50 Best Vacation Rentals in Oakland - Holiday Lettings - Cabins

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699 Vacation rentals

32

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 $212 / night

$994 - $1,473 / week

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from $212 / night

53

Oakland Vacation home rental

Garrett County / Oakland

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
Nestled among the trees in this quiet cul-de-sac, you'll find this beautifully decorated and spacious home which is part of the Mountainside Resort and Marine Club subdivision. Have complete access to tennis, basketball and volleyball courts found in a gorgeous mountain …see more

from $462 / night

$1,793 - $2,540 / week

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from $462 / 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 $262 / night

$1,045 - $1,274 / week

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from $262 / night

28

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
Enjoy the feeling of rustic mountain living in this cedar chalet. Cozy and inviting, this home is perfect for accommodating the extended family or group of friends. Wood-lined walls, cathedral ceilings and a beautiful stone fireplace greet you upon entering the main l …see more

from $337 / night

$1,443 - $2,243 / week

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from $337 / night

(1) Excellent 

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

$1,794 - $3,092 / week

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from $387 / 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 $247 / night

$1,024 - $1,494 / week

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from $247 / night

48

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

$1,843 - $2,618 / week

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from $412 / night

35

Vacation home in Oakland

Garrett County / Oakland

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
Waves and Moguls is a captivating 5 bedroom vacation home that is the ideal choice no matter what season you choose to visit. You will immediately feel a sense of home when you step inside the bright and lovely Great Room, sure to be a favorite gathering spot among fa …see more

from $362 / night

$1,543 - $2,173 / week

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from $362 / night

(6) Excellent 

43

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 $362 / night

$1,543 - $2,488 / week

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from $362 / night

17

Vacation home in Oakland

Garrett County / Oakland

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Treat your family and friends to an exceptional vacation experience at Golden Memories, a Deep Creek Lake vacation home that offers comfort, convenience and lots of charm! Relaxation comes naturally at this well-kept retreat. There is plenty of room for everyone to gat …see more

from $297 / night

$1,344 - $2,593 / week

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from $297 / night

(27) 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 - $1,200 / week

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Responds fast!
avg. 1 hour 30 minutes

from $200 / night

31

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 $896 / night

$3,491 - $5,689 / week

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from $896 / night

21

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 $247 / night

$974 - $1,244 / week

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from $247 / night

24

Vacation home in Oakland

Garrett County / Oakland

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
Beautifully decorated with a warm and cheery spirit Quiet Reflections is a lakefront townhome with room for everyone to relax and enjoy the lake views. The spacious main level invites you to get comfortable on the leather sofas and watch your favorite shows on the wal …see more

from $249 / night

$1,124 - $1,843 / week

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from $249 / night

24

Oakland Vacation home rental

Garrett County / Oakland

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
Let the adventure begin! Sunset Reflections is a cheerful 3 bedroom lakefront home that will allow you to experience a true Deep Creek getaway! The beautifully decorated Great Room is enhanced with cathedral style ceilings, an impressive stacked stone fireplace and floo …see more

from $322 / night

$1,373 - $2,593 / week

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from $322 / night

34

Vacation home in Oakland

Garrett County / Oakland

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Ask about children
  • Air conditioning
Letting go of everyday cares is effortless when you choose Breathe Easy for your Deep Creek vacation with family and friends. This spacious townhome in the centrally located Timberlake Village community is ready to host a fun and relaxing getaway. Decorated in muted e …see more

from $347 / night

$1,674 - $2,168 / week

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from $347 / night

27

Vacation home in Oakland

Garrett County / Oakland

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Tucked among towering trees, Knotty Pines offers you a classic mountain getaway with lots of opportunities to make lasting memories with your favorite people. Tastefully decorated, the great room will be a popular place to gather whether you are curling up on the sect …see more

from $247 / night

$1,194 - $1,525 / week

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from $247 / night

38

Oakland Vacation home rental

Garrett County / Oakland

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
Treat your family to an enchanted vacation experience at Morningside Lodge. This phenomenal 4 bedroom log home offers you and your family top notch comfort and style. Graceful hardwood floors flow throughout creating a warm ambiance but it is the spectacular lake views …see more

from $497 / night

$1,993 - $3,892 / week

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from $497 / night

(1) Excellent 

44

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

$2,373 - $3,448 / week

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from $597 / night

39

Vacation home rental

Garrett County / Oakland

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Make this lovely, lakefront rental your home away from home when you come to Deep Creek Lake and enjoy amenities like a hot tub, a dock with your own assigned slip, and shared tennis. You'll have the best of both worlds with easy access to the slopes and in-town conveni …see more

from $119 / night

$833 / week

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Responds fast!
avg. 22 minutes

from $119 / 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 $347 / night

$1,494 - $2,792 / week

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from $347 / night

51

Oakland Vacation home rental

Garrett County / Oakland

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
This chalet is the ideal place to relax and enjoy the spectacular views of the mountains. Located in a private, peaceful community of Mountainside, this home is just right for your vacation needs. Beautiful decor and attention to detail accent the cathedral ceiling and …see more

from $322 / night

$1,574 - $2,023 / week

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from $322 / night

28

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 $240 / night

$1,094 - $1,344 / week

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from $240 / night

44

Vacation home in Oakland

Garrett County / Oakland

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
Ski Season is premiere vacation home that offers guests the best of both worlds: indoor elegance and outdoor fun and adventure! This 4 bedroom lakefront home radiates luxury throughout. Step inside and take in the breathtaking lake views from the floor to ceiling window …see more

from $497 / night

$1,993 - $3,892 / week

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from $497 / night

45

Oakland Vacation home rental

Garrett County / Oakland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
Experience the pleasures of country living at this three-bedroom Oakland home, a dog-friendly Maryland escape with a private deck and firepit, its very own air hockey table, and a wondrous location close to Swallow Falls, the Yough River, and Deep Creek Lake. This two …see more

from $89 / night

$623 / week

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Responds fast!
avg. 22 minutes

from $89 / 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

$874 - $1,094 / week

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from $198 / night

27

Vacation home rental

Garrett County / Oakland

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
Surround yourself with natural beauty at this wonderful home located in the cozy, lakefront Timberloft community at the heart of Deep Creek Lake. Enjoy your first cup of coffee on the deck overlooking the lake. Delight in the spacious master suites that encompass beauti …see more

from $262 / night

$1,094 - $1,593 / week

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from $262 / night

13

Vacation home in Oakland

Garrett County / Oakland

4 12 7 nights min

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min
  • Child friendly
Summer skies or winter flurries, the time is always ‘Just Perfect’ for a trip to this charming 4 bedroom chalet! Merging together lake and mountain views creates an outdoor ambiance steeped in tranquility. Grill out on the back deck, set your sights on the majesty aroun …see more

from $213 / night

$1,489 - $2,320 / week

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from $213 / night

25

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
Fond, family memories will truly be made when you spend your Deep Creek getaway in the charismatic home known as Finn McCool's. This 5 bedroom home boasts a phenomenal lakefront with a private dock, ideal for swimming on hot summer days. After an exciting day of hiking …see more

from $462 / night

$1,843 - $3,791 / week

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from $462 / night

(5) Excellent 

Certificate of Excellence

27

Vacation home rental

Garrett County / Oakland

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • 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

Certificate of Excellence

from $120 / night

$800 / week

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Responds fast!
avg. 16 minutes

from $120 / 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
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 ent …see more

from $288 / night

$1,394 - $1,773 / week

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from $288 / night

(1)  

26

Vacation home in Oakland

Garrett County / Oakland

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
If luxury is what you have in mind, then look no further. Serenity Summit is an extravagant 5 bedroom duplex that boasts an immaculate interior. With 3 master suites available, this home is ideal for the multi-family or couple's retreat. Your Great Room boasts lustrous …see more

from $347 / night

$1,674 - $2,164 / week

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from $347 / night

(19) Very Good 

43

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
Memory Lane is a home designed to bring friends and family together for fun and laughter. Tucked among gracious, blossomed trees with a meticulously maintained lawn, you will truly feel like you have discovered your mountain oasis. Gather with loved ones in the Great Ro …see more

from $322 / night

$1,574 - $2,345 / week

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from $322 / 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

$3,191 - $5,290 / week

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from $798 / night

44

Vacation home rental

Garrett County / Oakland

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
For the chance to stay in one of Deep Creek’s most desired vacation homes, book a relaxing escape at Stargazer where peaceful days and starry nights are guaranteed. Mesmerizing from the second that you step inside, prepare to be swept away by the extraordinary lake view …see more

from $562 / night

$2,643 - $5,092 / week

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from $562 / 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 $247 / night

$1,044 - $1,574 / week

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from $247 / night

(3) Excellent 

18

Vacation home in Oakland

Garrett County / Oakland

5 16 7 nights min

  • 5 bedrooms
  • Sleeps 16
  • 7 nights min
  • Child friendly
Rother's Cove is a proven delight full of new surprises! This traditional lake home is a family-favorite destination for many groups that make this home their sanctuary, year after year. Start your own family tradition with a visit to charming Rother’s Cove! Inside the …see more

from $300 / night

$2,098 - $5,532 / week

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from $300 / 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

$1,993 - $2,873 / week

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from $472 / night

28

Oakland Vacation home rental

Garrett County / Oakland

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
Pack your bags and get ready to experience a true Deep Creek adventure when you choose to stay in the newly built log home Man Haus! This luxury log home will host 4 Master Suites making it an excellent choice for a couple’s retreat or an extended family getaway! Indoor …see more

from $547 / night

$2,393 - $4,341 / week

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from $547 / night

18

Vacation home in Oakland

Garrett County / Oakland

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
This charming mountain cabin sets the mood for an unforgettable vacation! The rustic furnishings and wood accents found throughout create a cozy getaway any time of year. The loft opens out onto the second story balcony for the perfect spot to enjoy morning coffee and c …see more

from $186 / night

$1,298 - $1,741 / week

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from $186 / night