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.
Grand Summit Hotel

Grand Summit Hotel

3 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Augusta (AUG)
8/10 Very Good! (234 reviews)
The staff were nice. The hotel rooms need some updating. The gift shop needs to be open for more days and hours.

Reviewed on Mar. 6, 2025

Spruce Point Inn

Spruce Point Inn

3.5 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Augusta (AUG)
8.8/10 Excellent! (344 reviews)
My daughter and I loved the Spruce Point Inn soooo much! It was a perfect weekend getaway spot to build our.relationship in peace and serenity and awe!

Reviewed on Oct. 14, 2024

Jordan Hotel

Jordan Hotel

3 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Augusta (AUG)
8.6/10 Excellent! (284 reviews)
Great property with lots of nice amenities but it’s time for an update, the rooms are looking tired. Also parking situation is horrible, nothing available in front of the hotel, we had to walk 10 minutes to get our car and it was 0 degrees/snowing out

Reviewed on Mar. 3, 2025

Maine Evergreen Hotel, Ascend Hotel Collection

Maine Evergreen Hotel, Ascend Hotel Collection

2.5 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Augusta (AUG)
9.2/10 Wonderful! (1,005 reviews)
Clean and tv worked well.

Reviewed on Feb. 28, 2025

Ready to book your vacation to Oakland?

 

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Oakland Hotel Deals

Cozy Long Pond Cottage: private mooring & shared dock
Cozy Long Pond Cottage: private mooring & shared dock
Rome
9.6/10 Exceptional! (11 reviews)
Trip
"Cute place"

Reviewed on Mar. 3, 2025

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Cozy Long Pond Cottage: private mooring & shared dock
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
Rome
9.6/10 Exceptional! (10 reviews)
A lovely place for a weekend
"We spent a beautiful fall weekend at Cedar Estates, the house was clean and very well equipped, as described in the listing. We enjoyed a nice campfire on Saturday night at the fire pit. Our 2 dogs really enjoyed exploring and running outside as well! Clean sheets and towels, hot water - lovely ..."

Reviewed on Oct. 23, 2024

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Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
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! (49 reviews)
Stay
"It was OK."

Reviewed on Oct. 23, 2024

Get rates
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
See all 477 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does an Oakland vacation package cost?
You’ll find cheap prices from CA $890 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?
To score cheap Oakland vacation packages, plan your trip outside of peak periods such as public holidays. You’ll generally find better availability and lower prices in the off-season or when it’s less busy.
How many days is enough for Oakland?
Generally, a handful of days is enough to visit the major sights during your Oakland vacation. However, if you prefer to have time to rest or take day trips, consider extending your trip.
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.
How to plan a trip to Oakland?

  1. Choose when to go: Check your calendar and get your bags packed. Your favorite season and the type of activities available will also help you decide when to visit Oakland.
  2. Set a budget: Consider costs such as flights, meals and transportation when working out how much to put aside for your trip to Oakland. Then, pick a property that fits your budget, whether that’s an economical option or a deluxe retreat.
  3. Set the duration of your trip: Start by making a list of all the attractions and activities you’d like to experience in Oakland. Then, estimate how long you’ll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Oakland vacation package.

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