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Holiday Rentals with Pools in Oakland

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    7 Matching Rentals in OaklandView all 237 rentals
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    Travellers to Oakland are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    37 Reviews
    5 Bedrooms, Sleeps 14Quick View
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    8 Bedrooms, Sleeps 26Quick View
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    5 Bedrooms, Sleeps 14Quick 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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 9Quick View
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    Pet friendly
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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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    11 Reviews
    4 Bedrooms, Sleeps 10Quick View
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    • Satellite TV
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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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 6Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Red Run 1A3 is an alluring 3 bedroom condominium located in the desirable Red Run Community. Summer days don't get better than this as you and your guests relish time spent swimming & playing from the nearby beach area or lounging lazily around the outdoor community swimming pool. Winter evenings...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    7 Bedrooms, Sleeps 18Quick View
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    About this property
    Your fairy tale vacation starts at Ever After! This lake front home promises a memorable vacation experience. Three floors of living space plus a separate carriage house with a 120 inch home theater and an oversized game room makes this property stand-out from the crowd.  The main level offers a...
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    Oakland, Garrett County 21550
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 18
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    5 Bedrooms, Sleeps 14Quick 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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Pet friendly
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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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    1 Review
    5 Bedrooms, Sleeps 12Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 1 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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    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    7 Bedrooms, Sleeps 18Quick View
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    Pet friendly
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    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,...
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    Oakland, Garrett County 21550
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 18
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    3 Bedrooms, Sleeps 8Quick 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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 8Quick View
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    Pet friendly
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    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 14Quick View
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    Pet friendly
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    Smoking allowed
    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    4 Bedrooms, Sleeps 10Quick 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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    6 Reviews
    4 Bedrooms, Sleeps 12Quick View
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    • Grill
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    Pet friendly
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    Excellent of 5 bubbles
    Reviewed 28 November 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...
    Excellent of 5 bubbles
    Reviewed 29 October 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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    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    6 Bedrooms, Sleeps 16Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    You will truly feel like you are in a magical place when you take in the exquisite lake and mountain views from the deck of Scenic Overlook. This marvelous 6 bedroom mountain home with all of the creature comforts of home combined with desirable vacation home amenities that you need for a fun...
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    Oakland, Garrett County 21550
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    4 Bedrooms, Sleeps 12Quick View
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    Pet friendly
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    Smoking allowed
    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, Sleeps 10Quick View
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    Pet friendly
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    Smoking allowed
    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 12Quick View
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    Pet friendly
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    Smoking allowed
    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Reviews
    6 Bedrooms, Sleeps 14Quick View
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    Pet friendly
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    Very good 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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    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, Sleeps 12Quick 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!...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, Sleeps 12Quick 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...
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    Oakland, Garrett County 21540
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, Sleeps 10Quick View
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    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....
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, Sleeps 16Quick View
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    About this property
    Mountain Meadow offers the perfect place to reunite with family and friends for that much needed Deep Creek Lake vacation. Offering an open floor plan, the spacious main level has a wall of windows with beautiful views as the focal point. Lots of natural light, gleaming hardwood floors and...
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    Oakland, Garrett County 21541
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    5 Bedrooms, Sleeps 14Quick 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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    5 Bedrooms, Sleeps 12Quick 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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    25 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 4 weeks 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...
    Excellent of 5 bubbles
    Reviewed 31 May 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...
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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...
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    Oakland, Garrett County 21550
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Reviews
    5 Bedrooms, Sleeps 12Quick View
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    Excellent 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...
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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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    2 Bedrooms, Sleeps 8Quick View
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    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 12Quick View
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    Pet friendly
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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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, Sleeps 15Quick 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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 15
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    4 Bedrooms, Sleeps 12Quick View
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    About this property
    Explore, relax and take a well-deserved break at Deep Breath! Convenient to area activities and attractions, it is the perfect home base for your Deep Creek Lake vacation. The spacious interior of this Craftsman-style home is brimming with attention to detail. Upon entering, a dual sided gas...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    16 Reviews
    4 Bedrooms, Sleeps 8Quick View
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    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Ready to discover your favorite Deep Creek vacation home? Everyone in your group will love the style, spaciousness and comfort of Just About Paradise! Offering plenty of indoor and outdoor gathering spaces, it is the perfect place for get-togethers.  Start your day with a home cooked breakfast --...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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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....
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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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...
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    Oakland, Garrett County 21541
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, Sleeps 12Quick View
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    Turn your dreams into reality when you choose to stay in the captivating 4 bedroom log home Shiver Me Timbers. Step inside the Main level and you will instantly be won over by the warm wood walls and gleaming hardwood floors that flow naturally throughout the cabin. The Great Room is gracefully...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Trailside Tranquility is a charming, craftsman-style vacation home combines style, comfort and a location that is convenient to the best of Deep Creek Lake. Step inside to find an open floorplan that makes gathering with family and friends entirely effortless. Warm and inviting, the great room is...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    13 Reviews
    4 Bedrooms, Sleeps 10Quick View
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    Excellent 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...
    Excellent 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...
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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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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...
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    Oakland, Garrett County 21541
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    About this property
    Nestled among the trees in this quiet cul-de-sac, you'll find this beautifully decorated and spacious home which is part of the Mountainside Resort and Marine Club subdivision. Have complete access to tennis, basketball and volleyball courts found in a gorgeous mountain setting. Delight in filtered...
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    Oakland, Garrett County 21541
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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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...
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    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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