Oakland, MD Vacation Homes from AED 566

A river flowing through a forest with a waterfall.

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Our top choices for Oakland vacation homes

Luxor Mountaintop Cabin-Castle at Deep Creek Lake

Oakland

AED 4,659 total

includes taxes & fees

29 Jul - 30 Jul

Serene 3BR Lodge - THE Lake View - Oakland

Oakland

AED 2,775 total

includes taxes & fees

12 Aug - 13 Aug

Rustic 3BR Farmhouse - Fire Pit- Oakland

Oakland

AED 1,396 total

includes taxes & fees

29 Jul - 30 Jul

Charming 2BR Townhouse - FIREPLACE - Oakland

Oakland

Steve L.

Rustic 3BR Cabin - HOT TUB - Oakland

Paradise Point

AED 1,960 total

includes taxes & fees

9 Aug - 10 Aug

Wisp View Retreat, Hot tub

Accident

AED 3,039 total

includes taxes & fees

2 Aug - 3 Aug

Rustic 3BR Cabin - HOT TUB - McHenry

McHenry

Ashley C.

AED 2,147 total

includes taxes & fees

9 Aug - 10 Aug

Minutes from LAKE - Ranch - Pets & Kids welcome - Secluded

McHenry

Jessica O.

AED 1,888 total

includes taxes & fees

28 Jul - 29 Jul

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Top Oakland Hotel Reviews

Baja Motel

10/10 Excellent

"Baja provided another great weekend stay for us at Deep Creek. It was a spacious, clean room with a great restaurant next door. After 3 stays this year, we continue to be impressed!"

Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing

10/10 Excellent

"David was great! The check in process and house information were easy to follow. He was always available when needing to communicate and responded within reason. The house was clean and it was the perfect set up to celebrate my friend’s bachelorette! We had a great time and recommend staying with them!"

Charming Dog Friendly Cottage w/ Dock & Fire Pit

10/10 Excellent

"Red cottage was a lovely place to stay! Property was clean and well appointed. The enclosed room had great views of the lake. Dogs loved watching the chipmunks outside. Wonderful to have the boat dock. Even without a boat or going out on the water, it was still nice to have a place to sit by the lake. One thing to note- if any of your guests have accessibility issues, they may have trouble, as there are stairs and there is little level lot outside."

New! Mountain Lake Access Home w/ Hot Tub!

8/10 Good

"We had a nice stay at this property with 6 adults and 3 children 11 and up. There was plenty of room for our group. The deck is lovely for a nice relaxing afternoon with a few cocktails, music and views of the lake through the trees. The dining table is a perfect size for family game nights and we enjoyed the air hockey, pool and foosball. The bedframes in the upstairs bedroom could use oiled or tightened as it squeaks very loudly anytime you move or roll over. The yard is mostly hill and it is difficult to get from the front of the property to the back from the outside. The fire pit is uneven and sloped, but we were able to enjoy it. Hot tub is a little bit beat up but everything works and the jets are nice and strong. The kitchen is well stocked with everything you need as well as an abundance of silver wear and utensils. Overall, this was a decent place to stay and our family enjoyed our long weekend."

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

10/10 Excellent

"Would absolutely recommend this house if you're considering a Deep Creek weekend. Check in process was extremely smooth, everything was clean and tidy when we arrived. Communication with the host was excellent from the time we booked until after we checked out. Our dog also loved it. I'm not entirely sure I've seen him more relaxed, although this was his first actual vacation that he's been on with us. Really easy walk to the lake side for fishing and swimming off the dock.If you have any questions about it, reach out. Terri was an excellent host."

AMAZING LAKE FRONT 7 BR Home, Hot Tub, Fire Pit, Dock, Pool Table, NEW FIRE PIT

10/10 Excellent

"This was an amazing property. The home is absolutely beautiful. The pictures on the website don't do it justice. Very spacious with lovely furnishings and comfortable beds.Perfect location on the lake. Very convenient to shops and excellent place to swim and kayak due to no wake zone.Great porches and outdoor space with great view of lake.Good communication with host."

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

10/10 Excellent

"The host was excellent! We were new to the area and he provided numerous suggestions for things to do in the area in both good weather and bad (rain was expected multiple times during the weekend). The tiny house was exactly as advertised - comfortable, well organized, and had great use of space! The outdoor areas were also well-configured and comfortable. We would definitely stay here again!"

Lakefront/Dock/Amazing views HotTub

10/10 Excellent

"Property itself was newly renovated, clean, and accommodating. Booking & communication from property management team was easy and proactive. Each king sized bedroom had updated and connecting bath then the two queen rooms shared a hall bath. If I had to really pick out any negatives for people to consider as part of their stay- the driveway is very steep and barely fit our family’s 3 SUV’s as it’s right on Garrett highway, which is also noisy from through traffic. The home is self is spacious vertically so there are a lot of steps to consider for family members and children. We unfortunately had a lot of rain during our stay and there weren’t any covered decks so everything was wet and there weren’t any dry areas for us to sit outside."

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Check prices for these dates

Our top choices for Oakland vacation homes

Luxor Mountaintop Cabin-Castle at Deep Creek Lake