Oakland Vacations from $452
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Your Oakland Vacation
There's no better way to embark on an adventure than with one of our vacation packages to Oakland. The rich history and eclectic style are just a couple of the convincing reasons to visit this captivating city. Make your trip to Oakland even more fun and exciting by going sightseeing. Colby College, Belgrade Lakes Chain and Waterville Opera House are among the leading attractions worth exploring. Expedia can help you escape the everyday. Tailor your vacation to Oakland to match your travel style, whatever that may look like.
The Latest Oakland vacation packages
Price found within the past 48 hours. Click for updated prices.
OneSixtyFive
Price was $1,088, price is now $890 per person
$890
per person
Feb 4 - Feb 8
found 7 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Augusta (AUG)
18.8/10 Exceptional! (142 reviews)
Clean, quiet, and comfortable. Very nice setting in the carriage house, enjoyable stay.
Reviewed on Nov 1, 2025
Colonial Inn Ellsworth
Price was $720, price is now $606 per person
$606
per person
Feb 4 - Feb 8
found 7 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Augusta (AUG)
15.2/10 Exceptional! (827 reviews)
The room was large and clean. In a convenient location - near restaurants, shopping, and sights. They had a fabulous breakfast - large selection of various foods.
Reviewed on Nov 13, 2025
Oakland Hotel Deals
Classy AF Home Steps from Colby and Trails
Oakland ME
10/10 Exceptional! (48 reviews)
Arthur's home was the perfect spot for us to visit our son at Colby- the house has everything you'd need to make dinner at home and is very comfortable. Loved being so close to Quarry Trails and so much nearby to enjoy in Waterville. Highly recommend and hope to come back soon for another extended ...
Reviewed on Sep 30, 2025
Sister A-Frame in Woods B
Oakland ME
$210 nightly
The price is $228 total per night from Nov 21 to Nov 22
$228 total
Nov 21 - Nov 22
Total with taxes and fees
10/10 Exceptional! (7 reviews)
Perfect for Colby visits
Reviewed on Nov 12, 2025
Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore
Oakland ME
$251 nightly
The price is $273 total per night from Nov 23 to Nov 24
$273 total
Nov 23 - Nov 24
Total with taxes and fees
10/10 Exceptional! (14 reviews)
This was the perfect house for a long weekend getaway! It had everything we needed & more. WiFi was slow but in the midst of a summer excursion or an ideal weathered day to have a bonfire it wouldn’t have mattered with all the outdoor activities that could be planned. I would totally rent this again, ...
Reviewed on Nov 10, 2025
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.
Find the Best Oakland Vacation Packages
Oakland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Augusta State Airport (AUG) |
Population | 2,600 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | First Congregational Church, Colby College and Belgrade Lakes Chain |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.