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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.
    All 249 Rentals in Oakland
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    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Letting go of everyday cares is effortless when you choose Breathe Easy for your Deep Creek vacation with family and friends. This spacious townhome in the centrally located Timberlake Village community is ready to host a fun and relaxing getaway. Decorated in muted earth tones, the spacious main...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    Appealing 5 Bedroom lakefront home close to all area attractions with hot tub1 / 30
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Reviewed January 4, 2018
    We loved this place. It was big and housed 5 families. Plenty of room for everyone. Kitchen had everything you needed. It was only a few minutes from the Wisp ski resort...
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    About this property
    Discover the beauty and uniqueness of Deep Creek Lake when you choose to stay in the captivating 5 bedroom lakefront home Crystal Lake. Ravishing lake views will greet you from every room of the main level, a delightful sight no matter what season you visit! Spend time catching up with family and...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    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...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Tucked among towering trees, Knotty Pines offers you a classic mountain getaway with lots of opportunities to make lasting memories with your favorite people. Tastefully decorated, the great room will be a popular place to gather whether you are curling up on the sectional sofa to watch TV or...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Breathtaking 6 Bedroom mountain home with exquisite lake & mountain views!1 / 44
    (1)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    Reviewed August 18, 2017
    This was the most amazing rental. We did not want to leave. From the moment we walked in the front door to the minute we had to depart we're perfect. The house is very...
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    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
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    Treat your family and friends to an exceptional vacation experience at Golden Memories, a Deep Creek Lake vacation home that offers comfort, convenience and lots of charm! Relaxation comes naturally at this well-kept retreat. There is plenty of room for everyone to gather together in the spacious...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Rich in Deep Creek history, this cottage was built as company housing for Deep Creek’s Hydro Electric Dam workers in 1925. Featuring private Youghiogheny River frontage in the protected Wild and Scenic Corridor, this home is completely unique in Deep Creek. Private yet within a five minute...
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    Oakland, Garrett County 21550
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Red Run Cabin1 / 22
    (27)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Reviewed October 11, 2017
    Great location, fantastic cabin, great weather for our trip - cool nights and mornings - perfect for walking our dog. We had a great time visiting the neighborhood and several...
    Reviewed August 30, 2017
    Family had fantastic time. Access to lake, No access to dock boat or our kayaks unless we hauled up a hill but there was plenty of space our dogs to swim...enough property you...
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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 - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    This chalet is the ideal place to relax and enjoy the spectacular views of the mountains. Located in a private, peaceful community of Mountainside, this home is just right for your vacation needs. Beautiful decor and attention to detail accent the cathedral ceiling and fireplace of the relaxing...
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    Oakland, Garrett County 21541
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Get the much deserved break that you crave when you stay at Bear Paws. This charming log cabin pairs total comfort with a convenient location! Featuring an open floorplan, the spacious main level is highlighted by vaulted ceilings and polished hardwood floors. Bear themed décor adds a playful...
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    Oakland, Garrett County 21550
    Cabin - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    About this property
    Fond, family memories will truly be made when you spend your Deep Creek getaway in the charismatic home known as Finn McCool's. This 5 bedroom home boasts a phenomenal lakefront with a private dock, ideal for swimming on hot summer days. After an exciting day of hiking and biking at Swallow Falls...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Waves and Moguls is a captivating 5 bedroom vacation home that is the ideal choice no matter what season you choose to visit. You will immediately feel a sense of home when you step inside the bright and lovely Great Room, sure to be a favorite gathering spot among family and friends. Cheerful...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Changed to: 'Canaima' is the name of the friendly spirit of the jungles of Venezuela and Brazil. It is also the site of the novel 'The Lost World' by Arthur Conan Doyle and the location of the 'Green Mansions', the place where Rima lived, in the beloved novel of William Hudson. Our cabin carries...
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    Oakland, Garrett County 21541
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    About this property
    Enjoy the feeling of rustic mountain living in this cedar chalet. Cozy and inviting, this home is perfect for accommodating the extended family or group of friends. Wood-lined walls, cathedral ceilings and a beautiful stone fireplace greet you upon entering the main level. The open floorplan...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    You will certainly learn to embrace the motto “Live It, Love It, Lake It” when you choose this charming mountain home for your Deep Creek getaway. Imagine sharing memories with your friends and family as you cozy up around the warm wood fireplace in the Great Room. This massive stone stacked...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    Centrally located getaway with hot tub & pool table!1 / 43
    (6)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    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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    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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Spectacular Lake and Sunrise Views! Relax & Get Away from it all at Valhalla!1 / 42
    (5)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Valhalla 'Hall of the Gods' is a spectacular 5 bedroom home that sits atop a beautiful mountain side. Step inside this wondrous home with large beams encompassing the great room and hardwoods that spread throughout the home. Enjoy exquisite views overlooking Deep Creek Lake while sipping your...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    All About the View is a remarkable lakefront home that encompasses all the qualities that make a vacation truly great. Its unique design, desirable amenities and ideal location combine to create the perfect venue for a vacation with family and friends. Gathering together in the Great Room will...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    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
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    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...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 3 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...
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    Oakland, Garrett County 21541
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Lakeside Chalet offers the most a mountain chalet setting can offer. Stay at this beautiful split lakefront property and enjoy the lush shades of green throughout the spring and summer seasons; then a backdrop bursting of colors in the fall. Entertain family and friends in the large open living...
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    Oakland, Garrett County 21541
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Get away from it all at this lovely home with multiple master suites and beautiful views! Nestled on a wooded hillside, you will love the feeling of seclusion while still being within five-minutes from Deep Creek Lake vacation activities. The great room greets you with lots of natural light,...
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    Oakland, Garrett County 21541
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    7 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    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
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 18
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Beautifully decorated with a warm and cheery spirit Quiet Reflections is a lakefront townhome with room for everyone to relax and enjoy the lake views. The spacious main level invites you to get comfortable on the leather sofas and watch your favorite shows on the wall-mounted flat screen. A wood...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Ski Season is premiere vacation home that offers guests the best of both worlds: indoor elegance and outdoor fun and adventure! This 4 bedroom lakefront home radiates luxury throughout. Step inside and take in the breathtaking lake views from the floor to ceiling windows. Expansive vaulted...
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    Oakland, Garrett County 21540
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Look no further! Whispering Pines is an extraordinary five bedroom home that will warmly welcome you and your family. Highlights of the spacious main level include gleaming hardwood floors, warm earth tones, and an open floor plan that is just right for spending time with your favorite people....
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Exquisite 5 Bedroom luxury townhome showcases elegant decor throughout!1 / 26
    (1)Terrible
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    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...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Located in the popular Blakeslee Community, Blue Waters is the perfect starting point for a great Deep Creek Lake vacation! Surrounded by a level lawn that is dotted with trees, you will love having outdoor space where the kids can run and play while staying within your sight as you relax on the...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    7 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    Pure vacation fun is what you will find when you choose St. Bart’s Retreat for your Deep Creek Lake getaway! This spacious lakefront home is close to favorite activities and offers lots of on-site amenities too. Upon entering the great room, the towering wall of windows with lake views will...
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    Oakland, Garrett County 21550
    Rental Home - 7 Bedrooms, 6 Bathrooms, Sleeps 18
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    If you want a classic Deep Creek Lake vacation with convenient lake access, look no further than Lakeview Cottage. This A-frame style home is ideal for a family getaway or a couples’ trip. Wood-lined walls create a warm ambiance in the great room, and a wall of windows lets in lots of natural...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    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...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Captivating Cabin located on wooded lot and short stroll to lake and dock!1 / 26
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed January 21, 2018
    This cabin was clean, convenient and totally as advertised. While not luxurious it has everything you need to enjoy a family ski weekend. It’s a quick scenic drive to Wisp, has...
    Reviewed October 6, 2017
    Everything was really good, location was very good centered perfectly.We all had a great time. I would definitly tell my freinds and family about it,and also book it again in...
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    About this property
    Newly renovated (2017) three bedroom two bath cabin that sits back from the road with plenty of parking . Cabin is situated on one acre of wooded grounds surrounded by large boulders and a pond. The stately stone fireplace is the centerpiece of this home. The soaring ceiling in the main living...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Explore the great outdoors or just sit back and relax at Creekside Cove, the perfect getaway for a fun-filled, memorable vacation.  Everyone in your group will love the style, spaciousness and classic mountain feel of this spacious chalet. The spacious main level has an open layout that is ideal...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    About this property
    There is no better place to reunite with friends and family than Nature’s Retreat. This spectacular 5 bedroom lakefront home offers all of the amenities of home and more! Glistening hardwood floors, a massive stone stacked fireplace and leather furnishings create a warm and comforting gathering...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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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...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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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
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Offering everything you need for a fun and relaxing vacation, Lake House is the perfect place to make your Deep Creek Lake vacation memories! The spacious main level is highlighted by gleaming hardwood floors, cathedral ceilings and a towering wall of windows that reveal lake views through the...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    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
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    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...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    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...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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