Oakland Vacations from $343

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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.
Bingham Motor Inn

Bingham Motor Inn

2 out of 5
Save 100% on your flight
Price was $441, price is now $343 per person
$343
per person
Oct 15 - Oct 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Augusta (AUG)
8.4/10 Very Good! (33 reviews)
An older motel that has been renovated inside. Staff was helpful. Appreciate the door key code for check in. There’s quite a bit of road noise.

Reviewed on Sep 1, 2025

Newagen Seaside Inn

Newagen Seaside Inn

3.5 out of 5
Save 100% on your flight
Price was $1,048, price is now $683 per person
$683
per person
Oct 5 - Oct 10
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
9.4/10 Exceptional! (317 reviews)
We had to upgrade to get a tv in our room. And, the sink area in the "regular" room had no room. The upgraded room had two sinks with spacious counter room and a tv. Both were bright and clean but the upgraded met more of our expectations, especially considering the price.

Reviewed on Aug 27, 2025

Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
Save 100% on your flight
Price was $777, price is now $510 per person
$510
per person
Oct 15 - Oct 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Augusta (AUG)
8.2/10 Very Good! (1,011 reviews)
It wasn’t a fancy place, but they had a heated pool, even though the Jacuzzi was empty, and a nice breakfast the next day

Reviewed on Aug 30, 2025

Jordan Hotel

Jordan Hotel

3 out of 5
Save 100% on your flight
Price was $619, price is now $486 per person
$486
per person
Oct 23 - Oct 28
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Augusta (AUG)
8.8/10 Excellent! (389 reviews)
The hotel is in a beautiful spot with views of mountains all around. This is basically a ski spot and we were there in the summer. The staff was very friendly and helpful. Th pool is way too warm maybe for the ski crowd but not for hot summer days. We sampled only one meal, the. Breakfast buffet. It was poor to mediocre. Really disappointing for this quality hotel. There are some excellent eateries nearby, cheaper and better food.

Reviewed on Aug 18, 2025

Hilton Garden Inn Auburn Riverwatch

Hilton Garden Inn Auburn Riverwatch

3 out of 5
Price was $677, price is now $569 per person
$569
per person
Nov 12 - Nov 17
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Augusta (AUG)
8.8/10 Excellent! (1,002 reviews)
Was advertised as having a gym we are both Avis gym people. No gym but they would give you a pas to the ymca across the road in a very questionable part of Auburn many many homeless sleeping on park benches or on the River Walk not worth what we pais

Reviewed on Aug 25, 2025

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Oakland Hotel Deals

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

Oakland
Get rates
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Cozy Long Pond Cottage: private mooring & shared dock

Cozy Long Pond Cottage: private mooring & shared dock

Rome
Get rates
Cozy Long Pond Cottage: private mooring & shared dock
Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.

Oakland
$214 nightly
The price is $233 total per night from Sep 3 to Sep 4
$233 total
Sep 3 - Sep 4
Total with taxes and fees
Central Maine Apartment offering 4 Seasons of Fun.
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.

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Frequently asked questions

How much does an Oakland vacation package cost?
You'll find cheap prices from $343 on Expedia for your Oakland break. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Oakland costs.
What are the cheapest months to go to Oakland?
October, November and December are great times to look for cheap Oakland vacation packages. Traveling in less busy periods means you can generally find reduced prices on flights and accommodations.
How many days is enough for Oakland?
With a well-organized itinerary, you can easily visit the main Oakland sights in a few days. But if you prefer to discover lesser-known spots or take day trips, think about booking your Oakland vacation for longer.
How to find the best Oakland package deals?
Start your search for an Oakland package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Oakland package deal straight away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Oakland escape underway.
Is it cheaper to book an Oakland vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Oakland vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Oakland?
If you have your Oakland vacation dates finalized, book as soon as you can to grab some awesome deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Oakland vacation packages?
Set off on your perfect trip to Oakland with help from our Book Now, Pay Later vacations. There's no need to save like crazy or hold off until payday — we've partnered with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can spread the total cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stick to your budget and snap up bargains while they last.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.