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Search Cottages in Oakland

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Featured Cottages in Oakland and around

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

10.0 out of 10, Exceptional, (10)
"The Tiny House was an awesome getaway space for us and our pupper. The space is very clean and well maintained. We loved the little touches of dog treats and small bottles of champagne greeting us upon check-in. The neighborhood is very quiet and hot tub was perfect for stargazing in the cold weather. Jeff provided a lot of information on local eateries and attractions that made us feel even more at home."
The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek

Close to everything DCL, fun for the whole family

9.8 out of 10, Exceptional, (26)
"The house was very conveniently located to all of our favorite activities for one. The check-in process was smooth and we were even allowed to check in a couple hours early which helped tremendously. The house was perfect for a weekend getaway with all the amenities we needed, a cozy living room, comfortable beds, and even some fun board games. We were looking forward to using the firepit outside which looked great, but it was just too cold so blankets and couches were the next best thing. I...
Close to everything DCL, fun for the whole family

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

Lucky 12

3.5 star property
Lucky 12

Oakland Retreat ~ 13 Mi to Deep Creek Lake!

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

Deep Breath

3.5 star property
Deep Breath

Serendipity

3.5 star property
Serendipity

Fox Den

3.5 star property
Fox Den

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

3.0 star property
Hot Tub & Dogs Welcome: Secluded Oakland Gem

Schmidt Lodge

3.5 star property
Schmidt Lodge

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

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

Lakefront Maryland Home - Deck, Grill & Pool Table

3.0 star property
Lakefront Maryland Home - Deck, Grill & Pool Table

Charming 2-bedroom cottage 2 minutes from Deep Creek Lake

2.0 star property
Charming 2-bedroom cottage 2 minutes from Deep Creek Lake
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

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

10.0 out of 10, Exceptional, (16)
"The house was beautiful and clean and in a great location (and smelled great too!). We arrived on Thanksgiving day and were pleasantly surprised to find a decorated Christmas tree lit by the fireplace. The house is a very convenient 10-15 minute drive to Oakland or McHenry. We loved sitting in the hot tub while it was snowing. Our granddaughter enjoyed the arcade game upstairs and was really excited about the bunk bed room. We had a wonderful stay and would love to come back in the warmer...
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Lakefront/Dock/Amazing views HotTub

9.8 out of 10, Exceptional, (40)
"Great central location right off busy Garrett Highway. Nice amenities, could even suit 3 distinct groups with sleeping for 14. Walk out lower level directly to the lake, steps away. Nice hot tub, dock and kayaks. Fun game table and some arcade games if children come along. Enjoyable evening by the fire pit with s'mores! Easy to find, easy to book, responsive owners."
Lakefront/Dock/Amazing views HotTub

Dog-friendly cabin with private hot tub, Ping-Pong & lake views

8.6 out of 10, Excellent, (77)
"A beautifully furnished cabin so close to the amenities and state parks of Deep Creek Lake. So well stocked with everything you need "
Dog-friendly cabin with private hot tub, Ping-Pong & lake views
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?
Reserving a cottage in Oakland is as simple as entering your travel dates and selecting an ideal place for outdoor fun and relaxation. From ritzy retreats to budget-friendly properties and cottages that offer amenities like laundry facilities, Expedia has something for all tastes. As for awesome deals? We’ve have them as well!
How can I find cheap cottages in Oakland?
With Expedia’s filter tool, comparing cheap cottages in Oakland couldn’t be simpler. To discover stays that are very pocket friendly, narrow your search by amenities, star rating and budget.
What is there to do in Oakland near my cottage?
If you’re eager to make the most of your time in Oakland, find your way to Herrington Manor State Park. It’s a hit among travellers and locals alike.