An aerial view of a coastal city with a harbor, marina, and residential area.

Parkside Vacations from $687

Book a Hotel + Flight or Car together to unlock savings

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.
  • A covered patio area with a table and chairs, a swimming pool, and a building in the background.
    Dec 10 - Dec 13

    Nautical Mile + Flight

    Wells
    3 nights
    2.5 star property
    8.6/10 - Excellent (26 reviews)
    Roundtrip • Tampa (TPA) - Portland (PWM)
    TPA - PWM • 1 stop PWM - TPA • 1 stop
    $821
    $687
    per traveler
    found 8 hours ago
    Nautical Mile
  • A spacious kitchen with a central island, wooden bar stools, and a long dining table.
    Jan 10 - Jan 16

    Blind Tiger Portland - Danforth Street. + Flight

    West End
    6 nights
    3.5 star property
    9.6/10 - Exceptional (206 reviews)
    Roundtrip • Orlando (MCO) - Portland (PWM)
    MCO - PWM • 1 stop PWM - MCO • 1 stop
    Save 100% on your flight
    $1,275
    $900
    per traveler
    found 1 day ago
    Blind Tiger Portland - Danforth Street.
  • A spa area with a hot tub, seating, and large windows.
    Dec 10 - Dec 13

    The Meadowmere Resort + Flight

    Ogunquit
    3 nights
    2.5 star property
    8.6/10 - Excellent (1,008 reviews)
    "We have stayed at the Meadowmere Resort a few times. We really love the location of this resort. It's super convenient to the main thoroughfare, too!"
    Reviewed November 10, 2026
    Roundtrip • Tampa (TPA) - Portland (PWM)
    TPA - PWM • 1 stop PWM - TPA • 1 stop
    $1,205
    $968
    per traveler
    found 8 hours ago
    The Meadowmere Resort
  • A multi-story building with a ground-floor shop and upper residential units.
    Dec 30 - Jan 3

    84 Main + Flight

    Kennebunk
    4 nights
    4.0 star property
    9.8/10 - Exceptional (58 reviews)
    "The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room."
    Reviewed July 17, 2026
    Roundtrip • Atlanta (ATL) - Portland (PWM)
    ATL - PWM • Nonstop PWM - ATL • Nonstop
    $1,042
    $870
    per traveler
    found 1 day ago
    84 Main
  • A spacious living room with a large dining table, comfortable seating, and large windows offering views of the city.
    Jan 15 - Jan 18

    The Docent's Collection at 121 Middle Street + Flight

    Downtown Portland
    3 nights
    3.5 star property
    9.6/10 - Exceptional (430 reviews)
    "The room was spacious, super clean, and well equipped. Good location in the Port. Nearby parking seems plentiful. The Docent calls itself an "aparthotel," meaning there aren't really hotel amenities. A lot of the communication with staff is done by text. Although, there was a human person at the door for most of our stay. Great choice, particularly for a long term stay given the swell kitchen, if you don't mind the concept."
    Reviewed November 10, 2026
    Roundtrip • Atlanta (ATL) - Portland (PWM)
    ATL - PWM • 1 stop PWM - ATL • 1 stop
    $1,032
    $863
    per traveler
    found 20 hours ago
    The Docent's Collection at 121 Middle Street

Where to stay in Parkside

Find the best Parkside areas and neighborhoods for the activities you enjoy most.
A large, historic building with a prominent clock tower and arched windows.

Downtown Portland

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

An aerial view of a coastal city with dense urban development, a marina, and a large body of water.

Old Port

Cobblestone streets, 19th-century brick buildings, and fishing piers define this district, offering boutiques, restaurants, and bars. Explore Post Office Park, Tommy's Park with its large mural, and stroll the Eastern Promenade Trail to East End Beach.

The Victoria Mansion Historic House Museum with a clear blue sky in the background.

West End

Distinguished by its well-preserved Victorian architecture, this downtown Portland neighborhood boasts the scenic Western Promenade park, offering views of the White Mountains, and several historic structures, such as the Gothic House and Morrill Mansion.

A historic building with a sign reading "Portland Museum of Art McLellan House."

Portland Arts District

The ample dining options and captivating waterfront views are top of the list for many visitors to Portland Arts District. A stop by Cross Insurance Arena or Portland Museum of Art might round out your trip.

An aerial view of a coastal town with houses, a parking lot, and a rocky shoreline.

West Bayside

If you're looking for some top things to see and do in West Bayside and surrounding area, you can visit Merrill Auditorium and Cross Insurance Arena.

Discover the most popular places to visit in Parkside

Deering Oaks Park

6.0/10 (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.
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What to do near Parkside

Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

$17
per traveler
100% of travelers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
See all activities near Parkside

Parkside Hotel Deals

A brick building with a white entrance and the name "THE FRANCIS" above the door.

The Francis

The Francis
3.5 star property
Parkside
9.4 out of 10, Exceptional, (418 reviews)
"Excellent stay! We were welcomed with complimentary blueberry wine and the concierge helped carry our bags to our room. Noting that they told us we'd receive a text with a link to order breakfast food, and we never received anything. Had to go down the street to purchase breakfast!"
$172 nightly
The price is $188
Nov 16 - Nov 17
Total with taxes and fees
The Francis
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.
See all properties in Parkside
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.