. Plenty of parking as part of SMCC campus. Short drive to downtown Portland and lots of stores around in South Portland. Very unique experience, would stay again without hesitation!
Reviewed on Dec 27, 2025
Inn By The Sea
Price was $1,123, price is now $856 per person
$856
per person
Apr 2 - Apr 7
found 22 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.4/10 Exceptional! (288 reviews)
Room was ready early friendly staff and room is better than expected
Reviewed on Nov 16, 2025
The Docent’s Collection – Thompson Block
Downtown Portland
Price was $884, price is now $676 per person
$676
per person
Mar 27 - Mar 30
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
Room was very clean, neat vibe, tons of space! Made coming back from
Reviewed on Jan 23, 2026
Cliff House Maine
Bald Head
Price was $1,308, price is now $1,024 per person
$1,024
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
Phenomenal service and food with stunning east coast views. A favorite for sure.
Reviewed on Jan 23, 2026
Portland Harbor Hotel
Downtown Portland
Price was $782, price is now $614 per person
$614
per person
Mar 27 - Mar 30
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Really nice room. Tub, separate shower, nice linens.
Reviewed on Feb 7, 2026
Where to stay in Parkside
Find the best Parkside areas and neighborhoods for the activities you enjoy most. Learn more about Parkside
Downtown Portland
4 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.
Parkside Hotel Deals
Longfellow Hotel
754 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$163 nightly
The price is $181 total per night from Feb 10 to Feb 11
$181 total
Feb 10 - Feb 11
Total with taxes and fees
9.4/10 Exceptional! (143 reviews)
We loved our stay. Great staff, room was nice, cafe very good and the Town Car service for rides, so convenient!
Reviewed on Jan 5, 2026
The Francis
747 Congress Street Portland ME
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $161 total per night from Feb 19 to Feb 20
$161 total
Feb 19 - Feb 20
Total with taxes and fees
9.4/10 Exceptional! (374 reviews)
Clean and great location
Reviewed on Jan 11, 2026
Knock on Wood | Airy Charm in Heart of Downtown
Portland ME
$318 nightly
The price is $346 total per night from Mar 5 to Mar 6
$346 total
Mar 5 - Mar 6
Total with taxes and fees
8.8/10 Excellent! (25 reviews)
Easy in and out. Beds were super comfortable
Reviewed on Oct 25, 2025
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.
Discover the most popular places to visit in Parkside
Deering Oaks Park
3/5(2 reviews)
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.
Fitzpatrick Stadium
Catch an event at Fitzpatrick Stadium during your trip to Portland. Amble around the area's waterfront or attend a sporting event.
Things to do
Portland Smartphone Audio Tour: Self-Guided Drive
$17
per traveler
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
$10
per traveler
Ultimate Portland Self-Guided Driving GPS Audio Tour
$17
per traveler
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.