Oakland Vacations

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Your Oakland Vacation

When a break in the city is calling, answer it with a vacation package to Oakland. The neighborhood of Blakeslee, which is good for nature, watersports and views, makes a terrific base for your adventures. Need some sightseeing tips for your trip to Oakland? Swallow Falls State Park and Herrington Manor State Park are two major attractions here. Check out Expedia's wide range of travel options and begin planning your ideal vacation to Oakland today.

Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
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Blakeslee

While there might not be top attractions in Blakeslee, you can explore the larger area and discover places like Deep Creek Lake and Deep Creek Lake State Park.

Find hotel + flight trips in Blakeslee

Oakland Essential Information

Language
English
Currency
U.S dollars
Population
1,900
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Herrington Manor State Park, Wolf Den Run State Park and Swallow Falls State Park

Oakland Hotel Deals

The Garrett Inn
The Garrett Inn
2.5 out of 5
17848 Garrett Highway, Oakland, MD
The price is $113 per night from Jun 9 to Jun 10
$113
$128 total
includes taxes & fees
Jun 9 - Jun 10
9.6/10 Exceptional! (319 reviews)
"Friendly staff , very clean , bathroom was small and sheets were a little rough. The room had a cozy farmhouse feel . I would definitely stay there again."

Reviewed on May 19, 2024

The Garrett Inn
Dog-friendly cabin with private hot tub, Ping-Pong & lake views
Dog-friendly cabin with private hot tub, Ping-Pong & lake views
Oakland
8.8/10 Excellent! (39 reviews)
Paradise heights
"Overall the property was great. Nice location. Pictures were accurate. Very clean property. Fully stocked kitchen. Minor things didn't work."

Reviewed on May 20, 2024

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Dog-friendly cabin with private hot tub, Ping-Pong & lake views
Riverside Suites
Riverside Suites
2 out of 5
1501 Maryland Hwy, Oakland, MD
Fully refundableReserve now, pay when you stay
The price is $134 per night from Jun 11 to Jun 12
$134
$153 total
includes taxes & fees
Jun 11 - Jun 12
9.2/10 Wonderful! (18 reviews)
"had a hard time getting into the office my wife took a gash out of her are on a piece of wood and had to request a band aide."

Reviewed on Jun 3, 2024

Riverside Suites
See all 866 properties in Oakland
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does an Oakland vacation package cost?
Explore the best of Oakland from as little as . We offer a great selection of hotels, flights and rental cars to suit every style and budget. Land even more discounts when you add some experiences or tours to your vacation package.
How do I get a cheap travel package to Oakland?
Find flights that suit your schedule, add a hotel room to your booking and see how much you save with an Oakland vacation package. It’s as simple as that! From hotels and flights to rental cars and activities, Expedia is where your cheap vacation begins. And with over 550 partner airlines and 1,000,000 hotels worldwide to choose from, you’ll never be short of choice.
Where should I stay in Oakland?
A trip to Oakland isn’t complete without paying a visit to Swallow Falls State Park, Herrington Manor State Park and Garrett Regional Medical Center. Spend your nights close to these top sights and make sightseeing easy.
What are the top hotels in Oakland?
If you’re thinking of staying in the Blakeslee neighborhood, some of your best options are Inn At Deep Creek and The Garrett Inn. The View is also a popular Oakland area. We recommend Oak Mar Motel or Grin Inn Bear It 3 Bedroom House if you prefer this part of town.
How far in advance should I book my Oakland vacation?
Reward yourself with the widest variety and the lowest prices by booking your trip to Oakland early. Airlines tend to advertise flight tickets anywhere up to a year prior to departure, so start your planning as soon as you can. That said, Expedia is committed to providing you with the best deals around, so it’s never a bad time to book your dream vacation!
What does an Expedia Oakland travel package include?
That depends on you. You can select from a range of Oakland packages, such as a rental car, flight and hotel. You can also book a flight with a hotel, or a flight with a rental car. Once you’ve made your booking, you can add the fun stuff like experiences and tours. Whatever your perfect Oakland break looks like, get ready to save!
What should I know before booking an Oakland travel package?
We already have low prices. However, you’ll score even better deals when you book your hotels, flights and car rentals together. With an Expedia travel package, you’ll get transparent pricing and tons of choice.
Can I choose my airline with an Oakland Expedia vacation package?
With a vacation package, you’re in charge. Whether you’re eager to fly to Oakland in coach or first class, simply pick from the available airline options. Expedia has access to more than 550 airline partners worldwide.
If I'm not able to travel, can I cancel my Oakland vacation package?
Yes you can, and we’re here to help. You may be able to change or cancel your Oakland vacation package for free within 24 hours of booking. However, you may incur a fee from your airline, hotel or car rental company if you booked more than 24 hours ago. If your travel plans suddenly change, look up our Customer Service Portal for more information.

Discover the most popular places to visit in Oakland

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Swallow Falls State Park

5/5(29 reviews)

Explore the great outdoors at Swallow Falls State Park, a lovely green space in Oakland. Amble around this family-friendly area's riverfront, or seek out the ski slopes.

Swallow Falls State Park
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Herrington Manor State Park

Explore the great outdoors at Herrington Manor State Park, a lovely green space in Oakland. While you're in the area, stroll along the lakeside.

Herrington Manor State Park
Image for Garrett Regional Medical Center

Garrett Regional Medical Center

Though Garrett Regional Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Oakland while you are here.

Garrett Regional Medical Center

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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.