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Holiday Homes and Apartments Oakland, MD

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    Travellers to Oakland are booking May dates now. Secure your holiday rental today, and have the perfect trip.
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    Studio, 3 Bathrooms, Sleeps 14 | Quick View
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    Studio, 4 Bathrooms, Sleeps 16 | Quick View
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    Studio, 3 Bathrooms, Sleeps 12 | Quick View
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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Red Run 1A3 is an alluring 3 bedroom condominium located in the desirable Red Run Community. Summer days don't get better than this as you and your guests relish time spent swimming & playing from the nearby beach area or lounging lazily around the outdoor community swimming pool. Winter evenings... View all property information
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    Oakland, Garrett County 21550
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    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    This chalet is the ideal place to relax and enjoy the spectacular views of the mountains. Located in a private, peaceful community of Mountainside, this home is just right for your vacation needs. Beautiful decor and attention to detail accent the cathedral ceiling and fireplace of the relaxing... View all property information
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    Oakland, Garrett County 21541
    1 / 17
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This four bedroom, four bath home has all you need for the perfect Deep Creek Lake getaway! Located in a community setting, take advantage of the community tennis courts and challenge a family member or friend to a match. In the warmer months, go to one of the local marinas and rent a watercraft... View all property information
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    Oakland, Garrett County 21550
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    4 of 5 bubbles (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    SPECIAL! Receive a Night FREE when Booking 3 Nights or More! Fox Den Lake House is an affordable, year-round, 2-bedroom, 1-bath vacation rental home with views of Deep Creek Lake from every room. Walk across the road to rent a boat or take a quick stroll down the street for some ice cream and... View all property information
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    Oakland, Garrett County 21550
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    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Live the lake life in luxurious style when you stay in this exquisite Creekside Townhome. Elegant décor flows throughout the home from the gleaming hardwood floors, the grand fireplaces, and lavish furnishings. Astounding lake views greet you from the Great Room which features a beautiful stone... View all property information
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    Oakland, Garrett County 21550
    1 / 27
    Studio, 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... View all property information
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    Oakland, Garrett County 21541
    1 / 16
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    • x
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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... View all property information
    Location Information
    Oakland, Garrett County 21550
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    1 / 30
    Studio, 5 Bathrooms, Sleeps 14 | Quick View
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    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... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 27
    Studio, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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... View all property information
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    Oakland, Garrett County 21550
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    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    What better way to experience a magical mountain getaway than a relaxing stay in a charming log cabin?Imagine arriving at your perfect little cabin tucked away in the quiet picturesque community of Yellowstone Village. Step inside and instantly fall in love with the dark hardwood floors and plush... View all property information
    Location Information
    Oakland, Garrett County 21550
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    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    Ready to experience a truly magnificent mountain vacation home? Schmidt Lodge is an inviting 3 bedroom log home located in a tranquil setting that reassures that you and your guests will experience the peaceful getaway that you seek! You and your guests will love the style, spaciousness, and cozy... View all property information
    Location Information
    Oakland, Garrett County 21550
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    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Imagine Vacationing in this Enchanting Home Right on the Shores of Deep Creek Lake with a Private Boat Dock! This charming and cozy 2 level, 3 bedroom, 2 full bath home nestled under towering pine trees in the heart of Deep Creek Lake is waiting for your family! The main level offers a full,... View all property information
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    Oakland, Garrett County 21550
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    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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,... View all property information
    Location Information
    Oakland, Garrett County 21541
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    Studio, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    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... View all property information
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    Oakland, Garrett County 21541
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Looking for that Cabin in the Woods Feel while Overlooking Deep Creek Lake? Find it at Owl’s Nest! This unique log cabin greets you with an inviting covered side porch which leads to a refreshing living room with a small fireplace, flat screen TV, warm furnishings, and a filtered lake view... View all property information
    Location Information
    Oakland, Garrett County 21550
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    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    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... View all property information
    Location Information
    Oakland, Garrett County 21541
    1 / 25
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    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... View all property information
    Location Information
    Oakland, Garrett County 21541
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    1 / 24
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 18
    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... View all property information
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    Oakland, Garrett County 21550
    1 / 43
    Studio, 5 Bathrooms, Sleeps 16 | Quick View
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    • x
    About this property
    The setting of this magnificent cedar chalet offers a quiet retreat for a restful vacation. The natural rock formations, wooded surroundings and beautiful mountain laurel create a serene location for relaxing and enjoying nature. The cathedral ceilings, grand windows and massive stone fireplace... View all property information
    Location Information
    Oakland, Garrett County 21541
    1 / 34
    Studio, 6 Bathrooms, Sleeps 16 | Quick View
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    • x
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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... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 42
    Studio, 5 Bathrooms, Sleeps 14 | Quick View
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    About this property
    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... View all property information
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    Oakland, Garrett County 21541
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • x
    About this property
    Immerse Yourself in this Original Deep Creek Lake Charmer with a Tranquil Lake Front Setting! From the minute you enter the driveway under the cover of the beautiful mature trees, you will feel the vintage charm this Deep Creek Lake original has with architectural touches of Frank Lloyd Wright.... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 27
    7 Bedrooms, 7 Bathrooms, Sleeps 18 | Quick View
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    About this property
    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... View all property information
    Location Information
    Oakland, Garrett County 21550 
    1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 7 | Quick View
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    About this property
    Reserve this adorable stone cottage with everything you will need to enjoy a quaint visit to Deep Creek Lake! Home Layout: Main Level: * Living Room - Wood Burning Fireplace, Queen Sleeper Sofa & Twin Roll-A-Way Bed * Kitchen * Dining Area * Bedroom - King Bed & Bunk Bed (2 Double Beds) *... View all property information
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    Oakland, Garrett County 21550
    1 / 8
    Studio, 5 Bathrooms, Sleeps 13 | Quick View
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    About this property
    Discover a truly delightful vacation experience when you choose Paddles & Poles for your Deep Creek Lake escape! Located in the lake front Silver Tree Landing community, this spacious, lake access home will be completely transformed for spring 2017 with new carpets, bedding, furniture, appliances... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 33
    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Your Deep Creek adventure starts here. Clear View is an amazing 4 bedroom home that showcases one of Deep Creek’s most premiere level lakefronts. Easily described as a “Vacationer’s Dream”, you and your guests will quickly fall in love with spectacular panoramic lake views that great you from the... View all property information
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    Oakland, Garrett County 21550
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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Known for its spacious common areas, sandy beach and quiet cove location, Four Hooppole is a lakefront community that offers ten acres of level manicured lawn. Guests staying here can enjoy the community tennis and basketball courts as well as the playground. It is off the beaten path but not far... View all property information
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    Oakland, Garrett County 21550
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    Studio, 7 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Currently under construction, Boulder House has a beautiful lakefront location that is within minutes from favorite things to do in Deep Creek Lake. Plans for this home include six master suites, a family room, a separate game room, and much more! You will love the convenience of having a private... View all property information
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    Oakland, Garrett County 21550
    1 / 25
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
    About this property
    Reserve Today - 3rd Night FREE! Step Back in Time and Find Peace and Quiet in this Cozy, Rustic Cabin, yet be Surrounded by All the Deep Creek Lake Resort Area has to Offer! This Deep Creek Lake Cabin is in the heart of the resort area within minutes to all restaurants and resort activities!... View all property information
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    Oakland, Garrett County 21550
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • x
    About this property
    This exceptional home fronting Deep Creek Lake with a private dock, community indoor pool, and so much more will make the perfect vacation spot! When you first see this home, you will say WOW! Walk under the cute covered front porch through the door to find a home that has the space for... View all property information
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    Oakland, Garrett County 21550
    1 / 26
    8 Bedrooms, 7 Bathrooms, Sleeps 26 | Quick View
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    About this property
    Reserve a Spring Getaway at Deep Creek Lake! Take Advantage of a 3 Night FREE during the 2017 Spring Season for Select Properties March 1st through May 18th! This Spectacular Lake Front Chalet is Waiting for Your Deep Creek Lake Getaway! Blueberry Hill is under NEW Ownership and Numerous UPDATES... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 27
    1 of 5 bubbles (1) Terrible
    4 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Reserve a Spring Getaway at Deep Creek Lake! Take Advantage of a 3 Night FREE during the 2017 Spring Season for Select Properties March 1st through May 18th! Enjoy Deep Creek Lake in this Original Bungalow Nestled between Towering Pines and Lush Rhododendrons with an Amazing Deck Space, Stone... View all property information
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    Oakland, Garrett County 21550
    1 / 24
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Reserve a Spring Getaway at Deep Creek Lake! Take Advantage of a 3 Night FREE during the 2017 Spring Season for Select Properties March 1st through May 18th! Luxury awaits you in this 3 level, 3,000 square foot, lakefront townhome in the heart of Deep Creek Lake with a Great Location!! * Wisp... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 14
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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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... View all property information
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    Oakland, Garrett County 21550
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    Dreaming of a Vacation to Deep Creek Lake and the Mountains? Well, you don’t have to Keep Dreaming if you Reserve “Keep Dreaming” Today! Fall in love with this natural log home in a quiet and private community just off Lakeshore Drive to escape from your stress while the resort area is just... View all property information
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    Oakland, Garrett County 21550
    1 / 24
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Porch
    • Parking
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Lake Access Mountain Chalet with Fireplaces, Hot Tub, & Community Amenities! Home Layout: Main Level: * Great Room - Wood Burning Fireplace & Queen Sleeper Sofa * Kitchen - Breakfast Bar * Dining Area * Bedroom - King Bed * Full Bath * Bedroom - (2) Queen Beds * Full Bath * Half Bath... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 26
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Parking
    • Air Conditioning
    • Porch
    • Internet Access
    • Washer
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Don't Miss Out on Staying in a Cute Log Cabin with a Year-Round Hot Tub Room & 2 Fireplaces! Home Layout: Main Level: * Living Room - Wood Burning Fireplace & Queen Sleeper Sofa * Kitchen * Dining Area * Bedroom - Queen Bed * Full Bath * Laundry Area Upper Level: * Bedroom - King Bed... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 26
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Satellite TV
    • Grill
    • Internet Access
    • Hot Tub
    • Porch
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy this Quaint and Cozy Deep Creek Lake Log Cabin for Your Vacation Getaway! Reserve TODAY for a 3rd Night FREE! This cute white washed home located in the Deep Creek Lake log cabin community of Yellowstone Village is waiting for your small family or romantic getaway. The covered front... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 24
    4 of 5 bubbles (1) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Grill
    • Hot Tub
    • Patio
    • Internet Access
    • DVD Player
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Are you Looking for a Mountain Chalet Very Close to Everything at Deep Creek Lake? You have found it in this stunning 3 level, 5 bedroom, 3 full bath home with a hot tub, two fireplaces, and a wrap around deck located in a quiet community! Walk up the steps and enter through the main level... View all property information
    Location Information
    Oakland, Garrett County 21550