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Holiday Rentals in Oakland

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    Travellers to Oakland are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    5 Bedrooms, Sleeps 12Quick View
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    5 Bedrooms, Sleeps 13Quick View
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    Escape to the relaxing sounds of nature at Yellowstone Village and ''Dan's Mountain'' conveniently located, yet off the beaten path, this beautiful log home offers a cozy, cabin feel while offering plenty of comfortable accommodations! There's plenty of room for a gathering with friends and family,...
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    Oakland, Garrett County 21541
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    14 Reviews
    8 Bedrooms, Sleeps 26Quick View
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    Unmatched in style and quality, this fantastic chalet sits lakeside on one of Deep Creek Lake's choicest coves. The interior boasts three spacious master suites, two fireplaces and an airy loft with a pool table. Savor the excellent view of the lake from inside or venture outdoors to swim or fish...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 26
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    11 Reviews
    5 Bedrooms, Sleeps 14Quick View
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    Papa Bear is a lovely home that will make you want to stay in the story forever. You will love relaxing in nicely decorated master suites and bedrooms. One room even overlooks the great room and windows are abundant throughout the house. The kitchen and dining room provide plenty of seating for the...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    Looking for vacation perfection? The search is over: Lake Chalet is ready to wow you! If you are seeking to settle somewhere with a convenient location and a wooded setting, this charming log-cabin style home is the one for you. Located in the picturesque Yellowstone Village, you are just minutes...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, Sleeps 6Quick 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Review
    5 Bedrooms, Sleeps 12Quick View
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    Greene Acres is calling! With elegant cathedral ceilings and floor-to-ceiling windows, the living areas of this charming log-style home hit all the right notes to create a stirring symphony you’ll want to listen to again and again. Lush, vibrant greenery surrounds you and provides privacy for...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, Sleeps 8Quick 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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    Oakland, Garrett County 21541
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    14 Reviews
    9 Bedrooms, Sleeps 28Quick View
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    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 masterpiece offers 100 feet of beautiful lakefront decorated with fragrant mountain laurel and towering hardwoods. Elegant...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 9 Bedrooms, 7 Bathrooms, Sleeps 28
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    12 Reviews
    8 Bedrooms, Sleeps 24Quick View
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    Elegant, Extravagant, Extraordinary…and the list goes on! Uncommon quality can be found in the smallest details of this grand chalet. Possessing a spectacular, sweeping view of Deep Creek Lake and its lush mountains, Peregrine’s Perch is a premium home that is flawless in design and filled with...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 24
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    3 Bedrooms, Sleeps 6Quick View
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    • Shared Outdoor Pool (Unheated)
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    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, Sleeps 16Quick View
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    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
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    5 Bedrooms, Sleeps 10Quick View
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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
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 6Quick View
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    • Mountain Views
    • Central Heating
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    About this property
    Newly renovated three bedroom two bath cabin that sits back from the road with plenty of parking . Cabin is situated on one acre of wooded grounds surrounded by large boulders and a small pond. The stately stone fireplace is the centerpiece of this home. The soaring ceiling in the main living...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 8Quick View
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    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 4Quick View
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    Experience the lake life from this charming two bedroom original log cabin. Inside is anything but rustic, with design elements throughout that where selected to highlight the vintage charm of this cottage while creating an updated feel. Enjoy a cozy meal at home or have dinner at the onsite...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, Sleeps 8Quick 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 8Quick View
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    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    7 Bedrooms, Sleeps 18Quick 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 
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 18
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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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    Oakland, Garrett County 21550
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    If you’re looking for a peaceful and relaxing, but fun and exciting, Deep Creek lake vacation, look no further than Sandy Beach Retreat. Nested in the woods of Stockslager road, the location of this home offers the quietest and peaceful setting, but is just a short drive away from the fun and...
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    2 Bedrooms, Sleeps 6Quick View
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    • Skiing: Property Is In A Ski Resort
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    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! From...
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    Oakland, Garrett County 21550
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, Sleeps 6Quick View
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    Nestled in the Yellowstone Village community, Tree Haus offers the best location for fun and entertainment. Just a couple minute drive to the hub of town, explore local shops and restaurants. With A/C and a wood burning fireplace, this home offers the most comfortable atmosphere all year round....
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    Oakland, Garrett County 21550
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Review
    2 Bedrooms, Sleeps 6Quick 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 nice...
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    Oakland, Garrett County 21550
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Reviews
    3 Bedrooms, Sleeps 9Quick View
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    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 Holiday Rental - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Located in the heart of Deep Creek, yet tucked away in the secluded Yellowstone Village community, Owl Cabin offers the best of both worlds! This welcoming two bedroom cabin offers the perfect setting to sit back, relax, and take your mind off the hustle and bustle of your daily routine. Enjoy a...
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    Oakland, Garrett County 21550
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 4Quick 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...
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    Oakland, Garrett County 21550
    Cabin Holiday Rental - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Skiing: Property Is In A Ski Resort
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    About this property
    Our comfortable newer log home is comfortable and large with over 3000 ft inside and over 2000 ft of deck around the home. The home is decorated with antiques but all the beds are new pillowtop and so you can relax and enjoy the quiet! A gourmet kitchen is available for you to use to cook your...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedrooms, Sleeps 6Quick View
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    • Skiing: Property Is In A Ski Resort
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    Pet friendly
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    About this property
    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 Holiday Rental - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 6Quick View
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    • Skiing: Property Is In A Ski Resort
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    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 porch...
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    Oakland, Garrett County 21550
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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