50 Best Vacation Rentals in Oakland - Holiday Lettings - Cabins

Close

Oakland

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

479 Vacation rentals

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 $308 / night

$1,295 - $2,593 / week

Book View

from $308 / 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 $314 / night

$1,408 - $2,792 / week

Book View

from $314 / 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

Book View

from $249 / 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

Book View

Responds fast!
avg. 1 hour 48 minutes

from $200 / 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 $198 / night

$874 - $1,124 / week

Book View

from $198 / night

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

Book View

from $347 / night

24

Home rental in Oakland

Garrett County / Oakland

4 9 2 nights min

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

from $350 / night

$2,450 / week

Book View

from $350 / night

52

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

Book View

from $412 / 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

Book View

from $322 / 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

Book View

from $249 / 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

$1,009 - $1,494 / week

Book View

from $247 / 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

Book View

from $347 / 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

Book View

from $462 / 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

Book View

from $798 / 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

Book View

from $597 / 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

Book View

from $198 / night

31

Vacation home in Oakland

Garrett County / Oakland

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
If you want a classic Deep Creek Lake vacation with convenient lake access, look no further than Lakeview Cottage. This A-frame style home is ideal for a family getaway or a couples’ trip. Wood-lined walls create a warm ambiance in the great room, and a wall of windows …see more

from $247 / night

$1,074 - $1,745 / week

Book View

from $247 / night

33

Vacation home in Oakland

Garrett County / Oakland

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Enjoy your next family vacation near the shore of beautiful Deep Creek Lake at this dog-friendly, well-appointed home in the woods complete with a furnished deck, a gas grill, and plenty of space for up to eight guests. This home is conveniently close to Garrett Highwa …see more

from $89 / night

$623 / week

Book View

Responds fast!
avg. 57 minutes

from $89 / night

(6) Excellent 

41

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

Book View

from $362 / night

(1)  

41

Vacation home in Oakland

Garrett County / Oakland

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
Head to Deep Creek Lake for a quiet vacation with family and friends, complete with all the conveniences that comes with being close to town. Your group will have ready access to the lake and the slopes, as well as in-town convenience. And to make your getaway complete, …see more

from $120 / night

$840 / week

Book View

Responds fast!
avg. 1 hour 2 minutes

from $120 / night

40

Vacation home in Oakland

Garrett County / Oakland

4 10 Min stay varies

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

from $447 / night

$1,873 - $3,791 / week

Book View

from $447 / night

34

Vacation home in Oakland

Garrett County / Oakland

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
Get away from it all at this lovely home with multiple master suites and beautiful views! Nestled on a wooded hillside, you will love the feeling of seclusion while still being within five-minutes from Deep Creek Lake vacation activities. The great room greets you with …see more

from $297 / night

$1,443 - $1,851 / week

Book View

from $297 / 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

Book View

from $387 / 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

Book View

from $896 / night

33

Oakland Vacation home rental

Garrett County / Oakland

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
Once in a Blue Moon is a brand new vacation home that is the ideal choice for your next Deep Creek Lake vacation! The convenient location puts you within minutes of restaurants, marinas, Deep Creek Lake State Park and much more. Beautifully decorated with upscale finis …see more

from $448 / night

$2,000 - $2,780 / week

Book View

from $448 / 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 $239 / night

$939 - $1,244 / week

Book View

from $239 / 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

Book View

from $297 / night

29

Vacation home in Oakland

Garrett County / Oakland

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Ready to discover your favorite Deep Creek vacation home? Everyone in your group will love the style, spaciousness and comfort of Just About Paradise! Offering plenty of indoor and outdoor gathering spaces, it is the perfect place for get-togethers.  Start your day wit …see more

from $337 / night

$1,574 - $1,993 / week

Book View

from $337 / night

27

Oakland Vacation home rental

Garrett County / Oakland

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
This cozy chalet is tucked among the trees offering a quiet setting for the peaceful escape that you deserve. Relax on the deck while taking in the beauty of the woodlands at this mountain getaway. Hummingbird Hill offers the restful atmosphere and comfortable surroundi …see more

from $337 / night

$1,473 - $2,493 / week

Book View

from $337 / 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

Book View

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

Book View

from $297 / 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

Book View

from $240 / night

26

Vacation cottage in Oakland

Garrett County / Oakland

2 8 Min stay varies

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

from $257 / night

$1,108 - $1,373 / week

Book View

from $257 / 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 $288 / night

$1,374 - $1,924 / week

Book View

from $288 / 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

Book View

from $288 / night

31

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
Lakeside Chalet offers the most a mountain chalet setting can offer. Stay at this beautiful split lakefront property and enjoy the lush shades of green throughout the spring and summer seasons; then a backdrop bursting of colors in the fall. Entertain family and friends …see more

from $312 / night

$1,194 - $2,193 / week

Book View

from $312 / 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 $242 / night

$958 - $1,593 / week

Book View

from $242 / 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 $124 / night

$868 / week

Book View

Responds fast!
avg. 40 minutes

from $124 / 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 $251 / night

$1,020 - $1,574 / week

Book View

from $251 / night

17

Vacation home in Oakland

Garrett County / Oakland

2 6 Min stay varies

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

from $165 / night

$790 - $938 / week

Book View

from $165 / night