50 Best Vacation Rentals in Oakland - Holiday Lettings - Cabins

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230 Vacation rentals

(6) Excellent 

40

Vacation home in Oakland

Garrett County / Oakland

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
Your Deep Creek tradition begins when you choose the delightful 4 bedroom chalet Swimming Bear Lodge for your next stay! Located on a large wooded lot, you will love being surrounded by nature in this tranquil setting. Step inside to the main level and immediately embr …see more

from $312 / night

$1395 - $2409 / week

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from $312 / night

27

Vacation home in Oakland

Garrett County / Oakland

7 18 Min stay varies

  • 7 bedrooms
  • Sleeps 18
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Pure vacation fun is what you will find when you choose St. Bart’s Retreat for your Deep Creek Lake getaway! This spacious lakefront home is close to favorite activities and offers lots of on-site amenities too. Upon entering the great room, the towering wall of windo …see more

from $798 / night

$3192 - $5290 / week

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from $798 / night

19

Vacation home in Oakland

Garrett County / Oakland

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
Rich in Deep Creek history, this cottage was built as company housing for Deep Creek’s Hydro Electric Dam workers in 1925. Featuring private Youghiogheny River frontage in the protected Wild and Scenic Corridor, this home is completely unique in Deep Creek. Private …see more

from $227 / night

$909 - $1144 / week

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from $227 / night

36

Vacation home in Oakland

Garrett County / Oakland

7 18 Min stay varies

  • 7 bedrooms
  • Sleeps 18
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Your fairy tale vacation starts at Ever After! This lake front home promises a memorable vacation experience. Three floors of living space plus a separate carriage house with a 120 inch home theater and an oversized game room makes this property stand-out from the crowd …see more

from $884 / night

$3491 - $5689 / week

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from $884 / night

(25) Excellent 

22

Oakland Vacation log cabin rental

Garrett County / Oakland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Red Run Cabin is a 1 story 3 bedroom cottage with a finished basement on an acre wooded lot near the west end of Deep Creek Lake, accomodating up to 6 people. It has lake access through the Red Run Restaurant property leading to a sandy beach and shallow lake bottom fa …see more

from $200 / night

$700 - $1100 / week

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from $200 / night

17

Oakland Vacation home rental

Garrett County / Oakland

4 11 7 nights min

  • 4 bedrooms
  • Sleeps 11
  • 7 nights min
  • Child friendly
Paradise is perfected at Providence at Penn Cove! This warm country home offers the ideal setting for an unforgettable Deep Creek Lake getaway! The beautifully landscaped backyard features a small pond, fire pit, and outdoor hot tub for the ultimate in relaxation and fu …see more

from $214 / night

$1497 - $2294 / week

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from $214 / night

25

Vacation home in Oakland

Garrett County / Oakland

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
Explore, relax and take a well-deserved break at Deep Breath! Convenient to area activities and attractions, it is the perfect home base for your Deep Creek Lake vacation. The spacious interior of this Craftsman-style home is brimming with attention to detail. Upon en …see more

from $240 / night

$1288 - $1693 / week

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from $240 / night

31

Vacation home in Oakland

Garrett County / Oakland

5 13 Min stay varies

  • 5 bedrooms
  • Sleeps 13
  • Min stay varies
  • Ask about children
You will certainly learn to embrace the motto “Live It, Love It, Lake It” when you choose this charming mountain home for your Deep Creek getaway. Imagine sharing memories with your friends and family as you cozy up around the warm wood fireplace in the Great Room. This …see more

from $347 / night

$1693 - $2488 / week

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from $347 / night

(15) Very Good 

20

Vacation home rental

Garrett County / Oakland

4 12 7 nights min

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min
  • Child friendly
  • Pet friendly
Nestled among the tall oaks and maples of the surrounding forest, Cedar Lodge offers privacy and seclusion along with the fun and excitement of a lake vacation. You’ll love the convenience of having the home’s lake access and community dock slip just a short walk away! …see more

from $224 / night

$1565 - $2887 / week

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from $224 / night

(18) Very Good 

13

Vacation home in Oakland

Garrett County / Oakland

3 11 7 nights min

  • 3 bedrooms
  • Sleeps 11
  • 7 nights min
  • Child friendly
  • Pet friendly
Sunny Escape is a showstopper! It doesn’t get any cuter and more charming than this original stone lakefront cottage. Loaded with great amenities, this three-bedroom Deep Creek home is surprisingly spacious, with level lakefront, sprawling lawn and private dock. Large w …see more

from $206 / night

$1436 - $3107 / week

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from $206 / night

(11) Very Good 

38

Oakland Vacation home rental

Garrett County / Oakland

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Come and relax at San~Stress, located in the wonderful community of Blakeslee. This property is adorned with hardwood floors, tongue and groove ceilings, and plenty of space for the whole family. The lower level family room is maxed out with a pool table, air hockey gam …see more

from $347 / night

$1616 - $2393 / week

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from $347 / night

27

Vacation home rental

Garrett County / Oakland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
Newly renovated (2017) three bedroom two bath cabin that sits back from the road with plenty of parking . Cabin is situated on one acre of wooded grounds surrounded by large boulders and a pond. The stately stone fireplace is the centerpiece of this home. The soaring …see more

from $150 / night

$950 / week

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avg. 1 hour 40 minutes

from $150 / night

27

Vacation home in Oakland

Garrett County / Oakland

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
Craftsman-style details, tasteful décor and a central location make Just Relax the perfect choice when you want to unwind at Deep Creek Lake. Step inside, and the first thing you will notice is the open floorplan that is ideal for entertaining. Natural light reflects o …see more

from $240 / night

$1288 - $1693 / week

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from $240 / night

(7) Excellent 

15

Vacation home rental

Garrett County / Oakland

6 15 7 nights min

  • 6 bedrooms
  • Sleeps 15
  • 7 nights min
  • Child friendly
This stunning Deep Creek vacation home is situated on a tranquil cove, offering a peaceful setting with incredible views. Just steps from the water’s edge, Telstar.gon has a large private dock and a deck that runs the length of the house, perfect for morning coffee, soa …see more

from $369 / night

$2576 - $6972 / week

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from $369 / night

22

Vacation home in Oakland

Garrett County / Oakland

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Pet friendly
A lifetime of family memories is just a phone call away when you choose to stay in the lovely 3 bedroom chalet known as Timber Trails. Truly a get away from it all home, you will love the private and peaceful setting while cherishing your close proximity to Oakland, Wis …see more

from $198 / night

$859 - $1124 / week

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from $198 / night

22

Home rental in Oakland

Garrett County / Oakland

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ask about children
  • Air conditioning
A truly amazing mountain home is just what you need for your relaxing getaway and Log Mahal will not disappoint. This custom crafted 5 bedroom home will quickly win you over with its unique style and décor. Love at first sight is a given when you enter the Great Room. L …see more

from $472 / night

$1993 - $2792 / week

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from $472 / night

30

Vacation home rental

Garrett County / Oakland

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Vivid and lively are two words that can describe the character displayed in Retro Lake Landing. Its originality is definitely one of a kind and will certainly put that extra little kick into your vacation. If you are looking for something different, fun and exciting, th …see more

from $285 / night

$1408 - $2093 / week

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from $285 / night

(37) Very Good 

28

Vacation home in Oakland

Garrett County / Oakland

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
American Pride is an inviting 5 bedroom 3 bath chalet nestled among the trees in one of the most requested communities in Deep Creek Lake. A few steps into the home and you will find yourself entering into the elegantly decorated Great Room which features large cathedra …see more

from $422 / night

$1972 - $3192 / week

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from $422 / night

41

Vacation home in Oakland

Garrett County / Oakland

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
When you step through the doors of Boxer Overlook, you will immediately be taken in by the unparalleled elegance this home showcases. Ideally located in a quiet community, this 5 bedroom chalet is perfect for large or multi-family gatherings. Offering an open concept fl …see more

from $412 / night

$1843 - $2534 / week

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from $412 / night

28

Vacation home in Oakland

Garrett County / Oakland

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
Is the clamor of city life wearing you down? Cedarwoods, a stunning 3 bedroom mountain chalet, is calling your name. Nestled away in the quiet community of Mountainside, this beautiful home offers the seclusion and privacy you crave. Boasting 3 spacious levels of living …see more

from $249 / night

$1216 - $1612 / week

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from $249 / night

(1) Very Good 

12

Vacation home rental

Garrett County / Oakland

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
Looking for a quiet wooded retreat? Log Heaven wraps you in nature's comforting embrace with the rich and rustic charm found throughout the space. One master suite and 3 additional bedrooms give your whole party enough space to spread out and then regroup in the living …see more

from $186 / night

$1301 - $1902 / week

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from $186 / night

26

Vacation home in Oakland

Garrett County / Oakland

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
Located on the shores of Deep Creek Lake, Majestic View is a delightful three bedroom townhouse with a name that says it all. Hardwood floors throughout the great room beautifully compliment the wall of windows that showcase breathtaking lake views that change with t …see more

from $249 / night

$1104 - $1794 / week

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from $249 / night

(9) Very Good 

15

Vacation home in Oakland

Garrett County / Oakland

8 24 7 nights min

  • 8 bedrooms
  • Sleeps 24
  • 7 nights min
  • Child friendly
Scenic Serenity offers an incredible lakefront setting and a location close to it all! This eight-bedroom Deep Creek vacation retreat is located on one of the most popular sections of the lake and offers commanding lake views from room to room. The home’s expansive back …see more

from $464 / night

$3245 - $6492 / week

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from $464 / night

(5) Very Good 

10

Oakland Vacation home rental

Garrett County / Oakland

5 14 7 nights min

  • 5 bedrooms
  • Sleeps 14
  • 7 nights min
  • Child friendly
  • Pet friendly
Looking for the ultimate vacation experience? Amazing Love has you covered! This five-bedroom vacation rental was recently remodeled and features a host of fantastic amenities, including an air hockey table, gas fireplace, pool table and wireless Internet. Plus, a fabul …see more

from $278 / night

$1946 - $4174 / week

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from $278 / night

19

Vacation home in Oakland

Garrett County / Oakland

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
Perched on a hillside overlooking Deep Creek Lake, this well-appointed home is the perfect starting point for a great vacation. Tasteful décor and a spacious layout create comfortable surroundings for your gathering of family and friends. Postcard views will greet you …see more

from $312 / night

$1493 - $1972 / week

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from $312 / night

20

Vacation cottage in Oakland

Garrett County / Oakland

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Pet friendly
Do you find yourself daydreaming about a romantic getaway in a charming lakefront home? Golden Retreat is perfect for a couple but is large enough for a small family. You’ll adore the comfortable furnishings and alluring appeal of the interior. Conveniently located a m …see more

from $314 / night

$1408 - $2792 / week

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from $314 / night

33

Vacation home in Oakland

Garrett County / Oakland

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
Get away from it all at this lovely home with rustic decor and beautiful views! This four bedroom home is nestled in the woods for a feeling of seclusion, with a large deck for enjoying the scenery! Relax in the hot tub or by one of the gas fireplaces, gather with your …see more

from $297 / night

$1443 - $1803 / week

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from $297 / night

30

Vacation home in Oakland

Garrett County / Oakland

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Discover the beauty and uniqueness of Deep Creek Lake when you choose to stay in the captivating 5 bedroom lakefront home Crystal Lake. Ravishing lake views will greet you from every room of the main level, a delightful sight no matter what season you visit! Spend time …see more

from $387 / night

$1794 - $3093 / week

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from $387 / night

22

Log cabin rental in Oakland

Garrett County / Oakland

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Get the much deserved break that you crave when you stay at Bear Paws. This charming log cabin pairs total comfort with a convenient location! Featuring an open floorplan, the spacious main level is highlighted by vaulted ceilings and polished hardwood floors. Bear the …see more

from $249 / night

$1008 - $1274 / week

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from $249 / night

36

Vacation home rental

Garrett County / Oakland

6 16 Min stay varies

  • 6 bedrooms
  • Sleeps 16
  • Min stay varies
  • Ask about children
  • Air conditioning
You will truly feel like you are in a magical place when you take in the exquisite lake and mountain views from the deck of Scenic Overlook. This marvelous 6 bedroom mountain home with all of the creature comforts of home combined with desirable vacation home amenities …see more

from $597 / night

$2372 - $3357 / week

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from $597 / night

(4) Good 

22

Oakland Vacation home rental

Garrett County / Oakland

5 15 7 nights min

  • 5 bedrooms
  • Sleeps 15
  • 7 nights min
  • Child friendly
  • Pet friendly
Enjoy fresh mountain air, tall trees, and stunning lakefront views at Paradise Lodge. This classic lodge-style lake home offers seclusion and privacy, yet boasts a location close to many stores, restaurants, and area hot spots. Paradise Lodge offers a multitude of ameni …see more

from $301 / night

$2105 - $3966 / week

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from $301 / night

19

Home rental in Oakland

Garrett County / Oakland

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
Let the adventure begin! Mother Nature will astound when you choose to stay in the captivating lakefront home known as Summer Haven! Imagine relaxing on the expansive wraparound deck as you take in the phenomenal lake views! Amenities abound inside the home as well; wh …see more

from $356 / night

$1673 - $3392 / week

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from $356 / night

42

Vacation home in Oakland

Garrett County / Oakland

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
Casa Montes (“House in the Mountains” in Latin) is an exquisite mountain retreat with over 1.5 acres of seasonal lake views and privacy, yet conveniently located within 5-minute walking distance of the lake, restaurants and shops.  Walk on a path to a pizzeria, a coffee …see more

from $412 / night

$1694 - $2662 / week

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from $412 / night

19

Vacation home in Oakland

Garrett County / Oakland

5 14 7 nights min

  • 5 bedrooms
  • Sleeps 14
  • 7 nights min
  • Child friendly
Life is good at Sylvan Sweet! This serene retreat will wrap you in the tranquility of a private wooded setting, yet keep you in close proximity to area activities, state parks, restaurants, and more! Situated on a peaceful cove at the edge of the lake, this home offers …see more

from $323 / night

$2260 - $5269 / week

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from $323 / night

23

Vacation home in Oakland

Garrett County / Oakland

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
If you are looking for a home that goes “Above and Beyond”, this 4 bedroom mountain home is the ideal choice for you and your family! Located on top of a quiet mountaintop, here you will find the privacy you need but still relish the close proximity to all area shopping …see more

from $297 / night

$1438 - $2129 / week

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from $297 / night

23

Vacation home in Oakland

Garrett County / Oakland

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
Tucked away on the end of Santa Fe Trail, welcome to your tranquil, private oasis. Santa Fe Getaway is an alluring 4 bedroom home that your family will want to return to season after season. Exquisite lake views greet you from many rooms of the home but it is outside on …see more

from $264 / night

$1108 - $1620 / week

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from $264 / night

28

Vacation home in Oakland

Garrett County / Oakland

4 12 7 nights min

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min
  • Child friendly
  • Pet friendly
Looking to get away with family and friends and enjoy a much needed escape from daily life? Look no further than Serenity Ridge! This newly decorated home offers entertainment for all! Simple elegance reigns supreme throughout the interior of the home, highlighted by ha …see more

from $201 / night

$1401 - $1958 / week

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from $201 / night

18

Oakland Vacation home rental

Garrett County / Oakland

3 10 7 nights min

  • 3 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
Magic is alive at Cochran’s Cabin! Experience the lake in an atmosphere only an authentic cabin can provide! This original Deep Creek log cabin has been thoroughly upgraded with modern amenities, yet maintains an old-world charm and simple simplicity that is apparent in …see more

from $248 / night

$1734 - $3026 / week

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from $248 / night

29

Oakland Vacation home rental

Garrett County / Oakland

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Pet friendly
Experience the beauty of Deep Creek Lake at Fox Den, a charming A-frame cottage that offers a treasured chance to unwind. Both romance-seekers and those in pursuit of inner peace will relish time spent at this classic mountain getaway. Highlighted by a wall of windows, …see more

from $198 / night

$874 - $1124 / week

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from $198 / night

(4) Good 

13

Oakland Vacation home rental

Garrett County / Oakland

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Child friendly
  • Pet friendly
LinLaurAl is a five-bedroom Deep Creek vacation rental with something for the whole family! Featuring 600 feet of level lakefront and plenty of privacy, this charming home is the perfect lakefront retreat. Enjoy warm summer mornings by stepping out of your master bedroo …see more

from $327 / night

$2286 - $4255 / week

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from $327 / night