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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.
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    7 Bedrooms, 7 Bathrooms, Sleeps 18 | Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    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
    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 / 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
    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 / 51
    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, 5 Bathrooms, Sleeps 14 | Quick View
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    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 / 23
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    About this property
    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
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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
    Location Information
    Oakland, Garrett County 21550
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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
    Location Information
    Oakland, Garrett County 21550
    1 / 17
    5 of 5 bubbles (24) 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
    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...
    Reviewed April 9, 2016
    So glad we found this cabin. Very cozy and super clean. Owner was very nice to deal with. We are looking forward to going back.
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    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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
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    5 Bedrooms, 3 Bathrooms, Sleeps 13 | Quick View
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    About this property
    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
    Location Information
    Oakland, Garrett County 21550
    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
    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...
    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 / 27
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    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
    Location Information
    Oakland, Garrett County 21540
    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
    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 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    If you are looking for a home that goes “Above and Beyond”, this 4 bedroom mountain home is the ideal choice for you and your family! Located on top of a quiet mountaintop, here you will find the privacy you need but still relish the close proximity to all area shopping, dining, and state parks!... View all property information
    Location Information
    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
    Location Information
    Oakland, Garrett County 21550
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    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
    Location Information
    Oakland, Garrett County 21550
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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
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    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
    Location Information
    Oakland, Garrett County 21550
    1 / 20
    5 of 5 bubbles (6) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Your Deep Creek tradition begins when you choose the delightful 4 bedroom chalet Swimming Bear Lodge for your next stay! Located on a large wooded lot, you will love being surrounded by nature in this tranquil setting. Step inside to the main level and immediately embrace the warmth and comfort of... View all property information
    Location Information
    Oakland, Garrett County 21550
    Reviewed November 28, 2015
    We had a wonderful time staying at this cabin. The place itself is awesome for a group--comfortably slept eight adults and five kids, with plenty of room for hanging out in the...
    Reviewed October 29, 2015
    This home was stunning! From the moment you pull in there is peace. The home is nestled in a wooded area the view of the lake and forest.. while sitting in the relaxing...
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    1 / 27
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    This cozy chalet is tucked among the trees offering a quiet setting for the peaceful escape that you deserve. Relax on the deck while taking in the beauty of the woodlands at this mountain getaway. Hummingbird Hill offers the restful atmosphere and comfortable surroundings that make you feel right... View all property information
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    Oakland, Garrett County 21541
    1 / 35
    5 of 5 bubbles (5) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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
    1 / 30
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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
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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 / 26
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Waves and Moguls is the ultimate definition of this captivating 5 bedroom townhome 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... View all property information
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    Oakland, Garrett County 21550
    1 / 22
    5 of 5 bubbles (8) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Surround yourself with nature in this majestic log home. Three master suites make it an excellent choice for couples as well as family gatherings. On the entry level, hardwood floors, cathedral ceilings and large windows adorn the great room, and the stone fireplace and stylish furnishings accent... View all property information
    Location Information
    Oakland, Garrett County 21550
    Reviewed August 17, 2015
    This was our second trip to Deep Creek Lake & we chose to stay right on the lake this time and were not disappointed. The house was beautiful. The location perfect - tucked away...
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    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
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    Oakland, Garrett County 21550
    1 / 40
    4.5 of 5 bubbles (19) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Memory Lane is a home designed to bring friends and family together for fun and laughter. Tucked among gracious, blossomed trees with a meticulously maintained lawn, you will truly feel like you have discovered your mountain oasis. Gather with loved ones in the Great Room where you can enjoy your... View all property information
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    Oakland, Garrett County 21541
    1 / 31
    5 Bedrooms, 4 Bathrooms, Sleeps 15 | Quick View
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    About this property
    Discover the perfect lake front getaway when you stay at Lake Shore Retreat! Offering all the comforts of home, this property boasts cathedral ceilings, expansive decks, and multiple gathering areas. Upon entering the main level, your eyes will immediately be drawn to the wall of windows that... 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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    About this property
    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 / 37
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Waterfront
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    • Pet-friendly
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    • x
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    • x
    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
    Location Information
    Oakland, Garrett County 21541
    1 / 28
    4.5 of 5 bubbles (37) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • ?
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    • x
    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
    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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    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Prepare yourself for a relaxing getaway when choose Bear Feet as your vacation getaway. Exploding with charm, this 3 bedroom townhome will easily beckon you to return time and time again. Step inside and appreciate the open floor plan and the wall of windows that boast extraordinary lake views.... 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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    • Pet-friendly
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    • ?
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    • x
    About this property
    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 / 19
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Let the adventure begin! Mother Nature will astound when you choose to stay in the captivating lakefront home known as Summer Haven! Imagine relaxing on the expansive wraparound deck as you take in the phenomenal lake views! Amenities abound inside the home as well; whether you are cuddled up in... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 27
    3 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Surround yourself with natural beauty at this wonderful home located in the cozy, lakefront Timberloft community at the heart of Deep Creek Lake. Enjoy your first cup of coffee on the deck overlooking the lake. Delight in the spacious master suites that encompass beautiful lake views. Relax in the... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 33
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    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 / 33
    8 Bedrooms, 8 Bathrooms, Sleeps 26 | Quick View
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    • Waterfront
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    • Private Indoor Pool
    • Sauna
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Come and stay at Deep Creek's premier lakefront property where dreams do come true, and the fun begins at this exquisite eight bedroom home known as Celebration at Deep Creek. From the moment that you step inside this luxurious mountain home you will be in awe. Walking through the foyer, you will... 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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    • Pet-friendly
    • Child-friendly
    • 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 / 16
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Home Sweet Cabin is a charismatic mountain home that rests in a quiet, peaceful cove. Expansive wooden cathedral ceilings highlight the stone fireplace and gives promises of nights spent bonding with family and friends. The open floor plan allows you to entertain your guests while preparing the... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 20
    4 of 5 bubbles (17) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    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
    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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    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Porch
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    • ?
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    • ?
    About this property
    The name 'Cozy Cabin' says it all... Enjoy the solitude of a modern log cabin offering a large yard and a wonderful covered porch for relaxation at it's finest! This cabin offers a 'man cave' in the basement with a large screen TV, Dry Bar with stools, comfortable overstuffed seating and a powder... View all property information
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    Oakland, Garrett County 21550
    1 / 28
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Hot Tub
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Oakland, Garrett County 21550
    1 / 11
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Your mountain vacation will be filled with magical memories when you choose to stay in the spectacular 3 bedroom log home known as Made It! You and your guests will immediately feel at home when you step through the front door. Luxurious décor compliments the gorgeous hardwood floors giving the... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • x
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    • Smoking allowed
    • x
    About this property
    Welcome Home Friends! Paradise at Penn Cove is a captivating 3 bedroom chalet that rests on quiet road overlooking Penn Cove. Upon entrance you will immediately feel the warm and cozy atmosphere of the Great Room. Expansive vaulted ceilings, floor to ceiling windows, and an immense stone stacked... View all property information
    Location Information
    Oakland, Garrett County 21550
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