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Oakland Holiday Homes

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    Travellers to Oakland are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 26
    7 Bedrooms, 7 Bathrooms, Sleeps 18 | Quick View
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    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Do you find yourself daydreaming about a romantic getaway in a charming lakefront home? Golden Retreat is perfect for a couple but is large enough for a small family. You’ll adore the comfortable furnishings and alluring appeal of the interior. Conveniently located a mere 5 minutes from Swallow... View all property information
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    Oakland, Garrett County 21550
    1 / 16
    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    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... View all property information
    Location Information
    Oakland, Garrett County 21550
    5 of 5 bubbles Reviewed 2 August 2016
    Lovely home and grounds. The house was comfortable for our large group that included young children, teenagers, parents and grandparents. Everyone had plenty of room. The main...
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    1 / 47
    7 Bedrooms, 7 Bathrooms, Sleeps 18 | Quick View
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    About this property
    If you are seeking a large spacious lakefront home, brimming with all desirable amenities, then we have the perfect home for you. Wynsome Run Lodge is a spectacular 7 bedroom home ideally located close to Deep Creek State Park, a movie theater, and area restaurants. The expansive Great Room,... View all property information
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    Oakland, Garrett County 21550
    1 / 32
    5 of 5 bubbles (6) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Your Deep Creek tradition begins when you choose the delightful 4 bedroom chalet Swimming Bear Lodge for your next stay! Located on a large wooded lot, you will love being surrounded by nature in this tranquil setting. Step inside to the main level and immediately embrace the warmth and comfort of... View all property information
    Location Information
    Oakland, Garrett County 21550
    5 of 5 bubbles Reviewed 29 November 2015
    We had a wonderful time staying at this cabin. The place itself is awesome for a group--comfortably slept eight adults and five kids, with plenty of room for hanging out in the...
    5 of 5 bubbles Reviewed 30 October 2015
    This home was stunning! From the moment you pull in there is peace. The home is nestled in a wooded area the view of the lake and forest.. while sitting in the relaxing...
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    1 / 18
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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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 vacation with family and friends. Gathering together in the Great Room will... View all property information
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    Oakland, Garrett County 21550
    1 / 38
    6 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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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 / 51
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    About this property
    On Top of the World perfectly defines the way you will feel when you step inside this exquisite 5 Bedroom mountain home. Recently remodeled throughout, this stunning home is located in the prestigious community of Mountainside and features one of the most breathtaking panoramic views of Deep Creek... View all property information
    Location Information
    Oakland, Garrett County 21550
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    1 / 26
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Located on the shores of Deep Creek Lake, Majestic View is a delightful three bedroom townhouse with a name that says it all. Hardwood floors throughout the great room beautifully compliment the wall of windows that showcase breathtaking lake views that change with the seasons. When you are not... View all property information
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    Oakland, Garrett County 21550
    1 / 38
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Treat your family to an enchanted vacation experience at Morningside Lodge. This phenomenal 4 bedroom log home offers you and your family top notch comfort and style. Graceful hardwood floors flow throughout creating a warm ambiance but it is the spectacular lake views that will take your breath... View all property information
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    Oakland, Garrett County 21550
    1 / 17
    5 of 5 bubbles (25) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
    Location Information
    Oakland, Garrett County 21550
    5 of 5 bubbles Reviewed 4 weeks ago
    This was our first trip to Deep Creek Lake. Red Run cabin is perfect for a small group, this trip was myself and my three teenagers. The cabin was great for a first-time trip...
    5 of 5 bubbles Reviewed 1 June 2016
    We had a wonderful time and the house is very well kept. The neighbors were friendly and the dogs loved it! Extremely pet friendly location. We went to swallow falls which was...
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    1 / 22
    5 of 5 bubbles (8) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Surround yourself with nature in this majestic log home. Three master suites make it an excellent choice for couples as well as family gatherings. On the entry level, hardwood floors, cathedral ceilings and large windows adorn the great room, and the stone fireplace and stylish furnishings accent... View all property information
    Location Information
    Oakland, Garrett County 21550
    5 of 5 bubbles Reviewed 17 August 2015
    This was our second trip to Deep Creek Lake & we chose to stay right on the lake this time and were not disappointed. The house was beautiful. The location perfect - tucked away...
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    1 / 42
    5 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Mountain Meadow offers the perfect place to reunite with family and friends for that much needed Deep Creek Lake vacation. Offering an open floor plan, the spacious main level has a wall of windows with beautiful views as the focal point. Lots of natural light, gleaming hardwood floors and... View all property information
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    Oakland, Garrett County 21541
    1 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    If you are looking for a home that goes “Above and Beyond”, this 4 bedroom mountain home is the ideal choice for you and your family! Located on top of a quiet mountaintop, here you will find the privacy you need but still relish the close proximity to all area shopping, dining, and state parks!... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 30
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    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... View all property information
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    Oakland, Garrett County 21550
    1 / 27
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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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
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    Oakland, Garrett County 21540
    1 / 42
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Casa Montes (“House in the Mountains” in Latin) is an exquisite mountain retreat with over 1.5 acres of seasonal lake views and privacy, yet conveniently located within 5-minute walking distance of the lake, restaurants and shops.  Walk on a path to a pizzeria, a coffee/breakfast spot, and to your... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 14
    4.5 of 5 bubbles (5) Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Fir Shore is a lovely and spacious log home that is just awaiting your arrival. A perfect home for the multi-family or a couples retreat, this home has 6 beautifully decorated bedrooms, 3 of which are master suites. Lacking nothing, this home offers something for everyone. The overstocked kitchen... View all property information
    Location Information
    Oakland, Garrett County 21550
    4 of 5 bubbles Reviewed 15 April 2013
    If you are just sleeping and eating in this house, and then headed out for a full day of whatever, then read no further, get this house, and don't worry about it. For some...
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    1 / 32
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    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... View all property information
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    Oakland, Garrett County 21550
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Prepare yourself for a relaxing getaway when choose Bear Feet as your vacation getaway. Exploding with charm, this 3 bedroom townhome will easily beckon you to return time and time again. Step inside and appreciate the open floor plan and the wall of windows that boast extraordinary lake views.... View all property information
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    Oakland, Garrett County 21550
    1 / 22
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    About this property
    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... View all property information
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    Oakland, Garrett County 21550
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Welcome View Point is an enchanting 5 bedroom home that offers plenty of privacy combined with lakefront luxuries. From the moment that you pull into the circular drive, you will know that you found your way home. Step into the Great Room and be awed by the impressive stone fireplace. Imagine... View all property information
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    Oakland, Garrett County 21550
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Nestled in the woods, Hideaway is an adorable A-frame mountain chalet that is the perfect getaway for a small family or a couple’s retreat. Recently renovated, this home offers a cozy Great Room with stylish furnishing and glistening hardwood floors. Family time will be spent watching your favorite... View all property information
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    Oakland, Garrett County 21550
    1 / 31
    5 Bedrooms, 4 Bathrooms, Sleeps 15 | Quick View
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    Discover the perfect lake front getaway when you stay at Lake Shore Retreat! Offering all the comforts of home, this property boasts cathedral ceilings, expansive decks, and multiple gathering areas. Upon entering the main level, your eyes will immediately be drawn to the wall of windows that... View all property information
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    Oakland, Garrett County 21550
    1 / 17
    4 of 5 bubbles (16) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
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    Oakland, Garrett County 21550
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Time and Again is genuinely true to its name. Once you have visited this beautifully constructed chalet, you will want to come back time and time again. Nestled close to the shoreline, it ensures that guests will enjoy many starry nights or lazy summer afternoons relaxing on the expansive deck that... View all property information
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    Oakland, Garrett County 21541
    1 / 28
    4.5 of 5 bubbles (37) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    About this property
    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... View all property information
    Location Information
    Oakland, Garrett County 21550
    5 of 5 bubbles Reviewed 19 February 2015
    We stayed at this location with 10 adults (5 couples) and it was perfect. For a group who loves to cook the kitchen was stocked with everything that was needed. The home felt like...
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    1 / 31
    5 Bedrooms, 3 Bathrooms, Sleeps 13 | Quick View
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    About this property
    You will certainly learn to embrace the motto “Live It, Love It, Lake It” when you choose this charming mountain home for your Deep Creek getaway. Imagine sharing memories with your friends and family as you cozy up around the warm wood fireplace in the Great Room. This massive stone stacked... View all property information
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    Oakland, Garrett County 21550
    1 / 36
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Look no further! Whispering Pines is an extraordinary five bedroom home that will warmly welcome you and your family. Highlights of the spacious main level include gleaming hardwood floors, warm earth tones, and an open floor plan that is just right for spending time with your favorite people.... View all property information
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    Oakland, Garrett County 21550
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Explore, relax and take a well-deserved break at Deep Breath! Convenient to area activities and attractions, it is the perfect home base for your Deep Creek Lake vacation. The spacious interior of this Craftsman-style home is brimming with attention to detail. Upon entering, a dual sided gas... View all property information
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    Oakland, Garrett County 21550
    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Welcome Home Friends! Paradise at Penn Cove is a captivating 3 bedroom chalet that rests on quiet road overlooking Penn Cove. Upon entrance you will immediately feel the warm and cozy atmosphere of the Great Room. Expansive vaulted ceilings, floor to ceiling windows, and an immense stone stacked... View all property information
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    Oakland, Garrett County 21550
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    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    Nestled among the trees in this quiet cul-de-sac, you'll find this beautifully decorated and spacious home which is part of the Mountainside Resort and Marine Club subdivision. Have complete access to tennis, basketball and volleyball courts found in a gorgeous mountain setting. Delight in filtered... View all property information
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    Oakland, Garrett County 21541
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Ready to discover your favorite Deep Creek vacation home? Everyone in your group will love the style, spaciousness and comfort of Just About Paradise! Offering plenty of indoor and outdoor gathering spaces, it is the perfect place for get-togethers.  Start your day with a home cooked breakfast --... View all property information
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    Oakland, Garrett County 21550
    1 / 18
    4.5 of 5 bubbles (6) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Turn your dreams into reality when you choose to stay in the captivating 4 bedroom log home Shiver Me Timbers. Step inside the Main level and you will instantly be won over by the warm wood walls and gleaming hardwood floors that flow naturally throughout the cabin. The Great Room is gracefully... View all property information
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    Oakland, Garrett County 21550
    1 / 37
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Hot Tub
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • x
    About this property
    Trailside Tranquility is a charming, craftsman-style vacation home combines style, comfort and a location that is convenient to the best of Deep Creek Lake. Step inside to find an open floorplan that makes gathering with family and friends entirely effortless. Warm and inviting, the great room is... View all property information
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    Oakland, Garrett County 21550
    1 / 28
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • ?
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    • x
    About this property
    Classic Americana is a marvelous 4 bedroom/ 2.5 bath lake access home that will surprise and delight you from the moment that you pull into the driveway. Enter from the covered front porch into the majestic Great Room. Embrace the country charm of the hardwood floors, the white washed wooden beamed... View all property information
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    Oakland, Garrett County 21550
    1 / 19
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
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    • x
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    • x
    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
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    Oakland, Garrett County 21550
    1 / 33
    8 Bedrooms, 8 Bathrooms, Sleeps 26 | Quick View
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    • Waterfront
    • Hot Tub
    • Satellite TV
    • DVD Player
    • Private Indoor Pool
    • Sauna
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    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... View all property information
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    Oakland, Garrett County 21550
    1 / 34
    5 of 5 bubbles (13) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Take your dream vacation at the luxurious Oz, located in the western part of Deep Creek Lake. Oz is the grand of lakefront properties with exquisite decor, a spacious layout, and fantastic ambiance. Oz has two sitting areas for the family to spread out with a large wood fireplace, separate dining... View all property information
    Location Information
    Oakland, Garrett County 21550
    5 of 5 bubbles Reviewed 6 November 2014
    Beautiful and clean home with plenty of amenities for a memorable vacation, inside and outside! Hotel bedding and comfort with large well stocked kitchen. Rooms are spread out...
    5 of 5 bubbles Reviewed 19 August 2014
    This is our second year at OZ and couldn't be more pleased. A fantastic vacation home with more amenities that I can list in one of the best locatiosn on the Lake. Working with...
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    1 / 21
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    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... View all property information
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    Oakland, Garrett County 21550
    1 / 30
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • ?
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    • x
    About this property
    Vivid and lively are two words that can describe the character displayed in Retro Lake Landing. Its originality is definitely one of a kind and will certainly put that extra little kick into your vacation. If you are looking for something different, fun and exciting, this would be the perfect... View all property information
    Location Information
    Oakland, Garrett County 21541
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Pet-friendly
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    • ?
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    • x
    About this property
    Get the much deserved break that you crave when you stay at Bear Paws. This charming log cabin pairs total comfort with a convenient location! Featuring an open floorplan, the spacious main level is highlighted by vaulted ceilings and polished hardwood floors. Bear themed décor adds a playful... View all property information
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    Oakland, Garrett County 21550
    1 / 23
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Tucked away on the end of Santa Fe Trail, welcome to your tranquil, private oasis. Santa Fe Getaway is an alluring 4 bedroom home that your family will want to return to season after season. Exquisite lake views greet you from many rooms of the home but it is outside on your large deck where you... View all property information
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    Oakland, Garrett County 21550
    1 / 17
    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Balcony
    • Skiing: Property Is...
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    • Washer
    • Mountain Views
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    What an Adorable Log Cabin! Home Layout: * Living Room - Wood Burning Fireplace * Kitchen * Dining Area * Bedroom - King Bed * Full Bath * Sunroom - Wood Burning Fireplace & Hot Tub * Laundry Area Upper Level: * Loft - Queen Bed * Bedroom - King Bed * Full Bath Lower Level: * Recreation Room -... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 28
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Is the clamor of city life wearing you down? Cedarwoods, a stunning 3 bedroom mountain chalet, is calling your name. Nestled away in the quiet community of Mountainside, this beautiful home offers the seclusion and privacy you crave. Boasting 3 spacious levels of living space, high vaulted ceilings... View all property information
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    Oakland, Garrett County 21550
    1 / 30
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Craftsman-style details, tasteful décor and a central location make Just Relax the perfect choice when you want to unwind at Deep Creek Lake. Step inside, and the first thing you will notice is the open floorplan that is ideal for entertaining. Natural light reflects off of gleaming hardwood... View all property information
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    Oakland, Garrett County 21550
    1 / 19
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Hot Tub
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    • x
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    • x
    About this property
    Rich in Deep Creek history, this cottage was built as company housing for Deep Creek’s Hydro Electric Dam workers in 1925. Featuring private Youghiogheny River frontage in the protected Wild and Scenic Corridor, this home is completely unique in Deep Creek. Private yet within a five minute... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 26
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Waves and Moguls is the ultimate definition of this captivating 5 bedroom townhome that is the ideal choice no matter what season you choose to visit. You will immediately feel a sense of home when you step inside the bright and lovely Great Room, sure to be a favorite gathering spot among family... View all property information
    Location Information
    Oakland, Garrett County 21550