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Oakland Vacation Rentals

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    Travelers to Oakland are booking August dates now. Secure your vacation rental today, and have the perfect trip.
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    Boasting new furnishings, modern upgrades and a cheerful color palette, Almost1 / 12
    (12)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    This gorgeous, rustic chalet promises the ultimate luxurious log cabin1 / 23
    (14)Very good
    9 Bedrooms, 7 Bathrooms, Sleeps 28 Quick View
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    Picture the quintessential vacation retreat: a wooden A-frame masterpiece where1 / 10
    (10)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    The log cabin experience is perfected at Creekside Lodge! Mixing together charming mountain-style details like knotted pine and stone with modern upgrades like upscale furniture and upgraded appliances, this log-style abode is the perfect fusion of rustic charm and upscale elegance! With four...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Refined elegance meets lakefront living at Making Memories! This exquisite home1 / 16
    (1)Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    This beautiful lake home delivers one warm welcome! From the moment you arrive, this home will surround you in an easy elegance for perfection that feels effortless. With a natural stone fireplace, cathedral ceilings, and windows overlooking nature, the great room will make you feel right at...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    Wild Yough Villa1 / 14
    (25)Excellent
    Studio, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Wild Yough is conveniently located near Swallow Falls & Herrington Manor State Parks, offering dynamic activities. Watch the Bald Eagle family snag a fish, watch Maple Syrup being made, take a canoe or paddle boat out on Herrington Manor Lake, or stroll the same Virgin Hemlock forest at Swallow...
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    Oakland, Garrett County 21550
    Rental Home - 2 Bathrooms, Sleeps 8
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    Light, bright, and airy, Magnificent View Point was built to please! With1 / 17
    (6)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Situated along a quiet peninsula, Magnificent View Point promises to provide the ideal perch for quiet lake mornings, busy days under the sun, and sunset views that will stay with you always! Stroll along the home’s massive back deck to take in the spectacular 180 degree lake views and wrap...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 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, 5 Bathrooms, Sleeps 11
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    Pet friendly
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    Smoking allowed
    About this property
    Conveniently located, yet off the beaten path, these Yellowstone Log Cabins (Property #s 359, 360, 365, and 367) offer cozy, quaint, and comfortable accommodations! All cabins are situated closely enough to one another for ideal couple retreats or single family getaways while offering a quiet...
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    Oakland, Garrett County 21541
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    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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    Blarney Stone Manor1 / 14
    (30)Very good
    Studio, 4 Bathrooms, Sleeps 6 Quick View
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    Relax on the Oversized Deck overlooking beautiful native stone landscaped area surrounded by trees. Blarney Stone Manor is nestled in a scenic woodland with abundant wildlife sure to entertain. Any chef will enjoy the spacious kitchen overlooking the dining table. Some of the fine finishes include...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
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    • Washer
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    • Central Heating
    • Housekeeping Included
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Waterfront
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    Pet friendly
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    Known for its spacious common areas, sandy beach and quiet cove location, Four Hooppole is a favorite lakefront community that offers ten acres of level manicured lawn and a fantastic swimming area. The main level of this well-appointed townhome features a spacious great room with lake views and...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Internet Access
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    Pet friendly
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    A fabulous vacation awaits you in the lovely classic cottage known as Clear Water View. You'll immediately be captivated by mesmerizing lake views and the beauty of the Great Room featuring expansive wood beamed cathedral ceilings and a massive native stone fireplace. The fully equipped kitchen has...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Relax, rejuvenate, and renew at Enchanted Lakefront! Bask in the summer air1 / 33
    (7)Very good
    8 Bedrooms, 8 Bathrooms, Sleeps 22 Quick View
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    Magic is alive at Enchanted Lakefront! When you step into the warm interior, or outside onto the impressive backyard stone patio, you will immediate fall under the home’s irresistible spell: one where every day cares are left behind and you emerge refreshed, renewed, and ready for adventure. In...
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    Oakland, Garrett County 21550 
    Rental Home - 8 Bedrooms, 8 Bathrooms, Sleeps 22
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    This cozy duplex is centrally located to all the activities Deep Creek has to1 / 8
    (4)Average
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Come away to a quiet retreat.  Wispering Ridge is a perfect getaway for a small family who wants to be close to everything the lake has to offer.  This duplex proves that you don't have to be large to have an incredible view of the lake.  An open great room, dining room, and kitchen give this home...
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    Oakland, Garrett County 21550 
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Treat yourself to a stay at The Herrington and let the endless amenities of1 / 77
    (2)Very good
    10 Bedrooms, 11 Bathrooms, Sleeps 34 Quick View
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    Looking for a royal retreat? The Herrington will make you will feel as if you are living in a castle. Whether on a family vacation or a business trip, The Herrington is equipped with multiple gathering rooms and meeting rooms. For family fun, play a game of pool, ping pong, or foosball in the game...
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    Oakland, Garrett County 21550 
    Rental Home - 10 Bedrooms, 11 Bathrooms, Sleeps 34
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
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    Pet friendly
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    Smoking allowed
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    Duffy's Oar House is the perfect Deep Creek Lake Cottage. It has the charm and charisma of original DCL,and the modern amenities that we have all grown to know and love! Situated on the western end of the lake, this home has a large level yard with a private dock that sits in a quiet cove with...
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    Oakland, Garrett County 21541
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Wonderful Upscale Cabin at Deep Creek Lake.1 / 14
    (2)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Mountain Views
    • Washer
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    • Porch
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    Pet friendly
    Kid friendly
    Smoking allowed
    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, 3 Bathrooms, Sleeps 9
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
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    Have the time of your life when stay at Donna’s Choice for your next Deep Creek vacation! Unwind in style at this bright and cheerful contemporary mountain home. Attention to detail is found throughout, and you will notice photos of local landmarks decorating the walls. The main level’s open...
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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 12 Quick View
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    Pet friendly
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    Tucked away among the trees just a short walk from the lake, you will find Woodland Retreat. Whether you spend a weekend or a week at this delightful vacation home, you wind up feeling relaxed and rejuvenated. The well-appointed main level offers ample space to spend time catching up with family...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Studio, 2 Bathrooms, Sleeps 8 Quick View
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    Affordable family fun awaits you at Bear Haven. The large back hard offers plenty of seating and trails for hiking. The expansive front deck affords a great place to enjoy the evening meal. A main level bedroom with private TV is joined by a sleep loft with plenty of additional bedding. The large...
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    Oakland, Garrett County 21550
    Rental Home - 2 Bathrooms, Sleeps 8
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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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    Windy Acres1 / 16
    (3)Very good
    Studio, 3 Bathrooms, Sleeps 12 Quick View
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    Conveniently located near Swallow Falls & Herrington Manor State Parks, Windy Acres offers so many relaxation opportunities. Start with an oversized front deck overlooking the horse field with Adirondak chairs, wonderful fire pit with nice seating or a relaxing hot tub on the side deck outside....
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    Oakland, Garrett County 21550
    Rental Home - 3 Bathrooms, Sleeps 12
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    Red Run Cabin1 / 21
    (2)Average
    Studio, 2 Bathrooms, Sleeps 6 Quick View
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    Relax at the picnic table, surrounded by evegreens and Rhododendron and feel like you are vacationing in your own park. Sitting mere minutes from Central Deep Creek Lake activities, this simple cabin in the woods is only a short walk to lovely beach area on the lake. Easy access to ASCI whitewater...
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    Oakland, Garrett County 21550
    Rental Home - 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Boulderdash brings you the relaxation you’ve been craving and the rest you deserve! Located in the popular Mountainside community, this home provides the perfect perch in which to unwind in peace and comfort. With two expansive decks, hot tub, and plenty of outdoor seating, you can gather your...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    The sun, the shade, the shore? All yours! Lakeshore Breeze is a delightful1 / 10
    (1)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Come catch some divine ‘Lakeshore Breeze’ at this cozy lakefront cabin! Boasting a prime location near McHenry Cove on Deep Creek Lake, this home is just a few miles away from all your favorite lake activities and destinations. And that is just if you can bear to leave! At the home, you will never...
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    Oakland, Garrett County 21550 
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Tolson Cabin is a treat! Experience the best of lake life from this charming two bedroom log cabin. Inside this home, you’ll find a delightful medley of modern amenities, upscale décor, and rustic stylings for an interior that is bursting with comfort. With rich wood walls and native stone...
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    Oakland, Garrett County 21550 
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Searching for a cozy getaway? Little Bear’s Den has you covered! Offering everything you need for vacation bliss, this log-style home features a perfect medley of rustic natural stylings and modern upgrades that will make you feel right at home. Pull in the driveway and let the experience begin!...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Is there anything better than Paradise Point? Let all your worries wash away the moment you walk through the door of this sprawling lakefront estate- only fun, sun and total relaxation are welcome here! Looking to come together to create treasured new memories? Paradise Point has it covered with...
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Check out this really cool townhome at Four Hooppole on the shores of Deep Creek Lake! The community offers around 10 acres of level manicured yard, community tennis court, community basketball court, playground, and one of the only sandy beaches with a roped off swimming area for your safety and...
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    Oakland, Garrett County 21550
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bold and beautiful, Lake's End is a dream come true. Bring all your favorite1 / 16
    (8)Very good
    8 Bedrooms, 6 Bathrooms, Sleeps 22 Quick View
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    Put an end to vacation disappointment at shining Lake's End! Busy minds and talented hands have created a true masterpiece of style and comfort just for you in the fantastic Silver Tree Landing community. Lake's End holds the key to every vacation dream you've ever had with soaring cathedral...
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    Oakland, Garrett County 21550 
    Rental Home - 8 Bedrooms, 6 Bathrooms, Sleeps 22
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Brimming with charm, By the Stream is Deep Creek Lake area vacation home that is ready to host your next getaway! So close to it all, yet just far enough away, you will love the wooded location that’s just around the corner from Wisp Resort. Enter the roomy main level to discover lots of living...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Bunbury Cottage is a quaint and charming Lincoln-lodge style home that1 / 9
    (3)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Want to try and solve a vacation riddle? What's charming and irresistible, immensely private, with 2 streams running on either side, and guaranteed to refresh your spirit? Here’s a hint: it's tucked away just off a winding country lane, surrounded by a magnificent age-old oaks and laurel? Answer:...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Conveniently located, yet off the beaten path, this Yellowstone Log Cabin is situated closely to Property Numbers 360, 364, 365, 366 and 367 making it ideal for group or extended family retreats as well as offering the cozy, quaint and comfortable accommodations for a single couple or family. The...
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    Location Information
    Oakland, Garrett County 21541
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    7 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    Experience the true meaning of gracious country living at St. Bart's Retreat. Bring all your favorite people; there's more than ample room at this magnificent lakefront chalet. Perched above the shimmering waters of Deep Creek Lake and facing due East, you will find nothing between you and the most...
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    Oakland, Garrett County 21550 
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 18
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Conveniently located, yet off the beaten path, these Yellowstone Log Cabins offer cozy, quaint, and comfortable accommodations! All cabins are situated closely enough to one another for ideal couple retreats or single family getaways while offering a quiet wooded setting. Lured Away offers an...
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    Oakland, Garrett County 21541
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
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    Smoking allowed
    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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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Studio, 3 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
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    Take a decent walk to the community lake access area where you will find a pavilion, picnic table, large grassy play area, and swimming and fishing access along the shoreline of Deep Creek Lake. Assigned boat slip for your vacation home is available here as well. Inside this modest chalet you will...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 3 Bathrooms, Sleeps 9
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Pet friendly
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    Unlike any other vacation retreat, Deer Pass offers the opportunity to escape the ordinary and transcend into greatness! It is not often you can enjoy coffee on your deck while watching deer graze at your lawns edge, the day unfolding quietly before you. Tasteful, upscale furnishings with a...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    Shenandoah1 / 41
    (21)Very good
    Studio, 4 Bathrooms, Sleeps 14 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
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    Relax in the Great Room or Rec Room taking in the panoramic lakeviews. Cozy up in front of the gas fireplace on those chilly evenings. Large kitchen overlooks Family Room. 2 Master Suites, each offering it's own private bathroom, balcony, and King bed. Separate loft game room offers pool table,...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 4 Bathrooms, Sleeps 14
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    Glamping-Uzes1 / 31
    (2)Excellent
    Studio, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
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    If you like the idea of falling asleep under the stars and roasting marshmallows around a campfire, but the hassles of pitching a tent and sleeping on bumpy ground just don't do it for you, then glamping, the new term being used for upscale - or glamorous - camping, could be your ideal vacation....
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - Sleeps 4
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    Glamping-Cortina1 / 32
    (2)Very good
    Studio, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
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    About this property
    If you like the idea of falling asleep under the stars and roasting marshmallows around a campfire, but the hassles of pitching a tent and sleeping on bumpy ground just don't do it for you, then glamping, the new term being used for upscale - or glamorous - camping, could be your ideal vacation....
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - Sleeps 4
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    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Patio
    • Grill
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    • Hot Tub
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    Studio, Sleeps 4 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you like the idea of falling asleep under the stars and roasting marshmallows around a campfire, but the hassles of pitching a tent and sleeping on bumpy ground just don't do it for you, then glamping, the new term being used for upscale - or glamorous - camping, could be your ideal vacation....
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Washer
    • Satellite TV
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    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Studio, Sleeps 4 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you like the idea of falling asleep under the stars and roasting marshmallows around a campfire, but the hassles of pitching a tent and sleeping on bumpy ground just don't do it for you, then glamping, the new term being used for upscale - or glamorous - camping, could be your ideal vacation....
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - Sleeps 4
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    Lazy Bear Lodge1 / 31
    (6)Excellent
    Studio, 4 Bathrooms, Sleeps 13 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in this Quality Log chalet nestled in a forest setting. When you are ready to explore you will be only 3 minutes from Swallow Falls State Park with Maryland's highest waterfall & 5 minutes from Herrington Manor State Park with lifeguarded beachy area, barbeque pits and hiking trails. Larger...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 4 Bathrooms, Sleeps 13
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