Oakland Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by KM Moore

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.

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Default Image

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 hotels in Mountainside

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

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
$88 nightly
The price is $101 total per night from Nov 25 to Nov 26
$101 total
Nov 25 - Nov 26
Total with taxes and fees
9.6/10 Exceptional! (407 reviews)
Cleanliness friendly staff

Reviewed on Nov 17, 2025

The Garrett Inn
Baja Motel

Baja Motel

2 out of 5
1501 Maryland Hwy Oakland MD
Fully refundableReserve now, pay when you stay
$180 nightly
The price is $206 total per night from Nov 26 to Nov 27
$206 total
Nov 26 - Nov 27
Total with taxes and fees
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 Oct 20, 2025

Baja Motel
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 Oct 23, 2025

Get rates
Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip
See all 820 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.

Find the Best Oakland Vacation Packages

Oakland Essential Information

Language
English
Currency
U.S dollars
Population
1,900
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Herrington Manor State Park, Wolf Den Run State Park and Swallow Falls State Park

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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?
If you're hoping to book a cheap Oakland vacation package, consider traveling in July, August and December. You're likely to find better rates on airfares and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Oakland?
Usually, a handful of days is enough to tick off the major attractions during your Oakland vacation. But if you'd like to have time to unwind or go on day tours, consider extending your trip.
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.
Does Expedia offer Book Now, Pay Later Oakland vacation packages?
Your Oakland break is meant to be an escape from your daily routine, not a source of money worries. So to allow you a little more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

Explore a world of travel with Expedia

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