50 Best Vacation Rentals in Garrett County - Holiday Lettings - Cabins

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Apartments McHenry
330 properties
Oakland
253 properties

Garrett County

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732 Vacation rentals

29

Vacation home in McHenry

Garrett County / McHenry

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
Gather the family and head to the mountains for a refreshing and unforgettable vacation at Deep Creek Village #44. This fabulous lakefront townhome has something to offer everyone all year around. For those that want to take advantage of some of Wisp's winter activities …see more

from $198 / night

$874 - $1,364 / week

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from $198 / 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 $328 / night

$1,461 - $2,593 / week

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from $328 / 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

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

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

(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

(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

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

30

Vacation home rental

Garrett County / McHenry

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
It's difficult to top this lake house's charm, location, and private dock slip across the road! Two stories of windows flood the living spaces with light, and the deck opens up to glimpses of the lake between the trees. Plus, you're welcome to bring the family dog along …see more

from $98 / night

$686 / week

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Responds fast!
avg. 42 minutes

from $98 / night

32

Vacation home with shared pool in McHenry

Garrett County / McHenry

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
Check out this updated, larger Ski Harbor end unit. Situated perfectly on a peninsula and lakefront, right by the tennis court and the indoor pool, hot tub and sauna! Best location in the development. This 4 Bedroom home has been updated and has 2 living areas with flat …see more

from $291 / night

$1,194 - $1,594 / week

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from $291 / night

35

McHenry Vacation home rental

Garrett County / McHenry

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Ask about children
  • Air conditioning
When you visit Deep Creek, By the Lake is where you want to be! Offering five master suites, this spacious home is a great choice for family vacations or a couples’ getaway. Located in the popular Lake Pointe community, you immediately notice the convenience of the loc …see more

from $553 / night

$2,183 - $3,772 / week

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from $553 / night

21

Vacation home with shared pool in McHenry

Garrett County / McHenry

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
Ski Harbor #7 is a tastefully furnished four-bedroom townhome located on Deep Creek Lake's most popular northern peninsula. It is ideal for the small family but spacious enough for the couple's retreat. Boasting magnificent mountain views, the spacious main level has a …see more

from $237 / night

$1,094 - $1,594 / week

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from $237 / 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

51

Vacation home in McHenry

Garrett County / McHenry

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
Breathe easy at Quiet Retreat, a welcoming Deep Creek Lake vacation rental home that is surrounded by towering trees and limitless adventures. The spacious main level has a bright and airy feel thanks to a massive wall of windows and well-chosen décor. Unwind on the l …see more

from $528 / night

$2,770 - $4,275 / week

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from $528 / 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

40

Vacation home in McHenry

Garrett County / McHenry

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
Tucked among the trees in the centrally located Gallatin Woods community, Keep Dreaming is a mountain getaway that is ready and waiting to host your family and friends! With outdoor space that will keep everyone happy, a wrap-around deck gives everyone room to relax an …see more

from $371 / night

$1,968 - $2,795 / week

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from $371 / 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 29 minutes

from $200 / 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

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

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. 42 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

(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

39

Home rental in Oakland

Garrett County / Oakland

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
Welcome to Fish Inn! This cozy four-bedroom, two bath lake house is ready for you and your friends and family to create fond memories of time together at Deep Creek Lake. Tucked among the trees, Fish Inn is a lake access home that is outfitted with everything you need …see more

from $344 / night

$1,494 - $1,793 / week

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from $344 / 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

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

25

McHenry Vacation home rental

Garrett County / McHenry

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
Experience a vacation in one of Deep Creek's most favored communities! Everyone in your group will fall in love with the location, pleasant décor throughout and the amazing level lakefront at Ski Harbor #26! This adorable townhome offers superb amenities and lots of rec …see more

from $262 / night

$1,446 - $2,520 / week

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from $262 / 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. 29 minutes

from $174 / night

(1) Excellent 

35

Home rental in McHenry with shared pool

Garrett County / McHenry

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Mountain Top Lodge is true to its name, situated in the premier Deep Creek Highlands, this brand new home features an amazing great room with a soaring cathedral ceiling, gas fireplace to ward off a cold winters night and a wall of windows to capture the beauty of the w …see more

from $381 / night

$1,619 - $2,538 / week

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from $381 / night

40

Vacation home in McHenry

Garrett County / McHenry

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
Nestled on the shores of Deep Creek Lake, Wispering Waters is an ideal choice for your next getaway with family and friends. Ideal for gathering with your favorite people, the main level has an open floor plan with scenic lake views and plenty of space for everyone to …see more

from $468 / night

$2,189 - $3,292 / week

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from $468 / 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

64

Vacation home accommodation

Garrett County / McHenry

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
An amazing view of the lake is just one of the many highlights of American Dream – a favorite Deep Creek Lake vacation home! Just one stay will leave you longing to return year after year. Faces will light up when you enter the spacious interior that boasts a massive …see more

from $560 / night

$2,394 - $3,104 / week

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from $560 / night

32

Vacation home in McHenry

Garrett County / McHenry

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Explore…relax…and take a much deserved break at Happy Trails! Off-the-beaten-path yet convenient to all the area’s attractions, this is the perfect place to start your Deep Creek Lake dream vacation. Exposed beams, wood accents and abundant natural light combine to cre …see more

from $297 / night

$1,344 - $1,674 / week

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from $297 / night

39

Vacation home in McHenry

Garrett County / McHenry

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
For your next family getaway, book a stay in this charming vacation home in the Maryland woods! Featuring a private hot tub, a game room, and incredible proximity to Wisp Mountain and Deep Creek Lake, this delightful rental is a sure bet for a family vacation for the ag …see more

from $167 / night

$1,169 / week

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Responds fast!
avg. 42 minutes

from $167 / 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

48

Vacation home in McHenry

Garrett County / McHenry

5 15 Min stay varies

  • 5 bedrooms
  • Sleeps 15
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Log Me Inn is a brand new log cabin home in the Biltmore Community. The cabin is situated among towering trees, in a gated community, on a cul de sac. You will love being surrounded by the beautiful natural setting. The spacious interior will have all of the 'bells and …see more

from $523 / night

$2,192 - $3,834 / week

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from $523 / night

(1) Very Good 

28

Vacation home with shared pool in McHenry

Garrett County / McHenry

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This Beautiful 3 Bedroom 2.5 bath town home with a wood burning fireplace sits across the street from the lake, views of the slopes and less than a 5 minutes from Wisp Resort. Perfectly located for all Deep Creek has to offer with many added benefits such as 325 feet of …see more

from $260 / night

$895 - $1,194 / week

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from $260 / 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

29

Vacation home in McHenry

Garrett County / McHenry

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Rock Lodge Cabin offers a serene mountain setting while providing convenient access to Deep Creek Lake activities. This modern log home has plenty of room for everyone with spacious gathering areas and ample outdoor space. An open concept makes the main level ideal …see more

from $328 / night

$1,524 - $1,973 / week

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from $328 / night

27

Vacation home with shared pool in McHenry

Garrett County / McHenry

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
Relax and enjoy your long awaited vacation at this lovely lakefront townhome. Conveniently located at the northern tip of the lake, this townhome provides the ideal location for lake activities and skiing. Just minutes from Wisp Ski and Golf Resort. Offering fun for all …see more

from $297 / night

$1,244 - $1,650 / week

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from $297 / night