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Holiday Homes in Oakland

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    Travellers to Oakland are booking February dates now. Secure your holiday rental today, and have the perfect trip.
    All 125 Rentals in Oakland
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 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...
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    21550, Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Ready to experience a truly magnificent mountain vacation home? Schmidt Lodge is an inviting 3 bedroom log home located in a tranquil setting that reassures that you and your guests will experience the peaceful getaway that you seek! You and your guests will love the style, spaciousness, and cozy...
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    21550, Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    About this property
    This exceptional home fronting Deep Creek Lake with a private dock, community indoor pool, and so much more will make the perfect vacation spot! Your family will feel right at home in this fabulous lakefront vacation home. Johnny Appleseed is the ideal vacation getaway for large families....
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    21550, Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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...
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    21550, Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    About this property
    Spend your vacation in a beautiful log home nestled in the woods in a new community off of Lake Shore Drive. Rocky Top is a 4 bedroom 3 bath property that intertwines nature with modern day conveniences. It boasts tongue and groove walls, wide hardwood plank floors, a great stone gas fireplace and...
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    21550, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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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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    21550, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Pet friendly
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    About this property
    Lake Chalet is the ultimate mountain oasis! Check out the hot tub room with fireplace, TV, and table! Looking for vacation perfection? The search is over: Lake Chalet is ready to wow you! If you are seeking to settle somewhere with a convenient location and a wooded setting, this charming...
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    21550, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    Enjoy having Mother Nature as your neighbor at Fancy Free. This lakefront chalet is tucked away in the private, small Heron Cove West community. Providing a much-needed break from everyday life, your vacation will be the source of wonderful memories you'll reflect on for years to come. The spacious...
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    21550, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 16
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    This cozy chalet is tucked among the trees offering a quiet setting for the peaceful escape that you deserve. Relax on the deck while taking in the beauty of the woodlands at this mountain getaway. Hummingbird Hill offers the restful atmosphere and comfortable surroundings that make you feel right...
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    21541, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
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    Pet friendly
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    Discover peaceful days and starry nights at Lakeside Vista, a charming Deep Creek Lake vacation home with picturesque lake views. When you are looking for a classic lake experience, this is a place where you can truly reconnect with your favorite people. On the main level, you will find the...
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    21550, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Grill
    • Waterfront
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    • Washer
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Mother Nature is always on the guest list at Sylvan Sweet thanks to a great yard and sunny windows! Life is good at Sylvan Sweet! This serene retreat will wrap you in the tranquility of a private wooded setting, yet keep you in close proximity to area activities, state parks, restaurants, and...
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    21550, Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Create new traditions and share special experiences with your favorite people when you vacation at Lakeside Memories! Overlooking Deep Creek Lake, this chalet-style home offers plenty of space for family gatherings or a couples' retreat. The main level great room offers beautiful views of the lake...
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    21550, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    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...
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    21550, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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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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    21550, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Memory Lane is a home designed to bring friends and family together for fun and laughter. Tucked among gracious, blossomed trees with a meticulously maintained lawn, you will truly feel like you have discovered your mountain oasis. Gather with loved ones in the Great Room where you can enjoy your...
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    21550, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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...
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    21550, Oakland, Garrett County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Check out this really cool townhome at Four Hooppole on the shores of Deep Creek Lake! The community offers around 10 acres of level manicured yard, community tennis court, community basketball court, playground, and one of the only sandy beaches with a roped off swimming area for your safety and...
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    21550, Oakland, Garrett County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Once starting your vacation at Beardise, you will want time to stand still to enjoy the many pleasures at Deep Creek Lake along with the view. This home offers the ultimate peaceful, easy feeling that will your stress from scheduled living to surrender! The only schedule needed is enjoying your...
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    21550, Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Prepare to be dazzled by the sophistication and grandeur that is Cedar Ridge. This alluring 3 bedroom split level lakefront is the perfect choice for the small family escape or for the couple's retreat. Located on the western end of the lake, the home provides you with a tranquil, serene setting, a...
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    21550, Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Prepare to be swept away by the majesty that is Overlook Point. Creature comforts surround you in the Great Room with expansive cathedral ceilings, bright open window and lustrous hardwood floors. Add in the addition of a cozy stone, gas fireplace, plush leather furnishings and a large flat screen...
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    21550, Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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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    21550, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Come and relax at San~Stress, located in the wonderful community of Blakeslee. This property is adorned with hardwood floors, tongue and groove ceilings, and plenty of space for the whole family. The lower level family room is maxed out with a pool table, air hockey game, mini bar, and stereo...
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    21550, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Changed to: 'Canaima' is the name of the friendly spirit of the jungles of Venezuela and Brazil. It is also the site of the novel 'The Lost World' by Arthur Conan Doyle and the location of the 'Green Mansions', the place where Rima lived, in the beloved novel of William Hudson. Our cabin carries...
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    21541, Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    A lifetime of family memories is just a phone call away when you choose to stay in the lovely 3 bedroom chalet known as Timber Trails. Truly a get away from it all home, you will love the private and peaceful setting while cherishing your close proximity to Oakland, Wisp Resort, and area shopping...
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    21550, Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    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. The...
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    21550, Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Offering an incredible 700 feet of waterfront, Sailor's Point invites you to unwind and feel at home on the shores of Deep Creek Lake. If your idea of a perfect vacation includes spending family time together in the game room, strolling along wooded community roads, and watching the sky fill with...
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    21550, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    If you want a classic Deep Creek Lake vacation with convenient lake access, look no further than Lakeview Cottage. This A-frame style home is ideal for a family getaway or a couples' trip. Wood-lined walls create a warm ambiance in the great room, and a wall of windows lets in lots of natural light...
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    21550, Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    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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    21550, Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    Currently under construction, Boulder House has a beautiful lakefront location minutes from favorite things to do in Deep Creek Lake. This home includes six master suites, family room, a separate game room, and much more! You will love the convenience of having a private dock, so bring your boat or...
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    21550, Oakland, Garrett County
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
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    Lakeshore Breeze1 / 29
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Reviewed 1 January 2017
    The house was advertised as sleeping 10, which, while physically possible, would be impracticle. We had a party of 6 and any more would have been a crowd. The house has only...
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    About this property
    The sun, the shade, the shore? All yours! Lakeshore Breeze is a rustic and warm waterfront oasis! Come catch some divine ‘Lakeshore Breeze' at this cozy lakefront cabin! Boasting a prime location near McHenry Cove on Deep Creek Lake, this home is just a few miles away from all your favorite lake...
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    21550 , Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    Letting go of everyday cares is effortless when you choose Breathe Easy for your Deep Creek vacation with family and friends. This spacious townhome in the centrally located Timberlake Village community is ready to host a fun and relaxing getaway. Decorated in muted earth tones, the spacious main...
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    21550, Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 11
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Patio
    • Housekeeping Included
    • Central Heating
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    • Hot Tub
    • DVD Player
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    Smoking allowed
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    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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    21550, Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    Don't Miss Out on Staying in a Cute Log Cabin with a Year-Round Hot Tub Room and Two Fireplaces! This adorable log cabin is waiting to make your Deep Creek Lake vacation memorable! Walk up the path and around the bushy pine tree to find a cozy, covered front porch peeking out between even more...
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    21550, Oakland, Garrett County
    Cabin Holiday Rental - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    21550, Oakland, Garrett County
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Treat yourself to this premier lakefront home located in quiet, yet prestigious Lake Forest Estates. Stoney Point offers many hard to find features making your stay at Deep Creek Lake a memory that will last a lifetime. Featuring a large LEVEL lakefront yard situated right on the shoreline, and...
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    21541, Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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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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    21550, Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    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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    21550, Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
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    • Waterfront
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    Smoking allowed
    About this property
    Look no further -- this place has it all! One Acre on the Lake and minutes from Wisp Ski Resort, Flip Flops & Mountain Tops is a place for all seasons. Relax by the Lake or hit the ski slopes. This beautiful lake front home located at the end of a cul-de-sac has everything you could want during...
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    21550, Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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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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    Location Information
    21550, Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 3 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
    Kid friendly
    Smoking allowed
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    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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    Location Information
    21550, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 drive to...
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    Location Information
    21550, Oakland, Garrett County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
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    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...
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    Location Information
    21541, Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
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    Home Sweet Cabin is a charismatic mountain home that rests in a quiet, peaceful cove. Expansive wooden cathedral ceilings highlight the stone fireplace and gives promises of nights spent bonding with family and friends. The open floor plan allows you to entertain your guests while preparing the...
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    Location Information
    21550, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    • Hot Tub
    • Housekeeping Included
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2018
    Looking for a weekend getaway with my friends, we stumbled upon this quaint mountain escape. We were all looking forward to weekend where we did not have to leave the house for...
    Reviewed 1 January 2018
    Fabulous accommodation. Has everything - outdoor fireplace, big porches, granite kitchen counters, water filter, sleeps around 12 or so, pool table, heated downstairs floor...
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    About this property
    Architecturally pleasing to the eye and the soul, this UNIQUE AND GORGEOUS 'GREEN HOME' boasts a 31' great room ceiling with 2 INTERIOR and 1 EXTERIOR (on deck) WOOD BURNING STACKED STONE FIREPLACES (also 31' tall) plus LARGE HOT TUB ON DECK and LARGE FIRE PIT in back yard. This serene gem backs to...
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    Location Information
    21550, Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
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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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    Location Information
    21550, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    9 Bedrooms, 8 Bathrooms, Sleeps 24 Quick View
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    21550, Oakland, Garrett County
    Holiday Rental House - 9 Bedrooms, 8 Bathrooms, Sleeps 24
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    Ski Solitude1 / 30
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Parking
    • Grill
    • Central Heating
    • Cable/satellite TV
    • Patio
    • Mountain Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 November 2018
    Had a very good stay in Captivating Cabin. My two concerns with any rental were swiftly taken care of, comfortable sofas and comfortable bed! Kitchen had good cookware and a...
    Reviewed 7 August 2018
    Cabin was very relaxing and comfortable. The grandchildren enjoyed the fire pit making smores. It was fully stocked with everything you would need.
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    About this property
    Classic lake cabin totally updated 2017! three bedroom two bath cabin that sits back from the road with plenty of parking . Cabin is situated on one acre of wooded grounds surrounded by large boulders and a pond. The stately stone fireplace is the centerpiece of this home. The soaring ceiling in...
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    Location Information
    21550, Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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