Oakland Vacations

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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.

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Find the Best Oakland Vacation Packages

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 SAR 331 per night from Nov 30 to Dec 1
SAR 331
SAR 377 total
30 Nov - 1 Dec
includes taxes & fees
9.6/10 Exceptional! (407 reviews)
Cleanliness friendly staff

Reviewed on 17 November 2025

The Garrett Inn
Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip

Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip

Oakland MD
10/10 Exceptional! (51 reviews)
Great location, property, house and owner communication - would definitely stay there again!

Reviewed on 23 October 2025

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Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip
Baja Motel

Baja Motel

2 out of 5
1501 Maryland Hwy Oakland MD
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (84 reviews)
Cute little motel
Super cute outside! Clean room, dated. TV took a bit to get set up. Fridge was good. Sleep was not the best. We had noisy late night guests above us until about 2:30. A train came by overnight and honked twice. The road noise settles down late.

Reviewed on 20 October 2025

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Baja Motel
See all 819 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.

Discover the most popular places to visit in Oakland

Gorgeous fall day! Lots of people, but there was room to walk

Swallow Falls State Park

5/5(29 reviews)

You can take time to visit Swallow Falls State Park during your travels to Oakland. Stroll along the riverfront in this family-friendly area, or seek out the ski slopes.

Swallow Falls State Park

Frequently asked questions

How do I find cheap flights to Oakland that have flexible change policies?
Search for low-cost flights to Oakland, then tick the "No change fee" box directly under the "Flexible change policies" heading. From then on it's smooth sailing. We get that travel plans change and flexibility matters, so you can book with confidence with Expedia.
Which airlines fly to Oakland?
Whether you're headed somewhere new or rendezvousing at a favorite vacation haunt, the following airlines will fly you into or near Oakland:

  • American Airlines - 7,098 flights to or near Oakland each month, including 6,885 flights to Ronald Reagan Washington National Airport (DCA) and 212 to Washington Dulles Intl. Airport (IAD) per month.
  • United Airlines - 6,077 flights to or near Oakland each month, including 5,270 flights to Washington Dulles Intl. Airport (IAD) and 806 to Ronald Reagan Washington National Airport (DCA) per month.
  • Delta Air Lines - 1,659 flights to or near Oakland each month, including 1,304 flights to Ronald Reagan Washington National Airport (DCA) and 355 to Washington Dulles Intl. Airport (IAD) per month.

How can I find cheap tickets to Oakland?
For an amazing deal to Oakland, book well in advance. Also take advantage of Expedia's handy "flexible dates" feature at the top of your search results. This will show you prices for nearby days. In the last seven days, was the lowest price for a flight to Oakland.
How much is a flight to Oakland?
In the last seven days, return airfares to Oakland sold for as little as and reached a maximum of . For one-way trips taking off from (), the lowest amount paid during this same period was just .
What are the most popular airports to fly into in Oakland?
Jet off to Oakland and you'll have a few top airports to select from. Below are three of the region's busiest:

  • Ronald Reagan Washington National Airport (DCA) - 11,147 flights per month.
  • Washington Dulles Intl. Airport (IAD) - 6,388 flights per month.
  • Morgantown Municipal Airport (MGW) - 165 flights per month.

When is the cheapest time to fly to Oakland?
If you're not fixed on what date you travel to Oakland, try to depart early on in the week. The most affordable day to take off is generally Tuesday, closely followed by Monday. Saturday is typically the priciest day, with many vacationers preferring to fly on weekends.
How much is a plane ticket to Oakland?
In the last seven days, plane tickets to Oakland cost between and . Prices usually rise as your travel date nears, so land yourself a bargain today.
What months are the cheapest to book a flight to Oakland?
February is an excellent month to get your hands on a bargain fare to Oakland. Bear in mind that the costliest time to purchase tickets in the States isn't the middle of summer, but the month of December.
How long is a flight to Oakland?
Your flight to Oakland could be long or it could be short depending on where your point of origin is. Before you cram your laptop with movies and TV shows, check out the average flight times for these top domestic routes:

  • Boston, MA (BOS-Logan Intl.) to Ronald Reagan Washington National Airport (DCA) - 1 hour and 44 minutes
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Ronald Reagan Washington National Airport (DCA) - 1 hour and 46 minutes
  • Chicago, IL (ORD-O'Hare Intl.) to Ronald Reagan Washington National Airport (DCA) - 1 hour and 51 minutes