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.
Greenleaf Inn
CA $997
per person
Oct 30 - Nov 3
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
9.6/10 Exceptional! (34 reviews)
This property is a MUST if you're in the Boothbay area! We really enjoyed everything about our stay! The room, the amenities, the service, the view, the treatment - it's DEFINITELY worth a visit!!
Reviewed on Aug 30, 2026
Ready to book your vacation to Oakland?
Oakland Hotel Deals
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Oakland ME
9.4/10 Exceptional! (77 reviews)
"A beautiful and serene location with great swimming and waterfront views. Highly recommend!"
Reviewed on Aug 29, 2026
Lakefront, dog-friendly cottage with screened porch, firepit, WiFi & lake access
Oakland ME
9.2/10 Wonderful! (15 reviews)
"I absolutely loved this cabin! The property was very well maintained and the cabin was incredibly clean and efficiently set up. Three things to consider - 1. The ladder to the loft is not dog-friendly if you have a medium to large size dog.2. The next door neighbors had 2 dogs off leash without a ..."
Reviewed on Jul 22, 2026
Cozy Long Pond Cottage: community access, private mooring & shared dock.
Rome ME
9.8/10 Exceptional! (28 reviews)
"Mala was a great host. We had a large group for a wedding in town, and there was ample space for all of us."
Reviewed on Aug 28, 2026
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.
Stay near popular Oakland attractions
Tree Spirits
You can enjoy a tasting or tour at Tree Spirits during your travels to Oakland. Make time to visit the shops and monuments while you're in the area.
Frequently asked questions
How much does an Oakland vacation package cost?
You'll find cheap prices from CA $997 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?
- 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.
- 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.
- 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.
- 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.
