Oakland Vacations from $492

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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.
Grand Summit Hotel

Grand Summit Hotel

3 out of 5
Price was $616, price is now $492 per person
$492
per person
Oct 22 - Oct 26
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Augusta (AUG)
8.2/10 Very Good! (272 reviews)
This is located in a ski- area and i was here in the off season. The hotel was conveniently located to several local pubs and restaurants. Family friendly but quiet i would visit again

Reviewed on Aug 17, 2025

Greenleaf Inn

Greenleaf Inn

2 out of 5
Price was $1,379, price is now $988 per person
$988
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
9.4/10 Exceptional! (9 reviews)
The location and view of this property was excellent. The staff gave good dining recommendations. The fire pit at night with s’mores was nice. We were given a nice bouquet of flowers at time of check in. The morning breakfast was a bit different. The kitchen was stocked with eggs, cream cheese, yogurt and condiments and pastries. You were responsible to make your own breakfast in the kitchen.

Reviewed on Jul 23, 2025

Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
Price was $697, price is now $518 per person
$518
per person
Oct 24 - Oct 28
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
8.2/10 Very Good! (1,011 reviews)
It was a nice place to stay! Quiet and clean. Agreeable personnel!

Reviewed on Aug 20, 2025

House near Acadia National Park

House near Acadia National Park

4 out of 5
Save 100% on your flight
Price was $1,648, price is now $1,286 per person
$1,286
per person
Oct 24 - Oct 28
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
9.8/10 Exceptional! (18 reviews)
This house was perfect for my girls trip. Close to bar harbor and Acadia national park. The home was clean and full of everything we need for our stay. Highly recommend this house! When I return to Bar Harbor I will be staying here again!

Reviewed on Jun 30, 2025

Jordan Hotel

Jordan Hotel

3 out of 5
Price was $618, price is now $493 per person
$493
per person
Oct 22 - Oct 26
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Augusta (AUG)
8.8/10 Excellent! (382 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

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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
9.4/10 Exceptional! (58 reviews)
"Beautiful lake, beautiful property, nice hiking"

Reviewed on Aug 16, 2025

Get rates
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.

Oakland
$226 nightly
The price is $246 total per night from Aug 21 to Aug 22
$246 total
Aug 21 - Aug 22
Total includes taxes and fees
9.8/10 Exceptional! (36 reviews)
"Cute!"

Reviewed on Aug 11, 2025

Central Maine Apartment offering 4 Seasons of Fun.
Cozy Farm Stay | Pet-Friendly & Peaceful

Cozy Farm Stay | Pet-Friendly & Peaceful

Oakland
$322 nightly
The price is $344 total per night from Sep 2 to Sep 3
$344 total
Sep 2 - Sep 3
Total includes taxes and fees
10/10 Exceptional! (4 reviews)
"The farmhouse was clean and charming. The kitchen was well-stocked. Kathleen was an excellent communicator. She went out of her way to make sure we were comfortable— including making a bonfire for smores! We loved getting to be with her sweet kitties and amazing donkeys, mule, and horse."

Reviewed on Aug 3, 2025

Cozy Farm Stay | Pet-Friendly & Peaceful
See all 520 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 $492 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.