Deals on vacations and trips to Oakland

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Top Oakland hotels deals

Sister A-Frame in Woods B

Sister A-Frame in Woods B

Oakland ME
$210 nightly
The price is $228 total per night
$228 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This cabin features a garden, laundry facilities, and barbecue grills. There's fun for all ages with a playground and an arcade/game room.
Kitchen
Washer
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 ME
$250 nightly
The price is $272 total per night
$272 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This guesthouse features a water park, limo/town car service, and a garden. Families will appreciate the playground and barbecue grills.
Pet friendly
Free WiFi
Cozy Long Pond Cottage: private mooring & shared dock

Cozy Long Pond Cottage: private mooring & shared dock

Rome ME
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This vacation home features a water park, laundry facilities, and barbecue grills.
Kitchen
Washer
My Valhalla Farm

My Valhalla Farm

3.5 out of 5
379 Belgrade Rd Oakland ME
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This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls, pet-sitting services, and litter boxes. There's a seasonal outdoor pool on site, and laundry facilities and barbecue grills are also offered.
Pool
Kitchen
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

2 out of 5
Oakland ME
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Charming apartment with waterfront access, modern comforts, and lakeside firepit

Charming apartment with waterfront access, modern comforts, and lakeside firepit

Oakland ME
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This apartment includes a garden and barbecue grills.
Kitchen
Washer
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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.

Tree Spirits

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 . 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.

Photos of local treasures

Browse Oakland vacation photos for more inspiration

Photo by Marc Maheu
Photo by Marc Maheu

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