Book Exclusive Oakland Vacation Packages

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Oakland flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Cod Cove Inn, BW Signature Collection

Cod Cove Inn, BW Signature Collection

2.5 out of 5
Price was CA $1,063, price is now CA $960 per person
CA $960
per person
Feb 9 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Augusta (AUG)
Book a stay at this business-friendly hotel in Edgecomb. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fort Edgecomb State Historical Site and Lincoln County Jail Museum are located nearby.
Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

2.5 out of 5
Price was CA $1,359, price is now CA $1,142 per person
CA $1,142
per person
Feb 9 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Augusta (AUG)
Book a stay at this family-friendly hotel in Augusta. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Turnpike Mall and Kennebec Ice Arena are located nearby.

Top Oakland hotels deals

Classy AF Home Steps from Colby and Trails

Classy AF Home Steps from Colby and Trails

Oakland ME
Get rates
Stay at this vacation home in Oakland. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Quarry Road Trails and Tree Spirits are located nearby.
Kitchen
Washer
Sister A-Frame in Woods B

Sister A-Frame in Woods B

Oakland ME
The price is CA $167 per night
CA $167
CA $316 total
Dec 9 - Dec 10
includes taxes & fees
Book a stay at this family-friendly cabin in Oakland. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Tree Spirits and Belgrade Lakes Chain are located nearby.
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
The price is CA $196 per night
CA $196
CA $377 total
Dec 9 - Dec 10
includes taxes & fees
Book a stay at this golf guesthouse in Oakland. Enjoy free WiFi, a water park, and breakfast (surcharge). Popular attractions Tree Spirits and Belgrade Lakes Chain are located nearby.
Pet-friendly
Free WiFi
Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.

Oakland ME
The price is CA $140 per night
CA $140
CA $333 total
Jan 5 - Jan 6, 2026
includes taxes & fees
Stay at this apartment in Oakland. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Belgrade Lakes Chain and Tree Spirits are located nearby.
Kitchen
Washer
My Valhalla Farm

My Valhalla Farm

3.5 out of 5
379 Belgrade Rd Oakland ME
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Stay at this vacation home in Oakland. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tree Spirits and Belgrade Lakes Chain are located nearby.
Pool
Kitchen
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

Oakland ME
Get rates
Stay at this cabin in Oakland. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Tree Spirits and Belgrade Lakes Chain are located nearby.
Kitchen
Air conditioning
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See all available properties in Oakland
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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

Oakland Vacations

Ready for your next memorable adventure? Make sure you don't miss out on any excitement in Oakland by learning a few basics about it before you dash off.

Oakland is a neighborhood in Augusta, the state capital of Maine. It's about 17 miles (27 kilometers) to the north of the middle of town.

Ready to meet some of the locals? 19,000 people call Augusta home.

Places to visit in Oakland

Skiing is one of the most popular activities in Augusta and a superb excuse to get out and discover more of this exciting region. Cross-country skiing is a second activity to add to your must-do list.

Where do you fly into for Oakland?

Are you ready to kick-start your next fantastic vacation? Well, Oakland is approximately 50 miles (80 kilometers) from Bangor International Airport (BGR).

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 CA $960. 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 161 kilometers from Oakland.
Which airport is best for Oakland?
Bangor Intl. Airport (BGR), 80 kilometers northeast of downtown Oakland, is most likely where you'll arrive. Your other choices are Augusta State Airport (AUG) (26 kilometers away from central Oakland) and Knox County Regional Airport (RKD) (72 kilometers 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