Oakdale Vacations from $691
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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.
The Docent's Collection at 178 Middle Street
Downtown Portland
Price was $1,172, price is now $906 per person
$906
per person
Jan 15 - Jan 18
found 16 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
9.8/10 Exceptional! (81 reviews)
room was very modern, however some areas did not look well cleaned (edge if the bed had some dried white liquid). the surrounding area has nice shops but is very sketchy at night. did not feel comfortable with the parking situation. also at 6am sounded like maintenance or cleaning crew was constantly in and out of the elevator making tons of noise. was good for a night but wouldnt stay again.
Reviewed on Oct 27, 2026
84 Main
Price was $1,015, price is now $825 per person
$825
per person
Dec 18 - Dec 22
found 11 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Portland (PWM)
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 on Jul 17, 2026
Where to stay in Oakdale
Find the best Oakdale areas and neighborhoods for the activities you enjoy most. Learn more about Oakdale
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.
Oakdale Hotel Deals
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $112 total per night from Dec 6 to Dec 7
$112 total
Dec 6 - Dec 7
Total with taxes and fees
9/10 Wonderful! (1,007 reviews)
"Great hotel. Conveniently located to everything"
Reviewed on Nov 6, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
$81 nightly
The price is $89 total per night from Nov 15 to Nov 16
$89 total
Nov 15 - Nov 16
Total with taxes and fees
8.2/10 Very Good! (1,855 reviews)
"Just stayed one night, everything was fine."
Reviewed on Nov 7, 2026
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $97 total per night from Nov 9 to Nov 10
$97 total
Nov 9 - Nov 10
Total with taxes and fees
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.
Stay near popular Oakdale attractions
Things to do
Vintage Fire Truck Sightseeing Tour of Portland Maine
$45
per adult
98% of travellers recommend
Portland, Maine: Tour in Vintage Fire Engine
$45
per adult
90% of travellers recommend
Portland, Maine: Hidden Histories Guided Walking Tour
$54
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.