Oakland Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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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
Aug 25 - Aug 29
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Augusta (AUG)
8.2/10 Very Good! (265 reviews)
Loved the gondola to the top of the mountain

Reviewed on Jul. 12, 2025

Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor

Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor

3 out of 5
per person
Aug 25 - Aug 29
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Augusta (AUG)
8.2/10 Very Good! (1,008 reviews)
Average hotel cross the board

Reviewed on Jul. 3, 2025

The Brunswick Hotel

The Brunswick Hotel

3 out of 5
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Augusta (AUG)
9.2/10 Wonderful! (796 reviews)
Beautiful Hotel! It was super peaceful!

Reviewed on Jul. 14, 2025

Newagen Seaside Inn

Newagen Seaside Inn

3.5 out of 5
per person
Aug 24 - Aug 28
found 12 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Augusta (AUG)
9.4/10 Exceptional! (298 reviews)
Abby and all the staff were all so helpful and welcoming! The Newagen Seaside Inn is so picturesque! We only spent one night there but wished we could have spent a week. The complimentary breakfast was delicious and the Tuesday evening lobster dinner was a great experience! Wished we lived closer! It was hands down the best place we stayed during our trip to New England!

Reviewed on Jul. 11, 2025

Mid-Town Motel

Mid-Town Motel

2 out of 5
per person
Aug 25 - Aug 29
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Augusta (AUG)
9/10 Wonderful! (159 reviews)
Very comfortable great location. We walked to everything.

Reviewed on Jul. 11, 2025

Ready to book your vacation to Oakland?

 

Choose your dates

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! (54 reviews)
East Pond Getaway
"Our family rented this camp on East Pond in Oakland for 5 days the week of July 4th. Check in was easy, and the property was as described. Kitchen is well stocked with pots and pans and cooking utensils. Camp included air conditioners which was great as we needed them on a few warm muggy nights. ..."

Reviewed on Jul. 10, 2025

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Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Oakland
6.6/10 (4 reviews)
Great cabin and location.
"Had a wonderful time. Loon Cove is exactly that, the Loons were everywhere. The cabin was comfortable and well appointed. I really enjoyed my stay. I have one criticism, the sheer curtains in the bedrooms and bathrooms need to have a privacy/darkening option. The sun comes up at 4:30am and the trash ..."

Reviewed on May 30, 2025

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Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
The Modern Maine Retreat
The Modern Maine Retreat
Oakland
9/10 Wonderful! (4 reviews)
Great space!
"Large house great for families. Plenty of parking space. Large bathrooms. Living room furniture is a little funky.One bedroom has to be walked through to get to master suite. Overall very pleasant stay."

Reviewed on Jul. 2, 2025

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The Modern Maine Retreat
See all 534 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 $803 on Expedia for your Oakland escape. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Oakland costs.
What are the cheapest months to go to Oakland?
The off-season is the best time to travel to Oakland if you're on a budget. Another tip for getting cheap Oakland vacation packages? Avoid visiting during public holidays and any major events.
How many days is enough for Oakland?
For your Oakland vacation, a handful of days will be enough to tour the top spots. Be sure to check out Common Street Arts --- it's one of the leading sights in this destination. If you're looking for more adventure, consider basing yourself here and heading off on some tours from Oakland.
How to find the best Oakland package deals?
Start your search for an Oakland package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Oakland package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Oakland getaway off to a flying start.
Is it cheaper to book an Oakland vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component individually. And you'll still get the freedom to create a tailored Oakland vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Oakland?
Secure amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Oakland trip.
How to plan a trip to Oakland?

  1. Choose when to travel: Check your schedule and get your bags packed. Your favourite time of year and the activities available will also help you decide when to vacation in Oakland.
  2. Set a budget: Factor in costs like flights, food and transportation when working out how much to set aside for your trip to Oakland. Then, select a hotel that fits your budget, whether that's an affordable stay or a deluxe getaway.
  3. Set the duration of your trip: Start by listing all the activities and sights you want to experience in Oakland. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalized Oakland vacation package.

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