Oakland Vacations from $561

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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.
Sonesta Essential Fairmont

Sonesta Essential Fairmont

2.5 out of 5
Price was $639, price is now $561 per person
$561
per person
Feb 13 - Feb 16
found 23 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Morgantown (MGW)
8.2/10 Very Good! (1,001 reviews)
Room was nice just little on the small side. Hotel was lovely. Staff was very pleasant.

Reviewed on Jan 7, 2026

Lakeview Golf Resort Townhouses

Lakeview Golf Resort Townhouses

4 out of 5
Price was $970, price is now $820 per person
$820
per person
Feb 13 - Feb 16
found 23 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Morgantown (MGW)
6.8/10 (20 reviews)
after sunset it is very dark to drive and very few dining options no restaurant onsite

Reviewed on Dec 2, 2024

Lakeview Golf Resort

Lakeview Golf Resort

3.5 out of 5
Price was $703, price is now $616 per person
$616
per person
Feb 13 - Feb 16
found 23 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Morgantown (MGW)
6.2/10 (889 reviews)
Staff was great! Enjoyed the room upgrade.

Reviewed on Dec 20, 2025

Hampton Inn & Suites Morgantown / University Town Centre

Hampton Inn & Suites Morgantown / University Town Centre

2.5 out of 5
Price was $725, price is now $640 per person
$640
per person
Feb 13 - Feb 16
found 23 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Morgantown (MGW)
9.4/10 Exceptional! (837 reviews)
The front desk assistant was so kind an informative

Reviewed on Jan 8, 2026

Sonesta Essential Morgantown

Sonesta Essential Morgantown

2.5 out of 5
Price was $661, price is now $585 per person
$585
per person
Feb 13 - Feb 16
found 23 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Morgantown (MGW)
7.4/10 Good! (1,001 reviews)
Clean room. Friendly staff coffee and baked cookies!

Reviewed on Dec 29, 2025

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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

The Garrett Inn

The Garrett Inn

2.5 out of 5
17848 Garrett Highway Oakland MD
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $123 total per night from Jan 11 to Jan 12
$123 total
Jan 11 - Jan 12
Total with taxes and fees
9.6/10 Exceptional! (412 reviews)
Room was clean. Staff was nice. Parking was perfect

Reviewed on Dec 14, 2025

The Garrett Inn
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

Oakland MD
8/10 Very Good! (66 reviews)
The place was as described and close to a lot of thsijgs

Reviewed on Nov 13, 2025

Get rates
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Oakland MD
9.4/10 Exceptional! (15 reviews)
My family and I, including our dog Harley, had a great stay. Terry was an amazing host. We had a weather related issue and she was super responsive and extremely helpful. This was our second stay at this property. It fits our needs and was perfect for a few days of skiing and playing in the snow. ...

Reviewed on Jan 5, 2026

Get rates
Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp
See all 816 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

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Frequently asked questions

How much does an Oakland vacation package cost?
You'll find cheap prices from $561 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.

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