
Oakland Vacations from $369
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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.
The Latest Oakland vacation packages
Price found within the past 48 hours. Click for updated prices.


Greenleaf Inn
Price was $2,004, price is now $1,703 per person
$1,703
per person
Nov 27 - Dec 1
found 22 hours ago
Roundtrip flight included
Denver (DEN) to Augusta (AUG)
8.8/10 Excellent! (11 reviews)
Great spot in Boothbay Harbor Maine. Walkable area to restaurants, boat excursions, shops and waterfront. Easy parking on premises. Check in time on our Expedia booked reservation states 2:00pm-4:00pm check in. We received a text message from the Inn manager letting us know check in was at 4:00pm and to send him a text when we were close to arrival. Other than the time difference check in was seamless and informative. Property manager was friendly and accommodating and walked us around the common areas of both buildings Admirals Quarters where the main office is and the greenleaf building where we stayed. They both have a shared kitchen area and living room dining room areas.
Our room was advertised as a private penthouse king with direct access to the sky deck. The room was on the small side but worked for our short stay and had fold out luggage storage which was convenient for our belongings. We had a small refrigerator as well. Bed was on the soft side which didn’t work well for me but was fine for my husband. Lots of light comes in early morning but we are early risers so no issue for us. The view out of the windows from the bed was beautiful. All upgrades were well done. Neighbors sliding door was right next to ours which accesses the shared deck. You could hear your neighbor as well when inside.
The property is set up with a sense of community most areas are shared including decks, chairs, grounds both inside and out. Typical of most Inn’s.
Reviewed on Aug 11, 2025


The Brunswick Hotel
Price was $806, price is now $692 per person
$692
per person
Dec 28 - Jan 1
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Augusta (AUG)
9.2/10 Wonderful! (852 reviews)
Lovely stay at the Brunswick Hotel. There were comfy beds and pillows and good water pressure in the shower. Our room was spacious. We were able to walk into town for dinner. The staff was very helpful when we left our sonicare toothbrush in the room to get it back to us. Breakfast was not included but was tasty.
Reviewed on Oct 22, 2025

Maine Evergreen Hotel, an Ascend Collection Hotel
Price was $578, price is now $507 per person
$507
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
9.2/10 Wonderful! (1,025 reviews)
Friendly staff, very clean and nice-sized room
Reviewed on Oct 23, 2025
Oakland Hotel Deals

Cozy Long Pond Cottage: private mooring & shared dock
Rome
9.8/10 Exceptional! (17 reviews)
Property is quiet, well laid out, and comfortable. Host is instantaneous with any concerns and/or recommendations. Lake can be seen from the property, and the beach is a short walk. Would definitely stay here again.
Reviewed on Sep 11, 2025

Sister A-Frame in Woods B
Oakland
$211 nightly
The price is $230 total per night from Oct 27 to Oct 28
$230 total
Oct 27 - Oct 28
Total with taxes and fees
10/10 Exceptional! (7 reviews)
Super clean, very new.
Reviewed on Oct 1, 2025

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Oakland
9.4/10 Exceptional! (64 reviews)
The stay was incredible! Better than I would’ve imagined from the listing :)
Reviewed on Oct 15, 2025
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.
Find the Best Oakland Vacation Packages
Oakland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Augusta State Airport (AUG) |
Population | 2,600 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | First Congregational Church, Colby College and Belgrade Lakes Chain |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.


















