
Oakdale Vacations from $358
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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.


Waldo Emerson Inn
Price was $653, price is now $550 per person
$550
per person
Dec 11 - Dec 13
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
8.8/10 Excellent! (357 reviews)
Our stay at the Waldo Emerson was nothing short of exceptional! From the moment we arrived, Amelia welcomed us with warm hospitality, and every detail of this charming property made us feel right at home.
The accommodations were comfortable and full of character, and the property itself is absolutely beautiful. Each morning, we looked forward to a delicious, fresh, and thoughtfully prepared breakfast that was the perfect start to our day.
What truly made our experience special were the wonderful sightseeing and dinner recommendations. Amelia and Ron are phenomenal hosts who go above and beyond to ensure their guests have a memorable stay. Their genuine warmth, local knowledge, and attention to detail made our visit to Kennebunkport even more enjoyable.
The Waldo Emerson is an outstanding choice for anyone looking for a charming bed and breakfast in Kennebunkport. We thoroughly enjoyed our stay and would gladly return. We highly recommend it to anyone seeking the perfect combination of comfort, charm, exceptional hospitality, and relaxation!
**A truly wonderful experience from start to finish!**
Reviewed on Oct 18, 2026

Portland Harbor Hotel
Downtown Portland
Price was $565, price is now $486 per person
$486
per person
Dec 18 - Dec 21
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.2/10 Wonderful! (1,851 reviews)
Location A+ with easy to walk to shops and restaurants.
Bedroom was clean and had great wooden armoire, small refrigerator.
Bathroom seemed clean but lighting very low. Water pressure could be improved.
All in all a great place to stay.
Reviewed on Nov 6, 2026


The Docent's Collection at 178 Middle Street
Downtown Portland
Price was $787, price is now $684 per person
$684
per person
Dec 18 - Dec 21
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) 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
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! (1,006 reviews)
"Very clean"
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

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

Harbor Lights and Sights Cruise
$61
per adult
90% of travellers recommend

Sunset Windjammer Cruise Along the Coast of Portland Maine
$77
per adult
92% of travellers recommend

Portland: Casco Bay Morning Lighthouse Cruise
$59
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.






















