Oakland Vacation Packages
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Your Oakland Vacation
When a fun city break is calling, answer it with a vacation package to Oakland. The neighborhood of Blakeslee, which is great for nature, watersports and views, makes a wonderful base for your adventures. If going to see the sights is a priority during your trip to Oakland, be sure to swing by popular attractions like Swallow Falls State Park and Herrington Manor State Park. No matter your travel plans or the size of your budget, putting together a tailored Oakland vacation is a cinch with Expedia.
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 Thousand Acres Lakeside Golf Course.
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.
Ready to book your vacation to Oakland?
Oakland Hotel Deals
Baja Motel
1501 Maryland Hwy Oakland MD
CA $156
CA $177 total
Sep 29 - Sep 30
includes taxes & fees
9/10 Wonderful! (136 reviews)
"na..............................."
Reviewed on Sep 28, 2026
The Garrett Inn
17848 Garrett Highway Oakland MD
Fully refundableReserve now, pay when you stay
CA $164
CA $195 total
Oct 29 - Oct 30
includes taxes & fees
Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp
Oakland MD
9.6/10 Exceptional! (23 reviews)
"It's hard to find a pet friendly place to stay where you and your pet feel comfortable so it was especially nice to find this place that seemed very welcoming for our pet. The host was wonderful and the lake view was marvelous."
Reviewed on Aug 30, 2026
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)
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.
Photo by Zhijiang Chen
Herrington Manor State Park
9.4/10 (12 reviews)
You can take time to visit Herrington Manor State Park during your travels to Oakland. While you're in the area, stroll along the lakeside.
Lower Deep Creek Heritage Conservation Fund Site
You can take time to visit Lower Deep Creek Heritage Conservation Fund Site during your travels to Oakland. While you're in the area, stroll along the lakeside.
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.
Broadford Park
Explore the great outdoors at Broadford Park, a lovely green space in Oakland. While you're in the area, stroll along the lakeside.
Ruth Enlow Library of Garrett County
After visiting Ruth Enlow Library of Garrett County, make a plan to see the other sights and activities in Oakland. While you're in the area, stroll along the lakeside.
Mountain Lake Park Town Hall
After visiting Mountain Lake Park Town Hall, make a plan to see the other sights and activities in Mountain Lake Park.
beach near Herrington Manor State Park
Why not spend a lazy afternoon at beach near Herrington Manor State Park during your trip to Oakland? While you're in the area, stroll along the lakeside.
Frequently asked questions
How much does an Oakland vacation package cost?
You can grab a vacation package to this top destination on Expedia. But how much your vacation to Oakland costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Oakland?
March, April and November are great times to look for cheap Oakland vacation packages. Choosing to travel in less busy months means you can generally find reduced prices on flights and hotels.
How many days is enough for Oakland?
With a well-planned itinerary, you can easily hit the main Oakland sights in a handful of days. But if you want to discover hidden gems or go on day tours, consider booking your Oakland vacation for longer.
How to find the best Oakland package deals?
Bagging a cheap Oakland package deal is easy with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can customize your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Oakland package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book an Oakland vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and stays individually. Better still, you can tailor your Oakland escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Oakland?
If you're planning a spontaneous Oakland vacation, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Oakland?
- Choose your dates: What you'd like to do in Oakland and your preferred season will help you decide when to travel.
- Figure out your budget: Make sure you have enough money to cover everything from dining out and transportation to flights and experiences. Your accommodations will probably be the largest expense during your trip to Oakland.
- Decide how long to go for: Now that you're more familiar with Oakland, you can work out the perfect length of your vacation. Put together a rough plan and give yourself enough time to get through everything on your must-do list.
- Bundle your accommodations and airfare: Once you've nailed down your dates and duration, book the right Oakland vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
