Parkside Vacations from $919

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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.
Newagen Seaside Inn

Newagen Seaside Inn

3.5 out of 5
Save 100% on your flight
Price was $1,362, price is now $919 per person
$919
per person
Aug 2 - Aug 7
found 18 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.4/10 Exceptional! (341 reviews)
IT WAS CHARMING AND BEAUTIFUL. The restaurant was wonderful, all the staff was first class, would love to go back.

Reviewed on Oct 14, 2025

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Save 100% on your flight
Price was $1,578, price is now $951 per person
$951
per person
Aug 2 - Aug 7
found 18 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9/10 Wonderful! (1,003 reviews)
Very convenient and helpful staff.

Reviewed on May 10, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $1,973, price is now $1,219 per person
$1,219
per person
Jul 15 - Jul 20
found 18 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
8.6/10 Excellent! (1,001 reviews)
Very well kept… great staff we had a great time

Reviewed on Apr 14, 2026

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $3,171, price is now $2,222 per person
$2,222
per person
Jul 15 - Jul 20
found 18 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.4/10 Exceptional! (1,003 reviews)
all was great. my favorite place!

Reviewed on Apr 29, 2026

Saco Bay Hotel

Saco Bay Hotel

2.5 out of 5
Price was $1,446, price is now $1,016 per person
$1,016
per person
Jul 19 - Jul 25
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
7.6/10 Good! (1,049 reviews)
The internet was not secure The room did not have room darkening drapes. Breakfast was good. TV not usefall no NBC,ABC,CBS channel and very few other channels to watch except old out of date programming.

Reviewed on May 11, 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

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.

Find hotels in Downtown Portland

Parkside Hotel Deals

Longfellow Hotel

Longfellow Hotel

4 out of 5
754 Congress St Portland ME
$244 nightly
The price is $270 total per night from May 17 to May 18
$270 total
May 17 - May 18
Total with taxes and fees
9.6/10 Exceptional! (160 reviews)
Everything was great!

Reviewed on May 11, 2026

Longfellow Hotel
The Francis

The Francis

3.5 out of 5
747 Congress Street Portland ME
$238 nightly
The price is $260 total per night from May 14 to May 15
$260 total
May 14 - May 15
Total with taxes and fees
9.4/10 Exceptional! (388 reviews)
Great location, comfortable bed, charming property, friendly and helpful staff.

Reviewed on May 1, 2026

The Francis
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$241 nightly
The price is $266 total per night from May 25 to May 26
$266 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (1,763 reviews)
Best location in Portland. The free bikes were the highlight, We went everywhere with them. Very convenient! The staff was very nice.

Reviewed on May 10, 2026

Portland Harbor Hotel
See all 2,402 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

State Theatre

State Theatre

The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.

State Theatre
Portland Museum of Art

Portland Museum of Art

Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.

Portland Museum of Art
East End Beach

East End Beach

Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.

East End Beach

Things to do

Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

$15
per traveler
Portland Smartphone Audio Tour: Self-Guided Drive
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.