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Oakland Maryland Vacation Rentals - Home
1 / 29

Oakland Home
5 Bedrooms / 4.5 Bathrooms / Sleeps 145 BR / 4.5 BA / Sleeps 14
Home / 5 Bedrooms / Sleeps 14

from

$300

/ night

Email Owner
Bedrooms:5
Bathrooms:4.5
Sleeps:14
Type:Home
Per night:$300 - $648
Per month:$9,000 - $19,440
Pets allowed:No
Internet:Yes

This exceptional home fronting Deep Creek Lake with a private dock, community pool, and so much more will make the perfect vacation spot! When you first see this home, you will say WOW! Walk under the cute covered front porch through the door to find a home that has the space...

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1 / 24

Oakland Cottage
2 Bedrooms / 1 Bathroom / Sleeps 62 BR / 1 BA / Sleeps 6
Cottage / 2 Bedrooms / Sleeps 6

from

$125

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Cottage
Per night:$125 - $173
Per month:$3,750 - $5,190
Pets allowed:Yes
Internet:Yes

Now 3rd Night FREE! Reserve Today! Fox Den Lake House is an affordable, year- round, 2- bedroom, 1- bath vacation rental home with views of Deep Creek Lake from every room. Walk across the road to rent a boat or take a quick stroll down the street for some ice cream and nice...

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1 / 37

Oakland Home
10 Bedrooms / 10 Bathrooms / Sleeps 3410 BR / 10 BA / Sleeps 34
Home / 10 Bedrooms / Sleeps 34
(2) Excellent 2 Reviews
Bedrooms:10
Bathrooms:10
Sleeps:34
Type:Home
Per night:$1,631 - $2,048
Per week:$11,414 - $14,335
Pets allowed:No
Internet:No

Looking for a royal retreat? With 17, 000 sq. ft., The Herrington will make you will feel as if you were living in a castle. From the circular driveway, beauti ful estate, and 11 acre lake, to the grand entryway, ballroom, and elaborate pool room, attention to detail and luxury...

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1 / 19

Oakland Home
9 Bedrooms / 8 Bathrooms / Sleeps 289 BR / 8 BA / Sleeps 28
Home / 9 Bedrooms / Sleeps 28
(14) Excellent 14 Reviews

from

$922

/ night

Email Owner
Bedrooms:9
Bathrooms:8
Sleeps:28
Type:Home
Per night:$922 - $1,356
Per week:$6,451 - $9,492
Pets allowed:No
Internet:No

If bigger is better, this fantastic chalet is the absolute best! Timberlodge excels in every way imaginable when it comes to your comfort and pleasure. This exquisite log home masterpiece offers 100 feet of beautiful lakefront decorated with fragrant mountain laurel and towering...

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1 / 15

Oakland Home
8 Bedrooms / 7 Bathrooms / Sleeps 268 BR / 7 BA / Sleeps 26
Home / 8 Bedrooms / Sleeps 26
(7) Excellent 7 Reviews

from

$462

/ night

Email Owner
Bedrooms:8
Bathrooms:7
Sleeps:26
Type:Home
Per night:$462 - $750
Per week:$3,233 - $5,248
Pets allowed:Yes
Internet:No

Avoid the ordinary! Thrilling Blueberry Hill is the pinnacle of vacation perfection. Ideally located, this charming pet friendly chalet is within a short stroll to restaurants, and within 3 miles of the state park, movie theaters, and other lake activities. Relax in lakefront...

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1 / 15

Oakland Home
8 Bedrooms / 8 Bathrooms / Sleeps 268 BR / 8 BA / Sleeps 26
Home / 8 Bedrooms / Sleeps 26
(8) Excellent 8 Reviews

from

$678

/ night

Email Owner
Bedrooms:8
Bathrooms:8
Sleeps:26
Type:Home
Per night:$678 - $1,060
Per week:$4,745 - $7,417
Pets allowed:No
Internet:No

This cedar and stone lakefront chalet offers the ultimate in elegance, comfort, and relaxation. With eight master suites and eight and a half bathrooms, Journey’s End offers the privacy and space that large groups will appreciate. An expansive dining table located off the kitchen...

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1 / 19

Oakland Home
8 Bedrooms / 8 Bathrooms / Sleeps 268 BR / 8 BA / Sleeps 26
Home / 8 Bedrooms / Sleeps 26
(14) Excellent 14 Reviews

from

$882

/ night

Email Owner
Bedrooms:8
Bathrooms:8
Sleeps:26
Type:Home
Per night:$882 - $1,317
Per week:$6,174 - $9,219
Pets allowed:No
Internet:No

Unmatched in style and quality, this fantastic chalet sits lakeside on one of Deep Creek Lake's choicest coves. Recently updated and repainted, the interior boasts three spacious master suites, two fireplaces and an airy loft with a pool table. Savor the excellent view of the lake...

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1 / 21

Oakland Home
9 Bedrooms / 9 Bathrooms / Sleeps 269 BR / 9 BA / Sleeps 26
Home / 9 Bedrooms / Sleeps 26
(9) Excellent 9 Reviews
Bedrooms:9
Bathrooms:9
Sleeps:26
Type:Home
Per night:$1,047 - $1,442
Per week:$7,326 - $10,088
Pets allowed:No
Internet:No

Look beyond the beautiful furnishings and the numerous amenities and you will find peaceful relaxation with incredible panoramic views of Deep Creek Lake and the surrounding mountains. Nestled “Under the Stars” in Mountainside, this recently redecorated chalet is sequestered ...

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1 / 16

Oakland Home
8 Bedrooms / 7 Bathrooms / Sleeps 258 BR / 7 BA / Sleeps 25
Home / 8 Bedrooms / Sleeps 25
(2) Excellent 2 Reviews

from

$462

/ night

Email Owner
Bedrooms:8
Bathrooms:7
Sleeps:25
Type:Home
Per night:$462 - $918
Per week:$3,230 - $6,424
Pets allowed:No
Internet:No

Superior in every way, Absolute Delight is an absolute dream! Located in the elite community of Alpine Shores, this spectacular 8- bedroom chalet reigns supreme in its lush wooded setting. An unbelievable western exposure is yours to enjoy from the total comfort and beauty of oversized...

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1 / 15

Oakland Home
6 Bedrooms / 7 Bathrooms / Sleeps 256 BR / 7 BA / Sleeps 25
Home / 6 Bedrooms / Sleeps 25
(24) Excellent 24 Reviews

from

$952

/ night

Email Owner
Bedrooms:6
Bathrooms:7
Sleeps:25
Type:Home
Per night:$952 - $1,274
Per month:$28,560 - $38,220
Pets allowed:Yes
Internet:Yes

Book your large family gathering for the Garrett County Agricultural Fair Week! Laurel Cove is now available August 1- August 8! Set against a backdrop of native laurel & the sparkling waters of Deep Creek Lake, Laurel Cove will surprise and dazzle you with its wide open ...

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Oakland Maryland Vacation Rentals - Home
1 / 19

Oakland Home
8 Bedrooms / 7 Bathrooms / Sleeps 248 BR / 7 BA / Sleeps 24
Home / 8 Bedrooms / Sleeps 24
(10) Very Good 10 Reviews

from

$794

/ night

Email Owner
Bedrooms:8
Bathrooms:7
Sleeps:24
Type:Home
Per night:$794 - $1,210
Per week:$5,553 - $8,465
Pets allowed:Yes
Internet:No

Multiply your vacation dreams a thousand times over at Awesome View! Aptly named, this magnificent home affords you a tranquil view of Deep Creek's natural surroundings and your dock offers a truly incredible view of the lake. This distinguished mountain chalet goes beyond the normal...

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Oakland Maryland Vacation Rentals - Home
1 / 18

Oakland Home
8 Bedrooms / 9 Bathrooms / Sleeps 248 BR / 9 BA / Sleeps 24
Home / 8 Bedrooms / Sleeps 24
(12) Excellent 12 Reviews

from

$979

/ night

Email Owner
Bedrooms:8
Bathrooms:9
Sleeps:24
Type:Home
Per night:$979 - $1,221
Per week:$6,847 - $8,544
Pets allowed:No
Internet:No

Elegant, Extravagant, Extraordinary…and the list goes on! Uncommon quality can be found in the smallest details of this grand chalet. Possessing a spectacular, sweeping view of Deep Creek Lake and its lush mountains, Peregrine’s Perch is a premium home that is flawless in...

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Oakland Maryland Vacation Rentals - Home
1 / 15

Oakland Home
8 Bedrooms / 5 Bathrooms / Sleeps 248 BR / 5 BA / Sleeps 24
Home / 8 Bedrooms / Sleeps 24
(8) Excellent 8 Reviews

from

$453

/ night

Email Owner
Bedrooms:8
Bathrooms:5
Sleeps:24
Type:Home
Per night:$453 - $743
Per week:$3,167 - $5,197
Pets allowed:No
Internet:No

Scenic Serenity offers an incredible lakefront setting and a location close to it all. This eight- bedroom Deep Creek vacation rental is on one of the most popular sections of the lake and offers commanding views from the great room and deck. A game room, multiple living areas, ...

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Oakland Maryland Vacation Rentals - Home
1 / 12

Oakland Home
8 Bedrooms / 7 Bathrooms / Sleeps 228 BR / 7 BA / Sleeps 22
Home / 8 Bedrooms / Sleeps 22
(7) Excellent 7 Reviews

from

$471

/ night

Email Owner
Bedrooms:8
Bathrooms:7
Sleeps:22
Type:Home
Per night:$471 - $910
Per week:$3,297 - $6,365
Pets allowed:No
Internet:No

Plan your Deep Creek getaway with a stay at the spacious and professionally decorated Enchantment. With amenities such as free high speed wireless internet, 2 dishwashers, 2 refrigerators, and the convenience of a washer/dryer, this custom log home has everything you will need...

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Oakland Maryland Vacation Rentals - Home
1 / 15

Oakland Home
8 Bedrooms / 6 Bathrooms / Sleeps 228 BR / 6 BA / Sleeps 22
Home / 8 Bedrooms / Sleeps 22
(8) Excellent 8 Reviews

from

$453

/ night

Email Owner
Bedrooms:8
Bathrooms:6
Sleeps:22
Type:Home
Per night:$453 - $743
Per week:$3,167 - $5,197
Pets allowed:Yes
Internet:No

Put an end to vacation disappointment at shining pet friendly Lake’s End! Busy minds and talented hands have created a true masterpiece of style and comfort just for you in the fantastic Silver Tree Landing community. Bold and beautiful, Lake’s End holds the key to every vacation...

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Oakland Maryland Vacation Rentals - Home
1 / 15

Oakland Home
8 Bedrooms / 7 Bathrooms / Sleeps 228 BR / 7 BA / Sleeps 22
Home / 8 Bedrooms / Sleeps 22
(3) Very Good 3 Reviews

from

$462

/ night

Email Owner
Bedrooms:8
Bathrooms:7
Sleeps:22
Type:Home
Per night:$462 - $750
Per week:$3,233 - $5,248
Pets allowed:Yes
Internet:No

Bursting with the promise of your most unforgettable vacation, Serendipity proudly awaits your inspection. This pet friendly chalet offers quality furnishings, cathedral ceiling, beautiful stone fireplaces and a family room with pool table. Enjoy unparalleled lake views from the...

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Oakland Maryland Vacation Rentals - Home
1 / 16

Oakland Home
7 Bedrooms / 7 Bathrooms / Sleeps 227 BR / 7 BA / Sleeps 22
Home / 7 Bedrooms / Sleeps 22
(11) Excellent 11 Reviews

from

$479

/ night

Email Owner
Bedrooms:7
Bathrooms:7
Sleeps:22
Type:Home
Per night:$479 - $790
Per week:$3,351 - $5,525
Pets allowed:No
Internet:No

Inspired by the majesty of its surroundings, Sundance offers enjoyment on a grand scale! Echoing the wide- open feel of the lake and mountains, this incredible chalet possesses immense, beautifully appointed rooms. You’ll be delighted to find you are within 5 minutes of restaurants...

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Oakland Maryland Vacation Rentals - Home
1 / 21

Oakland Home
7 Bedrooms / 6 Bathrooms / Sleeps 207 BR / 6 BA / Sleeps 20
Home / 7 Bedrooms / Sleeps 20
(9) Excellent 9 Reviews

from

$640

/ night

Email Owner
Bedrooms:7
Bathrooms:6
Sleeps:20
Type:Home
Per night:$640 - $952
Per week:$4,475 - $6,663
Pets allowed:Yes
Internet:No

Enter a world as nature intended- unspoiled, unhurried, unforgettable. Luxury takes on new meaning at “Drift Away, ” when surveying the immense rooms, well- equipped kitchen, superior furnishings and attention to every detail. Nearly every room offers stunning views. Your...

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Oakland Maryland Vacation Rentals - Home
1 / 15

Oakland Home
7 Bedrooms / 7 Bathrooms / Sleeps 207 BR / 7 BA / Sleeps 20
Home / 7 Bedrooms / Sleeps 20
(4) Excellent 4 Reviews

from

$556

/ night

Email Owner
Bedrooms:7
Bathrooms:7
Sleeps:20
Type:Home
Per night:$556 - $919
Per week:$3,891 - $6,428
Pets allowed:Yes
Internet:No

The discriminating guest will appreciate this luxurious pet friendly home. Waterfront Chateau is the ultimate rendezvous for family and friends. Located on a dead end street just 4 miles from Wisp, the setting is tranquil - - - away from the hustle and bustle. Enjoy the cool mountain...

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Oakland Maryland Vacation Rentals - Home
1 / 18

Oakland Home
7 Bedrooms / 6 Bathrooms / Sleeps 207 BR / 6 BA / Sleeps 20
Home / 7 Bedrooms / Sleeps 20
(3) Excellent 3 Reviews

from

$511

/ night

Email Owner
Bedrooms:7
Bathrooms:6
Sleeps:20
Type:Home
Per night:$511 - $853
Per week:$3,576 - $5,965
Pets allowed:No
Internet:No

A vacation you will never forget awaits you at Almost Aspen! Located on the lake front of scenic Deep Creek Lake this chalet is the ideal spot for a getaway any time of year. The interior of the home is complete with classic furnishings and lots of room for all of your friends and...

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Oakland Maryland Vacation Rentals - Home
1 / 15

Oakland Home
7 Bedrooms / 5 Bathrooms / Sleeps 187 BR / 5 BA / Sleeps 18
Home / 7 Bedrooms / Sleeps 18
(13) Excellent 13 Reviews

from

$440

/ night

Email Owner
Bedrooms:7
Bathrooms:5
Sleeps:18
Type:Home
Per night:$440 - $883
Per week:$3,080 - $6,176
Pets allowed:Yes
Internet:No

Perched on a hillside at the end of a quiet country road, Grand View overlooks shimmering blue lake water and the surrounding mountains. Recently redecorated, the stylish décor, hardwood floors and cathedral ceilings further enhance this already elegant chalet. Watch the sun rise...

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Oakland Maryland Vacation Rentals - Home
1 / 23

Oakland Home
7 Bedrooms / 7 Bathrooms / Sleeps 187 BR / 7 BA / Sleeps 18
Home / 7 Bedrooms / Sleeps 18
(9) Excellent 9 Reviews

from

$531

/ night

Email Owner
Bedrooms:7
Bathrooms:7
Sleeps:18
Type:Home
Per night:$531 - $772
Per week:$3,712 - $5,404
Pets allowed:No
Internet:No

Life is full of surprises an you will find the most wonderful ones at Hollywood! Recently completely revamped, this lovely lakefront chalet is sure to be a favorite. Glowing hardwood floors, lofty cathedral ceilings and a huge native stone fireplace create a feeling of spacious...

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Oakland Maryland Vacation Rentals - Home
1 / 21

Oakland Home
7 Bedrooms / 7 Bathrooms / Sleeps 187 BR / 7 BA / Sleeps 18
Home / 7 Bedrooms / Sleeps 18
(8) Excellent 8 Reviews

from

$446

/ night

Email Owner
Bedrooms:7
Bathrooms:7
Sleeps:18
Type:Home
Per night:$446 - $758
Per week:$3,122 - $5,301
Pets allowed:Yes
Internet:No

Experience the true meaning of gracious country living at St. Bart's Retreat. Bring all your favorite people; including the family dog! There's more than ample room at this magnificent lakefront chalet. Perched above the shimmering waters of Deep Creek Lake and facing due East, ...

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Oakland Maryland Vacation Rentals - Home
1 / 18

Oakland Home
6 Bedrooms / 5 Bathrooms / Sleeps 176 BR / 5 BA / Sleeps 17
Home / 6 Bedrooms / Sleeps 17
(14) Excellent 14 Reviews

from

$558

/ night

Email Owner
Bedrooms:6
Bathrooms:5
Sleeps:17
Type:Home
Per night:$558 - $772
Per week:$3,900 - $5,399
Pets allowed:Yes
Internet:No

Packed with amenities, Splash Mountain offers a spacious vacation home with superior looks inside and out. Situated atop Marsh Mountain on an expansive 3 ½ acres, this Deep Creek rental offers privacy and stuffing views. The home offers 6 bedrooms, as well as a state- of- the-...

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Oakland Maryland Vacation Rentals - Home
1 / 14

Oakland Home
6 Bedrooms / 4 Bathrooms / Sleeps 166 BR / 4 BA / Sleeps 16
Home / 6 Bedrooms / Sleeps 16
(9) Excellent 9 Reviews

from

$340

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:16
Type:Home
Per night:$340 - $649
Per week:$2,379 - $4,542
Pets allowed:Yes
Internet:No

Beautifully decorated with a woodland theme, this pet friendly lakefront resort home is one of a kind. Treat your family and friends to such amenities as pool table, hot tub, large rooms and quality furnishings. Your dog will love the screened porch, spacious decks with plenty...

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Oakland Maryland Vacation Rentals - Home
1 / 14

Oakland Home
5 Bedrooms / 6 Bathrooms / Sleeps 165 BR / 6 BA / Sleeps 16
Home / 5 Bedrooms / Sleeps 16
(2) Excellent 2 Reviews

from

$338

/ night

Email Owner
Bedrooms:5
Bathrooms:6
Sleeps:16
Type:Home
Per night:$338 - $656
Per week:$2,364 - $4,586
Pets allowed:No
Internet:No

Rother's Cove is a long time favorite that has undergone extensive updates that include the addition of central air, a gas fireplace and a 6th full bath. Ideally suited for a gathering of family and friends on a quiet cove with 3 private dock slips. The massive great room with cathedral...

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Oakland Maryland Vacation Rentals - Home
1 / 15

Oakland Home
6 Bedrooms / 4 Bathrooms / Sleeps 166 BR / 4 BA / Sleeps 16
Home / 6 Bedrooms / Sleeps 16
(20) Excellent 20 Reviews

from

$243

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:16
Type:Home
Per night:$243 - $393
Per week:$1,697 - $2,746
Pets allowed:No
Internet:No

If it’s a breathtaking view that you’re looking for, you’ll find it at Scenic Overlook. Truly spectacular, this mountainside chalet offers sweeping lake views from the upper and lower decks, as well as the great room, dining room and family room. Spacious and well- appointed,...

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Oakland Maryland Vacation Rentals - Home
1 / 14

Oakland Home
6 Bedrooms / 4 Bathrooms / Sleeps 166 BR / 4 BA / Sleeps 16
Home / 6 Bedrooms / Sleeps 16
(3) Excellent 3 Reviews

from

$339

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:16
Type:Home
Per night:$339 - $669
Per week:$2,367 - $4,678
Pets allowed:No
Internet:No

Translate serenity by the lake into a fantastic chalet, and Southern Comfort is the result. Located on 417 feet of gently sloping lakefront with rolling hills and scenic vistas, this beauty has incredible lake views visible from 4 of the 6 bedrooms. The 2 master suites opening onto...

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Oakland Maryland Vacation Rentals - Home
1 / 15

Oakland Home
6 Bedrooms / 5 Bathrooms / Sleeps 166 BR / 5 BA / Sleeps 16
Home / 6 Bedrooms / Sleeps 16
(7) Excellent 7 Reviews

from

$339

/ night

Email Owner
Bedrooms:6
Bathrooms:5
Sleeps:16
Type:Home
Per night:$339 - $601
Per week:$2,367 - $4,206
Pets allowed:No
Internet:No

Settled off of Glendale Road, Stone Crest is an ideal home for your vacation. The waters of its lakefront are central to the main body of the lake yet they are tucked back in the cove to avoid a lot of traffic. Comfortable and stylish interiors grace the entire house. The two master...

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Oakland Maryland Vacation Rentals - Home
1 / 13

Oakland Home
4 Bedrooms / 3 Bathrooms / Sleeps 154 BR / 3 BA / Sleeps 15
Home / 4 Bedrooms / Sleeps 15
(9) Excellent 9 Reviews

from

$202

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:15
Type:Home
Per night:$202 - $279
Per week:$1,409 - $1,952
Pets allowed:No
Internet:No

Riches of a different sort await you at sparkling Five Diamonds! It is prime location in desirable Lake Forest Estates offers an uncommon opportunity to truly experience the best Mother Nature has to offer any season of the year. The cheerful, cozy interior wraps you in a warm country-...

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Oakland Maryland Vacation Rentals - Home
1 / 21

Oakland Home
5 Bedrooms / 3 Bathrooms / Sleeps 155 BR / 3 BA / Sleeps 15
Home / 5 Bedrooms / Sleeps 15
(4) Very Good 4 Reviews

from

$232

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:15
Type:Home
Per night:$232 - $412
Per week:$1,622 - $2,878
Pets allowed:Yes
Internet:No

Enjoy the fresh mountain air and tall trees at this lodge home in a secluded location, yet convenient to stores, restaurants, a movie theatre, and the ski slopes. Paradise Lodge offers a multitude of amenities including a private dock and lakeside pavilion with both stairs and...

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Oakland Maryland Vacation Rentals - Home
1 / 16

Oakland Home
6 Bedrooms / 6 Bathrooms / Sleeps 156 BR / 6 BA / Sleeps 15
Home / 6 Bedrooms / Sleeps 15
(2) Excellent 2 Reviews

from

$339

/ night

Email Owner
Bedrooms:6
Bathrooms:6
Sleeps:15
Type:Home
Per night:$339 - $637
Per week:$2,367 - $4,454
Pets allowed:No
Internet:No

Visualize yourself standing at the railing of a spacious, sunlit deck, as you survey the expansive view of the lake and mountains that unfurl before you. Now make that vision a reality by choosing Sunset Pointe as your vacation destination. Within 10 minutes to skiing and golf, ...

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Oakland Maryland Vacation Rentals - Home
1 / 13

Oakland Home
6 Bedrooms / 5 Bathrooms / Sleeps 156 BR / 5 BA / Sleeps 15
Home / 6 Bedrooms / Sleeps 15
(9) Very Good 9 Reviews

from

$308

/ night

Email Owner
Bedrooms:6
Bathrooms:5
Sleeps:15
Type:Home
Per night:$308 - $558
Per week:$2,152 - $3,900
Pets allowed:No
Internet:No

Vibrant and uplifting, Tamaqua Lodge will lift your spirits to new heights. Beautifully appointed rooms accented with eye- catching flair and style provide ample space for your family and friends. Although interior rooms provide outstanding views, you'll want to escape to your expansive...

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Oakland Maryland Vacation Rentals - Home
1 / 14

Oakland Home
6 Bedrooms / 6 Bathrooms / Sleeps 156 BR / 6 BA / Sleeps 15
Home / 6 Bedrooms / Sleeps 15
(7) Excellent 7 Reviews

from

$371

/ night

Email Owner
Bedrooms:6
Bathrooms:6
Sleeps:15
Type:Home
Per night:$371 - $747
Per week:$2,595 - $5,229
Pets allowed:No
Internet:No

This stunning Deep Creek vacation rental is situated on a tranquil cove, offering a peaceful setting with incredible views. Just steps from the waters edge, Telstar. gon has a large, private dock and a deck that runs the length of the house, perfect for morning coffee, soaking...

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Oakland Maryland Vacation Rentals - Home
1 / 13

Oakland Home
6 Bedrooms / 6 Bathrooms / Sleeps 146 BR / 6 BA / Sleeps 14
Home / 6 Bedrooms / Sleeps 14
(8) Very Good 8 Reviews

from

$348

/ night

Email Owner
Bedrooms:6
Bathrooms:6
Sleeps:14
Type:Home
Per night:$348 - $606
Per week:$2,433 - $4,236
Pets allowed:Yes
Internet:No

Anytime is the perfect time to vacation at this striking pet friendly mountain chalet! Sunbathe and water ski in the warm summer months, crunch through carpets of multi- colored leaves in the glorious fall months, ski in a true winter wonderland filled with pristine snow and watch...

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Oakland Maryland Vacation Rentals - Home
1 / 9

Oakland Home
5 Bedrooms / 3 Bathrooms / Sleeps 145 BR / 3 BA / Sleeps 14
Home / 5 Bedrooms / Sleeps 14
(5) Very Good 5 Reviews

from

$224

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:14
Type:Home
Per night:$224 - $425
Per week:$1,568 - $2,974
Pets allowed:Yes
Internet:No

Amazing Love is the ultimate lakefront home that is sure to fit your Deep Creek vacation needs. This five- bedroom vacation rental was recently remodeled a features a host of amenities, including a dishwasher, microwave, washer/dryer and wireless Internet. Lounge on the colossal...

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Oakland Maryland Vacation Rentals - Home
1 / 15

Oakland Home
5 Bedrooms / 6 Bathrooms / Sleeps 145 BR / 6 BA / Sleeps 14
Home / 5 Bedrooms / Sleeps 14
(16) Excellent 16 Reviews

from

$328

/ night

Email Owner
Bedrooms:5
Bathrooms:6
Sleeps:14
Type:Home
Per night:$328 - $375
Per week:$2,291 - $2,625
Pets allowed:Yes
Internet:No

A place of repose, a place to reflect and to rekindle the spirit- - - that is the American Dream. Located on a quiet wooded lot atop Mountainside, the view knows no end and the essence of privacy and quietude surround you. This beautiful chalet boasts four master suites, a prow...

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Oakland Maryland Vacation Rentals - Home
1 / 14

Oakland Home
5 Bedrooms / 5 Bathrooms / Sleeps 145 BR / 5 BA / Sleeps 14
Home / 5 Bedrooms / Sleeps 14
(5) Excellent 5 Reviews

from

$278

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:14
Type:Home
Per night:$278 - $592
Per week:$1,944 - $4,142
Pets allowed:No
Internet:No

Changes in Attitude is more than just a name, it’s a promise! Vacationing in this lakefront retreat is a sure- fire cure for the work- weary. Tucked in the trees, you’ll find a wonderful balance of privacy and accessibility to area activities. The central location puts you ...

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Oakland Maryland Vacation Rentals - Home
1 / 12

Oakland Home
5 Bedrooms / 4 Bathrooms / Sleeps 145 BR / 4 BA / Sleeps 14
Home / 5 Bedrooms / Sleeps 14
(8) Excellent 8 Reviews

from

$194

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:14
Type:Home
Per night:$194 - $317
Per week:$1,352 - $2,219
Pets allowed:No
Internet:No

Perfectly situated in the heart of it all, Crosswinds combines ideal location with the right blend of comfort and style. Within a short walk you’ll find Silver Tree marina – the next best thing to having your own dock slip. Drive just a few miles further to reach state parks,...

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Oakland Maryland Vacation Rentals - Home
1 / 12

Oakland Home
5 Bedrooms / 5 Bathrooms / Sleeps 145 BR / 5 BA / Sleeps 14
Home / 5 Bedrooms / Sleeps 14
(3) Very Good 3 Reviews

from

$201

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:14
Type:Home
Per night:$201 - $385
Per week:$1,406 - $2,694
Pets allowed:No
Internet:No

Accept no substitute for the perfect family vacation! Only 20 yards from the water’s edge and your private dock, Crystal Lake will meet and exceed your expectations. Enjoy panoramic lake views while you cook out on the spacious deck or soak in the bubbling outdoor hot tub. Retreat...

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Oakland Maryland Vacation Rentals - Home
1 / 14

Oakland Home
5 Bedrooms / 6 Bathrooms / Sleeps 145 BR / 6 BA / Sleeps 14
Home / 5 Bedrooms / Sleeps 14
(3) Excellent 3 Reviews

from

$429

/ night

Email Owner
Bedrooms:5
Bathrooms:6
Sleeps:14
Type:Home
Per night:$429 - $873
Per week:$3,000 - $6,106
Pets allowed:No
Internet:No

A vacation retreat like this is a rare find. Diamond on the Lake is truly a gem, offering a grassy level lakefront with scenic lake views. The attention to detail, upscale furnishings, and abundant amenities is sure to satisfy the most discriminating guest. Your cares will simply...

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Oakland Maryland Vacation Rentals - Home
1 / 17

Oakland Home
5 Bedrooms / 4 Bathrooms / Sleeps 145 BR / 4 BA / Sleeps 14
Home / 5 Bedrooms / Sleeps 14
(7) Very Good 7 Reviews

from

$224

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:14
Type:Home
Per night:$224 - $364
Per week:$1,562 - $2,548
Pets allowed:No
Internet:No

If you’re looking for a lakefront retreat on Deep Creek Lake with plenty of room for family and friends, Edgewater is the vacation rental for you. This five- bedroom, four- bathroom home offers a peaceful wooded setting on a quiet cove that is perfect for fishing and swimming....

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Oakland Maryland Vacation Rentals - Home
1 / 14

Oakland Home
5 Bedrooms / 6 Bathrooms / Sleeps 145 BR / 6 BA / Sleeps 14
Home / 5 Bedrooms / Sleeps 14
(6) Excellent 6 Reviews

from

$255

/ night

Email Owner
Bedrooms:5
Bathrooms:6
Sleeps:14
Type:Home
Per night:$255 - $329
Per week:$1,784 - $2,303
Pets allowed:No
Internet:No

Its All Good will help you to release the stresses of life and recharge your batteries. This lake area home is situated on the peaceful Lake Shore drive. You can even catch glimpses of the lake through the trees. The lodge- like decor makes you feel right at home in the mountains ...

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Oakland Maryland Vacation Rentals - Home
1 / 13

Oakland Home
5 Bedrooms / 6 Bathrooms / Sleeps 145 BR / 6 BA / Sleeps 14
Home / 5 Bedrooms / Sleeps 14
(9) Excellent 9 Reviews

from

$302

/ night

Email Owner
Bedrooms:5
Bathrooms:6
Sleeps:14
Type:Home
Per night:$302 - $632
Per week:$2,108 - $4,421
Pets allowed:No
Internet:No

Let yourself be transported by Lake Shore Dreams to a place where the pace is a little slower, the stars shine brighter and air is crisp and clear. You’ll awake feeling completely refreshed and ready to tackle the many activities that are at your fingertips. Enjoy boating, swimming...

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Oakland Maryland Vacation Rentals - Home
1 / 16

Oakland Home
5 Bedrooms / 5 Bathrooms / Sleeps 145 BR / 5 BA / Sleeps 14
Home / 5 Bedrooms / Sleeps 14
(4) Excellent 4 Reviews

from

$263

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:14
Type:Home
Per night:$263 - $560
Per week:$1,838 - $3,914
Pets allowed:No
Internet:No

Pine Oasis offers everything one could need for a relaxing Deep Creek Lake vacation. This lakefront home boasts five bedrooms, a lovely kitchen, a game room, and a soaring stacked stone fireplace in the great room. Enjoy an expansive back deck, a cozy screened porch, and a perfectly...

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Oakland Maryland Vacation Rentals - Home
1 / 12

Oakland Home
5 Bedrooms / 5 Bathrooms / Sleeps 145 BR / 5 BA / Sleeps 14
Home / 5 Bedrooms / Sleeps 14
(4) Excellent 4 Reviews

from

$194

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:14
Type:Home
Per night:$194 - $303
Per week:$1,352 - $2,119
Pets allowed:Yes
Internet:No

The epitome of convenience inside and out, Quality Time combines an ideal location with classic décor and an array of amenities. Spend time with the important people in your life including the family dog while chatting by the fire or relaxing under the stars on the deck. Within ...

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Oakland Maryland Vacation Rentals - Home
1 / 18

Oakland Home
5 Bedrooms / 3 Bathrooms / Sleeps 145 BR / 3 BA / Sleeps 14
Home / 5 Bedrooms / Sleeps 14
(1) Excellent 1 Review

from

$253

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:14
Type:Home
Per night:$253 - $484
Per week:$1,765 - $3,384
Pets allowed:No
Internet:No

If you seek the perfect vacation retreat, Summer Song will be music to your ears! The house has been beautifully renovated in 2014 with new furniture, carpet, paint, furnishings, hot tub and new lakefront bedroom in the basement. Enjoy dining on the spacious deck offering lovely...

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Oakland Maryland Vacation Rentals - Home
1 / 12

Oakland Home
5 Bedrooms / 5 Bathrooms / Sleeps 145 BR / 5 BA / Sleeps 14
Home / 5 Bedrooms / Sleeps 14
(12) Excellent 12 Reviews

from

$237

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:14
Type:Home
Per night:$237 - $278
Per week:$1,658 - $1,942
Pets allowed:No
Internet:No

Close to state parks, restaurants and lake activities, Almost Heaven is a new vacation retreat that offers carefree convenience for your Deep Creek Lake getaway. All new furnishings and décor are featured throughout this spacious duplex. Pass the time with a game of pool, a dip...

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Oakland Maryland Vacation Rentals - Home
1 / 12

Oakland Home
5 Bedrooms / 5 Bathrooms / Sleeps 145 BR / 5 BA / Sleeps 14
Home / 5 Bedrooms / Sleeps 14
(18) Excellent 18 Reviews

from

$250

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:14
Type:Home
Per night:$250 - $317
Per week:$1,747 - $2,217
Pets allowed:No
Internet:No

When it’s time to unwind, It’s 5 O’clock Somewhere is the place to kick back, relax and enjoy the best of Deep Creek Lake. This brand new chalet features a wall of windows and a wrap around deck from which to enjoy the view of the lake and surrounding mountains. Well designed...

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Oakland Maryland Vacation Rentals - Home
1 / 14

Oakland Home
5 Bedrooms / 6 Bathrooms / Sleeps 145 BR / 6 BA / Sleeps 14
Home / 5 Bedrooms / Sleeps 14
(10) Excellent 10 Reviews

from

$406

/ night

Email Owner
Bedrooms:5
Bathrooms:6
Sleeps:14
Type:Home
Per night:$406 - $821
Per week:$2,840 - $5,744
Pets allowed:No
Internet:No

Brimming with amenities, It’s a Wonderful Life has everything you need for a fantastic Deep Creek getaway. With 2 flat screen TV’s, shuffleboard, foosball and a pool table, the game room provides hours of fun for all ages. Convenient amenities such as 3 dishwashers, 2 refrigerators...

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