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Oakland Rentals

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$10 - $500

Oakland Rentals

About Oakland

102 apartments

Red Run Cabin

Oakland log cabin

3 bedrooms / 2 bathrooms / sleeps 6

“Beautiful, clean home in a perfect setting!” My husband, two year old daughter, dog and I just returned from a five night stay at Red Run Cabin. The home, although nothing fancy, was beautiful and well kept. We generally always stay in cabins or cond

Responds fast! avg. 1 hour 38 minutes

$136

1 / 22

Responds fast! avg. 3 hours 11 minutes

$89

1 / 45

Swallow Falls Inn Cabin 1

Oakland house

1 bedroom / 1 bathroom / sleeps 4

“Relaxing” Loved the cabin and it's location, we will be returning.

$108

1 / 9

$250

1 / 54

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

Oakland house

3 bedrooms / 4 bathrooms / sleeps 10

$162

1 / 39

Captivating Cabin located on wooded lot and short stroll to lake and dock!

Oakland house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 10 minutes

$119

1 / 27

Mountain High

Oakland house

4 bedrooms / 4 bathrooms / sleeps 12

$100

1 / 36

Linwood

Oakland house

3 bedrooms / 2 bathrooms / sleeps 8

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

$34

1 / 18

Swallow Falls Inn Cabin 2

Oakland house

1 bedroom / 1 bathroom / sleeps 4

$108

1 / 7

Dog-friendly, lakefront log home on a quiet cove - front deck & shared dock

Oakland house

3 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 3 hours 44 minutes

$145

1 / 41

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

$45

1 / 10

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

Oakland house

3 bedrooms / 3 bathrooms / sleeps 10

$171

1 / 35

$89

1 / 30

Drift Away

Oakland house

7 bedrooms / 6 bathrooms / sleeps 20

“Fantastic venue for a family Thanksgiving!” The Drift away was the perfect venue for our family reunion/Thanksgiving. The house has multiple living areas, a nice game room area and plenty of outdoor space so that everybody could find somewhere to hang

$100

1 / 22

$167

1 / 40

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

$61

1 / 12

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

$68

1 / 13

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

$59

1 / 8

Summer Song

Oakland house

5 bedrooms / 3 bathrooms / sleeps 14

“Hot at the lake” The house was very nice and in a good location. Amenities were very good. Unfortunately, the air conditioning in the master bedroom was broken during the hottest week of the year. The real estate agent supplied with fans. However,

$100

1 / 48

Lake Shore Lodge

Oakland house

5 bedrooms / 6 bathrooms / sleeps 10

“We had a terrific time.” The house was beautiful. Deep Creek Lake is incredible. There is so much to do that we needed more time than a week.

$159

1 / 17

Bear Cove

Oakland house

3 bedrooms / 4 bathrooms / sleeps 10

“Great value” A group of us rented Bear Cove rented this for a bachelorette weekend. Spacious, clean, quiet and beautiful lake front property! This is great for a quiet get away!

$100

1 / 12

Sylvan Sweet

Oakland house

5 bedrooms / 5 bathrooms / sleeps 14

$110

1 / 19

Providence at Penn Cove

Oakland house

4 bedrooms / 4 bathrooms / sleeps 11

$77

1 / 17

NEW LISTING! Charming cabin w/split lake access dock & firepit

Oakland house

3 bedrooms / 1 bathroom / sleeps 8

Responds fast! avg. 3 hours 11 minutes

$163

1 / 35

Hilltop Happy Hour

Oakland house

4 bedrooms / 5 bathrooms / sleeps 10

$69

1 / 23

Magnificent View Point

Oakland house

4 bedrooms / 5 bathrooms / sleeps 12

“Magnificent” Magnificent View Point lives up to it's name. This was our 2nd stay at this beautiful lake front home. The home is beautifully decorated, bright & cheery. The kitchen is well equipped with everything you could possibly need. The large lot

$100

1 / 19

Swallow Falls Inn Cabin 3

Oakland house

2 bedrooms / 1 bathroom / sleeps 6

$124

1 / 10

Just Perfect

Oakland house

4 bedrooms / 3 bathrooms / sleeps 12

$97

1 / 13

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

$101

1 / 23

Sundance

Oakland house

7 bedrooms / 7 bathrooms / sleeps 22

“Relaxing in Comfortable Surroundings” My family, my two sisters and their families and our mother thoroughly enjoyed our stay at Sundance. The house is absolutely gorgeous, with plenty of room for a crowd. Although the weather didn't fully cooperate

$100

1 / 37

Responds fast! avg. 3 hours 11 minutes

$89

1 / 33

Mountaineer

Oakland house

3 bedrooms / 4 bathrooms / sleeps 8

“Great house, good value, Pet Friendly!” Our recent stay at Moutaineer was excellent as was the rental process through Railey Mountain Vacations. We arrived after check-in and the drop box system worked very well. I would advise those choosing Mounta

$28

1 / 20

Sunset Dream

Oakland house

4 bedrooms / 3 bathrooms / sleeps 12

“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

$110

1 / 26

Diamond on the Lake

Oakland house

5 bedrooms / 6 bathrooms / sleeps 14

“The Diamond Still Sparkles!” This is a beautiful place to stay - stunning sunsets - the house has everything you need (except a 2nd refrigerator and a chaise or more comfortable porch furniture). The screened in gazebo is delightful

$100

1 / 13

Lost Bearadise

Oakland house

3 bedrooms / 3 bathrooms / sleeps 8

$89

1 / 18

At Last

Oakland house

5 bedrooms / 5 bathrooms / sleeps 14

$100

1 / 60

Amazing Love

Oakland house

5 bedrooms / 3 bathrooms / sleeps 14

“see the water from the deck” This home really worked for my family. Plenty of room to spread out,plenty of bathrooms making little wait time for a shower. The deck was very comfortable with lots of seating.Often used the tables on the deck for playing

$114

1 / 12

Absolute Delight

Oakland house

8 bedrooms / 7 bathrooms / sleeps 25

“Great Time, Great Friends, and Great House” We had very good service, we booked Absolute Delight again for 2009, and we also stayed there in 2007. The house met all of our needs. Having 2 refrigerators was a plus for that size of a house. Also, we

$100

1 / 25
Viewing 38 of 102

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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