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Oakland Vacation Rentals

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    Travelers to Oakland are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    7 Bedrooms, 7 Bathrooms, Sleeps 18 | Quick View
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    5 of 5 bubbles (6) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    About this property
    On Top of the World perfectly defines the way you will feel when you step inside this exquisite 5 Bedroom mountain home. Recently remodeled throughout, this stunning home is located in the prestigious community of Mountainside and features one of the most breathtaking panoramic views of Deep Creek... View all property information
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    Oakland, Garrett County 21550
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Experience true lake life when you choose to stay in the enchanting home known as Bear's Dream. Tucked among tall trees and within walking distance to Deep Creek State Park, this home easily offers both the peace and privacy you seek. Embracing a cozy cabin spirit, you will instantly fall in love... View all property information
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    Oakland, Garrett County 21550
    1 / 17
    5 of 5 bubbles (25) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Red Run Cabin is a 1 story 3 bedroom cottage with a finished basement on an acre wooded lot near the west end of Deep Creek Lake, accomodating up to 6 people. It has lake access through the Red Run Restaurant property leading to a sandy beach and shallow lake bottom far out into the lake, making... View all property information
    Location Information
    Oakland, Garrett County 21550
    5 of 5 bubbles Reviewed 6 days ago
    This was our first trip to Deep Creek Lake. Red Run cabin is perfect for a small group, this trip was myself and my three teenagers. The cabin was great for a first-time trip...
    5 of 5 bubbles Reviewed May 31, 2016
    We had a wonderful time and the house is very well kept. The neighbors were friendly and the dogs loved it! Extremely pet friendly location. We went to swallow falls which was...
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    1 / 55
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Looking for the finest, most preeminent home to pamper you while on vacation? This stunning and impressive home has so many unique and elegant features, it will let you heartbroken when it is time to depart. From the moment you enter, you will be in awe of how delicately detailed every room has... View all property information
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    Oakland, Garrett County 21541
    1 / 30
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Vivid and lively are two words that can describe the character displayed in Retro Lake Landing. Its originality is definitely one of a kind and will certainly put that extra little kick into your vacation. If you are looking for something different, fun and exciting, this would be the perfect... View all property information
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    Oakland, Garrett County 21541
    1 / 18
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    All About the View is a remarkable lakefront home that encompasses all the qualities that make a vacation truly great. Its unique design, desirable amenities and ideal location combine to create the perfect venue for a vacation with family and friends. Gathering together in the Great Room will... View all property information
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    Oakland, Garrett County 21550
    1 / 17
    4 of 5 bubbles (16) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    El Dorado is a delightful lake cottage with cozy furnishings, warm pine walls, beamed cathedral ceilings and a beautiful stone fireplace. Stunning views of Deep Creek Lake can be seen from almost every room in this charming chalet. Relax in the bubbling hot tub after a day on the lake or fish off... View all property information
    Location Information
    Oakland, Garrett County 21550
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    1 / 31
    5 Bedrooms, 3 Bathrooms, Sleeps 13 | Quick View
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    You will certainly learn to embrace the motto “Live It, Love It, Lake It” when you choose this charming mountain home for your Deep Creek getaway. Imagine sharing memories with your friends and family as you cozy up around the warm wood fireplace in the Great Room. This massive stone stacked... View all property information
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    Oakland, Garrett County 21550
    1 / 23
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    When you step through the doors of Boxer Overlook, you will immediately be taken in by the unparalleled elegance this home showcases. Ideally located in a quiet community, this 5 bedroom chalet is perfect for large or multi-family gatherings. Offering an open concept floor plan, this home showcases... View all property information
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    Oakland, Garrett County 21550
    1 / 33
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Where memories Imagine sitting on the deck overlooking Deep Creek Lake with your mornings first cup of coffee and feeling your cares gently float away. Meander down the lit path to a stone patio and relax on the bench to take in the serene view of the lake. While away the hours in the bubbling hot... View all property information
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    Oakland, Garrett County 21541
    1 / 23
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Windsor House is the perfect choice for vacationers interested in Deep Creek Lake’s numerous attractions. Thanks to its convenient location, you’re within a short drive from state parks, skiing, restaurants, shops and many other lake activities. This home of distinction features tasteful décor... View all property information
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    Oakland, Garrett County 21550
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Classic Americana is a marvelous 4 bedroom/ 2.5 bath lake access home that will surprise and delight you from the moment that you pull into the driveway. Enter from the covered front porch into the majestic Great Room. Embrace the country charm of the hardwood floors, the white washed wooden beamed... View all property information
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    Oakland, Garrett County 21550
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    For the chance to stay in one of Deep Creek’s most desired vacation homes, book a relaxing escape at Stargazer where peaceful days and starry nights are guaranteed. Mesmerizing from the second that you step inside, prepare to be swept away by the extraordinary lake views that greet you from the... View all property information
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    Oakland, Garrett County 21550
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Craftsman-style details, tasteful décor and a central location make Just Relax the perfect choice when you want to unwind at Deep Creek Lake. Step inside, and the first thing you will notice is the open floorplan that is ideal for entertaining. Natural light reflects off of gleaming hardwood... View all property information
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    Oakland, Garrett County 21550
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    When you are ready to experience the best of Deep Creek Lake, make Wright Off the Lake your destination for family fun and relaxation! From the moment you enter, you will appreciate the stylish décor and attention to detail throughout this five bedroom townhome. An open concept means that it is... View all property information
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    Oakland, Garrett County 21550
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Casa Montes (“House in the Mountains” in Latin) is an exquisite mountain retreat with over 1.5 acres of seasonal lake views and privacy, yet conveniently located within 5-minute walking distance of the lake, restaurants and shops.  Walk on a path to a pizzeria, a coffee/breakfast spot, and to your... View all property information
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    Oakland, Garrett County 21550
    1 / 35
    5 of 5 bubbles (5) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Valhalla "Hall of the Gods" is a spectacular 5 bedroom home that sits atop a beautiful mountain side. Step inside this wondrous home with large beams encompassing the great room and hardwoods that spread throughout the home. Enjoy exquisite views overlooking Deep Creek Lake while sipping your... View all property information
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    Oakland, Garrett County 21550
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    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Do you find yourself daydreaming about a romantic getaway in a charming lakefront home? Golden Retreat is perfect for a couple but is large enough for a small family. You’ll adore the comfortable furnishings and alluring appeal of the interior. Conveniently located a mere 5 minutes from Swallow... View all property information
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    Oakland, Garrett County 21550
    1 / 27
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    Ski Season is premiere vacation home that offers guests the best of both worlds: indoor elegance and outdoor fun and adventure! This 4 bedroom lakefront home radiates luxury throughout. Step inside and take in the breathtaking lake views from the floor to ceiling windows. Expansive vaulted... View all property information
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    Oakland, Garrett County 21540
    1 / 19
    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... View all property information
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    Oakland, Garrett County 21550
    1 / 23
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    Sunrise is a spectacular 4 bedroom lakefront home that will quickly become host to your family’s favorite Deep Creek memories. From the moment that you begin pulling up to the home, you will embrace the charm of the serene tree lined drive. Offering over 4 acres of private lawn, outdoor enthusiasts... View all property information
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    Oakland, Garrett County 21550
    1 / 44
    7 Bedrooms, 7 Bathrooms, Sleeps 18 | Quick View
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    If you are seeking a large spacious lakefront home, brimming with all desirable amenities, then we have the perfect home for you. Wynsome Run Lodge is a spectacular 7 bedroom home ideally located close to Deep Creek State Park, a movie theater, and area restaurants. The expansive Great Room,... View all property information
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    Oakland, Garrett County 21550
    1 / 38
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Treat your family to an enchanted vacation experience at Morningside Lodge. This phenomenal 4 bedroom log home offers you and your family top notch comfort and style. Graceful hardwood floors flow throughout creating a warm ambiance but it is the spectacular lake views that will take your breath... View all property information
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    Oakland, Garrett County 21550
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Welcome View Point is an enchanting 5 bedroom home that offers plenty of privacy combined with lakefront luxuries. From the moment that you pull into the circular drive, you will know that you found your way home. Step into the Great Room and be awed by the impressive stone fireplace. Imagine... View all property information
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    Oakland, Garrett County 21550
    1 / 16
    5 of 5 bubbles (1) Excellent
    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... View all property information
    Location Information
    Oakland, Garrett County 21550
    5 of 5 bubbles Reviewed August 1, 2016
    Lovely home and grounds. The house was comfortable for our large group that included young children, teenagers, parents and grandparents. Everyone had plenty of room. The main...
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    1 / 32
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Logxurious is the ideal name for this 5 bedroom lakefront log home that exemplifies the definition of luxury living. Inside the lodge, guests are treated to a warm and charismatic Great Room which features gleaming hardwood floors, dark cherry wood vaulted beams, and a grand stone fireplace. Bright... View all property information
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    Oakland, Garrett County 21550
    1 / 14
    4.5 of 5 bubbles (5) Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Fir Shore is a lovely and spacious log home that is just awaiting your arrival. A perfect home for the multi-family or a couples retreat, this home has 6 beautifully decorated bedrooms, 3 of which are master suites. Lacking nothing, this home offers something for everyone. The overstocked kitchen... View all property information
    Location Information
    Oakland, Garrett County 21550
    4 of 5 bubbles Reviewed April 14, 2013
    If you are just sleeping and eating in this house, and then headed out for a full day of whatever, then read no further, get this house, and don't worry about it. For some...
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    1 / 38
    4.5 of 5 bubbles (11) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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... View all property information
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    Oakland, Garrett County 21550
    1 / 15
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Prepare for the “Wow!” when you walk into the breathtaking home known as Log Hut! The newly renovated 4 bedroom log home offers the best of both worlds both inside and out. The interior design that flows consistently throughout the home features refined and elegant décor, plush leather furnishings,... View all property information
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    Oakland, Garrett County 21550
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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.... View all property information
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    Oakland, Garrett County 21550
    1 / 28
    4.5 of 5 bubbles (37) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    About this property
    American Pride is an inviting 5 bedroom 3 bath chalet nestled among the trees in one of the most requested communities in Deep Creek Lake. A few steps into the home and you will find yourself entering into the elegantly decorated Great Room which features large cathedral ceilings, a massive stone... View all property information
    Location Information
    Oakland, Garrett County 21550
    5 of 5 bubbles Reviewed February 18, 2015
    We stayed at this location with 10 adults (5 couples) and it was perfect. For a group who loves to cook the kitchen was stocked with everything that was needed. The home felt like...
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    4 of 5 bubbles (17) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    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... View all property information
    Location Information
    Oakland, Garrett County 21550
    4 of 5 bubbles Reviewed October 14, 2013
    Rocky Top is a very nice cabin with enough privacy even though there are other cabins nearby. There is enough room to be comfortable without being in each others way. There were 9...
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    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... View all property information
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    Oakland, Garrett County 21541
    1 / 34
    5 of 5 bubbles (13) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Take your dream vacation at the luxurious Oz, located in the western part of Deep Creek Lake. Oz is the grand of lakefront properties with exquisite decor, a spacious layout, and fantastic ambiance. Oz has two sitting areas for the family to spread out with a large wood fireplace, separate dining... View all property information
    Location Information
    Oakland, Garrett County 21550
    5 of 5 bubbles Reviewed November 6, 2014
    Beautiful and clean home with plenty of amenities for a memorable vacation, inside and outside! Hotel bedding and comfort with large well stocked kitchen. Rooms are spread out...
    5 of 5 bubbles Reviewed August 18, 2014
    This is our second year at OZ and couldn't be more pleased. A fantastic vacation home with more amenities that I can list in one of the best locatiosn on the Lake. Working with...
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    1 / 21
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • x
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    There is no better place to reunite with friends and family than Nature’s Retreat. This spectacular 5 bedroom lakefront home offers all of the amenities of home and more! Glistening hardwood floors, a massive stone stacked fireplace and leather furnishings create a warm and comforting gathering... View all property information
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    Oakland, Garrett County 21550
    1 / 28
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
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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... View all property information
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    Oakland, Garrett County 21550
    1 / 25
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Located on the shores of Deep Creek Lake, Majestic View is a delightful three bedroom townhouse with a name that says it all. Hardwood floors throughout the great room beautifully compliment the wall of windows that showcase breathtaking lake views that change with the seasons. When you are not... View all property information
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    Oakland, Garrett County 21550
    1 / 24
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    You will see nothing but positive Changes in Attitude when you choose to stay in this spectacular 5 bedroom lakefront home. Step inside and immediately become swept away by the majestic lake views! This home has top of the line amenities that guarantee a fun and memorable vacation for all. The... View all property information
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    Oakland, Garrett County 21550
    1 / 19
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • x
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    Perched on a hillside overlooking Deep Creek Lake, this well-appointed home is the perfect starting point for a great vacation. Tasteful décor and a spacious layout create comfortable surroundings for your gathering of family and friends. Postcard views will greet you each morning as you prepare... View all property information
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    Oakland, Garrett County 21550
    1 / 22
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • x
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    • x
    About this property
    A truly amazing mountain home is just what you need for your relaxing getaway and Log Mahal will not disappoint. This custom crafted 5 bedroom home will quickly win you over with its unique style and décor. Love at first sight is a given when you enter the Great Room. Large vaulted ceilings... View all property information
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    Oakland, Garrett County 21550
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • x
    About this property
    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... View all property information
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    Oakland, Garrett County 21550
    1 / 18
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
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    • x
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    • x
    About this property
    Prepare to be swept away by the majesty that is Overlook Point. Creature comforts surround you in the Great Room with expansive cathedral ceilings, bright open window and lustrous hardwood floors. Add in the addition of a cozy stone, gas fireplace, plush leather furnishings and a large flat screen... View all property information
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    Oakland, Garrett County 21550
    1 / 35
    5 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    • x
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    • x
    About this property
    Enjoy an evening among the stars in this mountainside chalet. Refresh your spirit as you take in the beauty of each season from the expansive deck. The unique floor plan and open living space are a few of the many special features of this well-designed home. Mountain Meadow offers the perfect place... View all property information
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    Oakland, Garrett County 21541
    1 / 16
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • x
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    • x
    About this property
    Your magical mountain getaway begins with your stay in Strawberry Fields. Nestled in the heart of the Deep Creek action, you and your guests will love having so many adventurous options at your fingertips! With 3 levels of optimal living space, this amazing home is perfect for reuniting friends and... View all property information
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    Oakland, Garrett County 21550
    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • x
    About this property
    A lifetime of family memories is just a phone call away when you choose to stay in the lovely 3 bedroom chalet known as Timber Trails. Truly a get away from it all home, you will love the private and peaceful setting while cherishing your close proximity to Oakland, Wisp Resort, and area shopping... View all property information
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    Oakland, Garrett County 21550
    1 / 20
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • x
    About this property
    Caesar’s Hideaway is a warm and inviting home that is designed with the ease of entertainment in mind. Located in the heart of Deep Creek Lake, you and your guests will love the convenient location but fall in love with the mesmerizing lake views. Offering 4 levels of living space, there is more... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 23
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Tucked away on the end of Santa Fe Trail, welcome to your tranquil, private oasis. Santa Fe Getaway is an alluring 4 bedroom home that your family will want to return to season after season. Exquisite lake views greet you from many rooms of the home but it is outside on your large deck where you... View all property information
    Location Information
    Oakland, Garrett County 21550
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