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Holiday Rentals in Oakland, MD

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    ₹ 15,486 Average
    ₹ 65,000+
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    Travellers to Oakland are booking May dates now. Secure your holiday home today, and have the perfect trip.
    1 / 32
    Studio, 5 Bathrooms, Sleeps 12 | Quick View
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    Studio, 8 Bathrooms, Sleeps 26 | Quick View
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    Studio, 7 Bathrooms, Sleeps 18 | Quick View
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    1 / 38
    Studio, 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
    Location Information
    Oakland, Garrett County 21550
    1 / 23
    Studio, 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
    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
    5 of 5 bubbles Reviewed 1 June 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...
    5 of 5 bubbles Reviewed 9 April 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 / 35
    5 of 5 bubbles (5) Excellent
    Studio, 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
    Location Information
    Oakland, Garrett County 21550
    1 / 29
    Studio, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    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
    Location Information
    Oakland, Garrett County 21550
    1 / 22
    5 of 5 bubbles (8) Excellent
    Studio, 5 Bathrooms, Sleeps 12 | Quick View
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    • Hot Tub
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    • x
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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
    5 of 5 bubbles Reviewed 17 August 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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    1 / 30
    Studio, 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
    Location Information
    Oakland, Garrett County 21550
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    1 / 44
    Studio, 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
    1 / 16
    3 of 5 bubbles (1) Average
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Plan your next Deep Creek Lake vacation at Greene Acres. With elegant cathedral ceilings and beautiful floor to ceiling windows, the living areas of this home have the most breathtaking views. Step out on the spacious deck to soak up the sun and listen to the sounds of nature that surround you. For... View all property information
    Location Information
    Oakland, Garrett County 21550
    3 of 5 bubbles Reviewed 2 weeks ago
    While this home was very nice and clean, please note that while you clearly see a fireplace in the photos, there is a sign stating you cannot use it. When searching for homes for...
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    1 / 28
    4.5 of 5 bubbles (37) Very good
    Studio, 3 Bathrooms, Sleeps 14 | Quick View
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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
    5 of 5 bubbles Reviewed 18 February 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 / 37
    Studio, 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
    Location Information
    Oakland, Garrett County 21541
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    Studio, 5 Bathrooms, Sleeps 14 | Quick View
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    • Hot Tub
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    • x
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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
    Location Information
    Oakland, Garrett County 21550
    1 / 17
    4 of 5 bubbles (16) Very good
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
    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
    1 / 33
    Studio, 4 Bathrooms, Sleeps 14 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
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    • 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
    Location Information
    Oakland, Garrett County 21541
    1 / 38
    4.5 of 5 bubbles (11) Very good
    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
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    • Shared Outdoor Pool...
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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
    Location Information
    Oakland, Garrett County 21550
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    Studio, 5 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
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    • x
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    • x
    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 / 34
    5 of 5 bubbles (13) Excellent
    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • x
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    • x
    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 6 November 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 18 August 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 / 55
    Studio, 6 Bathrooms, Sleeps 14 | Quick View
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    • x
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    • x
    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
    Location Information
    Oakland, Garrett County 21541
    1 / 51
    Studio, 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
    Location Information
    Oakland, Garrett County 21550
    1 / 30
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
    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
    Location Information
    Oakland, Garrett County 21541
    1 / 40
    4.5 of 5 bubbles (19) Very good
    Studio, 4 Bathrooms, Sleeps 12 | Quick View
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    • x
    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
    Location Information
    Oakland, Garrett County 21541
    1 / 22
    Studio, 4 Bathrooms, Sleeps 12 | Quick View
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    • x
    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
    Location Information
    Oakland, Garrett County 21550
    1 / 16
    5 of 5 bubbles (1) Excellent
    Studio, 5 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • x
    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
    5 of 5 bubbles Reviewed 2 August 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 / 7
    3.5 of 5 bubbles (2) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    This cozy chalet with lake access is the perfect escape for couples or a small family. Decorated in a fun western style, guests will enjoy three comfortable bedrooms and two bathrooms. The tranquil wooded setting of this Deep Creek vacation rental will make you feel worlds away from it all, while... View all property information
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    Oakland, Garrett County 21550 
    1 / 22
    Studio, 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
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    Oakland, Garrett County 21550
    1 / 20
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
    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
    Location Information
    Oakland, Garrett County 21550
    1 / 20
    Studio, 5 Bathrooms, Sleeps 12 | Quick View
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    • x
    About this property
    If luxury is what you have in mind, then look no further. Serenity Summit is an extravagant 5 bedroom duplex that boasts an immaculate interior. With 3 master suites available, this home is ideal for the multi-family or couple's retreat. Your Great Room boasts lustrous hardwood floors, stylish... View all property information
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    Oakland, Garrett County 21550
    1 / 31
    Studio, 3 Bathrooms, Sleeps 13 | Quick View
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    • x
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    • x
    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 / 18
    3.5 of 5 bubbles (7) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Located on a large wooded lot, Linwood offers a quiet retreat. Enjoy your early morning coffee on the spacious deck or on those crisp evenings, or just relax in front of a glowing fire. Regardless of season, Linwood provides a comfortable and casual atmosphere with tongue and groove walls, stone... View all property information
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    Oakland, Garrett County 21550 
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • ?
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    • x
    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 it... View all property information
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    Oakland, Garrett County 21550
    1 / 21
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Welcome Home Friends! Paradise at Penn Cove is a captivating 3 bedroom chalet that rests on quiet road overlooking Penn Cove. Upon entrance you will immediately feel the warm and cozy atmosphere of the Great Room. Expansive vaulted ceilings, floor to ceiling windows, and an immense stone stacked... View all property information
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    Oakland, Garrett County 21550
    1 / 27
    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    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
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    Oakland, Garrett County 21550
    1 / 15
    Studio, 2 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    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
    1 / 20
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    Let the adventure begin! Sunset Reflections is a cheerful 3 bedroom lakefront home that will allow you to experience a true Deep Creek getaway! The beautifully decorated Great Room is enhanced with cathedral style ceilings, an impressive stacked stone fireplace and floor to ceiling windows which... View all property information
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    Oakland, Garrett County 21550
    1 / 16
    3.5 of 5 bubbles (3) Average
    6 Bedrooms, 6 Bathrooms, Sleeps 15 | Quick View
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    About this property
    Visualize yourself standing at the railing of a spacious, sunlit deck, as you survey the expansive view of the lake and mountains that unfurl before you. Now make that vision a reality by choosing Sunset Pointe as your vacation destination. Within 10 minutes to skiing and golf, this stunning... View all property information
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    Oakland, Garrett County 21550 
    1 / 23
    Studio, 5 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Oakland, Garrett County 21550
    1 / 28
    Studio, 6 Bathrooms, Sleeps 12 | Quick View
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    • Hot Tub
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Pack your bags and get ready to experience a true Deep Creek adventure when you choose to stay in the newly built log home Man Haus! This luxury log home will host 4 Master Suites making it an excellent choice for a couple’s retreat or an extended family getaway! Indoor creature comforts include... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 36
    Studio, 5 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Get away from it all at this lovely home with rustic decor and beautiful views! This four bedroom home is nestled in the woods for a feeling of seclusion, with a large deck for enjoying the scenery! Relax in the hot tub or by one of the gas fireplaces, gather with your family in the den for a game... View all property information
    Location Information
    Oakland, Garrett County 21541
    1 / 20
    4 of 5 bubbles (17) Very good
    Studio, 3 Bathrooms, Sleeps 12 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • 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
    4 of 5 bubbles Reviewed 15 October 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 / 14
    4.5 of 5 bubbles (5) Very good
    Studio, 5 Bathrooms, Sleeps 14 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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 14 April 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 / 22
    Studio, 5 Bathrooms, Sleeps 10 | Quick View
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    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Oakland, Garrett County 21550
    1 / 26
    Studio, 5 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
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    • x
    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 / 27
    Studio, 3 Bathrooms, Sleeps 12 | Quick View
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    • Waterfront
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • x
    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 / 10
    4 of 5 bubbles (5) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • x
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    • x
    About this property
    Looking for the ultimate vacation experience? Amazing Love has you covered! This five-bedroom vacation rental was recently remodeled and features a host of fantastic amenities, including an air hockey table, gas fireplace, pool table and wireless Internet. Plus, a fabulous outdoor hot tub! Step out... View all property information
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    Oakland, Garrett County 21550
    1 / 30
    4.5 of 5 bubbles (12) Very good
    8 Bedrooms, 9 Bathrooms, Sleeps 24 | Quick View
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    About this property
    Elegant, Extravagant, Extraordinary…and the list goes on! Uncommon quality can be found in the smallest details of this grand chalet. Possessing a spectacular, sweeping view of Deep Creek Lake and its lush mountains, Peregrine’s Perch is a premium home that is flawless in design and filled with... View all property information
    Location Information
    Oakland, Garrett County 21550 
    4 of 5 bubbles Reviewed 15 June 2011
    We had a wonderful week stay at Peregrine's Perch. Our group included an 84-year old, eight 18 year olds, parents, cousins and neighbors. The PROS: The house accommodated...
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    1 / 19
    Studio, 6 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • Smoking allowed
    • x
    About this property
    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 / 21
    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Escape the worries of everyday and give yourself a much deserved “Time Out” in this 4 bedroom mountain home. Centrally located close to all area attractions and tucked away in the prestigious community of Mountainside, location doesn’t get better than this. Expansive cathedral ceilings accented by... View all property information
    Location Information
    Oakland, Garrett County 21550