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Oakland Vacation Rentals

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    Travelers to Oakland are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 254 Rentals in Oakland
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    *Secluded & Quiet UNIQUE OUTSIDE FIREPLACE *XL HOT TUB*Pool Table-5 Star QUALITY1 / 56
    (5)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    8 Bedrooms, 10 Bathrooms, Sleeps 16 Quick View
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    Captivating Cabin located on wooded lot and short stroll to lake and dock!1 / 30
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Red Run Cabin1 / 22
    (29)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 11, 2018
    My family had a lot of fun staying at this house for a long weekend getaway! When the weather is hot, the house is warm and stuffy because there is only one small air...
    Reviewed May 7, 2018
    Had a wonderful time. Very peaceful and serene. The house is beatifully done and very homey. The pictures dont do it justice. Only downfall was it rained most of our stay...
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    About this property
    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 far out into the lake, making...
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    Oakland, Garrett County 21550
    Cabin - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Patio
    • Housekeeping Included
    • Central Heating
    • Washer
    • Hot Tub
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your mountain vacation will be filled with magical memories when you choose to stay in this spectacular 3 master suite bedroom log home. You and your guests will immediately feel at home when you step through the front door. Luxurious décor compliments the gorgeous hardwood floors giving the...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Offering unparalleled lake front elegance, Preston on the Lake is a premiere vacation home with amazing features inside and out. You will be immediately impressed as you drive up to the entrance of this stately retreat. The main level features a grand gathering space with cathedral ceilings, lake...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 7 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The setting of this magnificent cedar chalet offers a quiet retreat for a restful vacation. The natural rock formations, wooded surroundings and beautiful mountain laurel create a serene location for relaxing and enjoying nature. The cathedral ceilings, grand windows and massive stone fireplace...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 16
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    El Dorado is a delightful lake cottage with cozy furnishings, warm pine walls, beamed cathedral ceilings and a beautiful stone fireplace. Stunning views of Deep Creek Lake can be seen from almost every room in this charming chalet. Relax in the bubbling hot tub after a day on the lake or fish off...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For the chance to stay in one of Deep Creek's most desired vacation homes, book a relaxing escape at Stargazer where peaceful days and starry nights are guaranteed. Mesmerizing from the second that you step inside, prepare to be swept away by the extraordinary lake views that greet you from the...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Housekeeping Included
    • Internet Access
    • Cable/satellite TV
    • Parking
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With a great lakefront and convenient central location, Arrowhead #26 showcases the best of DCL! Arrowhead #26 is a showstopper! It doesn't get more convenient or cozy than this lakefront townhome. Loaded with great amenities, this three-bedroom home is surprisingly spacious, with a stunning level...
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    Oakland, Garrett County 21550
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
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    Pet friendly
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    About this property
    Offering everything you need for a fun and relaxing vacation, Lake House is the perfect place to make your Deep Creek Lake vacation memories! The spacious main level is highlighted by gleaming hardwood floors, cathedral ceilings and a towering wall of windows that reveal lake views through the...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Duffy's Oar House is the perfect Deep Creek Lake Cottage. It has the charm and charisma of original DCL,and the modern amenities that we have all grown to know and love! Situated on the western end of the lake, this home has a large level yard with a private dock that sits in a quiet cove with...
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    Oakland, Garrett County 21541
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
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    About this property
    Windsor House is the perfect choice for vacationers interested in Deep Creek Lake's numerous attractions. Thanks to its convenient location, you're within a short drive from state parks, skiing, restaurants, shops and many other lake activities. This home of distinction features tasteful décor that...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    Pet friendly
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    About this property
    Fond, family memories will truly be made when you spend your Deep Creek getaway in the charismatic home known as Finn McCool's. This 5 bedroom home boasts a phenomenal lakefront with a private dock, ideal for swimming on hot summer days. After an exciting day of hiking and biking at Swallow Falls...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    Pet friendly
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    About this property
    You will see nothing but positive Changes in Attitude when you choose to stay in this spectacular 5 bedroom lakefront home. Step inside and immediately become swept away by the majestic lake views! This home has top of the line amenities that guarantee a fun and memorable vacation for all. The...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
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    Pet friendly
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    About this property
    Welcome to The Quarterdeck – where you'll enjoy expansive decks, mountain views, and high-end finishes making your stay in Deep Creek one to be remembered. This recently and extensively updated large 5 bedroom, 4 full bathroom chalet-style home is the ideal choice if you're looking for a private,...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Tranquil Dreams1 / 17
    (4)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With natural foliage all around, Tranquil Dreams is a rustic delight with super close lake access! You can rest easy knowing that vacation perfection is assured at Tranquil Dreams! Your stay is destined to be restful at this four-bedroom chalet, situated along a quiet wooded finger of the lake....
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    Oakland, Garrett County 21550 
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Hot Tub
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    Pet friendly
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    About this property
    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, it is ideal for a group of couples or a family vacation. Highlights of the interior include new furnishings, 8 TVs, central...
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    Oakland, Garrett County 21550
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    Linwood1 / 18
    (7)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
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    Pet friendly
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    Smoking allowed
    About this property
    The traditional comforts and community amenities at Linwood make for proven vacation bliss! Let Linwood take your spirit to a place where everyday concerns are left behind and relaxation and felicity can take hold, unchecked and unencumbered. With tree covered lot, nearby lake access, and...
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    Oakland, Garrett County 21550 
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to one of Deep Creek's finest homes. Reverie is an exquisite 5 bedroom mountain home that will far exceed your expectations. Combining lavish décor with prime lakefront easily makes this home a Deep Creek gem. Floor to ceiling windows in the Great Room allow you and your guests to bask in...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    About this property
    Truly a treasure, Jewel in Paradise is a stunning lake front vacation home that is the perfect place to get away with family and friends. Perched on a hillside, stunning lake views are yours to enjoy! The spacious main level has an open floor plan with high-end finishes that is ideal for...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    About this property
    Currently undergoing updates, Solar Delight is a lake front vacation home that is sure to please your family and friends. Enhancements include kitchen upgrades as well as the addition of a fifth bedroom. From the expansive deck to the private dock, outdoor living is at its finest. You can enjoy...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    9 Bedrooms, 8 Bathrooms, Sleeps 24 Quick View
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    • Hot Tub
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    Pet friendly
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    About this property
    Bask in the glory of Sunset Delight! Able to accommodate large groups, this gorgeous home offers the ideal space for friendly get-togethers and family reunions, and also serves as a great home base for groups during corporate or church retreats. A towering stone fireplace, magnificent picture...
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    Oakland, Garrett County 21550
    Rental Home - 9 Bedrooms, 8 Bathrooms, Sleeps 24
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    About this property
    Looking for the finest, most preeminent home to pamper you while on vacation? This stunning and impressive home has so many unique and elegant features, it will let you heartbroken when it is time to depart. From the moment you enter, you will be in awe of how delicately detailed every room has...
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    Oakland, Garrett County 21550
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    With super close lake access and abundant privacy of the woods, Deer Pass is a proven delight! Unlike any other vacation retreat, Deer Pass offers the opportunity to escape the ordinary and transcend into greatness! It is not often you can enjoy coffee on your deck while watching deer graze at...
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    Oakland, Garrett County 21550
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    AAH Chalet1 / 23
    (13)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    About this property
    Aah Chalet! All your favorite activities are just down the road at this towering two level chalet! What would you say to the perfect lakefront home, in the perfect location, with the perfect list of amenities? You would say “Aah, Chalet!” You can have it all when you stay at this fantastic...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Pack your bags and get ready to experience a true Deep Creek adventure when you choose to stay in the newly built log home Man Haus! This luxury log home will host 4 Master Suites making it an excellent choice for a couple's retreat or an extended family getaway! Indoor creature comforts include...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    There is no better place to reunite with friends and family than Nature's Retreat. This spectacular 5 bedroom lakefront home offers all of the amenities of home and more! Glistening hardwood floors, a massive stone stacked fireplace and leather furnishings create a warm and comforting gathering...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Majestically situated right along the lakefront, this premier property will provide you with long lasting vacation memories. Enjoy star gazing and amazing views from the many decks or leave your stress behind while relaxing in the bubbling outdoor hot tub overlooking Deep Creek Lake. The spacious...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Have the time of your life when stay at Donna's Choice for your next Deep Creek vacation! Unwind in style at this bright and cheerful contemporary mountain home. Attention to detail is found throughout, and you will notice photos of local landmarks decorating the walls. The main level's open...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Logxurious is the ideal name for this 5 bedroom lakefront log home that exemplifies the definition of luxury living. Inside the lodge, guests are treated to a warm and charismatic Great Room which features gleaming hardwood floors, dark cherry wood vaulted beams, and a grand stone fireplace. Bright...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Prepare for the 'Wow!' when you walk into the breathtaking home known as Log Hut! The newly renovated 4 bedroom log home offers the best of both worlds both inside and out. The interior design that flows consistently throughout the home features refined and elegant décor, plush leather furnishings,...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Welcome to a True Cabin in the Woods Getaway!This cute and cozy 2 level private cabin in the woods just outside of historic Oakland and within minutes to Deep Creek Lake is waiting for you!Home Layout:Main Level:* Kitchen* Dining Area* Living Room - Queen Sleeper Sofa* Half BathLower Level:*...
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    Oakland, Garrett County 21550
    Cabin - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    A truly amazing mountain home is just what you need for your relaxing getaway and Log Mahal will not disappoint. This custom crafted 5 bedroom home will quickly win you over with its unique style and décor. Love at first sight is a given when you enter the Great Room. Large vaulted ceilings...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Sunrise is a spectacular 4 bedroom lakefront home that will quickly become host to your family's favorite Deep Creek memories. From the moment that you begin pulling up to the home, you will embrace the charm of the serene tree lined drive. Offering over 4 acres of private lawn, outdoor enthusiasts...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    American Pride is an inviting 5 bedroom 3 bath chalet nestled among the trees in one of the most requested communities in Deep Creek Lake. A few steps into the home and you will find yourself entering into the elegantly decorated Great Room which features large cathedral ceilings, a massive stone...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    True to its name, the good life awaits at La Bella Vita! This stunning, recently remodeled home promises an exceptional Deep Creek Lake vacation for your family and friends. With amazing lake views from almost every room and upscale décor throughout, this will quickly become a favorite spot to get...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 14
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    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 together in the Great Room will...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    No matter what time of year you visit, Four Seasons Chateau promises a Deep Creek vacation that will leave you longing to come back again and again. This well-appointed retreat offers style, comfort, and best of all, a convenient location that puts the best area activities at your fingertips....
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 14
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    8 Bedrooms, 8 Bathrooms, Sleeps 26 Quick View
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    Come and stay at Deep Creek's premier lakefront property where dreams do come true, and the fun begins at this exquisite eight bedroom home known as Celebration at Deep Creek. From the moment that you step inside this luxurious mountain home you will be in awe. Walking through the foyer, you will...
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    Oakland, Garrett County 21550
    Rental Home - 8 Bedrooms, 8 Bathrooms, Sleeps 26
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    At Last promises amazing lake views, fun adventures and treasured memories for your next Deep Creek Lake vacation! Conveniently located, this elegant log home is the ideal place to reconnect with family and friends. Upon entering the spacious main level, your eyes will be drawn to the wall of...
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    Oakland, Garrett County 21550
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
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    Home on the Ridge is a sweet and spacious dwelling with breathtaking mountain-lake views! Looking for a comfortable roost to rest the head? Someplace bright and cheery where relaxation and rejuvenation can take hold? Look no further than Home on the Ridge! Perched atop a quiet wooded community,...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    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 level. The open floorplan lends...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Time to kick back, relax, and enjoy Lazy Days. This charming and charismatic lakefront home is the ideal choice for the small family getaway or a couple's retreat. Located on top of Wisp Mountain, you will love the close proximity to Lodestone Golf Course, ASCI (The Adventure Sports Center...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Discover a truly delightful experience when you choose Paddles & Poles for your Deep Creek escape! Located in the lake front Silver Tree Landing community, this tastefully decorated home has all of the vacation essentials plus a lot more! A retreat for all seasons, the central location makes it...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Hemlock Chalet1 / 15
    (5)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
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    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At shaded and secluded Hemlock Chalet, you'll find a perfect fusion of nature and homey comforts! Hemlock Chalet is a hit! Located in the prestigious Blakeslee community, this marvelous chalet offers your favorite amenities and all the little luxuries you are looking for in a vacation retreat....
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    Location Information
    Oakland, Garrett County 21550 
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Located in the quiet Gallatin Woods community, Bears Lair is a spacious log home that puts the best of Deep Creek Lake at your fingertips. The main level exudes warmth with cathedral ceilings, hardwood floors and a stacked stone fireplace. You can unwind and watch TV by the glow of the fire with...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Located in the heart of Deep Creek Lake, Stone Crest offers a convenient location, spacious layout, and great amenities. As you enter the main level, take a moment to appreciate that wall windows, cathedral ceilings, and towering stone fireplace. This spacious home offers seamless indoor/outdoor...
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    Oakland, Garrett County 21550
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Perched on a mountainside with scenic views, Boulder Escape is a classic Deep Creek retreat with all of the amenities that make a vacation truly memorable! Inviting and comfortable, this handsome log home features a spacious, open floorplan on the main level with a centerpiece stone fireplace,...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    Invite your friends and family to Heavenly Grove, where convenience, comfort and style come together to create an amazing setting for Deep Creek Vacations. Located in the popular Blakeslee Community, you are off-the-beaten path but still close to the best of the area. This contemporary home makes...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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