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Oakland Vacation Rentals

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    Travelers to Oakland are booking December dates now. Secure your vacation rental today, and have the perfect trip.
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    7 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    7 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    About this property
    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, 7 Bathrooms, Sleeps 18
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    Firewood and snowshoes included! Close to all winter activities! Special rates!1 / 26
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    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...
    Reviewed September 10, 2017
    Looking for a home-base to relax in for a weekend at Deep Creek, this home had everything we could have asked for and more. Several comfortable beds in private bedrooms, a...
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Do you find yourself daydreaming about a romantic getaway in a charming lakefront home? Golden Retreat is perfect for a couple but is large enough for a small family. You’ll adore the comfortable furnishings and alluring appeal of the interior. Conveniently located a mere 5 minutes from Swallow...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Centrally located getaway with hot tub & pool table!1 / 41
    (6)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    Pet friendly
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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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    Breathtaking 6 Bedroom mountain home with exquisite lake & mountain views!1 / 43
    (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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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    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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    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
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    Pet friendly
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    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...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Pet friendly
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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, 5 Bathrooms, Sleeps 14
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    Wonderful Upscale Cabin at Deep Creek Lake.1 / 14
    (3)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Mountain Views
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    • Porch
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    Pet friendly
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    Smoking allowed
    Reviewed July 25, 2017
    Had a great time at the cabin! Very clean, peaceful, and relaxing! We would love to stay again! We are talking about going in the winter when we can use the fireplace. The...
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    About this property
    Our log home is situated on our private 1.5 acre lot so as to capture the best views of farm land and mountains. Enjoy your own peaceful getaway knowing that all lake and sport activities are just minutes away. We designed our cabin with comfort in mind--the first floor includes an inviting great...
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    Oakland, Garrett County 21550
    Cabin - 3 Bedrooms, 4 Bathrooms, Sleeps 9
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    About this property
    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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    3 Bedrooms, 4 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, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    About this property
    Let the adventure begin! Mother Nature will astound when you choose to stay in the captivating lakefront home known as Summer Haven! Imagine relaxing on the expansive wraparound deck as you take in the phenomenal lake views! Amenities abound inside the home as well; whether you are cuddled up in...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Creekside #91 / 24
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
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    • Mountain Views
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    Pet friendly
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    Smoking allowed
    About this property
    DCL at Creekside 9 - 19956 Garrett Highway, Oakland, Maryland 21550 - Deep Creek Lodging Company Luxury awaits you in this 3 level, 3,000 square foot, lakefront townhome in the heart of Deep Creek Lake with a Great Location!! * Day Use Boat Slip! * Arrowhead Market, Honi Honi Bar & Garrett 8...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Spectacular Lake and Sunrise Views! Relax & Get Away from it all at Valhalla!1 / 40
    (5)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    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...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Caesar’s Hideaway is a warm and inviting home that is designed with the ease of entertainment in mind. Located in the heart of Deep Creek Lake, you and your guests will love the convenient location but fall in love with the mesmerizing lake views. Offering 4 levels of living space, there is more...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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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 8 Quick View
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    Hidden from view, a true Treasure of the mountains awaits. This charming cabin is nestled amongst a soaring canopy of trees at Deep Creek Lake. Hidden Treasure features cozy comfort with all the extra amenities. As an added bonus, you can bring your dog on vacation too! Relax in the great room by...
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    Oakland, Garrett County 21541
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Red Run Cabin1 / 22
    (27)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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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    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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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    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, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    About this property
    This cozy chalet is tucked among the trees offering a quiet setting for the peaceful escape that you deserve. Relax on the deck while taking in the beauty of the woodlands at this mountain getaway. Hummingbird Hill offers the restful atmosphere and comfortable surroundings that make you feel right...
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    Oakland, Garrett County 21541
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Beautiful and Spacious 6 Bedroom w/Hot Tub and Dock Slip1 / 15
    (5)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Reviewed April 14, 2013
    If you are just sleeping and eating in this house, and then headed out for a full day of whatever, then read no further, get this house, and don't worry about it. For some...
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    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
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Waterfront
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    Majestically situated right along the lakefront, this premier property will provide you with long lasting vacation memories. Enjoy star gazing and amazing views from the many decks or leave your stress behind while relaxing in the bubbling outdoor hot tub overlooking Deep Creek Lake. The spacious...
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    Oakland, Garrett County 21541
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    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...
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    Oakland, Garrett County 21541
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    About this property
    Enjoy having Mother Nature as your neighbor at Fancy Free. This lakefront chalet is tucked away in the private, small Heron Cove West community. Providing a much-needed break from everyday life, your vacation will be the source of wonderful memories you’ll reflect on for years to come. The...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 16
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Discover your own Deep Creek Lake paradise when you stay at Lake Shore Paws! Great outdoor space and a convenient location make it the perfect choice for a fun and relaxing getaway. Vaulted ceilings and lots of windows highlight the spacious main level. It is easy to imaging spending crisp...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    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 10 Quick View
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    About this property
    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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    Time and Again is genuinely true to its name. Once you have visited this beautifully constructed chalet, you will want to come back time and time again. Nestled close to the shoreline, it ensures that guests will enjoy many starry nights or lazy summer afternoons relaxing on the expansive deck that...
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    Oakland, Garrett County 21541
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    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
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    7 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    If you are seeking a large spacious lakefront home, brimming with all desirable amenities, then we have the perfect home for you. Wynsome Run Lodge is a spectacular 7 bedroom home ideally located close to Deep Creek State Park, a movie theater, and area restaurants. The expansive Great Room,...
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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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    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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    Exceptional in every way, this newly built duplex creates a cozy vacation haven1 / 12
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    5 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    A real crowd pleaser, Dream On is a modern duplex that creates a unique vacation haven for any gathering. Professional décor, warm earth tone stylings, a gourmet kitchen and 7 flat screen TV's are just a few of the upscale amenities that enhance the attractive interior. Relax in the bubbling hot...
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    Oakland, Garrett County 21550 
    Rental Home - 5 Bedrooms, 1 Bathroom, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Escape to the relaxing sounds of nature at Yellowstone Village and ''Dan's Mountain'' conveniently located, yet off the beaten path, this beautiful log home offers a cozy, cabin feel while offering plenty of comfortable accommodations! There's plenty of room for a gathering with friends and family,...
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    Oakland, Garrett County 21541
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 1 Bathroom, Sleeps 11 Quick View
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    Paradise is perfected at Providence at Penn Cove! This warm country home offers the ideal setting for an unforgettable Deep Creek Lake getaway! The beautifully landscaped backyard features a small pond, fire pit, and outdoor hot tub for the ultimate in relaxation and fun. Plus, with the home’s...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 11
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Experience the beauty of Deep Creek Lake at Fox Den, a charming A-frame cottage that offers a treasured chance to unwind. Both romance-seekers and those in pursuit of inner peace will relish time spent at this classic mountain getaway. Highlighted by a wall of windows, wood accents, tasteful decor...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    Location Information
    Oakland, Garrett County 21541
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    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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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    The Deep Creek-3rd Night FREE!1 / 26
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Skiing: Property Is In A Ski Resort
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    About this property
    Take a Break from the Fast Pace of Life and Step Back into Time at “The Deep Creek.” Reserve TODAY for a 3rd Night FREE! This cozy and quaint 2 level, 2 bedroom, 2 full bath traditional log cabin is waiting for you! Whether you are looking for a romantic getaway or the perfect adventure for a...
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    Oakland, Garrett County 21550
    Cabin - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Located in the heart of the action, you and the family will quickly call Reardon’s Roost your home away from home, time after time. Imagine enjoying your morning coffee out on the deck as you take in the spectacular lake and mountain views before you. Catch a movie on the flat screen in the Great...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    Location Information
    Oakland, Garrett County 21541
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Is the clamor of city life wearing you down? Cedarwoods, a stunning 3 bedroom mountain chalet, is calling your name. Nestled away in the quiet community of Mountainside, this beautiful home offers the seclusion and privacy you crave. Boasting 3 spacious levels of living space, high vaulted ceilings...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Magic is alive at Cochran’s Cabin! Experience the lake in an atmosphere only an authentic cabin can provide! This original Deep Creek log cabin has been thoroughly upgraded with modern amenities, yet maintains an old-world charm and simple simplicity that is apparent in every nook and cranny....
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Welcome View Point is an enchanting 5 bedroom home that offers plenty of privacy combined with lakefront luxuries. From the moment that you pull into the circular drive, you will know that you found your way home. Step into the Great Room and be awed by the impressive stone fireplace. Imagine...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    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...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Looking to get away with family and friends and enjoy a much needed escape from daily life? Look no further than Serenity Ridge! This newly decorated home offers entertainment for all! Simple elegance reigns supreme throughout the interior of the home, highlighted by hardwood floors, plush home...
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    Location Information
    Oakland, Garrett County 21550 
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 12
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