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

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700 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

17

McHenry Vacation home rental

Garrett County / McHenry

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
Discover the simple pleasures in life when you choose to stay in captivating 4 bedroom/ 3 bath lakefront log home Woodhaven. Located on the McHenry cove, this wonderful home is the perfect proximity to the Wisp’s ski slopes in winter, Lodestone Golf Course, ASCI, & more …see more

from $262 / night

$1,244 - $1,993 / week

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from $262 / 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 $222 / night

$994 - $1,344 / week

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from $222 / 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

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

21

McHenry Vacation home rental

Garrett County / McHenry

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Pet friendly
Whether you seek rest and relaxation or fun and adventure, Deep Creek Village #29 is the ideal vacation home for your future Deep Creek vacation! Prepare to be blown away when you step inside this remodeled townhome which offer luxury living in the heart of McHenry. Wal …see more

from $187 / night

$895 - $1,419 / week

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from $187 / 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

(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

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

29

Vacation home rental

Garrett County / McHenry

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • 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 $89 / night

$623 / week

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Responds fast!
avg. 3 hours 1 minutes

from $89 / 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 $262 / night

$1,124 - $1,594 / week

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from $262 / 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

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

(1) Excellent 

48

McHenry Vacation home rental

Garrett County / McHenry

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Live luxuriously when you stay in the impressive 5 bedroom home known as Big Chill. This mammoth mountain home offers 3 levels of living space and more than enough room to host a large family gathering. Step inside and embrace the spacious Great Room which showcases st …see more

from $562 / night

$2,472 - $3,898 / week

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from $562 / 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

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. 3 hours 1 minutes

from $89 / night

(12) Very Good 

15

Home rental in McHenry

Garrett County / McHenry

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
All Seasons Getaway truly is a remarkable townhome to visit throughout all the seasons. Located in the heart of Deep Creek Lake, this home offers both stunning lake and ski slope views. Step into the Great Room and take in the warm décor and glistening hardwood floors. …see more

from $237 / night

$974 - $1,233 / week

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from $237 / night

16

Vacation home in McHenry

Garrett County / McHenry

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Lake living doesn’t get better than this! Blue Heron is a charming and delightful 3 bedroom home that offers a phenomenal lake front. Breathtaking lake views greet you from every angle the moment that you step in this one level of living home. The dark, glistening hard …see more

from $347 / night

$1,494 - $2,993 / 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

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 $422 / night

$1,993 - $3,292 / week

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from $422 / night

29

Vacation home in McHenry

Garrett County / McHenry

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Ask about children
  • Pet friendly
Welcome home friends and family! Village of the Wisp #12 is a delightful 3 bedroom ski in/ ski out townhome that will please any winter enthusiast. Offering 3 levels of living space, you and your family have more than ample room to move about. Bringing your swim/ ski ge …see more

from $230 / night

$1,124 - $2,077 / week

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from $230 / 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

29

Home rental in McHenry

Garrett County / McHenry

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
Situated in the Wisp Mountains most convienent ski-in/ski-out community, Ski Chalet holds the key to endless adventures. Located next to chairlift #4 and #5, the skiers in your group will be absolutely delighted with the convenient location when hitting the slopes. Thos …see more

from $312 / night

$1,394 - $3,572 / week

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from $312 / night

30

Vacation home in McHenry

Garrett County / McHenry

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
Sunset Terrace is an enchanting 3 bedroom lakefront home that promises to deliver vacation memories that will last a lifetime. Like the name implies, you and your guests will love sitting on the private dock in the evenings as you enjoy breathtaking sunsets. Bring your …see more

from $247 / night

$1,074 - $1,594 / week

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from $247 / night

31

Vacation home in McHenry

Garrett County / McHenry

6 16 Min stay varies

  • 6 bedrooms
  • Sleeps 16
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
The Treehouse is that log cabin on the lake in the mountains that you dreamt of as a child. Turn those dreams into reality at this gorgeous, unique hand-hewn log home. It nestles among mature pines on a gently sloping lakefront lot at the foot of Wisp Mountain within wa …see more

from $747 / night

$3,192 - $4,690 / week

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from $747 / 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 $288 / night

$1,293 - $1,674 / week

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from $288 / night

41

McHenry Vacation home rental

Garrett County / McHenry

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Find peace and relaxation at this charming cabin in the woods, a two-bedroom McHenry retreat with a private deck, sweeping views of the forest, and a wonderful location for hikers, golfers, skiers, anglers, and boating enthusiasts. Tucked away in a dense grove of trees …see more

from $64 / night

$448 / week

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Responds fast!
avg. 3 hours 1 minutes

from $64 / 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

25

Oakland Vacation home rental

Garrett County / Oakland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
Changed to: "Canaima" is the name of the friendly spirit of the jungles of Venezuela and Brazil. It is also the site of the novel "The Lost World" by Arthur Conan Doyle and the location of the "Green Mansions", the place where Rima lived, in the beloved novel of William …see more

from $301 / night

$1,344 - $1,727 / week

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from $301 / 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

(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

(1) Excellent 

42

McHenry Vacation home rental

Garrett County / McHenry

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
High-Skis' Villa is a premier chalet located on top of Wisp Mountain and walking distance to the Adventure Sports Center and future mountaintop village. The interconnecting hiking and biking trails through natural wooded landscapes are available to you during your vacat …see more

from $437 / night

$1,873 - $3,102 / week

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from $437 / night

13

Vacation home rental

Garrett County / McHenry

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Location can be key, especially for those that love to be in the heart of the action. Cedar Creek #15 is a beautiful 4 bedroom townhome that will warmly welcome you and your family from the moment that step inside. Gleaming hardwood floors flow throughout and the stylis …see more

from $222 / night

$924 - $1,405 / week

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from $222 / 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

29

Vacation home in McHenry

Garrett County / McHenry

4 13 Min stay varies

  • 4 bedrooms
  • Sleeps 13
  • Min stay varies
  • Ask about children
  • Pet friendly
Prepare to experience an unbelievable Deep Creek vacation when you choose to stay in the stunning mountain chalet Adlerskron. Perched high on a wooded hill, this home boasts lake and mountain views. Just a few steps into the Great Room and you will be in awe of the beau …see more

from $347 / night

$1,593 - $2,306 / week

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from $347 / night

(3) Excellent 

16

Vacation home in McHenry

Garrett County / McHenry

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Pet friendly
No matter the season, Happy Landing keeps adventure front and center for your Deep Creek Lake vacation! Centrally located along Marsh Hill Road, Wisp Resort is just a short walk or drive away. It could not be any easier to access the ski slopes, outdoor mountain coaster …see more

from $409 / night

$2,863 - $3,519 / week

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from $409 / 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

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 $297 / night

$1,174 - $1,711 / week

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from $297 / 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

35

Vacation home in McHenry

Garrett County / McHenry

2 10 Min stay varies

  • 2 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
Villages of Wisp 70 Bright Passage is a great option for your next Deep Creek Lake getaway! On crisp mountain nights, warm up by the fireplace in the great room or head to the lower level family room to watch your favorite team or a movie on the Blu Ray DVD Player. Th …see more

from $208 / night

$1,043 - $1,845 / week

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from $208 / night