Compare Oakland Vacation Rentals

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Oakland Rentals

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
8.8 mi from city center
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Deep Creek Retreat | 5BR + Hot Tub + Game Room

Deep Creek Retreat | 5BR + Hot Tub + Game Room

Oakland MD
8.49 mi from city center
At this vacation home, guests have access to a sauna, a hot tub, and an arcade/game room. Additional amenities include laundry facilities and barbecue grills.
Dog Friendly Cabin in the Woods, Hot Tub & Firepit

Dog Friendly Cabin in the Woods, Hot Tub & Firepit

Oakland MD
3.26 mi from city center
Guests staying at this cabin enjoy a hot tub and laundry facilities.
Hot Tub
Kitchen
The winter is coming !!!

The winter is coming !!!

Oakland MD
8.18 mi from city center
$414 nightly
The price is $439 total per night
$439 total
Jul 24 - Jul 25
Total with taxes and fees
Guests of this cabin enjoy a hot tub, an arcade/game room, and laundry facilities.
Serene Mountain Escape: Hot Tub, Foosball, Views

Serene Mountain Escape: Hot Tub, Foosball, Views

Oakland MD
6.46 mi from city center
This vacation home features a hot tub, an arcade/game room, and laundry facilities. Other amenities at this family-friendly vacation home include barbecue grills and a garden.
Sisters Treehouse

Sisters Treehouse

Oakland MD
8.77 mi from city center
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Beautiful Lakeside Cottage on Quiet Street with Private Dock, Kayaks & Fire Pit

Beautiful Lakeside Cottage on Quiet Street with Private Dock, Kayaks & Fire Pit

Oakland MD
7.4 mi from city center
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden. This smoke-free cottage also has a water dispenser.
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
8.8 mi from city center
Guests of this vacation home enjoy features like a gym, a hot tub, and an arcade/game room. Other amenities at this family-friendly vacation home include laundry facilities, a garden, and barbecue grills.
New! Mountain Lake Access Home w/ Hot Tub!

New! Mountain Lake Access Home w/ Hot Tub!

Oakland MD
8.72 mi from city center
This vacation home features a hot tub and barbecue grills.
That Special Place

That Special Place

Oakland MD
8.17 mi from city center
$462 nightly
The price is $490 total per night
$490 total
Aug 11 - Aug 12
Total with taxes and fees
At this cabin, guests have access to features like laundry facilities. This smoke-free cabin also has barbecue grills.
Timroc II, FIVE STAR REVIEWS! SHORT WALK TO THE LAKE, HOT TUB! PRIVATE 2 ACRES!

Timroc II, FIVE STAR REVIEWS! SHORT WALK TO THE LAKE, HOT TUB! PRIVATE 2 ACRES!

Oakland MD
6.98 mi from city center
Guests of this chalet enjoy a hot tub, an arcade/game room, and laundry facilities. Other amenities at this family-friendly chalet include barbecue grills and a garden.
Peaceful 2-bedroom cabin in charming Oakland perfect for relaxing getaway

Peaceful 2-bedroom cabin in charming Oakland perfect for relaxing getaway

Oakland MD
6.62 mi from city center
At this cabin, guests have access to features like laundry facilities. This smoke-free cabin also has a garden.
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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 Large Group Rentals

How to Book Vacation Rentals in Oakland



🏠 What is the best price for Oakland vacation rentals?

Oakland vacation rentals range in price, starting at $439 per night.


🏠 What types of vacation rentals in Oakland can I rent?

Orbitz offers a wide range of Oakland rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Oakland condo rentals.


🏠 Is it free to cancel my Oakland vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Oakland vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Oakland. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Oakland?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Oakland apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Oakland?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Oakland package deals will get you even more savings.