Oakdale Vacations from $378

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Your Oakdale Vacation

Our Oakdale vacation packages are a simple and practical way to organize and book your next retreat. Uncover the true character of this unique neighborhood without the pressure of planning everything yourself. Wondering what to see and do during your trip to Oakdale? Nearby attractions such as Portland Museum of Art, University of Southern Maine and Victoria Mansion are good places to start. Stop dreaming and start doing. When it's time to lock in your ideal vacation to Oakdale, Expedia will help you get there.

The Latest Oakdale Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Casco Bay Inn

Casco Bay Inn

2 out of 5
Price was $474, price is now $378 per person
$378
per person
Feb 17 - Feb 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
8/10 Very Good! (1,000 reviews)
The area was great! The room was clean and affordable.

Reviewed on Dec 7, 2025

Hilton Garden Inn Freeport Downtown

Hilton Garden Inn Freeport Downtown

3 out of 5
Save 100% on your flight
Price was $754, price is now $587 per person
$587
per person
Feb 17 - Feb 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9/10 Wonderful! (1,003 reviews)
The bartender was terrible. She was so busy talking to everyone that she messed up just about every order while we were there. Service was slow because she would not stop talking. We had the same issue with her last year!! We will absolutely stay there again but we will not patron the bar/restaurant again.

Reviewed on Dec 4, 2025

River View Resort

River View Resort

2.5 out of 5
Price was $1,359, price is now $1,076 per person
$1,076
per person
Jan 14 - Jan 20
found 11 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
8.8/10 Excellent! (297 reviews)
It was a basic suite-like motel. Could use an upgrade. Very 70s

Reviewed on Mar 30, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $914, price is now $732 per person
$732
per person
Feb 24 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (288 reviews)
Room was ready early friendly staff and room is better than expected

Reviewed on Nov 16, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $594, price is now $491 per person
$491
per person
Feb 24 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Lovely stay in a beautiful room, appreciated the upgrade. Easy walk to downtown activities.

Reviewed on Dec 12, 2025

Where to stay in Oakdale

Find the best Oakdale areas and neighborhoods for the activities you enjoy most. Learn more about Oakdale
State Street Church

Downtown Portland

4 out of top 10 points of interest in this area
4.5/5(326 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

Oakdale Hotel Deals

Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

2.5 out of 5
369 Maine Mall Road South Portland ME
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $73 total per night from Jan 11 to Jan 12
$73 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
8.8/10 Excellent! (1,646 reviews)
The room was nice and the staff were very nice.

Reviewed on Dec 8, 2025

Tru by Hilton Portland Airport Area
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $152 total per night from Jan 4 to Jan 5
$152 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.4/10 Exceptional! (1,542 reviews)
Yes, excellent service and we really enjoyed our stay.

Reviewed on Dec 4, 2025

Portland Regency Hotel & Spa
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $160 total per night from Dec 15 to Dec 16
$160 total
Dec 15 - Dec 16
Total with taxes and fees
9.2/10 Wonderful! (1,709 reviews)
Amazing. Everything was great!

Reviewed on Dec 11, 2025

Portland Harbor Hotel
See all 2,353 properties in Oakdale
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
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Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Oakdale

State Theatre showing street scenes as well as an individual femail

State Theatre

4.5/5(88 reviews)

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 showing art and interior views as well as a small group of people

Portland Museum of Art

4.5/5(255 reviews)

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 which includes general coastal views and a beach as well as a small group of people

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

Tour of Palace & Monument of Marrakech

Tour of Palace & Monument of Marrakech

$39
per adult
Tour of Palace & Monument of Marrakech
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

$10
per traveler
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

$17
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.