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Oakland Luxury Holiday Homes

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    Travellers to Oakland are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    38 Matching Rentals in OaklandView all 254 rentals
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    The Herrington1 / 77
    (2)Very good
    10 Bedrooms, 15 Bathrooms, Sleeps 34 Quick View
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    8 Bedrooms, 10 Bathrooms, Sleeps 16 Quick View
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    9 Bedrooms, 8 Bathrooms, Sleeps 24 Quick View
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    Under the Stars1 / 22
    (10)Very good
    9 Bedrooms, 9 Bathrooms, Sleeps 26 Quick View
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    Reviewed 6 August 2016
    Our extended family of 19, ranging in ages from 5-64 ( pretty spectacular that the kids are still able to, and desiring to, spend vacation with the adults !) spent our annual...
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    About this property
    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 
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 26
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    Peregrine's Perch1 / 30
    (12)Very good
    8 Bedrooms, 9 Bathrooms, Sleeps 24 Quick View
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    Reviewed 15 June 2011
    We had a wonderful week stay at Peregrine's Perch. Our group included an 84-year old, eight 18 year olds, parents, cousins and neighbors. The PROS:The house accommodated...
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    About this property
    The exquisite comfort of Peregrine's Perch spellbinds with a panorama that'll leave you speechless! Elegant, Extravagant, Extraordinary… the praises for this sensational estate go on and on! Uncommon quality can be found in the smallest details at this palatial home! Possessing a spectacular,...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 24
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    8 Bedrooms, 8 Bathrooms, Sleeps 26 Quick View
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    About this property
    Come and stay at Deep Creek's premier lakefront property where dreams do come true, and the fun begins at this exquisite eight bedroom home known as Celebration at Deep Creek. From the moment that you step inside this luxurious mountain home you will be in awe. Walking through the foyer, you will...
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    Oakland, Garrett County 21550
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 26
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    About this property
    Looking for the finest, most preeminent home to pamper you while on vacation? This stunning and impressive home has so many unique and elegant features, it will let you heartbroken when it is time to depart. From the moment you enter, you will be in awe of how delicately detailed every room has...
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    Oakland, Garrett County 21550
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    About this property
    Currently under construction, Boulder House has a beautiful lakefront location minutes from favorite things to do in Deep Creek Lake. This home includes six master suites, family room, a separate game room, and much more! You will love the convenience of having a private dock, so bring your boat or...
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    Oakland, Garrett County 21550
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
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    Timberlodge1 / 72
    (14)Very good
    9 Bedrooms, 7 Bathrooms, Sleeps 28 Quick View
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    About this property
    Extravagant comfort and mountain style reign supreme at Timberlodge! You'll love the private pool! If bigger is better, this fantastic chalet is the absolute best! Timberlodge excels in every way imaginable when it comes to your comfort and pleasure. This exquisite log home is a masterpiece of...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 9 Bedrooms, 7 Bathrooms, Sleeps 28
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    About this property
    Welcome to one of Deep Creek's finest homes. Reverie is an exquisite 5 bedroom mountain home that will far exceed your expectations. Combining lavish décor with prime lakefront easily makes this home a Deep Creek gem. Floor to ceiling windows in the Great Room allow you and your guests to bask in...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Ritz on the Lake1 / 19
    (14)Very good
    8 Bedrooms, 8 Bathrooms, Sleeps 26 Quick View
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    About this property
    With traditional comforts and extravagant luxuries, Ritz on the Lake delivers an exceptional stay! Unmatched in style and quality, this fantastic chalet rests along the stunning lakefront of one of Deep Creek Lake's favorite coves. The interior of this sprawling 8-bedroom estate boasts three...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 26
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    Awesome View1 / 38
    (11)Average
    8 Bedrooms, 7 Bathrooms, Sleeps 24 Quick View
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    About this property
    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 
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 24
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    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    About this property
    Putter Place is a brand new lake front home that invites you to unwind and make yourself at home! Your family and friends will be delighted when they enter this spacious, tastefully decorated waterfront property. Whether you are making breakfast in the kitchen or watching TV on the couch, the open...
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    Oakland, Garrett County 21550
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    About this property
    Located in the heart of Deep Creek Lake, Stone Crest offers a convenient location, spacious layout, and great amenities. As you enter the main level, take a moment to appreciate that wall windows, cathedral ceilings, and towering stone fireplace. This spacious home offers seamless indoor/outdoor...
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    Oakland, Garrett County 21550
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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    Drift Away1 / 22
    (9)Very good
    7 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    Reviewed 1 January 2012
    I would give this a rating of slightly below average. I was looking for a house to fit a group of 6 adults for New Years Eve weekend. The bedroom layout fit what I was looking...
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    About this property
    Relaxation takes hold at Drift Away, with its charming lakefront, indoor pool, and shaded lot! Enter a world as nature intended-unspoiled, unhurried, and unforgettable-- all just six minutes away from Wisp Resort! Luxury takes on new meaning at Drift Away! When surveying the immense rooms, you are...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 20
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    Bear Cove1 / 12
    (2)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    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 
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    7 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    About this property
    Discover Paradise at Deep Creek! This well-appointed chalet offers a level lake front, beautiful views and lots of fun amenities. It is the perfect starting point for an amazing vacation with family and friends. Paradise at Deep Creek effortlessly hosts your group with an abundance of comfortable...
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    Oakland, Garrett County 21550
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 18
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    7 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    Your fairy tale vacation starts at Ever After! This lake front home promises a memorable vacation experience. Three floors of living space plus a separate carriage house with a 120 inch home theater and an oversized game room makes this property stand-out from the crowd. The main level offers a...
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    Oakland, Garrett County 21550
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 18
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    5 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Offering unparalleled lake front elegance, Preston on the Lake is a premiere vacation home with amazing features inside and out. You will be immediately impressed as you drive up to the entrance of this stately retreat. The main level features a grand gathering space with cathedral ceilings, lake...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    When you want to be off-the-beaten-path and still have convenient access to favorite activities, look no further than Whisked-A-Way! Situated on the shores of Red Run Cove, this attractive home is equipped with all of the vacation essentials plus lots of fun extras! Kick-back and relax in the great...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Offering an incredible 700 feet of waterfront, Sailor's Point invites you to unwind and feel at home on the shores of Deep Creek Lake. If your idea of a perfect vacation includes spending family time together in the game room, strolling along wooded community roads, and watching the sky fill with...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    About this property
    Surround yourself with nature in this majestic log home. Three master suites make it an excellent choice for couples as well as family gatherings. On the entry level, hardwood floors, cathedral ceilings and large windows adorn the great room, and the stone fireplace and stylish furnishings accent...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    8 Bedrooms, 7 Bathrooms, Sleeps 26 Quick View
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    About this property
    This Spectacular Lake Front Chalet is Waiting for Your Deep Creek Lake Getaway! Unwined is under NEW Ownership and Numerous UPDATES are in Progress!   Have a large group or planning a small family reunion? Unwined is the perfect place to accommodate a large group! This home is located off of...
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    Oakland, Garrett County 21550
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 26
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Skydance is the place where lifetime memories are made! This beautifully crafted, lake front home features an expansive deck that invites you to sit back and take in gorgeous sunrises and scenic lake views. A grassy, level lawn that is dotted with trees features a charming wooden bridge that leads...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    About this property
    Recent Upgrades Include: * Large indoor pool (28') with indoor and outdoor hot tubs * 13 seat, 5 tier movie theater with 144' screen and surround sound * 5 fireplaces * 16 person custom dining room table, breakfast nook and 5 person breakfast bar * 3 living rooms * Massive bar with pool...
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    Oakland, Garrett County 21550
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 20
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    Enchanted Lakefront1 / 33
    (7)Very good
    8 Bedrooms, 8 Bathrooms, Sleeps 22 Quick View
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    About this property
    Large, lakefront luxury! Relax in Enchanted Lakefront's 6 master suites and outdoor stone patio! 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...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 22
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    Journey's End1 / 36
    (8)Excellent
    8 Bedrooms, 9 Bathrooms, Sleeps 26 Quick View
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    About this property
    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 
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 26
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    You will see nothing but positive Changes in Attitude when you choose to stay in this spectacular 5 bedroom lakefront home. Step inside and immediately become swept away by the majestic lake views! This home has top of the line amenities that guarantee a fun and memorable vacation for all. The...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    For the chance to stay in one of Deep Creek's most desired vacation homes, book a relaxing escape at Stargazer where peaceful days and starry nights are guaranteed. Mesmerizing from the second that you step inside, prepare to be swept away by the extraordinary lake views that greet you from the...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    No matter what time of year you visit, Four Seasons Chateau promises a Deep Creek vacation that will leave you longing to come back again and again. This well-appointed retreat offers style, comfort, and best of all, a convenient location that puts the best area activities at your fingertips....
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    There is no better place to reunite with friends and family than Nature's Retreat. This spectacular 5 bedroom lakefront home offers all of the amenities of home and more! Glistening hardwood floors, a massive stone stacked fireplace and leather furnishings create a warm and comforting gathering...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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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 
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 14
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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 Holiday Rental - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Pack your bags and get ready to experience a true Deep Creek adventure when you choose to stay in the newly built log home Man Haus! This luxury log home will host 4 Master Suites making it an excellent choice for a couple's retreat or an extended family getaway! Indoor creature comforts include...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Treat yourself to this premier lakefront home located in quiet, yet prestigious Lake Forest Estates. Stoney Point offers many hard to find features making your stay at Deep Creek Lake a memory that will last a lifetime. Featuring a large LEVEL lakefront yard situated right on the shoreline, and...
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    Oakland, Garrett County 21541
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Almost Aspen1 / 41
    (3)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    About this property
    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
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 20
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    Absolute Delight1 / 25
    (2)Very good
    8 Bedrooms, 7 Bathrooms, Sleeps 25 Quick View
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    Stylish and luxurious, Absolute Delight is an 8-bedroom lake estate with all your favorite amenities! Superior in every way, Absolute Delight is an absolute dream! Located in the elite community of Alpine Shores, this spectacular 8-bedroom chalet reigns supreme with its lush wooded setting and top...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 25
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    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    True to its name, the good life awaits at La Bella Vita! This stunning, recently remodeled home promises an exceptional Deep Creek Lake vacation for your family and friends. With amazing lake views from almost every room and upscale décor throughout, this will quickly become a favorite spot to get...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 14
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