Oakland Vacation Packages
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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.
Top Oakland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Brunswick Hotel
Price was CA $1,245, price is now CA $1,215 per person
CA $1,215
per person
May 16 - May 21
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Augusta (AUG)
9.4/10 Exceptional! (916 reviews)
Clean room, friendly staff, in walking distance to everything great view
Reviewed on Mar 20, 2026
Oakland Hotel Deals
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Oakland ME
9.4/10 Exceptional! (66 reviews)
Loved our stay!
Reviewed on Nov 9, 2025
Cozy Long Pond Cottage: community access, private mooring & shared dock.
Rome ME
10/10 Exceptional! (22 reviews)
The cottage was beautiful. Everything inside was new or in new condition. The host was also excellent. During our stay we conversed like we were old friends. Cottage was surprisingly well stocked. I would literally want to stay there again.
Reviewed on Jan 17, 2026
Peaceful Farmhouse Retreat- Pets welcome
Oakland ME
The price is CA $279 per night from Mar 27 to Mar 28
CA $279
CA $504 total
Mar 27 - Mar 28
includes taxes & fees
10/10 Exceptional! (11 reviews)
Kathleen is an incredibly thoughtful and gracious host. From coffee and oatmeal on the kitchen counter to a tea pot filled with water upon our late night arrival, Kathleen had thoughtful touches throughout. The kitchen was well equipped, towels were plentiful, and we even had a fun visit with the ...
Reviewed on Mar 17, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
