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Oakland Vacation Rentals

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    Travelers to Oakland are booking February dates now. Secure your vacation rental today, and have the perfect trip.
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    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    You’ll love the setting of Willow Point, a cozy cottage with sprawling1 / 14
    (11)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 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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    About this property
    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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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Waves and Moguls is a captivating 5 bedroom vacation home that is the ideal choice no matter what season you choose to visit. You will immediately feel a sense of home when you step inside the bright and lovely Great Room, sure to be a favorite gathering spot among family and friends. Cheerful...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Studio, 3 Bathrooms, Sleeps 9 Quick View
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    About this property
    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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    Colorful, vibrant, and fun! That’s Tamaqua Lodge- check out the large deck and1 / 21
    (11)Average
    6 Bedrooms, 1 Bathroom, Sleeps 15 Quick View
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    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. Although outstanding views can be seen throughout the interior of the home thanks to ample...
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    Oakland, Garrett County 21550 
    Rental Home - 6 Bedrooms, 1 Bathroom, Sleeps 15
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    Extravagant comfort and mountain style reign supreme at Timberlodge! You’ll1 / 23
    (14)Very good
    9 Bedrooms, 1 Bathroom, Sleeps 28 Quick View
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    If bigger is better, this fantastic chalet is the absolute best! Timberlodge excels in every way imaginable when it comes to your comfort and pleasure. This exquisite log home is a masterpiece of design offering 100 feet of beautiful lakefront decorated with fragrant mountain laurel and towering...
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    Oakland, Garrett County 21550 
    Rental Home - 9 Bedrooms, 1 Bathroom, Sleeps 28
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    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
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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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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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    When you come to stay at Wispering Ridge, you get the best in both convenience1 / 8
    (4)Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Come away to a quiet retreat! Wispering Ridge is the perfect getaway for your small family getaway or a reunion among close friends. This duplex proves that you don't have to be large to have an incredible view of the lake. An open great room, dining room, and kitchen give this home a spacious...
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    Oakland, Garrett County 21550 
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    The lodge-like decor and gleaming cherry wood of It’s All Good help you enjoy1 / 14
    (6)Excellent
    5 Bedrooms, 1 Bathroom, Sleeps 14 Quick View
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    Why worry? It’s All Good! Find release from the stresses of daily life and recharge your batteries with an escape to this cozy five bedroom chalet. Cloaked in rich earth tones and cherry wood, this home is as warm and welcoming as could be! Situated along Lake Shore Drive, you can even catch...
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    Oakland, Garrett County 21550 
    Rental Home - 5 Bedrooms, 1 Bathroom, Sleeps 14
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    Captivating 4 Bedroom Log home with private hot tub!1 / 19
    (6)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Turn your dreams into reality when you choose to stay in the captivating 4 bedroom log home Shiver Me Timbers. Step inside the Main level and you will instantly be won over by the warm wood walls and gleaming hardwood floors that flow naturally throughout the cabin. The Great Room is gracefully...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Find time to reconnect with family and friends at Trees, Breeze and Skis! This classic mountain chalet invites you to relax and enjoy the beauty of the Deep Creek Lake area. Great outdoor space and a wrap-around deck greet you upon your arrival. It is easy to imagine starting your day with a hot...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • DVD Player
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    Located in the heart of Deep Creek Lake, Stone Crest offers a convenient location, spacious layout, and great amenities. As you enter the main level, take a moment to appreciate that wall windows, cathedral ceilings, and towering stone fireplace. This spacious home offers seamless indoor/outdoor...
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    Oakland, Garrett County 21550
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    4 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    The log cabin experience is perfected at Creekside Lodge! Mixing together charming mountain-style details like knotted pine and stone with modern upgrades like upscale furniture and upgraded appliances, this log-style abode is the perfect fusion of rustic charm and upscale elegance! With four...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 10
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    6 Bedrooms, 1 Bathroom, Sleeps 14 Quick View
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    Unlike any other vacation retreat, Deer Pass offers the opportunity to escape the ordinary and transcend into greatness! It is not often you can enjoy coffee on your deck while watching deer graze at your lawns edge, the day unfolding quietly before you. Tasteful, upscale furnishings with a...
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    Oakland, Garrett County 21550
    Rental Home - 6 Bedrooms, 1 Bathroom, Sleeps 14
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    Treat yourself to a stay at The Herrington with the luxury estate’s private1 / 77
    (2)Very good
    10 Bedrooms, 1 Bathroom, Sleeps 34 Quick View
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    Looking for a royal retreat? The Herrington will make you will feel as if you are living in a castle. Whether on a family vacation or a business trip, The Herrington is equipped with multiple gathering rooms and meeting rooms. For family fun, play a game of pool, ping pong, or foosball in the game...
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    Oakland, Garrett County 21550 
    Rental Home - 10 Bedrooms, 1 Bathroom, Sleeps 34
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    Immerse in nature! Life is unspoiled and unforgettable at the lakefront of Just1 / 18
    (2)Very good
    4 Bedrooms, 1 Bathroom, 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 
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    Magical details and quality furnishings combine with a charming level lakefront1 / 18
    (3)Excellent
    5 Bedrooms, 1 Bathroom, 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 
    Rental Home - 5 Bedrooms, 1 Bathroom, Sleeps 16
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    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    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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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
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    About this property
    Newer 2200-square-foot, custom, log cabin with three-sided wrap deck nestled on one+ acre in Deerfield off of Mayhew Inn Road. Beautiful trees and ferns with room to breath. Three miles from Swallows Falls, 2 miles to horseback riding stables and 5 miles to State Park Beach which has full water...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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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
    Rental Home - 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    What better way to experience a magical mountain getaway than a relaxing stay in a charming log cabin?Imagine arriving at your perfect little cabin tucked away in the quiet picturesque community of Yellowstone Village. Step inside and instantly fall in love with the dark hardwood floors and plush...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Changed to: 'Canaima' is the name of the friendly spirit of the jungles of Venezuela and Brazil. It is also the site of the novel 'The Lost World' by Arthur Conan Doyle and the location of the 'Green Mansions', the place where Rima lived, in the beloved novel of William Hudson. Our cabin carries...
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    Oakland, Garrett County 21541
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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 21541
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 2 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
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Spacious Chalet with Sunset Lake Views1 / 43
    (1)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    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
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Check out this really cool townhome at Four Hooppole on the shores of Deep Creek Lake! The community offers around 10 acres of level manicured yard, community tennis court, community basketball court, playground, and one of the only sandy beaches with a roped off swimming area for your safety and...
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    Oakland, Garrett County 21550
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 6 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
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    Walk to the waterfalls and explore the winding trails around Swallow Falls Inn1 / 7
    (4)Average
    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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Tees-n-Skis delights with high-end furnishings, fun amenities, and favorable1 / 9
    (9)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 12 Quick View
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    Summer and winter shine in equal measure when you come for a stay at Tees-n-Skis! This fantastic craftsman-style home was built to fulfill all your four-season vacation dreams. Clean lines, modern details, and professional décor combine to create an atmosphere of quiet sophistication, apparent in...
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    Oakland, Garrett County 21550 
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 12
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    The traditional comforts and community amenities at Linwood make for proven1 / 18
    (7)Average
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Let Linwood take your spirit to a place where everyday concerns are left behind and relaxation and felicity can take hold, unchecked and unencumbered. With tree covered lot, nearby lake access, and community dock slip, this three bedroom abode is the perfect place to get away from the daily grind....
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    Oakland, Garrett County 21550 
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 8
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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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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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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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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
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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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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Rustic and warm, Bunbury Cottage is a charming Lincoln-lodge style home with1 / 20
    (3)Average
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    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
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Gather together at Lake’s End! There's space for everyone at this magnificent1 / 16
    (8)Very good
    8 Bedrooms, 1 Bathroom, Sleeps 22 Quick View
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    Put an end to vacation disappointment at shining Lake's End! Busy minds and talented hands have created a true masterpiece of style and comfort just for you in the fantastic Silver Tree Landing community. Lake's End holds the key to every vacation dream you've ever had with soaring cathedral...
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    Location Information
    Oakland, Garrett County 21550 
    Rental Home - 8 Bedrooms, 1 Bathroom, Sleeps 22
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
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    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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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Smoking allowed
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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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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
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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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    Location Information
    Oakland, Garrett County 21541
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    The perfect home base for your Deep Creek experience, LakeStar Chalet is a brand new and conveniently located within minutes from favorite activities. Brimming with log home charm, the main level offers an open layout that is ideal for spending time with family and friends. A stunning...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Measures have been taken to make this cabin handicap accessible so our friends who may be limited to a wheelchair can still enjoy this outdoor experience! Nearby Tipi can be rented by guests of Stanley only with rental of Stanley. An upcharge of $25 per night applies for Tipi rental and includes 3...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    Let Montana East work its magic! This opulent estate will spirit you away to a place where every day concerns are left behind and wishes are always indulged. Escape to any one of the five oversized bedrooms to enjoy some well-deserved R&R for an enchanting mountain escape. Or, gather everyone...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 1 Bathroom, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Central Heating
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    Pet friendly
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    Smoking allowed
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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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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Kid friendly
    Smoking allowed
    About this property
    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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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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