Oakland Vacations

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Find the Best Oakland Vacation Packages

Oakland Hotel Deals

Cozy Long Pond Cottage: private mooring & shared dock

Cozy Long Pond Cottage: private mooring & shared dock

Rome ME
9.8/10 Exceptional! (21 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 17 January 2026

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Cozy Long Pond Cottage: private mooring & shared dock
Charming Guest House on Farm - Pets Welcome

Charming Guest House on Farm - Pets Welcome

Oakland ME
The price is AED 716 per night from Feb 11 to Feb 12
AED 716
AED 1,346 total
11 Feb - 12 Feb
includes taxes & fees
10/10 Exceptional! (8 reviews)
It was a great stay. The house is very comfortable

Reviewed on 29 January 2026

Charming Guest House on Farm - Pets Welcome
Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore

Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore

2 out of 5
Oakland ME
The price is AED 621 per night from Mar 2 to Mar 3
AED 621
AED 1,133 total
2 Mar - 3 Mar
includes taxes & fees
9.8/10 Exceptional! (18 reviews)
Yes, thank you again Diane

Reviewed on 11 January 2026

Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore
See all 523 properties in Oakland
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.

Frequently asked questions

How do I find cheap flights to Oakland that have flexible change policies?
By using our handy "No change fee" filter, that's how. Simply enter your travel dates, click the "Search" button, then tick the box under the "Flexible change policies" heading (to the left of your screen). Expedia makes it a cinch to find flexible, cheap flights to Oakland.
Which airlines fly to Oakland?
Let Cape Air get you there. This leading carrier operates 91 flights per month to Augusta State Airport (AUG), an Oakland gateway.
How can I find cheap tickets to Oakland?
You'll always pick up an unbeatable deal with Expedia, but our "flexible dates" feature makes it that much easier. Enter your preferred flight date, then click on the flexible dates link above to see a list of prices for nearby days. was the cheapest price for a flight to Oakland in the last seven days.
How much is a flight to Oakland?
If you were traveling one way from (), you could've locked in an affordable ticket for in the last seven days. Round-trip flights to Oakland ranged from only to over the same period.
What are the most popular airports to fly into in Oakland?
Start organizing your Oakland vacation by reserving a seat on one of the 91 flights every month to Augusta State Airport (AUG). This is the region's main entry point.
When is the cheapest time to fly to Oakland?
If you'd rather spend your money exploring the delights of Oakland rather than on flying there, take off early in the week. The cheapest day to fly is generally Tuesday, with Monday a close second. With many people traveling over the weekend, Saturday tends to have the costliest fares.
How much is a plane ticket to Oakland?
In the last seven days, flights to Oakland ranged from to .
What months are the cheapest to book a flight to Oakland?
An excellent month to book cheap fares to Oakland is February. Keep in mind that in the U.S, the most expensive time to purchase a ticket is the month of December.