Oakland, MD Vacation Homes from ￥33,405

A sandy beach with a rocky shoreline, trees with autumn foliage, and a lake under a partly cloudy sky.

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

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Oakland vacation homes

A cozy cabin interior with leather recliners, a stone fireplace, and a wooden wall with cabin rules posted.

1. Captain's Quarters Deep Creek Log Cabin Oasis

Oakland

Brendan P.

￥58,229 total

includes taxes & fees

Oct 28 - Oct 29

2. Dar's Deep Creek Log Cabin Timber Hideaway

Oakland

￥90,090 total

includes taxes & fees

Nov 8 - Nov 9

A neatly made bed with a grey textured blanket, a headboard with a vertical light fixture, and a painting of a forest scene on the wall.

3. Newly Renovated Lakefront Home with Private Dock, Hot Tub & Beautiful Lake Views

Oakland

￥137,261 total

includes taxes & fees

Oct 27 - Oct 28

A covered outdoor patio with tables and chairs, a wooden deck, and a view of the surrounding greenery.

4. Private Lodge sleeps 31 guests Spectacular Views

Oakland

Jocelyn M.

￥231,215 total

includes taxes & fees

Oct 26 - Oct 27

A wooden deck with railings and string lights, leading to a house with a porch and a window.

5. Near Wisp & Lake• Private • Fire Pit • Pets & Kids

McHenry

Jessica O.

A kitchen with a central island, a dining table, and a refrigerator.

6. Glendale Getaway: Nostalgic not Fancy

Swanton

Jason M.

￥38,411 total

includes taxes & fees

Nov 8 - Nov 9

A cabin with a porch, a grill, and a deck.

7. 3BR - Cozy Cabin - Hot Tub

McHenry

A bedroom with a bed, two bedside tables, a wall-mounted painting, and a nightstand.

8. Wisp View Retreat, Hot tub

Accident

￥113,519 total

includes taxes & fees

Oct 26 - Oct 27

View all properties

Find vacation rentals that suit your style

Cabins

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Top Oakland Hotel Reviews

Dog Friendly Cabin in the Woods, Hot Tub & Firepit

8/10 Good

"We had a good time, weather was perfect, dogs had fun too!"

Charming Dog Friendly Cottage w/ Dock & Fire Pit

8/10 Good

"The Red Cottage was a nice place to stay on our four night vacation away with our dog. The house was clean and did not smell of pets at all. Our dog adjusted well to the change of scenery and being in the mountains with new smells. The house was clean and well-stocked with kitchen supplies. Even with the request to bring paper products, there was a bag left for us with a roll of paper towels, two rolls of toilet paper, and mini dish and laundry soap, which was a nice surprise. The sleep number bed was super comfortable and we slept amazingly well. The proximity to downtown McHenry and Oakland is perfect, with lots of places to stop and explore within a short distance of the house. This was the perfect time of year to visit with Autumn Glory in full swing at Deep Creek. Our only complaint is the highway noise at the edge of the property was too much and made it hard to sit outside to enjoy the view. We enjoyed the hot tub very much, yet the last night we were there, the hot tub temp dropped to 95 degrees and the bubble stopped working. Given everything was so well maintained, this is sure to be quickly repaired."

The Garrett Inn

8/10 Good

"When we arrived to the Garrett Inn, we were able to check in, and were given a key to the room, and told where to park (each room's number was plainly painted on the space for each room, however, due to the configuration of the parking lot vs the way the room's were situated, the parking spaces were off-set from the individual rooms, so when parked for the room assigned, the space was two spaces offset. The room was well appointed, two full beds, a bathroom with a pocket door, a small table with two chairs. There was a microwave and room size refrigerator in the corner of the room, with coffee fixings and a coffee pot. The beds were firm but slept good. However, there was a bit of car noise from the busy highway (Rt 219), but it calmed down after about 11 pm. There was a great restaurant across the street, and also about a quarter of a mile down the road from the motel, both served great food. This motel was perfect for those who were exploring the local area and require a base to work from, this motel is perfect. It's not a chain motel, but it's quaint and fills all the basic needs of a motel."

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

10/10 Excellent

"Great, open property. Very clean. Fire pit was awesome! Lake access was perfect. Bill was amazing. If we needed anything, he was there in less than 5 minutes. We will definitely re-book!"

Lakefront/Dock/Amazing views HotTub

10/10 Excellent

"The guest house was absolutely beautiful. The space was exactly what we needed. We had room to gather and do things as a larger group but also had the space to be alone if we wanted to. The views are amazing, the house was clean, the bedrooms and bathrooms were wonderful as well. We thoroughly enjoyed our stay. I appreciated the quick response when I had questions both before and during our stay. I would absolutely recommend this property to anyone and would also stay again!"

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

10/10 Excellent

"This place is exceptional! Very cozy, the beds are comfy, and that's including the sofa bed. Plenty of linens, towels and essentials. The fire pit was perfect, although we did not use the hot tub. Loved everything about this place, centrally located, it's clean and tidy, a lot of little extras, including vinyl records, a turntable, and games to play. We had a wonderful anniversary weekend getaway! Jeff is an ideal host. I HIGHLY recommend this place. Give it a try. You won't be disappointed!!"

Find out more about Oakland

Oakland Vacation Homes information

Number of reviews	185
Accommodation	477 Vacation Homes
Lowest Price	￥33,405
Highest Price	￥279,379

Explore a world of travel with Expedia

More ways to book

Book Vacation Homes in Oakland on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Oakland vacation homes

1. Captain's Quarters Deep Creek Log Cabin Oasis

2. Dar's Deep Creek Log Cabin Timber Hideaway

3. Newly Renovated Lakefront Home with Private Dock, Hot Tub & Beautiful Lake Views

4. Private Lodge sleeps 31 guests Spectacular Views