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Vacation Rentals in Oakland, MD

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    All 207 Rentals in Oakland
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    Travellers to Oakland are booking June dates now. Secure your vacation rental today, and have the perfect trip.
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    $383
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    1 / 18
    3 Bedrooms / 2 Bathrooms / Sleeps 10
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    $291
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    1 / 8
    3 Bedrooms / 3 Bathrooms / Sleeps 10
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    $3,208
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    4 Bedrooms / 5 Bathrooms / Sleeps 12
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    $5,646
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    1 / 16
    5 Bedrooms / 5 Bathrooms / Sleeps 12
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    About this property
    Bedding: King, King, Queen, Queen, Bunk and 2 Twins Your Deep Creek adventure awaits! Reverie is an exquisite 5 bedroom home that will far exceed your expectations. Floor to ceiling windows in the Great Room allow you and your guests to bask in the sheer beauty of the lake from every angle. Lavish... View all property information
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    Location Information
    Oakland, Garrett County 21550
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    $891
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    1 / 21
    7 Bedrooms / 7 Bathrooms / Sleeps 18
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
    • Hot Tub
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
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    About this property
    Bedding: King, King, King, Queen, Queen, Queen, Queen, 2 Double Rollaways 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... View all property information
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    Location Information
    Oakland, Garrett County 21550
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    1 / 15
    4.5 of 5 stars (5) Very good
    4 Bedrooms / 5 Bathrooms / Sleeps 12
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    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Kick up your heels and celebrate at Martini Mountain! Perfect for entertaining, this spacious home is ideal for a get-together of family and friends. The great room is highlighted by soaring cathedral ceilings and a wall of windows. Enjoy meals outside or in, as the dining room opens to the... View all property information
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    Location Information
    Oakland, Garrett County 21550
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    1 / 13
    5 of 5 stars (8) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    Amenities & Details
    • Fireplace
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Consign your cares to oblivion with a stay at this pet friendly lakefront log home. Truly charming, you’ll find yourself surrounded with quality furnishings and imaginative décor. Relax in total comfort in the romantic glow from your fireplace. Equally relaxing will be time spent outdoors on your... View all property information
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    Location Information
    Oakland, Garrett County 21550
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