Oakland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Marc Maheu
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    Save up to CA $775 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

Jordan Hotel

Jordan Hotel

3 out of 5
per person
Jun. 30 - Jul. 6
Roundtrip flight included
Montreal (YUL) to Augusta (AUG)
8.2/10 Very Good! (202 reviews)
Amenities are much nicer on paper than reality

Reviewed on Apr. 10, 2024

Mid-Town Motel

Mid-Town Motel

2 out of 5
per person
Jun. 30 - Jul. 6
Roundtrip flight included
Montreal (YUL) to Augusta (AUG)
8.8/10 Excellent! (88 reviews)
Absolutely adorable!

Reviewed on Feb. 19, 2024

Unity Sky Lodge

Unity Sky Lodge

3 out of 5
per person
Jun. 30 - Jul. 6
Roundtrip flight included
Montreal (YUL) to Augusta (AUG)
9/10 Wonderful! (16 reviews)
If you are going to Northern Maine, Jackman Maine you have to stay at Sky Lodge - Main Lodge is a gem, a beautiful time stood still lodge - we stayed in a cabin across the street - Oh My - every thing you need and more - just a very special place. Loved it.

Reviewed on Jun. 25, 2021

Prices and availability subject to change. Additional terms may apply.

Oakland Hotel Deals

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 (3 reviews)
Great Cabin!
"Everything we had hoped for. :)"

Reviewed on Oct. 22, 2023

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Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Cozy Long Pond cottage, private mooring and community beach. Bring your boat!
Cozy Long Pond cottage, private mooring and community beach. Bring your boat!
Rome
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Cozy Long Pond cottage, private mooring and community beach. Bring your boat!
Central Maine Apartment offering 4 Seasons of Fun.
Central Maine Apartment offering 4 Seasons of Fun.
Oakland
The price is CA $158 per night from Apr. 23 to Apr. 24
CA $158
CA $359 total
includes taxes & fees
Apr 23 - Apr 24
9.8/10 Exceptional! (25 reviews)
Good stay
"This was such an awesome place To stay. They had snacks and coffee. Enjoyed all the special touches!"

Reviewed on Oct. 9, 2023

Central Maine Apartment offering 4 Seasons of Fun.
See all 447 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.

Explore other types of vacation packages

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?
Custom build your Oakland vacation package from an affordable CA $1,114. Choose from any combination of flights, hotels and rental cars to craft the getaway you’ve been dreaming about for ages. Remember to add on a few experiences or tours!
How do I get a cheap travel package to Oakland?
Booking a hotel and flight together with Expedia won’t just save precious time — it’ll save you money too. An Oakland vacation package makes it a breeze to put together your ideal trip. With more than 550 airlines throughout the world to choose from, finding flights that fit your busy schedule won’t be a problem. In addition to that, we’ve got over 1,000,000 hotels globally to take your pick of. Now that’s what we call choice. Whatever your budget, Expedia puts the world within your reach.
Where should I stay in Oakland?
If you’ll be checking out Thomas College, maximize your time sightseeing and find a place to stay nearby. It’s one of the best attractions in Oakland.
What are the top hotels in Oakland?
When it comes to comfortable and convenient places to stay in Oakland, you can’t beat Lake Front With Amazing Sunsets On Mcgrath Pond. Browse its deals and pick up a bargain.
How far in advance should I book my Oakland vacation?
Reserving your flights early with Expedia means one less thing to worry about. Most carriers display prices up to a year in advance. This is often the cheapest time to book. If circumstances have left you booking late, last-minute deals to Oakland occasionally appear a few weeks before departure.
What does an Expedia Oakland travel package include?
From hotels and flights to rental cars, Expedia can help you put together an Oakland package that suits you. Heading off for a few weeks? Look into a hotel, rental car and flight bundle. If you’re taking a quick break, a hotel and airfare deal may suit you better. Activities can also be added once you’ve made your booking. Our travel packages make it easy to plan and save.
Can I choose my airline with an Oakland Expedia vacation package?
Yes — that’s one of the best things about an Expedia vacation package. You get to decide. We have more than 550 partner airlines globally, so you have loads of choice when putting together your Oakland getaway.
If I'm not able to travel, can I cancel my Oakland vacation package?
It’s difficult to predict what the future holds, so it’s comforting to know that you can cancel or change your Oakland vacation package. If your booking was made in the last 24 hours, you may be eligible for a refund. If it’s an older booking, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to find out more.

Discover the most popular places to visit in Oakland

Image for Tree Spirits

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.

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