Compare Oakland Cottage Rentals

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Featured Cottages in Oakland

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
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden. This smoke-free cottage also has a water dispenser.
The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek

The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek

Oakland MD
This cottage features a hot tub and a garden. This smoke-free cottage also has barbecue grills.
Pool
Hot Tub
Close to everything DCL, fun for the whole family

Close to everything DCL, fun for the whole family

Oakland MD
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Private Family Home w/ Deck, Porch + Forest Views!

Private Family Home w/ Deck, Porch + Forest Views!

3 out of 5
Oakland MD
This cottage features free WiFi in public areas and barbecue grills. Free parking is included with your stay.
Lucky 12 by Taylor Made Deep Creek

Lucky 12 by Taylor Made Deep Creek

3.5 out of 5
82 MOUNTAINVIEW CT Oakland MD
Guests staying at this cottage enjoy free WiFi in public areas, a hot tub, and barbecue grills. If you decide to drive, there's free parking.
Oakland Retreat ~ 13 Mi to Deep Creek Lake!

Oakland Retreat ~ 13 Mi to Deep Creek Lake!

3 out of 5
Oakland MD
Guests of this cottage have access to free WiFi in public areas. If you decide to drive, there's free parking.
Kitchen
Pet friendly
Bear on the Lake

Bear on the Lake

3 out of 5
19976 Garrett Hwy Oakland MD
Guests staying at this cottage enjoy a marina, free WiFi in public areas, and a library. You can put free parking to good use if you drive.
In The Middle by Taylor Made Deep Creek

In The Middle by Taylor Made Deep Creek

3 out of 5
426 Pergin Farm Road Oakland MD
Guests of this cottage have access to free WiFi in public areas. Free parking is included with your stay.
Somewhere by Taylor Made Deep Creek

Somewhere by Taylor Made Deep Creek

3 out of 5
3053 Lake Shore Drive Oakland MD
Guests staying at this cottage enjoy a marina, free WiFi in public areas, and a library. There's free parking if you drive. This smoke-free cottage also has barbecue grills.
Kitchen
Dryer
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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.

Hotel Options in Oakland

    Baja Motel

    Baja Motel

    1501 Maryland Hwy Oakland MD
    $125 nightly
    The price is $143 total per night from Jun 1 to Jun 2
    $143 total
    Jun 1 - Jun 2
    Total with taxes and fees
    9/10 Wonderful! (97 reviews)
    The Garrett Inn

    The Garrett Inn

    17848 Garrett Highway Oakland MD
    $124 nightly
    The price is $142 total per night from May 31 to Jun 1
    $142 total
    May 31 - Jun 1
    Total with taxes and fees
    9.6/10 Exceptional! (434 reviews)
    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
    8.2/10 Very Good! (75 reviews)

Cottages

Book a cottage in Oakland
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Oakland. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Oakland better.

Cottage apartments in Oakland range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Oakland
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Oakland and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Oakland cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Oakland. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Oakland Cottages essential information

Accommodation
27 Cottages
Lowest Price
$142
Highest Price
$143
Popular accommodation
Beautiful Lakeside Cottage on Quiet Street with Private Dock, Kayaks & Fire Pit, The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek, Close to everything DCL, fun for the whole family, Private Family Home w/ Deck, Porch + Forest Views!, Lucky 12 by Taylor Made Deep Creek, Oakland Retreat ~ 13 Mi to Deep Creek Lake!, Bear on the Lake, In The Middle by Taylor Made Deep Creek, Somewhere by Taylor Made Deep Creek