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.
Days Inn by Wyndham Brunswick Bath Area

Days Inn by Wyndham Brunswick Bath Area

2 out of 5
per person
Apr. 24 - Apr. 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Augusta (AUG)
7.8/10 Good! (1,001 reviews)
Quiet, clean and affordable

Reviewed on Jan. 25, 2025

OneSixtyFive

OneSixtyFive

3 out of 5
per person
Apr. 24 - Apr. 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Augusta (AUG)
9.6/10 Exceptional! (112 reviews)
A lovely restored 1839 mansion with beautiful individually furnished rooms and a fabulous ground floor bar, living room & dining room. Would definitely go back.

Reviewed on Nov. 13, 2024

Condos at Fairlawn

Condos at Fairlawn

3 out of 5
per person
Apr. 24 - Apr. 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Augusta (AUG)
7.6/10 Good! (27 reviews)
Golf package was not as good as it should have been

Reviewed on Sep. 6, 2024

Jordan Hotel

Jordan Hotel

3 out of 5
per person
Apr. 18 - Apr. 21
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Augusta (AUG)
8.6/10 Excellent! (284 reviews)
Ski in/ski out with ski licker was great

Reviewed on Jan. 26, 2025

Econo Lodge

Econo Lodge

2 out of 5
per person
Apr. 24 - Apr. 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Augusta (AUG)
7.2/10 Good! (322 reviews)
Was able to get checked in quickly and was informed of the amenities quickly and accurately.

Reviewed on Jan. 26, 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
9.8/10 Exceptional! (8 reviews)
Renter
"Very good stay."

Reviewed on Jan. 22, 2025

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Cozy Long Pond Cottage: private mooring & shared dock
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
The price is CA $201 per night from Feb. 2 to Feb. 3
CA $201
CA $385 total
includes taxes & fees
Feb 2 - Feb 3
10/10 Exceptional! (2 reviews)
The Perfect Stay
"The home is perfectly appointed and Diane has put a lot of thought into making your stay special. The view of the snow covered lake was beautiful. I can only imagine how wonderful it would be in the summer."

Reviewed on Jan. 19, 2025

Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore
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
See all 470 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 $865 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.