Updating...

Enter dates for more accurate prices

Oakland Rentals

Filter

Oakland Rentals

About Oakland

251 apartments

Charming, Dog Friendly A-Frame Close to Activities!

Oakland house

3 bedrooms / 2 bathrooms / Sleeps 8

$185

1 / 32

Breathtaking 6 Bedroom mountain home with exquisite lake & mountain views!

Oakland house

6 bedrooms / 4 bathrooms / Sleeps 16

$392

1 / 44

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 30 minutes

$136

1 / 22

Conveniently located, spacious townhome with hot tub & pool table!

Oakland house

5 bedrooms / 4 bathrooms / Sleeps 11

$347

1 / 34

Want it all? Mountain High delivers! Mountain setting, lake access, and plush

Oakland house

4 bedrooms / 4 bathrooms / Sleeps 12

$400

1 / 35

Responds fast! avg. 17 minutes

$173

1 / 38

Brand New Home, 4 Master Suites, Outdoor Kitchen with Pizza Oven!

Oakland house

6 bedrooms / 5 bathrooms / Sleeps 16

$603

1 / 35

Chalet with Private Dock & Central Location

Oakland house

5 bedrooms / 3 bathrooms / Sleeps 14

$271

1 / 28

Lake Access Home Close to Activities, Restaurants & Shops

Oakland house

4 bedrooms / 5 bathrooms / Sleeps 12

$299

1 / 53

Responds fast! avg. 17 minutes

$89

1 / 45

Appealing 5 Bedroom lakefront home close to all area attractions with hot tub

Oakland house

5 bedrooms / 4 bathrooms / Sleeps 14

$375

1 / 30

Warm & Inviting home with amazing lake views!

Oakland house

4 bedrooms / 3 bathrooms / Sleeps 12

$299

1 / 23

Mountaintop Chalet with Spacious Deck & Central Location

Oakland house

4 bedrooms / 3 bathrooms / Sleeps 10

$314

1 / 51

Conveniently located log cabin with outdoor hot tub!

Oakland log cabin

2 bedrooms / 2 bathrooms / Sleeps 8

$249

1 / 22

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

Oakland house

3 bedrooms / 2 bathrooms / Sleeps 10

Responds fast! avg. 17 minutes

$147

1 / 41

Conveniently located cabin with fire pit & dock slip - close to state parks!

Oakland house

3 bedrooms / 2 bathrooms / Sleeps 10

$247

1 / 27

Perfect for an intimate escape, Swallow Falls Inn Cabin 4 is your ideal home

Oakland house

3 bedrooms / 2 bathrooms / Sleeps 8

$151

1 / 10

Charming, dog friendly home across quiet street from the lake!

Oakland house

3 bedrooms / 3 bathrooms / Sleeps 10

$297

1 / 17

Lakefront home close to area activities!

Oakland house

7 bedrooms / 7 bathrooms / Sleeps 18

$741

1 / 31

Cute & Inviting 3 Bedroom with an incredible lakefront!

Oakland cottage

3 bedrooms / 2 bathrooms / Sleeps 8

$339

1 / 20

Captivating 2 Bedroom cottage with hot tub offers amazing river access!

Oakland house

2 bedrooms / 1 bathroom / Sleeps 6

$239

1 / 21

Spectacular 5 Bedroom home lovingly furnished w/ Hot Tub!

Oakland house

5 bedrooms / 4 bathrooms / Sleeps 10

$348

1 / 35

Boasting modern upgrades and a cheerful color palette, Almost Heaven is ready

Oakland house

5 bedrooms / 5 bathrooms / Sleeps 14

“wonderful” when we got in the house we was so happy we didnt want to leave the house was very pretty all the rooms we very nice.. the bottom line is we love the house...

$65

1 / 12

Centrally located getaway with hot tub & pool table!

Oakland house

4 bedrooms / 3 bathrooms / Sleeps 12

$256

1 / 43

Extravagant comfort and mountain style reign supreme at Timberlodge! You’ll

Oakland house

9 bedrooms / 7 bathrooms / Sleeps 28

“Great Stay” Had a blast at Timberlodge. Highly recommended. Slept 23 of us comfortably. Lake right out back. Great stay!

$1,104

1 / 56

$261

1 / 12

Astounding & secluded mountain chalet with lake views!

Oakland house

3 bedrooms / 2 bathrooms / Sleeps 10

$349

1 / 39

“beautiful weekend” our group has rented this home several times and it is always very clean. we rent this home because we look for 5 couples to have their own private bedroom & bath & it is difficult to find very many homes that met our needs w/ quee

$429

1 / 12

Cheerful & Inviting 3 Bedroom Home w/ Hot Tub in the heart of Deep Creek!

Oakland house

3 bedrooms / 3 bathrooms / Sleeps 8

$224

1 / 18

The name says it all! Open pastures, rolling hills, and blue skies follow you

Oakland house

4 bedrooms / 3 bathrooms / Sleeps 12

$329

1 / 13

5 Bedroom Immaculate Chalet with Dock Slip and Community Indoor Pool

Oakland house

5 bedrooms / 3 bathrooms / Sleeps 14

“A great family Thanksgiving at american Pride” Spent a wonderful 3 nights at american Pride for Thanksgiving 2013. We had twelve people, 7 adults and 5 children. It housed us all very comfortably, the kitchen was well equipped and a great time was had

$414

1 / 51

Where can you revel in the ambience of wood fires and water views? Glistening

Oakland house

4 bedrooms / 4 bathrooms / Sleeps 12

“Awesome Time in an awesome Home with awesome Friends!!!” Our recent stay in Glistening Waters was pleasant from the scenery to the fun activities at the local resort. The home was clean and comfortable and exactly what we were hoping for. Although the

$357

1 / 14

Is it the quiet cove, the sandy beach, or the stone fire pit? You decide the

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!

$377

1 / 12

Beautiful Lake Views, Short Walk to Dock

Oakland house

3 bedrooms / 3 bathrooms / Sleeps 10

$242

1 / 27

Lake It Easy! Updated and spacious, this charming home boasts a great central

Oakland house

3 bedrooms / 1 bathroom / Sleeps 10

$145

1 / 8

Relaxation takes hold at Drift Away, with its charming lakefront, indoor pool

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

$858

1 / 22

Alluring 3 Bedroom home featuring premiere lakefront!

Oakland house

3 bedrooms / 2 bathrooms / Sleeps 8

$308

1 / 26

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

Oakland house

3 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 51 minutes

$119

1 / 27
Viewing 38 of 251

About Oakland

×

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.

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more