Parkside Vacations from $683

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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 Meadowmere Resort

The Meadowmere Resort

$683
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
8.6/10 Excellent! (1,009 reviews)
Evalina Hotel

Evalina Hotel

Downtown Portland
Save 100% on your flight
$1,792
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
10/10 Exceptional! (7 reviews)
It was our first time visiting Portland, and the Evalina exceeded our expectations. The location is perfect, right on Commercial Street, with plenty of restaurants and shops nearby. The ferry and cruise ports are also just a 5–10 minute walk away, making it easy to visit the different islands. The suite was comfortable and thoughtfully equipped with everything we could need, including an umbrella for rainy days, coffee and a French press, tea, a washer and dryer, and so much more. Communication was excellent throughout our stay as well. We truly enjoyed our visit, and the next time we’re in Portland, the Evalina will be our first choice!

Reviewed on Aug 8, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

Moody
$939
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9/10 Wonderful! (1,017 reviews)
We checked in a bit early, and we were greeted with ice tea and a smile. A very nice group of folks working and the breakfast was better than expected. We would absolutely stay here again.

Reviewed on Aug 11, 2026

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

West End
Save 100% on your flight
$1,960
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (128 reviews)
Inn By The Sea

Inn By The Sea

Save 100% on your flight
$1,811
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (327 reviews)
(+) Location Dog Friendly Food Parking Everything you would expect from a luxury hotel - it is pricy. Nothing negative.

Reviewed on Aug 2, 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

4 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.

Find hotels in Downtown Portland
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.

Find hotels in Old Port
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
$444 nightly
$491 total
Sep 1 - Sep 2
Total with taxes and fees
Longfellow Hotel
Clarion Pointe South Portland

Clarion Pointe South Portland

675 Main Street I-95 South Portland ME
Fully refundable
$93 nightly
$101 total
Sep 9 - Sep 10
Total with taxes and fees
Clarion Pointe South Portland
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

738 Main Street South Portland ME
Fully refundable
$96 nightly
$105 total
Aug 17 - Aug 18
Total with taxes and fees
6.4/10 (1,044 reviews)
"The room had a horrible smell. The door didn’t lock. There were holes in the wall covered in spackling."

Reviewed on Aug 11, 2026

Quality Inn & Suites South Portland
See all 2,480 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

Fitzpatrick Stadium

Catch an event at Fitzpatrick Stadium during your trip to Portland. Amble around the area's waterfront or attend a sporting event.
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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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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 Lighthouse Boat Cruise with Oysters & Prosecco

Portland Explorer: Boat Cruise with Oysters & Prosecco

$137
per adult
Portland Explorer: Boat Cruise with Oysters & Prosecco
Portland, Maine: Tour in Vintage Fire Engine

Portland, Maine: Tour in Vintage Fire Engine

$45
per adult
90% of travellers recommend
Portland, Maine: Tour in Vintage Fire Engine
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.