Oakland Holidays
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Your Oakland Holiday
When a city break is calling, answer it with a holiday package to Oakland. The neighbourhood of Blakeslee, which is great for nature, watersports and views, makes a great base for your adventures. If taking in the sights is a must during your trip to Oakland, be sure to swing by big-name attractions like Swallow Falls State Park and Herrington Manor State Park. No matter your travel plans or budget, organising a tailored Oakland holiday is a cinch with Expedia.
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
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
Blakeslee 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.
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
Silver Ridge 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.
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.
Oakland Holiday
Oakland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 1,900 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | Herrington Manor State Park, Wolf Den Run State Park and Swallow Falls State Park |
Our pick of the best Oakland Hotel Deals
Baja Motel
1501 Maryland Hwy Oakland MD
Fully refundableReserve now, pay when you stay
AU$168
28 Sept - 29 Sept
includes taxes & fees
9/10 Wonderful! (127 reviews)
"Good clean room Some road noise Nice sleeping though"
Reviewed on 14 Sept 2026
The Garrett Inn
17848 Garrett Highway Oakland MD
AU$238
16 Sept - 17 Sept
includes taxes & fees
9.6/10 Exceptional! (459 reviews)
"Took a hot shower and the steam set off the fire alarm now they are charging me 300+ dollars even tho I called the front desk to let them know what happened"
Reviewed on 14 Sept 2026
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 30 Aug 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)
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.
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.
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.
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.
Veteran's Park
Veteran's Park is just one of the places to see in Oakland, so why not enjoy the other things to explore during your travels? While you're in the area, stroll along the lakeside.
Oakland Town Hall
After visiting Oakland Town Hall, make a plan to see the other sights and activities in Oakland. While you're in the area, stroll along the lakeside.
Glades Park
After visiting Glades Park, make a plan to see the other sights and activities in Oakland. While you're in the area, stroll along the lakeside.
Frequently asked questions
How much does an Oakland holiday 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 holiday 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 holiday packages and you could score some great off-season deals.
How many days is enough for Oakland?
With a well-organised 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 holiday 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 customise 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 travelling on a weekday, when prices are usually lower.
Is it cheaper to book an Oakland holiday as a package?
An Expedia holiday 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 holiday package to Oakland?
If you've got your Oakland holiday 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, favourite 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 holiday 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.
