Photo by KM Moore

Search Cottages in Oakland

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

Compare 14 Cottages in Oakland with updated reviews, rates, and availability.

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 | Microwave, dishwasher, cookware/dishes/utensils, paper towels

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 | Fridge, microwave, oven, stovetop

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!
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
Schmidt Lodge
House, Multiple Beds, Hot Tub | Private kitchen | Fridge, microwave, oven, stovetop

Schmidt Lodge

3.5 star property
Schmidt Lodge
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 | Fridge, microwave, oven, stovetop

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.
Don't see what you're looking for?
See all available properties in Oakland
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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,
Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village
Exterior

Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village

10.0 out of 10, Exceptional, (429)
"My expectations were exceeded. This cabin lives up to Deep Creek reputation; offering the most sought after amenities. The property was well-stocked with what you’d need daily. It was like staying a cabin from Animal Crossing, IYKYK."
Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village
Private cabin with hot tub, outdoor dining, and fireplace
Exterior

Private cabin with hot tub, outdoor dining, and fireplace

9.6 out of 10, Exceptional, (37)
"Views are amazing. Cabin is cozy and comfortable. Unfortunately the hot tub was not clean. Didn't want to bother anyone with the weather we were having. Would have been nice if we could have used it, but overall would definitely stay here again. Very close to just about anything you would want to do or need."
Private cabin with hot tub, outdoor dining, and fireplace
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.