Oakland Cottages

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 cottages

A single-story house with a stone facade and a front porch, surrounded by a well-maintained lawn and trees.

1. Woodland Cottage, Fire Pit & Park Pass

Oakland

Chander R.

includes taxes & fees

11 Nov - 12 Nov

A small cabin with a wooden staircase leading to a door, surrounded by a gravel path and a wooden fence.

2. SwimSpa, 3 bd 2 ba! River! Trails! 14 acres!

Friendsville

includes taxes & fees

11 Nov - 12 Nov

A rustic cabin with a wooden deck and a flag, surrounded by autumn foliage.

3. Cozy Anchors Away Cabin Hideaway w/ Fire Pit!

Parsons

Jack

includes taxes & fees

11 Dec - 12 Dec

A single-story house with a covered porch, a small garden with various plants and a pumpkin, and a lawn in the background.

4. Country Roads Cottage w/ fenced in yard close to state forests and WVU!

Bruceton Mills

Diana S.

includes taxes & fees

16 Nov - 17 Nov

A two-story house with a covered porch and a small deck, surrounded by lush greenery and a clear blue sky.

5. Spacious riverfront cottage with full kitchen, cozy charm, and Casselman views.

Grantsville

Mitchum

includes taxes & fees

23 Nov - 24 Nov

A two-story house with a stone facade and a blue roof.

6. Private Home in Garrett County, surrounded by trees, fields and farmland.

Grantsville

Carolin M.

includes taxes & fees

11 Nov - 12 Nov

A rustic cabin with a stone foundation, a wooden porch, and a sloped roof.

7. Pura Vida - Spacious Woodland Retreat

Ohiopyle

Joe W.

includes taxes & fees

11 Nov - 12 Nov

A wooden cabin with a porch, two Adirondack chairs, and a hanging swing.

8. Parsons Cabin w/ Fire Pit & River Access!

Parsons

includes taxes & fees

13 Nov - 14 Nov

A wooden cabin with a covered porch, wooden chairs, and a view of a forested area.

9. Parsons Semper Fi Cabin w/ Fire Pit!

Parsons

Philip

includes taxes & fees

7 Dec - 8 Dec

View all properties

Find holiday 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

10/10 Excellent

"The house was very cute and private. Had everything you needed and plenty of space for the four ladies in our group. The hot tub was very nice even with the temperature in the 30s. We would love to stay again!"

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

10/10 Excellent

"I can't say enough good things about this property! From the very moment we booked, we got a super thoughtful message with great recommendations..Jeff even followed with some specific suggestions for the Halloween weekend! Location couldn't have been better and it was one of the cleanest, coziest, most welcoming property I've stayed at.We want to come back soon!"

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."

Find out more about Oakland