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Oakland Holiday Rentals

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    Travellers to Oakland are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 254 Rentals in Oakland
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    Red Run Cabin1 / 22
    (29)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Captivating Cabin located on wooded lot and short stroll to lake and dock!1 / 30
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    8 Bedrooms, 10 Bathrooms, Sleeps 16 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Patio
    • Housekeeping Included
    • Central Heating
    • Washer
    • Hot Tub
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your mountain vacation will be filled with magical memories when you choose to stay in this spectacular 3 master suite bedroom log home. You and your guests will immediately feel at home when you step through the front door. Luxurious décor compliments the gorgeous hardwood floors giving the...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
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    About this property
    Pack your bags and get ready to experience a true Deep Creek adventure when you choose to stay in the newly built log home Man Haus! This luxury log home will host 4 Master Suites making it an excellent choice for a couple's retreat or an extended family getaway! Indoor creature comforts include...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    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...
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    Oakland, Garrett County 21550
    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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    • Hot Tub
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    About this property
    Fond, family memories will truly be made when you spend your Deep Creek getaway in the charismatic home known as Finn McCool's. This 5 bedroom home boasts a phenomenal lakefront with a private dock, ideal for swimming on hot summer days. After an exciting day of hiking and biking at Swallow Falls...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Hot Tub
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    About this property
    This brand new log home is situated in a wooded community that is off-the-beaten-path yet still within minutes from Deep Creek Lake activities. Offering four master suites, it is ideal for a group of couples or a family vacation. Highlights of the interior include new furnishings, 8 TVs, central...
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    Oakland, Garrett County 21550
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Hot Tub
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    Pet friendly
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    About this property
    The setting of this magnificent cedar chalet offers a quiet retreat for a restful vacation. The natural rock formations, wooded surroundings and beautiful mountain laurel create a serene location for relaxing and enjoying nature. The cathedral ceilings, grand windows and massive stone fireplace...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    About this property
    Majestically situated right along the lakefront, this premier property will provide you with long lasting vacation memories. Enjoy star gazing and amazing views from the many decks or leave your stress behind while relaxing in the bubbling outdoor hot tub overlooking Deep Creek Lake. The spacious...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    Pet friendly
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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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    When you want to be off-the-beaten-path and still have convenient access to favorite activities, look no further than Whisked-A-Way! Situated on the shores of Red Run Cove, this attractive home is equipped with all of the vacation essentials plus lots of fun extras! Kick-back and relax in the great...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    5 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    Pet friendly
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    About this property
    Offering unparalleled lake front elegance, Preston on the Lake is a premiere vacation home with amazing features inside and out. You will be immediately impressed as you drive up to the entrance of this stately retreat. The main level features a grand gathering space with cathedral ceilings, lake...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 14
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
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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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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    About this property
    Currently undergoing updates, Solar Delight is a lake front vacation home that is sure to please your family and friends. Enhancements include kitchen upgrades as well as the addition of a fifth bedroom. From the expansive deck to the private dock, outdoor living is at its finest. You can enjoy...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
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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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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    Pet friendly
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    Smoking allowed
    About this property
    Invite your friends and family to Heavenly Grove, where convenience, comfort and style come together to create an amazing setting for Deep Creek Vacations. Located in the popular Blakeslee Community, you are off-the-beaten path but still close to the best of the area. This contemporary home makes...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Oakland, Garrett County 21550
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
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    8 Bedrooms, 8 Bathrooms, Sleeps 26 Quick View
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    • Hot Tub
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    Pet friendly
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    Smoking allowed
    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 26
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    About this property
    You will see nothing but positive Changes in Attitude when you choose to stay in this spectacular 5 bedroom lakefront home. Step inside and immediately become swept away by the majestic lake views! This home has top of the line amenities that guarantee a fun and memorable vacation for all. The...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    7 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    So close to it all, yet just far enough away, Friday's Escape is a Deep Creek retreat that is perfect for all seasons. Providing spacious accommodations for friends and family looking to spend quality time together, there is plenty of room to spread out in the large great room, which features a...
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    Oakland, Garrett County 21550
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 18
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
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    Prepare for the 'Wow!' when you walk into the breathtaking home known as Log Hut! The newly renovated 4 bedroom log home offers the best of both worlds both inside and out. The interior design that flows consistently throughout the home features refined and elegant décor, plush leather furnishings,...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    About this property
    Mountain memories start here! Highland Retreat is a marvelous 5 bedroom lakefront home that combines elegant décor with a bevy of fun amenities. Located on the western end of the lake, you and your guests will love cooling off on hot summer days by swimming and splashing from your very own private...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
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    About this property
    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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    Oakland, Garrett County 21541
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
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    About this property
    Windsor House is the perfect choice for vacationers interested in Deep Creek Lake's numerous attractions. Thanks to its convenient location, you're within a short drive from state parks, skiing, restaurants, shops and many other lake activities. This home of distinction features tasteful décor that...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    No matter what time of year you visit, Four Seasons Chateau promises a Deep Creek vacation that will leave you longing to come back again and again. This well-appointed retreat offers style, comfort, and best of all, a convenient location that puts the best area activities at your fingertips....
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 14
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Looking for the finest, most preeminent home to pamper you while on vacation? This stunning and impressive home has so many unique and elegant features, it will let you heartbroken when it is time to depart. From the moment you enter, you will be in awe of how delicately detailed every room has...
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    Oakland, Garrett County 21550
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    9 Bedrooms, 8 Bathrooms, Sleeps 24 Quick View
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    Bask in the glory of Sunset Delight! Able to accommodate large groups, this gorgeous home offers the ideal space for friendly get-togethers and family reunions, and also serves as a great home base for groups during corporate or church retreats. A towering stone fireplace, magnificent picture...
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    Oakland, Garrett County 21550
    Holiday Rental House - 9 Bedrooms, 8 Bathrooms, Sleeps 24
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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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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    Oakland, Garrett County 21541
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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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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    Oakland, Garrett County 21541
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Perched on a mountainside with scenic views, Boulder Escape is a classic Deep Creek retreat with all of the amenities that make a vacation truly memorable! Inviting and comfortable, this handsome log home features a spacious, open floorplan on the main level with a centerpiece stone fireplace,...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    For the chance to stay in one of Deep Creek's most desired vacation homes, book a relaxing escape at Stargazer where peaceful days and starry nights are guaranteed. Mesmerizing from the second that you step inside, prepare to be swept away by the extraordinary lake views that greet you from the...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    7 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    Your fairy tale vacation starts at Ever After! This lake front home promises a memorable vacation experience. Three floors of living space plus a separate carriage house with a 120 inch home theater and an oversized game room makes this property stand-out from the crowd. The main level offers a...
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    Oakland, Garrett County 21550
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 18
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    All About the View is a remarkable lakefront home that encompasses all the qualities that make a vacation truly great. Its unique design, desirable amenities and ideal location combine to create the perfect venue for a vacation with family and friends. Gathering together in the Great Room will...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Duffy's Oar House is the perfect Deep Creek Lake Cottage. It has the charm and charisma of original DCL,and the modern amenities that we have all grown to know and love! Situated on the western end of the lake, this home has a large level yard with a private dock that sits in a quiet cove with...
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    Oakland, Garrett County 21541
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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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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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Putter Place is a brand new lake front home that invites you to unwind and make yourself at home! Your family and friends will be delighted when they enter this spacious, tastefully decorated waterfront property. Whether you are making breakfast in the kitchen or watching TV on the couch, the open...
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    Oakland, Garrett County 21550
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    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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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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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    Oakland, Garrett County 21550
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, 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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    Oakland, Garrett County 21550
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Have the time of your life when stay at Donna's Choice for your next Deep Creek vacation! Unwind in style at this bright and cheerful contemporary mountain home. Attention to detail is found throughout, and you will notice photos of local landmarks decorating the walls. The main level's open...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Truly a treasure, Jewel in Paradise is a stunning lake front vacation home that is the perfect place to get away with family and friends. Perched on a hillside, stunning lake views are yours to enjoy! The spacious main level has an open floor plan with high-end finishes that is ideal for...
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    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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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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    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    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....
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    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    A truly amazing mountain home is just what you need for your relaxing getaway and Log Mahal will not disappoint. This custom crafted 5 bedroom home will quickly win you over with its unique style and décor. Love at first sight is a given when you enter the Great Room. Large vaulted ceilings...
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    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Entirely charming and conveniently located, Sage Mountain Retreat is a brand new Deep Creek Lake vacation rental that is ready to host your next getaway! Three master suites make it a great option for a couples' getaway or a family vacation. You will love this conveniently located home from the...
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    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    True to its name, the good life awaits at La Bella Vita! This stunning, recently remodeled home promises an exceptional Deep Creek Lake vacation for your family and friends. With amazing lake views from almost every room and upscale décor throughout, this will quickly become a favorite spot to get...
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    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    About this property
    If luxury is what you have in mind, then look no further. Serenity Summit is an extravagant 5 bedroom duplex that boasts an immaculate interior. With 3 master suites available, this home is ideal for the multi-family or couple's retreat. Your Great Room boasts lustrous hardwood floors, stylish...
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    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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