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Oakland Rentals

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Oakland Rentals

About Oakland

854 Houses

Linwood

Oakland house

3 bedrooms / 2 bathrooms / sleeps 8

“Rental for wedding party” Plenty of space, nice locations, big patio and deck

Price per night from

$37

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Cabin in the Woods (DCL)

Oakland log cabin

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$81

1 / 21

Responds fast! avg. 3 hours 9 minutes

Price per night from

$264

1 / 56

Deer Pass

Oakland house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$219

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Home on the Ridge

Oakland house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$77

1 / 15

Owl Cabin

Oakland log cabin

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$175

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Arrowhead #26

Oakland condo

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$132

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Hemlock Chalet

Oakland house

3 bedrooms / 2 bathrooms / sleeps 12

“Great cabin, clean and beautiful!” The Hemlock Chalet was a wonderful place to relax and enjoy Deep Creek. Though it is a bit of drive to the mountain, the cabin was clean, beautifully decorated, and spacious. My friends and I had a blast.

Price per night from

$57

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NEW LISTING! Spacious home w/convenient location & hot tub, near lake & dining

Oakland house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 2 hours 49 minutes

Price per night from

$145

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AAH Chalet

Oakland house

5 bedrooms / 3 bathrooms / sleeps 12

“Ahh Chalet” Raileys Mountain Lake Rental was great as usual. Very easy check in and check out process. We had two issues at the begining of the week and all it took was one phone call and they were resolved that same day aAH Chalet was a great lake

Price per night from

$121

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Wispering Ridge

Oakland house

2 bedrooms / 3 bathrooms / sleeps 6

“Great location, great view” The townhome was spotless. We love to cook and the kitchen was well equipped. Linens were provided and that was a great help. Location just off 219 but we had a great view of Deep Creek Lake. Only problem for elderly guest

Price per night from

$65

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Paradise Chalet (DCL)

Oakland log cabin

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$163

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Winter View (DCL)

Oakland house

4 bedrooms / 2 bathrooms / sleeps 11

Price per night from

$181

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Creature Comforts

Oakland house

6 bedrooms / 4 bathrooms / sleeps 16

“Spectacularly awesome!” It's not often when an entire family can get away during the holidays for some R & R! A last minute decision was made and Railey Mountain Vacation, specifically "Creature Comforts" vacation home provided the venue for our famil

Price per night from

$216

1 / 20

Harmony

Oakland house

4 bedrooms / 3 bathrooms / sleeps 12

“Great views of deep creek” Excellent location. Cleanliness of home was not very good. In need of thorough cleaning, especially carpet in pool room. To much dust on tables and drawers.

Price per night from

$59

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Tranquil Dreams

Oakland house

4 bedrooms / 3 bathrooms / sleeps 10

“Fun Stay” Many amenities (toilet paper, cleaning supplies, grilling materials, camping gear) were already provided when we arrived, making for a nice, care-free vacation. Beautiful location. Wonderful living space. Billiards table, fire pit, and hot

Price per night from

$64

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Baldwins Domain

Oakland house

3 bedrooms / 4 bathrooms / sleeps 8

“Very nice house. Private location.” We really enjoyed the house. It was very pretty inside and out and very roomy for a 3 BR house. The location was very secluded, so if you're looking for privacy while also being right on the lake, this house it g

Price per night from

$73

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Sylvan Sweet

Oakland house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$121

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Dog-friendly lakefront home w/ hot tub, dock, shared tennis - near the slopes!

Oakland house

3 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 2 hours 49 minutes

Price per night from

$162

1 / 39

Almost Heaven

Oakland condo

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$115

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Simply Cozy (DCL)

Oakland condo

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$242

1 / 27

Triple-T Lodge

Oakland house

4 bedrooms / 3 bathrooms / sleeps 12

“First class all the way” Beautiful home, great location, near to everything! Railey Vacation Rentals is on top of their game. From arrival to departure everything was absolutely perfect. If something was needed, it was handled by Railey immediately

Price per night from

$50

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The Whitetail (DCL)

Oakland log cabin

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$128

1 / 22

Dream On

Oakland house

5 bedrooms / 4 bathrooms / sleeps 10

“Tons of room for family fun!” Dream on is a great property with many upgrades you may have at home. The kitchen was fully stocked with the essentials needed for cooking a big meal. The open layout allows the whole family to gather in one place. The

Price per night from

$52

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Tranquil home w/ private hot tub & game room - close to lake access

Oakland house

5 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 2 hours 49 minutes

Price per night from

$159

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Summerside

Oakland house

5 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$111

1 / 20

Windy Acres (DCL)

Oakland log cabin

3 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$166

1 / 30

Lake It Easy

Oakland house

3 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$56

1 / 8

Responds fast! avg. 2 hours 49 minutes

Price per night from

$120

1 / 33

Edgewater

Oakland house

5 bedrooms / 4 bathrooms / sleeps 14

“Very nice place to stay.” Very nice house with a great location right on the water. Loved the hot tub and pool table, nice additions.

Price per night from

$68

1 / 17

Log Heaven

Oakland house

4 bedrooms / 4 bathrooms / sleeps 10

“Weekend Getaway with friends” We had a very nice stay at Log Heaven. It must have been newly renovated because it was just beautiful. Fun times with friends. We recommend a stay at this cabin and we will surely be back. The only thing is that it did

Price per night from

$77

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Sunset Dream

Oakland house

4 bedrooms / 3 bathrooms / sleeps 14

“Nice layout and beauutiful location.” This was a nice house that seems to be undergoing some renovation. We were there during a virtually snowless ski vacation - but the house provided a great home base for reconnecting with family and enjoying the a

Price per night from

$121

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Dog-friendly cabin in the woods with hot tub, furnished deck, & pool table

Oakland house

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 49 minutes

Price per night from

$159

1 / 35

Tree house

Oakland log cabin

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$114

1 / 25

Dog-friendly lakefront cabin w/ private dock and great views - close to skiing

Oakland house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 49 minutes

Price per night from

$146

1 / 41

Bella Vista

Oakland house

5 bedrooms / 3 bathrooms / sleeps 12

“Great House Great Location” House was fantastic. Plumbing system needs some work as the water came out brown on the first couple times we turned it on.

Price per night from

$71

1 / 17

Peregrine's Perch

Oakland house

8 bedrooms / 9 bathrooms / sleeps 24

“Another amazing trip” Weve stayed at this property multiple times and it still amazes us how much of a great time we have with a house full of amenities. You almost never have to leave with all the things to do.

Price per night from

$947

1 / 30

Arctic Retreat

Oakland house

3 bedrooms / 2 bathrooms / sleeps 8

“our stay felt like we was at home” My overall review is the place was actualy better than deepvillage when we came june 25,2010

Price per night from

$75

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About Oakland

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Located in the beautiful mountains of western Maryland, Oakland is the perfect woodland escape. Be the first to see the sun hit the green hills from your vacation home's bedroom balcony, then walk just minutes to Deep Creek Lake, perfect for boating, tubing, hiking, and swimming. Feel free to bring the water skis and kayak as there is plenty of space inside your vacation rental to store your equipment. While you are here, spend a day at Swallow Falls State Park, home to some of Maryland's most beautiful natural scenery. Hike along trails with panoramic views of rocky gorges, flowing rapids, and Muddy Creek Falls, a thrashing 53-foot waterfall. The park offers a large picnic area with a pavilion and playground, as well as nature programs, boat rentals, and a beach for swimming during the summer.

Here are a few additional suggestions of things to do in the area:

  • Visit Maryland's Historic B&O Train Station: This authentic 1884 train station has been restored to its original Queen Anne condition. The train speaks to Oakland's old, small town feel and adjoins a shop that sells baked goods, candles and maple syrup.
  • See a show at Our Town Theatre: This little production company offers great local and imported talent. Be sure to check the current schedule while visiting, and catch great comedies, dramas, and more.
  • Visit the county's Historical Society Museum: Like the train station, the historical museum is a great place to learn about the area's history and get a feel for small town life in another era.
  • Play golf: Champion caliber Deep Creek golf courses offer some of the best greens in the state. After a day of golf, spend an afternoon indulging in a pedicure at a luxury Deep Creek spa.
  • Go horseback riding: Several private stables in the state park area offer one-on-one lessons or trail rides with a friendly knowledgeable guide.
  • Experience Deep Creek skiing: In the winter, Deep Creek offers pristine, powdery trails perfect for both cross country and downhill skiing.

Experience the best of Oakland and the Deep Creek Lake area by staying in your own private luxury vacation rental. A trendy winter condo or summer apartment rental may be perfect for a long weekend getaway with friends. You may also decide to host your family and friends for a barbeque at your lakeside vacation home or mountain cabin. While you're visiting Oakland, make the most of your stay by scheduling a visit to nearby Swanton or McHenry.

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