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 $1,956, price is now CA $1,787 per person
CA $1,787
per person
Jun 11 - Jun 17
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) 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
Bluebird Ocean Point Inn
Ocean Point
Price was CA $803, price is now CA $772 per person
CA $772
per person
Jul 1 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Augusta (AUG)
8.8/10 Excellent! (556 reviews)
Thank you for another great stay, 37 years and counting! Clean updated rooms, friendly staff, morning coffee and the most amazing key lime pie on the planet.
Reviewed on Oct 23, 2025
Fairfield Inn & Suites by Marriott Brunswick Freeport
Price was CA $1,653, price is now CA $1,590 per person
CA $1,590
per person
Jun 11 - Jun 17
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to Augusta (AUG)
8.8/10 Excellent! (448 reviews)
Great stay great staff great location
Reviewed on Apr 1, 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
Stunning Belgrade Lakes Waterfront Retreat – Dock, Kayaks & Breathtaking Views!
Rome ME
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.
