Parkside Vacations from $750
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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.
Ogunquit River Inn & Suites
Moody
Save 100% on your flight
Price was $1,074, price is now $750 per person
$750
per person
Jul 29 - Aug 1
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
9/10 Wonderful! (1,011 reviews)
This ida beautiful hotel close to all beaches, dining, and shopping in ogunquit and wells. It is unique because it sits on a hill. Everything was great. The only reason for 4 stars is all the stairs. Be sure you know where your room is located because you might end up dragging your stuff up and down some steep and lengthy stair cases.
Reviewed on Jun 24, 2026
Blind Tiger Portland - Danforth Street.
West End
Save 100% on your flight
Price was $1,587, price is now $1,127 per person
$1,127
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (185 reviews)
This property oozed charm, and the manager was so friendly and helpful. Loved everything about my stay here.
Reviewed on Jun 26, 2026
The Meadowmere Resort
Price was $1,160, price is now $827 per person
$827
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Price was good for the amenities offered and location. Our room was just recently renovated.
Reviewed on Jun 22, 2026
Inn By The Sea
Save 100% on your flight
Price was $2,628, price is now $1,956 per person
$1,956
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (319 reviews)
We just love it there. It is our happy place. Beautiful grounds, comfortable, friendly and downy to earth staff. Wonderful place!
Reviewed on Jun 26, 2026
Grasshopper Inn
Price was $1,595, price is now $1,241 per person
$1,241
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
9.8/10 Exceptional! (73 reviews)
We had a fantastic stay at Grasshopper Inn and will definitely return when back in the area. Clean, friendly staff and brilliant location.
Reviewed on Oct 22, 2025
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(328 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
$357 nightly
The price is $395 total per night from Jun 29 to Jun 30
$395 total
Jun 29 - Jun 30
Total with taxes and fees
9.6/10 Exceptional! (172 reviews)
"The staff was excellent. The rooms were a little tight. The area around the hotel seemed a little sketchy but it was safe."
Reviewed on Jun 22, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$349 nightly
The price is $386 total per night from Jul 5 to Jul 6
$386 total
Jul 5 - Jul 6
Total with taxes and fees
9.4/10 Exceptional! (1,780 reviews)
"Staff was very accommodating to checking in, valet, storing luggage. Breakfast was delicious!"
Reviewed on Jun 26, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
$261 nightly
The price is $289 total per night from Jul 5 to Jul 6
$289 total
Jul 5 - Jul 6
Total with taxes and fees
9.4/10 Exceptional! (1,248 reviews)
"The air conditioning doesn’t stay on. The thermostat goes down to 64 but the temperature wouldn’t go below 69 which made it pretty warm to try and sleep."
Reviewed on Jun 26, 2026
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.
Stay near popular Parkside attractions
Things to do
Vintage Fire Truck Sightseeing Tour of Portland Maine
$45
per adult
98% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.