Oakland Vacation Packages 2026 from $788

Oakland flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

The Brunswick Hotel

$788

per person

Jul 5 - Jul 9

found 6 hours ago

Roundtrip flight included

Dallas (DFW) to Augusta (AUG)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, a terrace, and a lobby fireplace are also offered.

Bluebird Ocean Point Inn

Ocean Point

$1,097

per person

Jun 24 - Jun 30

found 4 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Augusta (AUG)

This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.

Topside Inn

$1,009

per person

Jun 26 - Jun 29

found 19 hours ago

Roundtrip flight included

Chicago (ORD) to Augusta (AUG)

A bar/lounge and a garden are featured at this hotel, along with free self parking. Guests will appreciate free perks like full breakfast and WiFi in public areas. A snack bar/deli, luggage storage, and concierge services are also on offer.

Smuggler's Cove Inn

Save 100% on your flight

$1,183

per person

Jul 11 - Jul 18

found 12 hours ago

Roundtrip flight included

Chicago (ORD) to Augusta (AUG)

A private beach and an outdoor pool are featured at this hotel. Enjoy a meal from the restaurant and perks like free on-the-go breakfast and free self parking. A bar/lounge, a terrace, and a garden are also provided.

OneSixtyFive

$851

per person

Jun 27 - Jul 2

found 9 hours ago

Roundtrip flight included

Chicago (ORD) to Augusta (AUG)

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. Luggage storage and concierge services are also provided.

Top Oakland hotels deals

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

Oakland ME

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This cottage featured laundry facilities and barbecue grills.

Kitchen

Dryer

Cozy Long Pond Cottage: community access, private mooring & shared dock.

Rome ME

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This vacation home featured laundry facilities and barbecue grills.

Kitchen

Washer

Pool, fire pit & dogs welcome, close to lakes and trails - Maine Farm Getaway

Oakland ME

$338 nightly

$359 total

May 5 - May 6

Total with taxes and fees

This vacation home features an outdoor pool and a hot tub. Laundry facilities and barbecue grills are also provided.

Pool

Hot Tub

Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College

Rome ME

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This cottage features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore

Oakland ME

$394 nightly

$430 total

May 5 - May 6

Total with taxes and fees

This guesthouse features limo/town car service, a garden, and barbecue grills.

Pet friendly

Free WiFi

The Cottage at Whispering Pines - Short Stroll to the Village!!!

Rome ME

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This cottage features laundry facilities.

Washer

Dryer

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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.

Popular places to visit

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 are vacation packages to Oakland?

You might be pleasantly surprised — you could find yourself in Oakland for as little as $788. Let Travelocity save you time and money with our amazing vacation packages. With hotels, flights and experiences all ready to be snapped up, why put it off?

How long should my Oakland vacation be?

Many travelers choose to stay around 8 nights in Oakland. But what's right for them mightn't be right for you. Whether you opt to stay for a couple of days or a couple of weeks, you'll love discovering all the wonderful things that this place has to offer.

Where can I get the best vacation package deals for Oakland?

You'll come across a terrific range of Oakland package deals on Travelocity. With as many as 400 partner airlines and 1,000,000 properties worldwide, arranging the ultimate escape will be easy.

Why should I purchase my Oakland vacation package with Travelocity?

Whether you're planning a weeks-long vacation or a last-minute escape, we have plenty of alluring destinations to choose from at a good price. In addition, we provide 24/7 assistance, top-notch service and a Price Match Guarantee. Save yourself time and money and reserve your dream vacation today.

Can I save money on my Oakland car rental if I combine it with my hotel or flight?

You most certainly can — bundle your hotel, flight and car into an Oakland vacation package and you'll save a ton. With so many places to explore in and around Oakland, that set of wheels will make exploring easy. Once you've slid into the driver's seat, put the stereo on and make your way to Franconia Notch State Park, a renowned attraction roughly 100 mi from Oakland.

Which airport is best for Oakland?

Bangor Intl. Airport (BGR), 50 mi northeast of downtown Oakland, is most likely where you'll arrive. Your other choices are Augusta State Airport (AUG) (16 mi away from central Oakland) and Knox County Regional Airport (RKD) (45 mi away from central Oakland).

Where should I stay when visiting Oakland?

If you're after somewhere to base yourself, take a look at the Cozy Long Pond cottage, private mooring and community beach. Bring your boat!. It's the top choice for many visitors.