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Vacation Rentals in Oakland, MD

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    Travellers to Oakland are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 23
    5 of 5 stars (9) Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 18 | Quick View
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    1 / 8
    3 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    1 / 16
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    $336
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    1 / 14
    4.5 of 5 stars (4) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    From
    $1,928
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    About this property
    Sleep peacefully knowing that your vacation will be restful at Tranquil Dreams. This four bedroom chalet is situated on a quiet, wooded finger of the lake. After enjoying the lake, return to the chalet and grill out, play pool in the rec room while you watch the big game or relax in the hot tub.... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 14
    5 of 5 stars (7) Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 15 | Quick View
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    $3,613
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    About this property
    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 up the sunshine, and... View all property information
    Location Information
    Oakland, Garrett County
    1 / 27
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    $539
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    About this property
    Live the lake life in luxurious style when you stay in this exquisite Creekside Townhome. Elegant décor flows throughout the home from the gleaming hardwood floors, the grand fireplaces, and lavish furnishings. Astounding lake views greet you from the Great Room which features a beautiful stone... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 21
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
    From
    $608
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    • Waterfront
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Parking
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Ski Season is premiere vacation home that offers guests the best of both worlds: indoor elegance and outdoor fun and adventure! This 4 bedroom lakefront home radiates luxury throughout. Step inside and take in the breathtaking lake views from the floor to ceiling windows. Expansive vaulted... View all property information
    Location Information
    Oakland, Garrett County 21540
    1 / 14
    4.5 of 5 stars (3) Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    $3,295
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    About this property
    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 a deck and a two... View all property information
    Location Information
    Oakland, Garrett County
    1 / 21
    3 of 5 stars (4) Average
    5 Bedrooms, 3 Bathrooms, Sleeps 15 | Quick View
    From
    $2,258
    / Week
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    • Hot Tub
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    • Child-friendly
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    • Elder access
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    About this property
    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 a path for more... View all property information
    Location Information
    Oakland, Garrett County
    1 / 9
    5 of 5 stars (7) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
    From
    $1,431
    / Week
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    • Air Conditioning
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    • Pet-friendly
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    About this property
    Ready for a little R&R? Restful Retreat possesses all of the essentials for a soothing and fun vacation experience. Gleaming hardwood floors, artful craftsmanship and beautiful décor create an inviting atmosphere that makes you feel instantly at ease. The unique two sided fireplace emits a soft... View all property information
    Location Information
    Oakland, Garrett County
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    1 / 10
    4.5 of 5 stars (8) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $358
    / Night
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    • Hot Tub
    • Shared Outdoor Pool...
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    • Pet-friendly
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    • Child-friendly
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    About this property
    Regardless of weather or time of year, good times are to be had at Blue Waters! This warm and inviting home offers such versatility as a relaxing quiet setting for a couple or a gathering place for family and friends. Blue Waters features a large great room with vaulted ceiling, native stone... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 18
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    From
    $555
    / Night
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    • Air Conditioning
    • DVD Player
    • Parking
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    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 gathering of family and friends. Gathering with friends and family in the Great... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 13
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    From
    $344
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    • Air Conditioning
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    • Pet-friendly
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    About this property
    You are about to discover Deep Creek’s Best Kept Secret when you choose to stay in this delightful 2 bedroom lake access home. Walking upstairs to your Great Room, you will instantly fall in love with the immaculate and modern décor throughout. Dark glistening hardwood floors combine with plush... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 27
    5 of 5 stars (5) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    From
    $1,033
    / Night
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    • Air Conditioning
    • Grill
    • DVD Player
    • Hot Tub
    • Sauna
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Valhalla 'Hall of the Gods' is a spectacular 5 bedroom home that sits atop a beautiful mountain side. Step inside this wondrous home with large beams encompassing the great room and hardwoods that spread throughout the home. Enjoy exquisite views overlooking Deep Creek Lake while sipping your... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 22
    6 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
    From
    $693
    / Night
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    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 that you need for a fun... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 19
    4.5 of 5 stars (12) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
    From
    $1,831
    / Week
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    • Air Conditioning
    • Hot Tub
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    If you and your dog have a longing for wide open spaces, filled with the sights and sounds of nature, remember Forget-Me-Not when selecting your pet friendly vacation destination! Splendid serenity awaits you at this enchanting haven with it’s spacious lawn and surrounding woodlands. With room... View all property information
    Location Information
    Oakland, Garrett County
    1 / 6
    2.5 of 5 stars (3) Poor
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    From
    $916
    / Week
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    • Pet-friendly
    • Wheelchair access
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    About this property
    Get away from it all in this rustic cabin located near Swallow Falls State Park, where you can visit Muddy Creek Falls, one of Deep Creek’s most popular sites. Swimming, fishing, and hiking are all conveniently located close by. Comfortably furnished inside, this charming log cabin is the perfect... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 32
    5 of 5 stars (1) Excellent
    1 Bedroom, Sleeps 4 | Quick View
    From
    $118
    / Night
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    Amenities & Details
    • Outdoor Dining Area
    • Grill
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    If you like the idea of falling asleep under the stars and roasting marshmallows around a campfire, but the hassles of pitching a tent and sleeping on bumpy ground just don't do it for you, then glamping, the new term being used for upscale - or glamorous - camping, could be your ideal vacation.... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 18
    4.5 of 5 stars (12) Very good
    8 Bedrooms, 9 Bathrooms, Sleeps 24 | Quick View
    From
    $9,532
    / Week
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    • Air Conditioning
    • Sauna
    • Hot Tub
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    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 design and filled with... View all property information
    Location Information
    Oakland, Garrett County
    1 / 10
    4.5 of 5 stars (7) Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    From
    $891
    / Night
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    Amenities & Details
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
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    About this property
    Just high enough to host some of Deep Creek's finest views courtesy of your private balcony; just close enough to walk - not drive - to boating, dining, and shopping; and just private enough to feel that you are safely tucked away at the wood's edge - this gorgeous condominium home offers a truly... View all property information
    Location Information
    Oakland, Garrett County 21550
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    1 / 11
    5 of 5 stars (1) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
    From
    $1,793
    / Week
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    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    When looking for a peaceful retreat this home offers everything you need. The interior has three levels of living space with a beautiful kitchen that opens up to the living room with a large stone fireplace reaching to cathedral ceilings. The lower level with a bar area and foosball table provides... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 20
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
    From
    $2,273
    / Week
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    • Air Conditioning
    • Hot Tub
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    • Pet-friendly
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    • Child-friendly
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    About this property
    'Mountain High' is a breathtaking private hideaway retreat nestled on 2 acres located in the Mountainside Community in Deep Creek Lake, Maryland (5 minutes from Wisp Resort) with Lake Access at the exclusive Mountainside Marina Club. This 4 Bedroom, 3 1/2 Bath home accommodates up to 12 guests... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 27
    5 of 5 stars (1) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
    From
    $905
    / Night
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    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    At Last! Your vacation is right around the corner and here is the perfect spot to make the most of every moment away. This beautiful chalet has it all; a central location, level lakefront and large grassy yard, beautiful architecture, spacious living areas, upscale appliances, an expansive deck,... View all property information
    Location Information
    Oakland, Garrett County
    1 / 11
    3 Bedrooms, 1 Bathroom, Sleeps 10 | Quick View
    From
    $290
    / Night
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    • Hot Tub
    • DVD Player
    • Parking
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    A lifetime of memories is waiting for you and your family when you choose the enchanting home Restintyme for you next stay at Deep Creek Lake. Unique in design, this delightful 3 bedroom home is ideal for the small family or couple’s retreat. Warm, comforting décor combined with gleaming hardwood... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 15
    4 of 5 stars (8) Very good
    8 Bedrooms, 6 Bathrooms, Sleeps 22 | Quick View
    From
    $4,409
    / Week
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    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    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 dream you’ve ever... View all property information
    Location Information
    Oakland, Garrett County
    1 / 16
    4.5 of 5 stars (11) Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 22 | Quick View
    From
    $4,665
    / Week
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    • Hot Tub
    • Air Conditioning
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    • Pet-friendly
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    • Child-friendly
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    About this property
    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 and shopping and... View all property information
    Location Information
    Oakland, Garrett County
    1 / 29
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
    From
    $692
    / Night
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    • Hot Tub
    • Grill
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Fun In the Sun is exactly what you will have from the moment you arrive until you depart when you stay in this fabulous 5 bedroom lakefront log home. Featuring prime Deep Creek lakefront, you will constantly be amazed by the exquisite lake views before you! Step into the Great Room and take in the... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 10
    4.5 of 5 stars (10) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
    From
    $2,337
    / Week
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    • Hot Tub
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Absolutely elegant, Creekside Townhomes epitomize the classic luxury of lakefront living. Hardwood floors, two fireplaces, tasteful décor, multiple jetted tubs and a gourmet kitchen are just a few of the highlights of the spacious interior. Enjoy lake views from the deck, lower level patio or from... View all property information
    Location Information
    Oakland, Garrett County
    1 / 11
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    $400
    / Night
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    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Your mountain vacation will be filled with magical memories when you choose to stay in the spectacular 3 bedroom log home known as Made It! 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... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 15
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
    From
    $413
    / Night
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    • Air Conditioning
    • Hot Tub
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Perched on a hillside overlooking Deep Creek Lake, this well-appointed home is the perfect starting point for a great vacation. Tasteful décor and a spacious layout create comfortable surroundings for your gathering of family and friends. Postcard views will greet you each morning as you prepare... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 11
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    From
    $330
    / Night
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    • Grill
    • DVD Player
    • Parking
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Bedding: Queen, Queen, Queen & Bunk w/trundle, Queen, Twin Sleeper Sofa Deep Creek adventures are waiting for you! Bear Feet is an astonishing 3 bedroom townhome that offers breathtaking lake views while putting you right in the heart of the action. Boasting 2 master suites, this home if ideal for... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 4
    5 Bedrooms, 4 Bathrooms, Sleeps 15 | Quick View
    From
    $748
    / Night
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    • Grill
    • DVD Player
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Great Location Additional amenities include: pool table, dock/boat-slip, 8 TVs, non-smoking only, high speed & wireless internet, free unlimited long distance, washer and dryer, saturday summer check-in, parking for 5 vehicles, jacuzzi tub (over-sized), towels and linens provided. View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 21
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
    From
    $519
    / Night
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    • Washer
    • Mountain Views
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Escape to a tranquil setting to relax or enjoy community tennis, hot tub and outdoor fire pit. Minutes to all other lake amenities This 5 bedroom, 4.5 bath chalet offers amazing home amenities and a beautiful view of the mountainous Deep Creek Lake area. The interior of the home has a modern... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 6
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $413
    / Night
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    • DVD Player
    • Grill
    • Parking
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Bedding: King; Double; Double, 2 Twin Rollaways 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... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 14
    5 of 5 stars (2) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Sauna
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    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 ceilings, a... View all property information
    Location Information
    Oakland, Garrett County
    1 / 10
    3 of 5 stars (4) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Enjoy the original cabin at Deep Creek Lake, family owned for over 60 years! This home is complete with a fireplace and post & beam ceilings in the living room. This home has all the luxuries of home - flat screen TV & internet with all the comforts of Deep Creek. Lakefront with views abound & a... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 15
    5 of 5 stars (6) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Walls of windows showcase spectacular, up close, lake views from every room! This spacious home boasts the finest of materials from the kitchen and baths to the large screen TV surround sound systems. Everyone will be eager to go outside to play when they see the grassy level lawn that leads to... View all property information
    Location Information
    Oakland, Garrett County
    1 / 18
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Experience the lake in an atmosphere only an authentic cabin can provide. Cochran’s Cabin makes an ideal mountain getaway for a couple or small family. The charming interior features a great room and lower level family room, three bedrooms, hardwood floors, and a cozy fireplace. Step outside to... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Satellite TV
    • Central Heating
    • Grill
    • Internet Access
    • Washer
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Are You Looking for a Quiet & Peaceful Getaway, yet Close to Everything? This quaint 3 bedroom, 1.5 bath one-level home will provide you with a vacation reminiscent of simpler times. Enjoy spending quality time with your loved ones without distraction. An open floor plan allows for family... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Bedding: Queen, Double, 3 Twins Tucked away in a quiet secluded cove at the Southern end of Deep Creek Lake sits Turtle Cove. This charming 3 bedroom cottage is the ideal home for a family getaway. The large shaded trees and sloping lakefront with a private dock add to the general serene ambiance... View all property information
    Location Information
    Oakland, Garrett County 21550