Oakland Holidays

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Our guide on 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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Mountainside

Mountainside might not have many top sights, but Deep Creek Lake and Deep Creek Lake State Park are two attractions nearby that you can check out.

Find hotel + flight trips in Mountainside

Our pick of the best Oakland Hotel Deals

The Garrett Inn
The Garrett Inn
2.5 out of 5
17848 Garrett Highway, Oakland, MD
Fully refundableReserve now, pay when you stay
The price is NZ$210 per night from 28 May to 29 May
NZ$210
per night
28 May - 29 May
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 19 May 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! (37 reviews)
Great Woodland Location
"Family and dogs enjoyed stay in this well-equipped cabin with a beautifiul working wood fireplace."

Reviewed on 7 Mar. 2024

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Dog-friendly cabin with private hot tub, Ping-Pong & lake views
Cozy, family-friendly, lakeview condo with gas grill & firepit
Cozy, family-friendly, lakeview condo with gas grill & firepit
Oakland
7.2/10 Good! (19 reviews)
lake view condo
"Cute for 2 people, but if you have trouble with steps look for a different location. Bed in main bedroom was VERY tall off the ground and hard to get into for a 5 foot tall woman. Clean property, but although sleeps 6 is stated in rental, it was comfortable for myself and my friend on our girls weekend. ..."

Reviewed on 1 May 2024

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Cozy, family-friendly, lakeview condo with gas grill & firepit
See all 863 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.

Frequently asked questions

How much does an Oakland holiday 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 holiday 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 holiday package. It’s as simple as that! From hotels and flights to rental cars and activities, Expedia is where your cheap holiday 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 Centre. 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 neighbourhood, 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 holiday?
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 holiday!
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 holiday package?
With a holiday 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 holiday package?
Yes you can, and we’re here to help. You may be able to change or cancel your Oakland holiday 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

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
Image for Herrington Manor State Park

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

If Garrett Regional Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Oakland.

Garrett Regional Medical Center

More holiday ideas

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.