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Oakland Holiday Homes

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    Travellers to Oakland are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    All 276 Rentals in Oakland
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    8 Bedrooms, 9 Bathrooms, Sleeps 26 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Spacious Chalet with Sunset Lake Views1 / 43
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    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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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 21541
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Magic is alive at Cochran’s Cabin! Experience the lake in an atmosphere only an authentic cabin can provide! This original Deep Creek log cabin has been thoroughly upgraded with modern amenities, yet maintains an old-world charm and simple simplicity that is apparent in every nook and cranny....
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    Red Run Cabin1 / 13
    (2)Average
    Studio, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Relax at the picnic table, surrounded by evegreens and Rhododendron and feel like you are vacationing in your own park. Sitting mere minutes from Central Deep Creek Lake activities, this simple cabin in the woods is only a short walk to lovely beach area on the lake. Easy access to ASCI whitewater...
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    Oakland, Garrett County 21550
    Condo/Apartment - 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 1 Bathroom, Sleeps 14 Quick View
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    This new construction will wow you at every turn! Located along a quiet cove, your private dock is just a short walk away; all you have to do is stroll across the street and you’re there! Bear Foot Cove features a massive deck, perfect for group meals, sun bathing, and enjoying the great outdoors....
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 1 Bathroom, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Conveniently located, yet off the beaten path, this Yellowstone Log Cabin is situated closely to Property Numbers 360, 364, 365, 366 and 367 making it ideal for group or extended family retreats as well as offering the cozy, quaint and comfortable accommodations for a single couple or family. The...
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    Oakland, Garrett County 21541
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Attractive & Inviting 4 Bedroom home with hot tub in prestigious community!1 / 36
    (11)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
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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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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Like the classic film that shares its name, It’s a Wonderful Life will take you on a journey of self-discovery and inspire you to grab your loved ones, hold them close, and spend your days wrapped in the warmth of their love. With five bedrooms, spacious back yard, and plentiful seating around the...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 14
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    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 inside, warmed by the wood stove or making a hearty breakfast in the cabin’s full kitchen,...
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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 8 Quick View
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    Leisure time is perfected at Just Breathe Inn! Spellbinding and spectacular, this lakefront chalet is rich with charm. You’ll feel rested and ready for adventure when you take in a morning sunrise from the beautiful hardwood deck, the home’s natural beauty surrounding you. Find time to appreciate...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Leave everyday life behind when you escape to Break Away Chalet, a centrally located vacation home in the heart of Deep Creek Lake. Situated on a partially wooded lot in a quiet community, your stress will instantly begin to disappear when you step out of the car. The spacious main level is...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Is the clamor of city life wearing you down? Cedarwoods, a stunning 3 bedroom mountain chalet, is calling your name. Nestled away in the quiet community of Mountainside, this beautiful home offers the seclusion and privacy you crave. Boasting 3 spacious levels of living space, high vaulted ceilings...
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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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    Looking for a quiet wooded retreat? Log Heaven wraps you in nature's comforting embrace with the rich and rustic charm found throughout the space. One master suite and 3 additional bedrooms give your whole party enough space to spread out and then regroup in the living room while enjoying a movie...
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    Oakland, Garrett County 21550 
    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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    Located in the heart of it all, Arrowhead 15 is the perfect choice for a family vacation or a Deep Creek Lake getaway with friends. You will love being able to walk to restaurants, a full-service market, the movie theater and nightlife! Easy lake access and lots of community outdoor space is a...
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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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    If you like the idea of falling asleep under the stars and roasting marshmallows around a campfire, but the hassles of pitching a tent and sleeping on bumpy ground just don't do it for you, then glamping, the new term being used for upscale - or glamorous - camping, could be your ideal vacation....
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    Oakland, Garrett County 21550
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
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    About this property
    4+ nights for your stay? Message us for special discounted rates. Escape the hustle of metro living and enjoy the solitude that is offered by Yough Mountain Resort! with 48+ miles of private gravel roads for biking and hiking, hundreds of acres of surrounding Garrett State Forest, and abundant...
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    Oakland, Garrett County 21550
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 9
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Offering easy, one-level living, this charming townhome has breathtaking lake views and a central location that is ideal for Deep Creek getaways! The glow of the fire in the pellet stove is a warm welcome when you kick-back in the great room and gaze out at the lake and mountains. Watch TV on the...
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    Oakland, Garrett County 21550
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 1 Bathroom, Sleeps 12 Quick View
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    Summer skies or winter flurries, the time is always ‘Just Perfect’ for a trip to this charming 4 bedroom chalet! Merging together lake and mountain views creates an outdoor ambiance steeped in tranquility. Grill out on the back deck, set your sights on the majesty around you, unwind in the hot tub,...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 12
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    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 stone fireplace! Then, linger for a moment on the spacious back deck to take in the glinting water and...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Outside or in, Crosswinds is the ideal choice for your next Deep Creek Lake vacation! Within a short walk from the home’s front door, you'll have easy access to the home’s lake access point - including a picturesque picnic area for you and your guests - as well as the neighboring Silver Tree...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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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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    Oakland, Garrett County 21541
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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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 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 wooded setting. Lured Away offers an...
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    Oakland, Garrett County 21541
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Looking for the ultimate vacation experience? Amazing Love has you covered! This five-bedroom vacation rental was recently remodeled and features a host of fantastic amenities, including an air hockey table, gas fireplace, pool table and wireless Internet. Plus, a fabulous outdoor hot tub! Step out...
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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 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, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    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 - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    Dog-friendly, lakefront log home on a quiet cove - front deck & shared dock1 / 41
    (1)Terrible
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Head to Deep Creek Lake for a quiet vacation with family and friends, complete with all the conveniences that comes with being close to town. Your group will have ready access to the lake and the slopes, as well as in-town convenience. And to make your getaway complete, you can bring the family dog...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    8 Bedrooms, 7 Bathrooms, Sleeps 22 Quick View
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    Bursting with promise, Serendipity is a vacation retreat unlike anything you have ever seen! Come in, take a look around, and let amazement take hold; every corner of this magnificent lake estate is sure to impress! Top quality furnishings, cathedral ceilings, and beautiful stone fireplaces combine...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 22
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Greene Acres is calling! With elegant cathedral ceilings and floor-to-ceiling windows, the living areas of this charming log-style home hit all the right notes to create a stirring symphony you’ll want to listen to again and again. Lush, vibrant greenery surrounds you and provides privacy for...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Studio, 3 Bathrooms, Sleeps 9 Quick View
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    4+ nights for your stay? Message us for special discounted rates. Take a decent walk to the community lake access area where you will find a pavilion, picnic table, large grassy play area, and swimming and fishing access along the shoreline of Deep Creek Lake. Assigned boat slip for your vacation...
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    Oakland, Garrett County 21550
    Condo/Apartment - 3 Bathrooms, Sleeps 9
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Experience pure fun and relaxation when you choose Pura Vida for your next Deep Creek Lake vacation! Upon your arrival, you will be charmed by the wrap-around deck and wooded surroundings of this tastefully decorated chalet. A wall of windows fills the great room with natural light. The open floor...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    LinLaurAl is a five-bedroom Deep Creek vacation rental with something for the whole family! Featuring 600 feet of level lakefront and plenty of privacy, this charming home is the perfect lakefront retreat. Enjoy warm summer mornings by stepping out of your master bedroom onto the spacious balcony...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Rother's Cove is a proven delight full of new surprises! This traditional lake home is a family-favorite destination for many groups that make this home their sanctuary, year after year. Start your own family tradition with a visit to charming Rother’s Cove! Inside the home, traditional touches,...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
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    Relaxing Location with Private Dock1 / 33
    (1)Average
    4 Bedrooms, 3 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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    Oakland, Garrett County 21541
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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    5 Bedrooms, 4 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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    4+ nights for your stay? Message us for special discounted rates. Come breathe fresh mountain air at this completely renovated 4 bedroom 2 full bath getaway nestled in the Youghiogheny Mountain Resort. This property has much to offer whether you are looking for a family vacation or romantic getaway...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    About this property
    Discover your own Deep Creek Lake paradise when you stay at Lake Shore Paws! Great outdoor space and a convenient location make it the perfect choice for a fun and relaxing getaway. Vaulted ceilings and lots of windows highlight the spacious main level. It is easy to imaging spending crisp...
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    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Waterfront
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    Pet friendly
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    Smoking allowed
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    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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    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Known for its spacious common areas, sandy beach and quiet cove location, Four Hooppole is a favorite lakefront community that offers ten acres of level manicured lawn and a fantastic swimming area. The main level of this well-appointed townhome features a spacious great room with lake views and...
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    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Want to try and solve a vacation riddle? What's charming and irresistible, immensely private, with 2 streams running on either side, and guaranteed to refresh your spirit? Here’s a hint: it's tucked away just off a winding country lane, surrounded by a magnificent age-old oaks and laurel? Answer:...
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    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Wild Yough Villa1 / 22
    (25)Excellent
    Studio, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Washer
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4+ nights for your stay? Message us for special discounted rates. Wild Yough is conveniently located near Swallow Falls & Herrington Manor State Parks, offering dynamic activities. Watch the Bald Eagle family snag a fish, watch Maple Syrup being made, take a canoe or paddle boat out on Herrington...
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    Location Information
    Oakland, Garrett County 21550
    Condo/Apartment - 2 Bathrooms, Sleeps 8
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    8 Bedrooms, 9 Bathrooms, Sleeps 24 Quick View
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    Elegant, Extravagant, Extraordinary… the praises for this sensational estate go on and on! Uncommon quality can be found in the smallest details at this palatial home! Possessing a spectacular, sweeping view of Deep Creek Lake, Peregrine’s Perch is a premium home that is flawless in design and...
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    Location Information
    Oakland, Garrett County 21550 
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 24
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    Shenandoah1 / 47
    (22)Very good
    Studio, 4 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
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    • Waterfront
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4+ nights for your stay? Message us for special discounted rates. Relax in the Great Room or Rec Room taking in the panoramic lakeviews. Cozy up in front of the gas fireplace on those chilly evenings. Large kitchen overlooks Family Room. 2 Master Suites, each offering it's own private bathroom,...
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    Location Information
    Oakland, Garrett County 21550
    Condo/Apartment - 4 Bathrooms, Sleeps 14
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    6 Bedrooms, 6 Bathrooms, Sleeps 15 Quick View
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    Visualize yourself standing at the railing of a spacious sunlit deck, as you survey the expansive view of the lake and mountains unfurling before you. Now make that vision a reality! Choose Sunset Pointe as your next Deep Creek Lake vacation destination: you’ll be glad you did! Located within an...
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    Location Information
    Oakland, Garrett County 21550 
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 15
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hidden Cove Getaway welcomes you to Deep Creek Lake with spacious rooms, a convenient location and fun amenities. A dramatic wall of windows fills the main level with natural light creating an inviting ambiance from the moment you enter. Hardwood floors, tasteful furnishings and cathedral...
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    Location Information
    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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    The seasons have never been more beautiful than at Always in Season! Sunbathe and water ski in the warm summer months, celebrate fall with a hike through bright leaves, patter gently through pristine snow for a spectacular Deep Creek winter, and watch as Mother Nature wakes from her winter nap to...
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    Location Information
    Oakland, Garrett County 21550 
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Sauna
    • Grill
    • Internet Access
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    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4+ nights for your stay? Message us for special discounted rates. Relax in this well cared for vintage Deep Creek lodge. 5 bedrooms, 2 living areas, expansive deck overlooking the firepit and horse shoe pit are just some of the amenities you are sure to enjoy while vacationing at Almost Heaven....
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    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Warm & Cozy 4 Bedroom Log Home w/ elegant furnishings in private setting!1 / 38
    (17)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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