Oakland Vacations from $432

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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.
Grand Summit Hotel
OneSixtyFive
Jordan Hotel
The Brunswick Hotel
Comfort Inn Ellsworth - Bar Harbor
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Oakland Hotel Deals

Cozy Long Pond Cottage: private mooring & shared dock

Cozy Long Pond Cottage: private mooring & shared dock

Rome ME
9.8/10 Exceptional! (20 reviews)
House had everything needed! Thanks.

Reviewed on Jan 3, 2026

Cozy Long Pond Cottage: private mooring & shared dock
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
$251 nightly
The price is $273 total per night from Jan 21 to Jan 22
$273 total
Jan 21 - Jan 22
Total with taxes and fees
9.8/10 Exceptional! (16 reviews)
Yes, thank you again Diane

Reviewed on Jan 11, 2026

Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore
Charming Guest House on Farm - Pets Welcome

Charming Guest House on Farm - Pets Welcome

Oakland ME
$345 nightly
The price is $367 total per night from Jan 21 to Jan 22
$367 total
Jan 21 - Jan 22
Total with taxes and fees
10/10 Exceptional! (7 reviews)
Very accommodating host. Loved everything about it. Highly recommend

Reviewed on Jan 5, 2026

Charming Guest House on Farm - Pets Welcome
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

Things to do near Oakland

Oakland, Maine, is perfect for outdoor and romantic getaways, offering stunning scenery and a variety of activities. Visitors can enjoy the beautiful lakeside park, engage in educational experiences, and explore the local ski fields. With options for exciting day trips and numerous recreational areas, there's plenty to do and see in Oakland, making it an ideal destination for all types of travelers.

Shopping

In Oakland, you'll find local gems like Liberty Tool Company and Morse's Sauerkraut for unique gifts. If you're up for a drive, the Turnpike Mall, 16 miles away, offers a vibrant shopping experience with various stores and entertainment options.

Recreation

Experience the serene beauty of Belgrade Lakes Golf, just 8 miles from Oakland, where you can enjoy a relaxing day on the greens. For excitement, visit Kennebec Ice Arena, 17 miles away, for thrilling ice skating. Finally, immerse yourself in culture at Johnson Hall, 22 miles from Oakland, with enchanting performances.

Adventure

Experience the breathtaking Kennebec River Rail Trail, a scenic hiking trail 16 miles from Oakland, perfect for outdoor enthusiasts. For winter sports, visit Eaton Mountain, also 16 miles away, offering thrilling skiing opportunities. Alternatively, enjoy the slopes at Titcomb Mountain Ski Area, located 23 miles from Oakland.

Nightlife

Oakland offers a cozy nightlife with charming local bars. Check out the Lakeside Tavern for a relaxed atmosphere and tasty pub fare. For live music and dancing, visit the Oakland Community Center, where you'll find local bands and a friendly crowd enjoying the night.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Oakland

Oakland, Maine, is a charming destination perfect for outdoor and romantic getaways. Visitors can explore historic colleges, scenic lakes, and event venues that highlight the area's culture and natural beauty. Notable attractions include the Oakland Arena, Museum, and Zoo, providing a variety of experiences for travelers seeking adventure and relaxation. Enjoy the picturesque landscapes and vibrant community that make Oakland a delightful spot to visit.

  • Colby College: Explore the beautiful campus of Colby College, a historic institution just 3 miles from Oakland. Immerse yourself in its vibrant culture, with stunning architecture and art exhibitions that reflect the rich history and academic excellence of this renowned liberal arts college.
  • Kennebec River: Enjoy the picturesque scenery along the Kennebec River, located 5 miles away. Perfect for outdoor enthusiasts, the river offers opportunities for kayaking, fishing, and picturesque walking trails, allowing you to connect with nature in a serene setting.
  • Waterville Opera House: Experience a night of entertainment at the Waterville Opera House, also 5 miles away. This historic venue hosts a variety of performances, providing a romantic atmosphere for enjoying live music and theater in the heart of the city.

Best time to go to Oakland

The best time to visit Oakland can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Oakland falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Oakland falls in January, visitor numbers are moderately low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January19.9°F (-6.7°C)Light RainMostly CloudyModerately LowSlightly Low
February21.6°F (-5.8°C)Light RainMostly CloudyAverageAverage
March29.8°F (-1.2°C)Light RainMostly CloudyAverageAverage
April42.1°F (5.6°C)Light RainMostly CloudyAverageAverage
May54.0°F (12.2°C)Light RainMostly SunnyAverageAverage
June61.9°F (16.6°C)Light RainMostly SunnyModerately HighAverage
July68.9°F (20.5°C)Light RainMostly SunnyModerately HighSlightly High
August67.6°F (19.8°C)Light RainMostly SunnyModerately HighSlightly High
September60.6°F (15.9°C)Light RainMostly SunnyAverageAverage
October49.3°F (9.6°C)Light RainMostly SunnyAverageSlightly High
November36.7°F (2.6°C)Light RainMostly SunnyModerately LowSlightly Low
December27.3°F (-2.6°C)Light RainMostly CloudyModerately LowSlightly Low

Tips to save on your trip to Oakland

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Oakland.
  • Consider traveling to Oakland during the low season (November to January) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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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Frequently asked questions

How much does an Oakland vacation package cost?
You'll find cheap prices from $432 on Expedia for your Oakland break. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Oakland costs.
What are the cheapest months to go to Oakland?
October, November and December are great times to look for cheap Oakland vacation packages. Traveling in less busy periods means you can generally find reduced prices on flights and accommodations.
How many days is enough for Oakland?
With a well-organized itinerary, you can easily visit the main Oakland sights in a few days. But if you prefer to discover lesser-known spots or take day trips, think about booking your Oakland vacation for longer.
How to find the best Oakland package deals?
Start your search for an Oakland package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Oakland package deal straight away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Oakland escape underway.
Is it cheaper to book an Oakland vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Oakland vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Oakland?
If you have your Oakland vacation dates finalized, book as soon as you can to grab some awesome deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Oakland vacation packages?
Set off on your perfect trip to Oakland with help from our Book Now, Pay Later vacations. There's no need to save like crazy or hold off until payday — we've partnered with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can spread the total cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stick to your budget and snap up bargains while they last.

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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.