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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Featured Cottages in Oakland and around

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

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

10.0 out of 10, Exceptional, (15)
"The Tiny House was exactly what we needed to get away for peace and the beauty of the outdoors. The house was equipped with everything we needed and some special treats that spoiled us during our stay"
The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek
Quaint dog-friendly retreat near the lake w/ wood stove, gas grill, & large yard
Outdoor dining

Quaint dog-friendly retreat near the lake w/ wood stove, gas grill, & large yard

9.0 out of 10, Wonderful, (42)
"Pros: Good location, quiet neighborhood with lots of deer, nice supply of start-up toiletries. Partial A/C was enough to keep house cool during heatwave. Comfortable master bed with its own A/C vent. Cons: Need a 4-wheel drive to navigate some steeple crush & run roads. House has small water tank, and owner wants renters to wait 30 minutes between shower use. Kitchen is very bare bones - bring your own cleaning supplies, foil, very few pans. Some safety concerns if need to take your pet outside...
Quaint dog-friendly retreat near the lake w/ wood stove, gas grill, & large yard
Close to everything DCL, fun for the whole family
Terrace/patio

Close to everything DCL, fun for the whole family

9.8 out of 10, Exceptional, (27)
"Conveniently close to Wisp Resort and very cozy place!"
Close to everything DCL, fun for the whole family
Oakland Retreat ~ 13 Mi to Deep Creek Lake!
House (3 Bedrooms) | Private kitchen

Oakland Retreat ~ 13 Mi to Deep Creek Lake!

3.0 star property
Oakland Retreat ~ 13 Mi to Deep Creek Lake!
Lucky 12
Exterior

Lucky 12

3.5 star property
Lucky 12
Deep Breath
House, Multiple Beds, Hot Tub | Private kitchen

Deep Breath

3.5 star property
Deep Breath
Private Family Home w/ Deck, Porch + Forest Views!
Terrace/patio

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

3.0 star property
Private Family Home w/ Deck, Porch + Forest Views!
Schmidt Lodge
House, Multiple Beds, Hot Tub | Private kitchen

Schmidt Lodge

3.5 star property
Schmidt Lodge
Hot Tub & Dogs Welcome: Secluded Oakland Gem
Interior

Hot Tub & Dogs Welcome: Secluded Oakland Gem

3.0 star property
Hot Tub & Dogs Welcome: Secluded Oakland Gem
Lakefront Maryland Home - Deck, Grill & Pool Table
Outdoor dining

Lakefront Maryland Home - Deck, Grill & Pool Table

3.0 star property
Lakefront Maryland Home - Deck, Grill & Pool Table
Fox Den
House, Multiple Beds, Hot Tub | Spa

Fox Den

3.5 star property
Fox Den
Convenient Cabin 3BR 1.5 BA, King Bed, Grill, more
Interior

Convenient Cabin 3BR 1.5 BA, King Bed, Grill, more

Convenient Cabin 3BR 1.5 BA, King Bed, Grill, more
Charming 2-bedroom cottage 2 minutes from Deep Creek Lake
Private kitchen

Charming 2-bedroom cottage 2 minutes from Deep Creek Lake

2.0 star property
Charming 2-bedroom cottage 2 minutes from Deep Creek Lake
Serendipity
House, Multiple Beds, Hot Tub | Private kitchen

Serendipity

3.5 star property
Serendipity
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.
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Other property types in Oakland

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

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

8.6 out of 10, Excellent, (43)
"We had a great time, the location was great and the place was clean"
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
Dog-friendly house on the lake, central AC, & EV charger
View from property

Dog-friendly house on the lake, central AC, & EV charger

8.6 out of 10, Excellent, (50)
"The inside of the house was very clean and very tastefully decorated. The view was out of this world! The one thing that we would like to note, is that prior guests left large dog poop on the balcony that was not cleaned up by the staff. In addition, there was a bag of dog poop left in front of the home. Everything else was excellent and we still appreciate it being dog-friendly."
Dog-friendly house on the lake, central AC, & EV charger
Modern house on the lake with private dock, hot tub, air hockey & central AC
TV, fireplace

Modern house on the lake with private dock, hot tub, air hockey & central AC

7.8 out of 10, Good, (17)
"Nice spot. A little loud with the highway and would have liked to have been able to use hottub but it didnt look clean. Otherwise great spot, super convenient for popping around the lake area."
Modern house on the lake with private dock, hot tub, air hockey & central AC
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.

Frequently asked questions

Why book your cottage in Oakland with Expedia?
We think a getaway should be a piece of cake, so if you’re on the lookout for cottages in Oakland at a competitive price, Expedia has got you covered. Keep costs down and select a thrifty option far away from the hustle and bustle, or splurge on an upscale cottage to pamper your loved ones.
How can I find cheap cottages in Oakland?
With Expedia’s handy filter tool, booking cheap cottages in Oakland couldn’t be simpler. To find stays that’ll make your wallet smile, refine your search results by star rating, amenities and budget.
What is there to do in Oakland near my cottage?
If you’re ready to fill up your itinerary in Oakland, make tracks to Swallow Falls State Park. It’s a winner among travellers and locals alike.