Oakland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by KM Moore
  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

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.

Top Oakland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
River House Lodge
Cannon Hill Inn
Sonesta Essential Morgantown
Hotel Morgan a Wyndham Hotel
Sonesta Essential Fairmont

Where to stay in Oakland

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

Ready to book your vacation to Oakland?

 

Choose your dates

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
The price is CA $149 per night from Apr 15 to Apr 16
CA $149
CA $170 total
Apr 15 - Apr 16
includes taxes & fees
9.6/10 Exceptional! (425 reviews)
Check-in was smooth, parking spot reserved for room was nice. Clean and cute room.

Reviewed on Apr 2, 2026

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

Baja Motel

2 out of 5
1501 Maryland Hwy Oakland MD
Fully refundableReserve now, pay when you stay
The price is CA $153 per night from Apr 20 to Apr 21
CA $153
CA $175 total
Apr 20 - Apr 21
includes taxes & fees
9/10 Wonderful! (92 reviews)
The clerk was able to shift my room to the first floor at the last minute. I have a difficult time with stairs. It was extra nice.

Reviewed on Apr 12, 2026

Baja Motel
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.

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.