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Oakland Holiday Rentals

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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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    *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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    Ski Solitude1 / 30
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Red Run Cabin1 / 44
    (29)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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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    • DVD Player
    • Grill
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    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, 4 Bathrooms, Sleeps 11 Quick View
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    • Cable/satellite TV
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    • Private Garden
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our 2 year young chalet offers rustic charm, yet decorated for today! Close to docks and lake you will find nature & zen and plenty of land to romp and play. Fully stocked kitchen with linens provided, native stone fireplace, 4 bedrooms and 4 baths. Newly finished basement offers second tv, pool...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    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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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    Intimate and inviting, Swallow Falls Inn Cabin 1 echoes with the wild resonance of the waterfalls! Get away to Swallow Falls Inn Cabin 1! Located near the state park, you are just a walk away from one of Deep Creek's most popular sites and home to Maryland's largest waterfalls! Muddy Creek Falls...
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    Oakland, Garrett County 21550
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
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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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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Emerald Bay1 / 13
    (5)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Waterfront
    • Washer
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    • Cable/satellite TV
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Emerald Bay gives you everything: an expansive lakefront, large deck and plenty of indoor comforts! A gorgeous lake view greets you at Emerald Bay! This beautiful chalet, located along quiet Paradise Point, features a quiet lakefront, sunny views, and open skies for an utterly ideal lakefront...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    About this property
    Enjoy the feeling of rustic mountain living in this cedar chalet. Cozy and inviting, this home is perfect for accommodating the extended family or group of friends. Wood-lined walls, cathedral ceilings and a beautiful stone fireplace greet you upon entering the main level. The open floorplan lends...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    About this property
    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Swallow Falls Cabin 21 / 7
    (4)Average
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 June 2016
    It is a shame that you can not take your pet there anymore. We enjoyed going there for the last five years. It is not like they offer much, ( wifi, hot tubes, swimming, Air for...
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    About this property
    Walk to the waterfalls and explore the winding trails around Swallow Falls Inn Cabin 2! Swallow Falls Inn Cabin 2 is a rustic wonder! With charming log-cabin exterior and porch swing, you will feel awash with a feeling of warm welcome from the moment you arrive! Whether you are spending the day...
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    Oakland, Garrett County 21550
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
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    Pet friendly
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    About this property
    Discover a truly delightful experience when you choose Paddles & Poles for your Deep Creek escape! Located in the lake front Silver Tree Landing community, this tastefully decorated home has all of the vacation essentials plus a lot more! A retreat for all seasons, the central location makes it...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lakefront home with level yard located in the convenient quiet cove of Paradise Point.  Relax on the deck with a drink or join the fun on the private dock of this home.  Offering plenty of room with 4 bedrooms and 2 1/2 baths for your family vacation.  Close to restaurants and shopping. The...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    Pet friendly
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    About this property
    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 12 Quick View
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    • Hot Tub
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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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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Grill
    • Waterfront
    • Internet Access
    • Washer
    • Housekeeping Included
    • Parking
    • Hot Tub
    Suitability
    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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    Oakland, Garrett County 21550
    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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    • Hot Tub
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    Pet friendly
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    About this property
    Experience the beauty of Deep Creek Lake at Fox Den, a charming A-frame cottage that offers a treasured chance to unwind. Both romance-seekers and those in pursuit of inner peace will relish time spent at this classic mountain getaway. Highlighted by a wall of windows, wood accents, tasteful decor...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    About this property
    Skydance is the place where lifetime memories are made! This beautifully crafted, lake front home features an expansive deck that invites you to sit back and take in gorgeous sunrises and scenic lake views. A grassy, level lawn that is dotted with trees features a charming wooden bridge that leads...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 13
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    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Hot Tub
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    Pet friendly
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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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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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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    Oakland, Garrett County 21550
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Tucked among the trees in the centrally located Gallatin Woods community, Keep Dreaming is a mountain getaway that is ready and waiting to host your family and friends! With outdoor space that will keep everyone happy, a wrap-around deck gives everyone room to relax and enjoy the scenery. Warm up...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    8 Bedrooms, 10 Bathrooms, Sleeps 16 Quick View
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    This brand new home is designed with amazing vacations in mind! Eight master suites, a private indoor pool and a convenient lake front location make this the perfect choice for any trip to Deep Creek Lake. High end décor will fill the spacious interior that includes multiple living areas where you...
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    Oakland, Garrett County 21550
    Holiday Rental House - 8 Bedrooms, 10 Bathrooms, Sleeps 16
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    Baldwins Domain1 / 46
    (3)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
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    With community perks and tranquil wooded setting, serenity can always be found at Baldwin's Domain! Pure mountain air mixes with comforting home-style touches at Baldwin's Domain to create an appealing signature aesthetic. Catch the view from the sunny living room and stay warm beside the home's...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Brimming with charm, By the Stream is Deep Creek Lake area vacation home that is ready to host your next getaway! So close to it all, yet just far enough away, you will love the wooded location that's just around the corner from Wisp Resort. Enter the roomy main level to discover lots of living...
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    Oakland, Garrett County 21550
    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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    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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    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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    Oakland, Garrett County 21550
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
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    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Brimming with charm and convenience, Some Kind of Wonderful is a Craftsman-style home that is ready and waiting to host your next Deep Creek vacation! Get together with your favorite people in the spacious main level where you will feel instantly at home during your time in the mountains. The open...
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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 12 Quick View
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    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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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Tamaqua Lodge1 / 21
    (13)Average
    6 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    Pet friendly
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    Reviewed 18 September 2018
    TAMAQUA LODGE review: 12 of us (4 adults & 8 20-24 year old) stayed at Tamaqua Lodge 8/4-8/11/18. PROS: Close to water; private dock; 6 bedrooms; 5 1/2 baths; location-close...
    Reviewed 8 March 2017
    We had a wonderful family reunion with 13 people in this spacious home with cathedral ceilings and a superb lake view!The dining table was big enough for everyone so we could...
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    About this property
    Colorful, vibrant, and fun! That's Tamaqua Lodge- check out the large deck and stunning lakefront! Joyful and uplifting, Tamaqua Lodge will elevate your spirits to new heights! Beautifully appointed rooms accented with eye-catching flair and style provide ample space for your family and friends....
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    Oakland, Garrett County 21550 
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 15
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Hidden from view, a true Treasure of the mountains awaits. This charming cabin is nestled amongst a soaring canopy of trees at Deep Creek Lake. Hidden Treasure features cozy comfort with all the extra amenities. As an added bonus, you can bring your dog on vacation too! Relax in the great room by...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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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    Oakland, Garrett County 21550
    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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    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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    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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    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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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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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, 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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    10 Bedrooms, 8 Bathrooms, Sleeps 20 Quick View
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    Twin Retreats offers an ideal gathering place for family and friends at Deep Creek Lake! Two spacious homes are side-by-side making it easy to spend quality time with your favorite people. The convenient location puts you within minutes of restaurants, marinas, Deep Creek Lake State Park and much...
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    Oakland, Garrett County 21550
    Condo/Apartment - 10 Bedrooms, 8 Bathrooms, Sleeps 20
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Conveniently located, yet off the beaten path, these Yellowstone Log Cabins (Property #s 359, 360, 365, and 367) offer cozy, quaint, and comfortable accommodations! All cabins are situated closely enough to one another for ideal couple retreats or single family getaways while offering a quiet...
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    Oakland, Garrett County 21541
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Once in a Blue Moon is a brand new vacation home that is the ideal choice for your next Deep Creek Lake vacation! The convenient location puts you within minutes of restaurants, marinas, Deep Creek Lake State Park and much more. Beautifully decorated with upscale finishes, you can spend evenings by...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 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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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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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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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Escape to the relaxing sounds of nature at Yellowstone Village and ''Dan's Mountain'' conveniently located, yet off the beaten path, this beautiful log home offers a cozy, cabin feel while offering plenty of comfortable accommodations! There's plenty of room for a gathering with friends and family,...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Head to Take-A-Break for unforgettable Deep Creek Lake vacations throughout all four seasons! Located in a friendly community, you will love having the lake right across the street! The spacious main level is bright and airy with cathedral ceilings and a massive wall of windows that reveal lake...
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    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 8
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