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Oakland Vacation Rentals

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    Travelers to Oakland are booking November dates now. Secure your vacation rental today, and have the perfect trip.
    All 138 Rentals in Oakland
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Sundance1 / 37
    (11)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 22 Quick View
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    Cedar Lodge1 / 20
    (15)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    At Last1 / 60
    (5)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    About this property
    At Last! This premium estate is absolutely laden with top-of-the-line amenities and upgrades! A Signature Collection home! Come winter, come summer, come autumn, come spring, Deep Creek Lake is never more beautiful than from the shores of At Last! Here, the sun sparkles over calm waters and time...
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    Oakland, Garrett County 21550 
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    Lake Shore Lodge1 / 17
    (5)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    About this property
    Beautiful inside and out, it's hard to believe the unrivaled excellence of stunning Lake Shore Lodge! Experience the thrill of a Deep Creek Lake vacation at this spectacular lakefront retreat. Lake Shore Lodge is simply brimming with promise for a vacation filled with bright new memories to last a...
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    Oakland, Garrett County 21550 
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    Emerald Bay1 / 13
    (5)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    About this property
    Emerald Bay gives you everything: an expansive lakefront, large deck and plenty of indoor comforts! A gorgeous lake view greets you at Emerald Bay! This beautiful chalet, located along quiet Paradise Point, features a quiet lakefront, sunny views, and open skies for an utterly ideal lakefront...
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    Oakland, Garrett County 21550 
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Baldwins Domain1 / 12
    (3)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    With community perks and tranquil wooded setting, serenity can always be found at Baldwin's Domain! Pure mountain air mixes with comforting home-style touches at Baldwin's Domain to create an appealing signature aesthetic. Catch the view from the sunny living room and stay warm beside the home's...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Magnificent View Point1 / 19
    (6)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Light and bright with ample windows and level lakefront, Magnificent View Point was built to please! 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!...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    Want it all? Mountain High delivers! Mountain setting, lake access, and plush furnishings? Got it! A Signature Collection home! Mountain High is the ideal choice for your next Deep Creek Lake getaway. Nestled on 2 acres in the Mountainside Community, you are just minutes away from local shopping,...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    LinLaurAl1 / 13
    (4)Average
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    About this property
    LinLaurAl is a charming and private pastoral oasis that includes a level lakefront among tall trees! LinLaurAl is a five-bedroom Deep Creek vacation rental with something for the whole family! Featuring 600 feet of level lakefront and plenty of privacy, this charming home is the perfect lakefront...
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    Oakland, Garrett County 21550 
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Bunbury Cottage1 / 35
    (3)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Rustic and warm, Bunbury Cottage is a charming Lincoln-lodge style home with lots to offer! 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...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lake's End1 / 71
    (8)Very good
    8 Bedrooms, 6 Bathrooms, Sleeps 22 Quick View
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    Gather together at Lake's End! There's space for everyone at this magnificent lakefront chalet! 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...
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    Oakland, Garrett County 21550 
    Rental Home - 8 Bedrooms, 6 Bathrooms, Sleeps 22
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    It's A Wonderful Life1 / 44
    (10)Very good
    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    It's A Wonderful Life is brimming with amenities, including a spectacular back patio and lakefront! Like the classic film that shares its name, It's a Wonderful Life will take you on a journey of self-discovery and inspire you to grab your loved ones, hold them close, and spend your days wrapped...
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    Oakland, Garrett County 21550 
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 14
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    Creature Comforts1 / 20
    (9)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    The modern and stylish touches of Creature Comforts make this home the envy of all others! Don't miss the comforting splendor of this fabulous lakefront resort home! Creature Comforts promises to provide a series of little luxuries and patent charms guaranteed to make you feel relaxed and warm....
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    Oakland, Garrett County 21550 
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    Diamond on the Lake1 / 13
    (4)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Diamond on the Lake's plush upscale furnishings, stylish décor, and premium lakefront are sure hits! A Signature Collection home! Pay attention: vacation retreats like this are hard to find! Diamond on the Lake is truly a gem, offering a grassy level lakefront with scenic lake views, upscale home...
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    Oakland, Garrett County 21550 
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 14
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    Bear Cove1 / 12
    (2)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Is it the quiet cove, the sandy beach, or the stone fire pit? You decide the best part of Bear Cove! Rest and rejuvenation wait at Bear Cove! This spacious three-bedroom home is settled along a quiet section of the lake, a place where you can take a morning stroll along community roads or sip...
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    Oakland, Garrett County 21550 
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    Crowd Pleaser1 / 14
    (11)Very good
    4 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    Sacrifice nothing at Crowd Pleaser! There is so much to do and so much to see here! Looking to satisfy a variety of vacation needs? Crowd Pleaser is the solution! Offering convenient location, nearby lake access, and a modern interior, this home is a must! Perhaps the best feature? All four...
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    Oakland, Garrett County 21550 
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 11
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    Tamaqua Lodge1 / 21
    (12)Average
    6 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    Colorful, vibrant, and fun! That's Tamaqua Lodge- check out the large deck and stunning lakefront! Joyful and uplifting, Tamaqua Lodge will elevate your spirits to new heights! Beautifully appointed rooms accented with eye-catching flair and style provide ample space for your family and friends....
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    Oakland, Garrett County 21550 
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 15
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    Scenic Serenity1 / 15
    (9)Very good
    8 Bedrooms, 6 Bathrooms, Sleeps 24 Quick View
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    Centrally located and blessed with lake views, you'll love simmering in Scenic Serenity's hot tub! A Signature Collection home! Scenic Serenity offers an incredible lakefront setting and a location close to it all! This eight-bedroom Deep Creek vacation retreat is located on one of the most...
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    Oakland, Garrett County 21550 
    Rental Home - 8 Bedrooms, 6 Bathrooms, Sleeps 24
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    Almost Aspen1 / 41
    (3)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    Location, location, location- Almost Aspen has it! Plus, seven large bedrooms and tons of amenities! A Signature Collection home! A vacation you will never forget awaits you at Almost Aspen! Located on the lakefront of scenic Deep Creek Lake, this expansive chalet is the ideal spot for a getaway...
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    Oakland, Garrett County 21550
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 20
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Intimate and inviting, Swallow Falls Inn Cabin 1 echoes with the wild resonance of the waterfalls! Get away to Swallow Falls Inn Cabin 1! Located near the state park, you are just a walk away from one of Deep Creek's most popular sites and home to Maryland's largest waterfalls! Muddy Creek Falls...
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    Oakland, Garrett County 21550
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Experience the Magic of Deep Creek Lake in a Comfortable & Cozy Log Cabin in Yellowstone Village! From the minute you arrive at this warm and inviting 2 bedroom, 1 full bath home, you will escape to a simpler time with all the modern conveniences you desire. The main level envelops you with the...
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    Oakland, Garrett County 21550
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Serendipity1 / 46
    (3)Average
    8 Bedrooms, 7 Bathrooms, Sleeps 22 Quick View
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    Serendipity! This splendid lake house showcases a sunlit interior, level lakefront, and large deck! Bursting with promise, Serendipity is a vacation retreat unlike anything you have ever seen! Come in, take a look around, and let amazement take hold; every corner of this magnificent lake estate is...
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    Oakland, Garrett County 21550 
    Rental Home - 8 Bedrooms, 7 Bathrooms, Sleeps 22
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    Edgewater1 / 17
    (8)Average
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Edgewater is your own private oasis! You'll love the hot tub overlooking quiet cove waters! For lakefront living full of perks, look no further than Edgewater. When you book a stay at this three-level family home, you get five bedrooms, four bathrooms, and the home's peaceful wooded setting all to...
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    Oakland, Garrett County 21550 
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Under the Stars1 / 22
    (10)Very good
    9 Bedrooms, 9 Bathrooms, Sleeps 26 Quick View
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    Life is better “Under the Stars”! Check out the spectacular sweeping views and two private pools! Nestled “Under the Stars” in the popular Mountainside community, this premier mountain home is sequestered away from the beaten track, only minutes away from skiing, state parks and restaurants, as...
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    Oakland, Garrett County 21550 
    Rental Home - 9 Bedrooms, 9 Bathrooms, Sleeps 26
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    This exceptional home fronting Deep Creek Lake with a private dock, community indoor pool, and so much more will make the perfect vacation spot! Your family will feel right at home in this fabulous lakefront vacation home. Johnny Appleseed is the ideal vacation getaway for large families....
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    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    Remedy1 / 27
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Come on over to Remedy! The fire is warm, the lakefront cool, and the nights always star studded! This beautiful Deep Creek Lake chalet will be the remedy to all of your vacation troubles! The classic feel of this warm and rustic lake home is highlighted by tasteful updates and colorful accents...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    About this property
    This Unique Chalet with Exceptional Architectural Details and Spacious Outdoor Areas is Calling Your Name! Home Layout: Main Level: Kitchen - Breakfast Bar Seating for 4 Living Room - Fireplace - Queen Sleeper Sofa Dining Area Bedroom - Queen Bed Bedroom - Duo Bunk Bed Full Bath Upper...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 11
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    Journey's End1 / 36
    (8)Excellent
    8 Bedrooms, 9 Bathrooms, Sleeps 26 Quick View
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    Bright and expansive, this 8-bedroom home is a great place to come together. Journey's End rocks! This cedar and stone lakefront chalet offers the ultimate in elegance, comfort, and relaxation! With eight master suites and eight and a half bathrooms, Journey's End offers the privacy and space you...
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    Oakland, Garrett County 21550 
    Rental Home - 8 Bedrooms, 9 Bathrooms, Sleeps 26
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    Swallow Falls Inn Cabin 21 / 7
    (4)Average
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Walk to the waterfalls and explore the winding trails around Swallow Falls Inn Cabin 2! Swallow Falls Inn Cabin 2 is a rustic wonder! With charming log-cabin exterior and porch swing, you will feel awash with a feeling of warm welcome from the moment you arrive! Whether you are spending the day...
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    Oakland, Garrett County 21550
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    With a great lakefront and convenient central location, Arrowhead #26 showcases the best of DCL! Arrowhead #26 is a showstopper! It doesn't get more convenient or cozy than this lakefront townhome. Loaded with great amenities, this three-bedroom home is surprisingly spacious, with a stunning level...
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    Oakland, Garrett County 21550
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Dream On1 / 12
    (10)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Dream On is rich with contemporary charm! This newly built duplex is a vacationer's haven! 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...
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    Oakland, Garrett County 21550 
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Rother's Cove1 / 18
    (3)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Magical details and quality furnishings combine with a charming level lakefront at Rother's Cove! Rother's Cove is a proven delight full of new surprises! This traditional lake home is a family-favorite destination for many groups that make this home their sanctuary, year after year. Start your...
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    Oakland, Garrett County 21550 
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 16
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    With super close lake access and abundant privacy of the woods, Deer Pass is a proven delight! 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...
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    Oakland, Garrett County 21550
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Lake It Easy! Updated and spacious, this charming home boasts a great central location at the lake! This beautiful townhome will make your next Deep Creek Lake getaway a memorable one! The comfortable furnishings and stylish decor fuse to create a ‘home away from home' with three levels of...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Spacious enough for a family reunion or a truly memorable holiday celebration, this warm and welcoming cabin in the woods comes with a well-appointed deck and a covered patio with a forest view, an outdoor hot tub, wood-burning fireplace, pool table, and a romantic, in-room Jacuzzi. Up to 10 guests...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Awesome View1 / 19
    (11)Average
    8 Bedrooms, 7 Bathrooms, Sleeps 24 Quick View
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    Awesome View is the perfect place to swim, stay, and play! The indoor pool always delights! Get it all at Awesome View! Just beyond the tree line of this magnificent estate, get ready for a very special treat: sweeping, panoramic views of Deep Creek envelop you from the home's private dock. This...
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    Oakland, Garrett County 21550 
    Rental Home - 8 Bedrooms, 7 Bathrooms, Sleeps 24
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    Pet friendly
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    Don't Miss Out on Staying in a Cute Log Cabin with a Year-Round Hot Tub Room and Two Fireplaces! This adorable log cabin is waiting to make your Deep Creek Lake vacation memorable! Walk up the path and around the bushy pine tree to find a cozy, covered front porch peeking out between even more...
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    Oakland, Garrett County 21550
    Cabin - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Waterfront Chateau1 / 14
    (4)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    Waterfront Chateau delights with a tranquil wooded setting, charming lakefront, and sunny interior! The discriminating guest will appreciate this luxurious lakefront home! Waterfront Chateau is the ultimate rendezvous destination for a getaway among family and friends. Located on a dead end street...
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    Oakland, Garrett County 21550 
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 20
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    Paradise Lodge1 / 22
    (4)Average
    5 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
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    Some of the best lake views can be found at Paradise Lodge! This home is full of timeless appeal! Enjoy fresh mountain air, tall trees, and stunning lakefront views at Paradise Lodge. This classic lodge-style lake home offers seclusion and privacy, yet boasts a location close to many stores,...
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    Oakland, Garrett County 21550 
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 15
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    What an adorable log cabin home! Whitewater Lodge is a three-bedroom log home in the picturesque Yellowstone Village cabin community in the central Deep Creek area. Inside, the charming wood styling, open layout, and fun vacation amenities transform this charming little cabin into a modern retreat...
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    Oakland, Garrett County 21550
    Cabin - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Dog-friendly, lakefront log home on a quiet cove - front deck & shared dock1 / 41
    (1)Terrible
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    • Grill
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    • Patio
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Head to Deep Creek Lake for a quiet vacation with family and friends, complete with all the conveniences that comes with being close to town. Your group will have ready access to the lake and the slopes, as well as in-town convenience. And to make your getaway complete, you can bring the family dog...
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    Location Information
    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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    About this property
    Waltzing Moose Lodge is a Spectacular Lake Access Mountain Log Chalet Perched on Top of Mountainside Overlooking Deep Creek Lake! Take in the breathtaking views and feel like you're standing on top of the world! From the minute you enter this luxurious home, you realize all the comforts you are...
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    Oakland, Garrett County 21550
    Cabin - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    Amazing Love1 / 29
    (5)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Smoking allowed
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    The dramatic wood ceilings and warm décor of Amazing Love make for vacation perfection! Looking for the ultimate vacation experience? Amazing Love has you covered! This five-bedroom vacation rental was recently remodeled and features a host of fantastic amenities, including an air hockey table,...
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    Location Information
    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
    Delight in this richly appointed lake access home in the prestigious Blakeslee community with a boat slip and hot tub! Home Layout Main Level: Great Room - Gas Burning Fireplace Kitchen - Breakfast Bar Dining Area Half Bath Sitting Room Bedroom - Queen Bed Sunroom - Outdoor Seating Indoor...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    At Creekside Lodge, the mountain aesthetic is perfected with rich colors and rugged natural textures! 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...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Beautiful Lake Access Chalet with Boat Slip, Hot Tub, Fireplace & Recreation Room! Home Layout: Main Level: * Great Room - Wood Burning Fireplace * Kitchen * Dining Area * Bedroom - King Bed * Bedroom - Queen Bed * Full Bath Upper Level: * Loft Area - Twin Chase Lounger * Bedroom - King Bed &...
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    Oakland, Garrett County 21550
    Cabin - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 Cinemas are conveniently within walking distance! Welcome to your perfect vacation! This gorgeous and...
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    Location Information
    Oakland, Garrett County 21550
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lakefront home with level yard located in the convenient quiet cove of Paradise Point.  Relax on the deck with a drink or join the fun on the private dock of this home.  Offering plenty of room with 4 bedrooms and 2 1/2 baths for your family vacation.  Close to restaurants and shopping. The...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Thank your “Lucky Stars” for this cozy cabin! You'll love the indoor hot tub and dual fireplaces! Days of delight and cozy nights await at Lucky Stars! This charming three bedroom cabin—one of the largest homes in the tranquil Yellowstone community—is everything you are looking for in a Deep...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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