50 Best Vacation Rentals in Oakland - Holiday Lettings - Cabins

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227 Vacation rentals

40

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 $390 / night

$1716 - $2472 / week

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from $390 / night

26

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

$3392 - $5512 / week

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from $884 / night

15

Vacation home in Oakland

Garrett County / Oakland

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
Prepare yourself for a relaxing getaway when choose Bear Feet as your vacation getaway. Exploding with charm, this 3 bedroom townhome will easily beckon you to return time and time again. Step inside and appreciate the open floor plan and the wall of windows that boast …see more

from $237 / night

$973 - $1495 / week

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from $237 / night

12

Vacation cottage in Oakland

Garrett County / Oakland

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Pet friendly
Nestled in the woods, Hideaway is an adorable A-frame mountain chalet that is the perfect getaway for a small family or a couple’s retreat. Recently renovated, this home offers a cozy Great Room with stylish furnishing and glistening hardwood floors. Family time will be …see more

from $247 / night

$1074 - $1343 / week

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from $247 / 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

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 - $1943 / week

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from $297 / night

(25) Excellent 

17

Oakland Vacation log cabin rental

Garrett County / Oakland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • 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

26

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
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 $238 / night

$1274 - $1644 / week

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from $238 / night

21

Home rental in Oakland

Garrett County / Oakland

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
Welcome Home Friends! Paradise at Penn Cove is a captivating 3 bedroom chalet that rests on quiet road overlooking Penn Cove. Upon entrance you will immediately feel the warm and cozy atmosphere of the Great Room. Expansive vaulted ceilings, floor to ceiling windows, an …see more

from $241 / night

$998 - $1495 / week

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from $241 / night

(9) Very Good 

12

Oakland Vacation home rental

Garrett County / Oakland

5 14 7 nights min

  • 5 bedrooms
  • Sleeps 14
  • 7 nights min
  • Child friendly
Outside or in, Crosswinds is the ideal choice for your next Deep Creek Lake vacation! Within a short walk from the home’s front door, you'll have easy access to the home’s lake access point - including a picturesque picnic area for you and your guests - as well as the n …see more

from $236 / night

$1649 - $2607 / week

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from $236 / night

(4) Good 

8

Oakland Vacation home rental

Garrett County / Oakland

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Come away to a quiet retreat.  Wispering Ridge is a perfect getaway for a small family who wants to be close to everything the lake has to offer.  This duplex proves that you don't have to be large to have an incredible view of the lake.  An open great room, dining room …see more

from $129 / night

$901 - $1126 / week

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from $129 / 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 $300 / night

$1415 - $1901 / week

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from $300 / 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

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
Look no further! Whispering Pines is an extraordinary five bedroom home that will warmly welcome you and your family. Highlights of the spacious main level include gleaming hardwood floors, warm earth tones, and an open floor plan that is just right for spending time …see more

from $293 / night

$1395 - $1993 / week

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from $293 / night

47

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
If you are seeking a large spacious lakefront home, brimming with all desirable amenities, then we have the perfect home for you. Wynsome Run Lodge is a spectacular 7 bedroom home ideally located close to Deep Creek State Park, a movie theater, and area restaurants. The …see more

from $861 / night

$3392 - $5311 / week

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from $861 / night

37

Home rental in Oakland

Garrett County / Oakland

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
Trailside Tranquility is a charming, craftsman-style vacation home combines style, comfort and a location that is convenient to the best of Deep Creek Lake. Step inside to find an open floorplan that makes gathering with family and friends entirely effortless. Warm and …see more

from $287 / night

$1395 - $1773 / week

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from $287 / night

19

Vacation home in Oakland

Garrett County / Oakland

5 14 7 nights min

  • 5 bedrooms
  • Sleeps 14
  • 7 nights min
  • Child friendly
This serene retreat will get you away from it all, yet is still in close proximity to activities, state parks and restaurants. Situated on a peaceful cove close to the dam, this home offers the perfect spot to enjoy the lake while fishing, swimming or going out on a boa …see more

from $284 / night

$1984 - $4849 / week

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from $284 / night

(4) Excellent 

13

Vacation home in Oakland

Garrett County / Oakland

5 14 7 nights min

  • 5 bedrooms
  • Sleeps 14
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Pay attention: vacation retreats like this are hard to find! Diamond on the Lake is truly a gem, offering a grassy level lakefront with scenic lake views, upscale home furnishings, and everything you could possible want in a vacation home. The attention to detail, styli …see more

from $460 / night

$3215 - $7151 / week

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from $460 / night

(5) Very Good 

14

Vacation home in Oakland

Garrett County / Oakland

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ask about children
  • Air conditioning
Fir Shore is a lovely and spacious log home that is just awaiting your arrival. A perfect home for the multi-family or a couples retreat, this home has 6 beautifully decorated bedrooms, 3 of which are master suites. Lacking nothing, this home offers something for everyo …see more

from $541 / night

$2315 - $2792 / week

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from $541 / night

18

Vacation home in Oakland

Garrett County / Oakland

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
All About the View is a remarkable lakefront home that encompasses all the qualities that make a vacation truly great. Its unique design, desirable amenities and ideal location combine to create the perfect venue for a vacation with family and friends. Gathering togethe …see more

from $422 / night

$1808 - $3871 / week

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from $422 / 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

$1674 - $2393 / week

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from $347 / 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 $312 / night

$1389 - $2673 / week

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from $312 / night

24

Oakland Vacation home rental

Garrett County / Oakland

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ask about children
  • Air conditioning
You will see nothing but positive Changes in Attitude when you choose to stay in this spectacular 5 bedroom lakefront home. Step inside and immediately become swept away by the majestic lake views! This home has top of the line amenities that guarantee a fun and memorab …see more

from $537 / night

$2192 - $4485 / week

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from $537 / night

16

Vacation home in Oakland

Garrett County / Oakland

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
Your magical mountain getaway begins with your stay in Strawberry Fields. Nestled in the heart of the Deep Creek action, you and your guests will love having so many adventurous options at your fingertips! With 3 levels of optimal living space, this amazing home is perf …see more

from $215 / night

$995 - $1123 / week

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from $215 / night

42

Vacation home in Oakland

Garrett County / Oakland

5 16 2 nights min

  • 5 bedrooms
  • Sleeps 16
  • 2 nights min
  • Ask about children
  • Air conditioning
Mountain Meadow offers the perfect place to reunite with family and friends for that much needed Deep Creek Lake vacation. Offering an open floor plan, the spacious main level has a wall of windows with beautiful views as the focal point. Lots of natural light, gleamin …see more

from $397 / night

$1593 - $2192 / week

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from $397 / night

38

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 $589 / night

$2372 - $3114 / week

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from $589 / night

(6) Excellent 

32

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 embra …see more

from $312 / night

$1395 - $2173 / week

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from $312 / night

(1) Excellent 

16

Vacation home in Oakland

Garrett County / Oakland

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
Welcome to one of Deep Creek’s finest homes. Reverie is an exquisite 5 bedroom mountain home that will far exceed your expectations. Combining lavish décor with prime lakefront easily makes this home a Deep Creek gem. Floor to ceiling windows in the Great Room allow you …see more

from $537 / night

$2278 - $5120 / week

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from $537 / night

24

Home rental in Oakland

Garrett County / Oakland

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Newer 2200-square-foot, custom, log cabin with three-sided wrap deck nestled on one+ acre in Deerfield off of Mayhew Inn Road. Beautiful trees and ferns with room to breath. Three miles from Swallows Falls, 2 miles to horseback riding stables and 5 miles to State Park B …see more

from $350 / night

$2450 / week

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from $350 / night

30

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 $238 / night

$1239 - $1644 / week

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from $238 / night

(7) Very Good 

17

Vacation home in Oakland

Garrett County / Oakland

5 14 7 nights min

  • 5 bedrooms
  • Sleeps 14
  • 7 nights min
  • Child friendly
For lakefront living full of perks, look no further than Edgewater. When you book a stay at this three-level family home, you get five bedrooms, four bathrooms, and the home's peaceful wooded setting all to yourself. Located along a quiet corner of the lake, the home’s …see more

from $224 / night

$1565 - $2941 / week

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from $224 / 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 $451 / night

$1922 - $2772 / week

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from $451 / night

22

Log cabin rental in Oakland

Garrett County / Oakland

2 8 2 nights min

  • 2 bedrooms
  • Sleeps 8
  • 2 nights min
  • 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 $222 / night

$944 - $1193 / week

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from $222 / night

25

Vacation home in Oakland

Garrett County / Oakland

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
Home Sweet Cabin is a charismatic mountain home that rests in a quiet, peaceful cove. Expansive wooden cathedral ceilings highlight the stone fireplace and gives promises of nights spent bonding with family and friends. The open floor plan allows you to entertain your g …see more

from $250 / night

$917 - $1273 / week

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from $250 / 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 - $1543 / week

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from $264 / 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

7

Vacation home in Oakland

Garrett County / Oakland

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Pet friendly
Located in the heart of the action, you and the family will quickly call Reardon’s Roost your home away from home, time after time. Imagine enjoying your morning coffee out on the deck as you take in the spectacular lake and mountain views before you. Catch a movie on t …see more

from $165 / night

$789 - $894 / week

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from $165 / night

(1) Excellent 

16

Home rental in Oakland

Garrett County / Oakland

4 12 7 nights min

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min
  • Child friendly
  • Pet friendly
This beautiful lake home delivers one warm welcome! From the moment you arrive, this home will surround you in an easy elegance for perfection that feels effortless. With a natural stone fireplace, cathedral ceilings, and windows overlooking nature, the great room will …see more

from $409 / night

$2857 - $5603 / week

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from $409 / 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 $283 / night

$1293 - $1995 / week

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from $283 / 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
Ready to discover your favorite Deep Creek vacation home? Everyone in your group will love the style, spaciousness and comfort of Just About Paradise! Offering plenty of indoor and outdoor gathering spaces, it is the perfect place for get-togethers.  Start your day wit …see more

from $347 / night

$1600 - $1943 / week

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from $347 / night

1