50 Best Vacation Rentals in Oakland - Holiday Lettings - Cabins

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732 Vacation rentals

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 $328 / night

$1,461 - $2,593 / week

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from $328 / night

28

Oakland Vacation home rental

Garrett County / Oakland

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
Brimming with charm and convenience, Some Kind of Wonderful is a Craftsman-style home that is ready and waiting to host your next Deep Creek vacation! Get together with your favorite people in the spacious main level where you will feel instantly at home during your ti …see more

from $297 / night

$1,443 - $1,725 / week

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from $297 / night

(6) Excellent 

45

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 $387 / night

$1,674 - $2,488 / 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

$1,009 - $1,274 / week

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from $249 / night

49

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 $456 / night

$2,009 - $2,618 / week

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from $456 / 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 Community. You will have complete access to tennis, basketball and volleyball courts found in a gorgeous mountain setting. Ente …see more

from $462 / night

$1,793 - $2,540 / week

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from $462 / night

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 $262 / night

$994 - $1,473 / week

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from $262 / night

(28) 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 37 minutes

from $200 / night

(1) Excellent 

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 $272 / night

$1,293 - $1,525 / week

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from $272 / 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 $347 / night

$1,593 - $2,023 / week

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from $347 / 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 $348 / night

$1,651 - $2,168 / week

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from $348 / 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 $894 / night

$3,370 - $5,290 / week

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from $894 / 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. 1 hour 26 minutes

from $89 / 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 $362 / night

$1,443 - $2,243 / week

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from $362 / night

42

Home rental in Oakland

Garrett County / Oakland

6 16 Min stay varies

  • 6 bedrooms
  • Sleeps 16
  • Min stay varies
  • Ask about children
  • Air conditioning
This brand-new log home is situated in a wooded community that is off-the-beaten-path yet still within minutes from Deep Creek Lake activities. Offering four master suites and incredible outdoor living space, every aspect was designed with memorable vacations in mind! …see more

from $603 / night

$2,592 - $3,321 / week

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from $603 / night

(6) Excellent 

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

from $120 / night

$800 / week

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Responds fast!
avg. 54 minutes

from $120 / night

24

Vacation home in Oakland

Garrett County / Oakland

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Pet friendly
Explore…relax…and take a well-deserved break at Lake View! Centrally located, this is the perfect place to start your dream vacation at Deep Creek Lake. Situated on a gently sloping lakefront lot, this charming cottage offers beautiful views from almost every room. Fri …see more

from $299 / night

$1,394 - $1,924 / week

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from $299 / night

(4) Excellent 

54

Ski home to rent in Oakland

Garrett County / Oakland

5 13 Min stay varies

  • 5 bedrooms
  • Sleeps 13
  • Min stay varies
  • Nearest beach 8 mi
  • Ski
  • Child friendly
Architecturally pleasing to the eye and the soul, this UNIQUE AND GORGEOUS 'GREEN HOME' boasts a 31' great room ceiling with 2 INTERIOR and 1 EXTERIOR (on deck) WOOD BURNING STACKED STONE FIREPLACES (also 31' tall) plus LARGE HOT TUB ON DECK and LARGE FIRE PIT in back y …see more

from $250 / night

$1,850 / week

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from $250 / night

34

Oakland Vacation home rental

Garrett County / Oakland

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
Discover peaceful days and starry nights at Lakeside Vista, a charming Deep Creek Lake vacation home with picturesque lake views. When you are looking for a classic lake experience, this is a place where you can truly reconnect with your favorite people. On the main le …see more

from $363 / night

$1,719 - $2,924 / week

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from $363 / 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 $925 / night

$3,393 - $5,689 / week

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from $925 / night

(2) Excellent 

12

Vacation home in Oakland

Garrett County / Oakland

3 10 7 nights min

  • 3 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
Rest and rejuvenation wait at Bear Cove! This spacious three-bedroom home is settled along a quiet section of the lake, a place where you can take a morning stroll along community roads or sip your coffee in peace at the water’s edge. A place defined by quietude, refle …see more

from $378 / night

$2,641 - $4,459 / week

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from $378 / 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 $487 / night

$1,893 - $3,791 / week

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from $487 / 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 $648 / night

$2,593 - $3,448 / week

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from $648 / 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

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 $383 / night

$1,671 - $2,173 / week

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from $383 / night

26

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

(1)  

25

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 $362 / night

$1,693 - $2,164 / week

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from $362 / 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

46

Vacation home in Oakland

Garrett County / Oakland

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ask about children
  • Air conditioning
At Last promises amazing lake views, fun adventures and treasured memories for your next Deep Creek Lake vacation! Conveniently located, this elegant log home is the ideal place to reconnect with family and friends. Upon entering the spacious main level, your eyes wi …see more

from $598 / night

$3,110 - $6,863 / week

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from $598 / night

(8) Excellent 

54

Home rental in Oakland

Garrett County / Oakland

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
Surround yourself with nature in this majestic, recently renovated log home. Four master suites make it an excellent choice for couples as well as family gatherings. On the entry level, hardwood floors, cathedral ceilings and large windows adorn the great room, and the …see more

from $647 / night

$2,493 - $4,771 / week

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from $647 / 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 $285 / night

$1,995 - $2,497 / week

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from $285 / night

54

Oakland Vacation home rental

Garrett County / Oakland

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Invite your friends and family to Heavenly Grove, where convenience, comfort and style come together to create an amazing setting for Deep Creek Vacations. Located in the popular Blakeslee Community, you are off-the-beaten path but still close to the best of the area. …see more

from $437 / night

$1,973 - $3,092 / week

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from $437 / night

28

Vacation home in Oakland

Garrett County / Oakland

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • 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

(4) Very Good 

75

Home accommodation in Oakland

Garrett County / Oakland

5 14 7 nights min

  • 5 bedrooms
  • Sleeps 14
  • 7 nights min
  • Child friendly
Pine Oasis offers everything one needs for a relaxing Deep Creek Lake vacation! This lakefront home boasts five bedrooms, as well as an open kitchen, game room, and soaring stacked stone fireplace; this charming estate makes it easy to spend time together, making new me …see more

from $395 / night

$2,759 - $5,808 / week

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from $395 / 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

22

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

35

Vacation home in Oakland

Garrett County / Oakland

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly
Spacious enough for a family reunion or a truly memorable holiday celebration, this warm and welcoming cabin in the woods comes with a well-appointed deck and a covered patio with a forest view, an outdoor hot tub, wood-burning fireplace, pool table, and a romantic, in- …see more

from $174 / night

$1,218 / week

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Responds fast!
avg. 3 hours 19 minutes

from $174 / night

40

Home rental in Oakland

Garrett County / Oakland

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Bring the whole family together at this chalet-style Oakland home, complete with a game room, two furnished patios, and a private hot tub. The family dogs are also welcome for a small nightly fee! Just up the road, Deep Creek Lake is an exceptional fishing destination, …see more

from $169 / night

$1,183 / week

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Responds fast!
avg. 2 hours 34 minutes

from $169 / 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 $492 / night

$2,693 - $5,473 / week

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from $492 / 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 $314 / night

$1,250 - $1,743 / week

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from $314 / night