Oakland Vacations from $1,241

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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.

The Latest Oakland vacation packages

Price found within the past 48 hours. Click for updated prices.
Paradise Found

Paradise Found

3.5 out of 5
The View
Price was $1,410, price is now $1,241 per person
$1,241
per person
Jan 2 - Jan 5
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Morgantown (MGW)
No reviews
Under the Stars

Under the Stars

3.5 out of 5
Mountainside
Save 100% on your flight
Price was $4,707, price is now $4,075 per person
$4,075
per person
Jan 2 - Jan 5
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Morgantown (MGW)
8/10 Very Good! (1 review)
Grand Chestnut Lodge

Grand Chestnut Lodge

3.5 out of 5
Save 100% on your flight
Price was $3,669, price is now $3,193 per person
$3,193
per person
Jan 2 - Jan 5
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Morgantown (MGW)
No reviews
St. Bart's Retreat

St. Bart's Retreat

4 out of 5
Save 100% on your flight
Price was $2,351, price is now $2,047 per person
$2,047
per person
Jan 2 - Jan 5
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Morgantown (MGW)
No reviews
VVS - Very Very Special

VVS - Very Very Special

3.5 out of 5
Save 100% on your flight
Price was $3,296, price is now $2,872 per person
$2,872
per person
Jan 2 - Jan 5
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Morgantown (MGW)
No reviews
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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.

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

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

Baja Motel

Baja Motel

2 out of 5
1501 Maryland Hwy, Oakland, MD
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $142 total per night from Oct 14 to Oct 15
$142 total
Oct 14 - Oct 15
Total with taxes and fees
8.8/10 Excellent! (79 reviews)
"10 out of 10. Clean, large room. Very nice staff"

Reviewed on Sep 28, 2025

Baja Motel
The Garrett Inn

The Garrett Inn

2.5 out of 5
17848 Garrett Highway, Oakland, MD
$108 nightly
The price is $123 total per night from Oct 13 to Oct 14
$123 total
Oct 13 - Oct 14
Total with taxes and fees
9.6/10 Exceptional! (403 reviews)
"Close proximity to Deep Creek Lake. Great accommodation at a reasonable cost."

Reviewed on Oct 1, 2025

The Garrett Inn
New: Lakefront Luxury Home with Private Indoor Heated Pool!

New: Lakefront Luxury Home with Private Indoor Heated Pool!

Oakland
9.4/10 Exceptional! (11 reviews)
"House was great! Large enough for our big group"

Reviewed on Jul 27, 2025

Get rates
New: Lakefront Luxury Home with Private Indoor Heated Pool!
See all 861 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.

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

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Frequently asked questions

How much does an Oakland vacation package cost?
You'll find cheap prices from $1,241 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

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.