Parkside Vacations from $680

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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.
Nautical Mile

Nautical Mile

$680
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
8.6/10 Excellent! (24 reviews)
I've stayed at the Nautical Mile many times! The rooms are perfect for a get-away! The pool is always ready to cool off in and the people, both working at the Nautical Mile and guests are very friendly.

Reviewed on Sep 8, 2026

The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

Downtown Portland
$818
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (61 reviews)
This loft was perfect! We will be back and stay longer!!

Reviewed on Sep 25, 2026

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

West End
$683
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (129 reviews)
Beautiful place

Reviewed on Sep 20, 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

Downtown Portland
$733
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (382 reviews)
Evalina Hotel

Evalina Hotel

Downtown Portland
$854
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
10/10 Exceptional! (11 reviews)
Better than expected. This new property was in a great location. Easy to walk to restaurants and shopping. Comfortable bed, nice bathroom and a sitting area with sofa, chair and tv. I was a little concerned because we could hear music from a nearby bar, but everything stopped by 10 o’clock. Would return.

Reviewed on Sep 25, 2026

Where to stay in Parkside

Find the best Parkside areas and neighborhoods for the activities you enjoy most. Learn more about Parkside
A tree-lined pathway leading to a brick building with a sign reading "Mercy Hospital Service Entrance".

Downtown Portland

5 out of top 10 points of interest in this area

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

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A marina with boats docked, a wooden pier, and a red brick building with balconies.

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.

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A lighthouse on a rocky shore with a sailboat in the distance.

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.

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A large, cream-colored building with white columns and a white picket fence in front.

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.

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A red brick building with Gothic architectural features, including pointed arches and a cross on top.

East Bayside

Bordered by Franklin Street and Washington Avenue, East Bayside offers a community arts venue, Mayo Street Arts, and the relaxing green space of Kennedy Park. Explore nearby Old Port and Munjoy Hill.

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Parkside Hotel Deals

Longfellow Hotel

Longfellow Hotel

754 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$334 nightly
$370 total
Oct 27 - Oct 28
Total with taxes and fees
9.6/10 Exceptional! (192 reviews)
"This hotel is amazing. Friendly staff- really good food and the spa was great."

Reviewed on Sep 21, 2026

Longfellow Hotel
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

738 Main Street South Portland ME
Fully refundable
$82 nightly
$90 total
Oct 25 - Oct 26
Total with taxes and fees
6.4/10 (1,138 reviews)
"Just an average stay. Nothing special just a room."

Reviewed on Sep 25, 2026

Quality Inn & Suites South Portland
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

80 John Roberts Rd. South Portland ME
Fully refundable
$93 nightly
$101 total
Oct 25 - Oct 26
Total with taxes and fees
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
See all 2,463 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.
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Stay near popular Parkside attractions

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.
See properties

Fitzpatrick Stadium

Catch an event at Fitzpatrick Stadium during your trip to Portland. Amble around the area's waterfront or attend a sporting event.
See properties

Neal S. Dow House

You can spend time exploring the galleries in Neal S. Dow House during your trip to Portland. Stroll along the waterfront or attend a sporting event in the area.
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Things to do

Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

$77
per adult
90% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Portland: Casco Bay Morning Lighthouse Cruise

Portland: Casco Bay Morning Lighthouse Cruise

$59
per adult
80% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
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.