Oakland Vacation Homes

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Vacation Homes in Oakland

Don't see what you're looking for?
See all available properties in Oakland
View all properties
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.

Hotel Options in Oakland

    Baja Motel

    Baja Motel

    1501 Maryland Hwy Oakland MD
    $110 nightly
    The price is $126 total per night from Dec 12 to Dec 13
    $126 total
    Dec 12 - Dec 13
    Total with taxes and fees
    The Garrett Inn

    The Garrett Inn

    17848 Garrett Highway Oakland MD
    $111 nightly
    The price is $127 total per night from Nov 17 to Nov 18
    $127 total
    Nov 17 - Nov 18
    Total with taxes and fees
    Cove Creek Lodge

    Cove Creek Lodge

    19638 Garrett Hwy Oakland MD
    $176 nightly
    The price is $201 total per night from Nov 18 to Nov 19
    $201 total
    Nov 18 - Nov 19
    Total with taxes and fees

Oakland Vacation Homes

Book vacation homes in Oakland
Next time you take a group getaway top Oakland, don’t confine your friends and family to one or two hotel rooms. Instead, snag a deal on a full-sized house and get the best of both worlds. Vacation home rentals are perfect for families and large groups that want to live like locals on vacation. Whether you are searching for a villa that pulls out all the stops or a four-bedroom house to host the best summer vacation ever, Orbitz has a variety of Oakland vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.

Homes for every Oakland vacation
If you’re planning a vacation with a lot of people, you’ll want room to stretch out, and a rental home has plenty of space. Many vacation homes also come with everything you’ll need for a proper getaway, like kitchens with every gadget you can think of, along with updated furnishings, fancy spa tubs and balconies. You may even wind up in a rental home that has a sprawling backyard for barbecues, games and general relaxation. These rentals offer the added bonus of putting you right in the thick of things in Oakland; instead of going to a small hotel room at the end of a busy day, you’re going home.

Vacations are all about creating lasting memories, and a Oakland rental home makes it easy to create good ones. Whether you’re getting the college crowd back together or bringing along your folks and your kids, a trip to Oakland is sure to be a winner.

Oakland Vacation Homes essential information

Accommodation
469 Vacation Homes
Lowest Price
$126
Highest Price
$201
Popular accommodation
Modern Deep Creek Lakefront Home, Movie Theater, Hot Tub, 7BR/6BA, Sleeps 16, Mountain Escape | Hot Tub | Game Room | Fire Pit, Charming 2BR Townhouse - FIREPLACE - Oakland, Serene 3BR Lodge - THE Lake View - Oakland, Lakefront/Dock/Amazing views HotTub, Sisters Treehouse, Rustic 3BR Farmhouse - Fire Pit- Oakland, Deep Creek Gem w/ Views, Fire Pit & Pool Table, Captain's Quarters Deep Creek Log Cabin Oasis

More to Explore