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
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.
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.
Paradise Point
If you're looking for some top things to see and do in Paradise Point and surrounding area, you can visit Deep Creek Lake and Deep Creek Lake State Park.
Silver Ridge
While Silver Ridge isn't home to many top sights, Deep Creek Lake and Deep Creek Lake State Park are some notable places to visit nearby.
The View
While there might not be top attractions in The View, you can explore the larger area and discover places like Deep Creek Lake and Deep Creek Lake State Park.
Find the Best Oakland Vacation Packages
Oakland Hotel Deals
Baja Motel
1501 Maryland Hwy Oakland MD
Fully refundableReserve now, pay when you stay
NT$3,703
NT$4,222 total
Oct 29 - Oct 30
includes taxes & fees
The Garrett Inn
17848 Garrett Highway Oakland MD
Fully refundableReserve now, pay when you stay
NT$5,030
NT$5,735 total
Oct 20 - Oct 21
includes taxes & fees
9.6/10 Exceptional! (464 reviews)
"When we arrived to the Garrett Inn, we were able to check in, and were given a key to the room, and told where to park (each room's number was plainly painted on the space for each room, however, due to the configuration of the parking lot vs the way the room's were situated, the parking spaces were ..."
Reviewed on 2026/10/19
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.
Stay near popular Oakland attractions
Swallow Falls State Park
9.8/10 (138 reviews)
Maryland's highest free-falling waterfall cascades 53 feet at Swallow Falls State Park. Wander through ancient hemlock forests and listen to the soothing rush of water along well-maintained trails.
Photo by Zhijiang Chen
Herrington Manor State Park
9.4/10 (12 reviews)
Nestled in Garrett County, Herrington Manor State Park features a pristine 53-acre lake for swimming, boating, and fishing. Reserve one of the 20 furnished log cabins for a woodland retreat with access to scenic trails.
Ruth Enlow Library of Garrett County
The Ruth Enlow Library has served as Oakland's literary hub since 1915, offering resources and community programs. Browse the diverse collection or join their seasonal reading events in this welcoming space.
Lower Deep Creek Heritage Conservation Fund Site
This 106.5-acre park offers tranquil trails through lush Maryland landscapes for both leisurely strolls and challenging hikes. Explore diverse ecosystems and seasonal beauty with comfortable shoes and water in hand.
Mount Nebo Wildlife Management Area
You can take time to visit Mount Nebo Wildlife Management Area during your travels to Oakland. While you're in the area, stroll along the lakeside.
Herrington Manor Recreation Area Reservoir
Nestled in Garrett County, Herrington Manor State Park offers a serene 53-acre lake and rustic log cabins. Paddle across calm waters in summer or glide through snowy trails on cross-country skis during winter months.
Oakland Golf Course
Enjoy a round of golf in Oakland at Oakland Golf Course. While you're in the area, stroll along the lakeside.
Broadford Park
Nestled around a scenic lake in Oakland, Broadford Park offers family-friendly swimming, boating, and trails. Rent a kayak for a peaceful afternoon or reserve a pavilion for a premium lakeside picnic experience.
Frequently asked questions
How much does an Oakland vacation package cost?
You'll find cheap prices on Expedia for your Oakland getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Oakland costs.
What are the cheapest months to go to Oakland?
You're likely to find lower rates and greater availability in March, April and November. Take a look at our cheap Oakland vacation packages and you could score some great off-season deals.
How many days is enough for Oakland?
With a well-organized itinerary, you can easily hit the most popular Oakland sights in a few days. But if you prefer to venture off the beaten track or go on day tours, consider booking your Oakland vacation for longer.
How to find the best Oakland package deals?
Finding a cheap Oakland package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most economical Oakland package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book an Oakland vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and hotels individually. Better still, you can tailor your Oakland escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Oakland?
If you've got your Oakland vacation dates locked in, book early to score some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Oakland?
- Choose the perfect time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to travel to Oakland.
- Plan your budget wisely: As well as the price of your stay, you should consider other expenses too. These include transportation, flights and food. Also, set aside a little extra for unexpected costs that could arise during your trip to Oakland.
- Set the duration of your trip: Start by making a list of all the attractions you'd like to get to in Oakland. Then, estimate how long you'll need at each, including any travel time.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to choose an Oakland vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
