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Vacation Rentals in Oakland, MD

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    Travelers to Oakland are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 17
    5 of 5 bubbles (24) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 16
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 14
    5 of 5 bubbles (3) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Tucked away at the end of quiet Lake Forest Drive, Glistening Waters lives up to its name. A nice level lakefront greets you as you walk out the front door. Trees surround the area to provide privacy and serenity. Inside, you will find fresh décor and quality furnishings to make you feel at home. A... View all property information
    Location Information
    Oakland, Garrett County 21550 
    1 / 15
    5 of 5 bubbles (7) Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 15 | Quick View
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    About this property
    This stunning Deep Creek vacation rental is situated on a tranquil cove, offering a peaceful setting with incredible views. Just steps from the waters edge, Telstar.gon has a large, private dock and a deck that runs the length of the house, perfect for morning coffee, soaking up the sunshine, and... View all property information
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    Oakland, Garrett County 21550 
    1 / 22
    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
    Location Information
    Oakland, Garrett County 21550
    1 / 14
    5 of 5 bubbles (6) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    About this property
    It's All Good will help you to release the stresses of life and recharge your batteries. This lake area home is situated on the peaceful Lake Shore drive. You can even catch glimpses of the lake through the trees. The lodge-like decor makes you feel right at home in the mountains yet surrounds you... View all property information
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    Oakland, Garrett County 21550 
    1 / 14
    3.5 of 5 bubbles (9) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Located on a quiet road with a marvelous level lakefront, Morning Breeze is the perfect spot for your next family vacation. The great room boasts a cathedral ceiling, stone fireplace and french doors opening onto the flagstone deck with a bubbling hot tub. A pool table and expansive windows... View all property information
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    Oakland, Garrett County 21550
    1 / 18
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Experience the lake in an atmosphere only an authentic cabin can provide - an original Deep Creek log cabin that has been thoroughly upgraded with modern amenities. Cochran's Cabin makes an ideal mountain-lake getaway for a romantic couple, a family, or even two families - private bedrooms for the... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 11
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Key to Paradise is set on a secluded and peaceful lot, making guests feel like they are worlds away from it all. This charming cabin in the woods features three bedrooms and three bathrooms, with a large and unique master suite. An incredible two-story fireplace built from native stone is the... View all property information
    Location Information
    Oakland, Garrett County 21550
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    1 / 9
    5 of 5 bubbles (9) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Transition from one season to the next without missing a beat - Tees-n-Skis can fulfill your vacation dreams all year long. Clean lines, professional décor and attention to detail create an atmosphere of quiet sophistication throughout this Craftsman style home. Indulge your need to relax with a... View all property information
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    Oakland, Garrett County 21550 
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • DVD Player
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    • ?
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    • x
    Location Information
    Oakland, Garrett County 21550
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Grill
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    • Hot Tub
    • Patio
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    • Satellite TV
    • Central Heating
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    Location Information
    Oakland, Garrett County 21550
    1 / 30
    4.5 of 5 bubbles (12) Very good
    8 Bedrooms, 9 Bathrooms, Sleeps 24 | Quick View
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    About this property
    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... View all property information
    Location Information
    Oakland, Garrett County 21550 
    4 of 5 bubbles Reviewed June 15, 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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    1 / 16
    3.5 of 5 bubbles (3) Average
    6 Bedrooms, 6 Bathrooms, Sleeps 15 | Quick View
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    About this property
    Visualize yourself standing at the railing of a spacious, sunlit deck, as you survey the expansive view of the lake and mountains that unfurl before you. Now make that vision a reality by choosing Sunset Pointe as your vacation destination. Within 10 minutes to skiing and golf, this stunning... View all property information
    Location Information
    Oakland, Garrett County 21550 
    1 / 12
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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 your coffee in peace at the water’s edge. A place defined by quietude, reflection, and ease. Simple... View all property information
    Location Information
    Oakland, Garrett County 21550 
    1 / 22
    4 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
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    • Patio
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    • x
    • ?
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    • x
    About this property
    Reserve the Perfect Deep Creek Lake Getaway! This cute home is close to everything the Deep Creek Lake resort area has to offer, plus you have a boat slip and lake access! Walk up the steps onto the large lake side deck and open the glass door to the earth-toned great room with cathedral... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 18
    4 of 5 bubbles (1) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    About this property
    If you seek the perfect vacation retreat, Summer Song will be music to your ears! The house has been beautifully renovated in 2014 with new furniture, carpet, paint, furnishings, hot tub and new lakefront bedroom in the basement. Enjoy dining on the spacious deck offering lovely lake views. The... View all property information
    Location Information
    Oakland, Garrett County 21550 
    1 / 5
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Is there anything better than Paradise Point? Let all your worries wash away the moment you walk through the door of this sprawling lakefront estate- only fun, sun and total relaxation are welcome here! Looking to come together to creature treasured new memories? Paradise Point has it covered with... View all property information
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    Oakland, Garrett County 21550
    1 / 21
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Mountain High is ideal for your next Deep Creek Lake getaway. Nestled on 2 acres in the Mountainside Community, you are just minutes away from local shopping, dining, and activities. Enjoy soaking in the outdoor hot tub, relax by 2 stone fireplaces or enjoy a full game room including a pool table,... View all property information
    Location Information
    Oakland, Garrett County 21550
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    1 / 10
    4 of 5 bubbles (6) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Mountaineer is a delightful three-bedroom chalet on a wooded lot in the Mountainside Community. With a stylish and comfortable décor, this Deep Creek retreat feels like a home away from home in the middle of a mountain paradise. A charming covered front porch, an outdoor hot tub, and wood-burning... View all property information
    Location Information
    Oakland, Garrett County 21550 
    1 / 15
    4.5 of 5 bubbles (4) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Sleep peacefully knowing that your vacation will be restful at Tranquil Dreams.  This four bedroom chalet is situated on a quiet, wooded finger of the lake. After enjoying the lake, return to the chalet and grill out, play pool in the rec room while you watch the big game or relax in the hot tub.... View all property information
    Location Information
    Oakland, Garrett County 21550 
    1 / 14
    4.5 of 5 bubbles (8) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    No matter cheery summer skies or frosty winter flurries- or something in the middle- good times are always to be had at Blue Waters! This warm home invites you in a plethora of options and ways in which to spend the day. Gather together with family and friends in the large great room to take in... View all property information
    Location Information
    Oakland, Garrett County 21550 
    1 / 13
    5 of 5 bubbles (4) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    About this property
    A vacation retreat like this is a rare find. Diamond on the Lake is truly a gem, offering a grassy level lakefront with scenic lake views. The attention to detail, upscale furnishings, and abundant amenities is sure to satisfy the most discriminating guest. Your cares will simply disappear whether... View all property information
    Location Information
    Oakland, Garrett County 21550 
    5 of 5 bubbles Reviewed July 16, 2016
    Diamond on the Lake was delightful! Beautiful sunsets...beautiful yard! The home is spectacular, with a screened in gazebo eating area. We take our children and grandchildren...
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    1 / 9
    4.5 of 5 bubbles (13) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Forget the fast lane and rediscover a slower pace of life when you come for a stay at Break Away Chalet! Grab the kids, load up the car, and begin your journey towards a new you: ready to unplug, unwind, and unhook from the hustle and bustle of daily life. As soon as you open the door of this... View all property information
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    Oakland, Garrett County 21550 
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Look no further for your destination for relaxation! Perched atop a quiet wooded community, Home on the Ridge is the perfect place to sit back and unwind. Whether spending time with family or friends, this lovely 3 bedroom home offers all you will need! Take a walk outside on the spacious deck to... View all property information
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    Oakland, Garrett County 21550
    1 / 14
    4.5 of 5 bubbles (3) Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Translate serenity by the lake into a fantastic chalet, and Southern Comfort is the result. Located on 417 feet of gently sloping lakefront with rolling hills and scenic vistas, this beauty has incredible lake views visible from 4 of the 6 bedrooms. The 2 master suites opening onto a deck and a two... View all property information
    Location Information
    Oakland, Garrett County 21550 
    1 / 28
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    Considering a much needed getaway to spend time with family and friends? Look no further than Serenity Ridge! This newly decorated home offers entertainment for all!. The simple elegance of the décor is further enhanced by hardwood floors and the glowing warmth of the fireplace. Offering 2 master... View all property information
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    Oakland, Garrett County 21550 
    1 / 17
    5 of 5 bubbles (14) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Nestled among the tall oaks and maples, this remodeled chalet offers privacy and seclusion within a short walk to the lake. The spacious deck and backyard fire pit set the stage -roast marshmallows, share your favorite stories, rekindle friendship and laugh till your sides hurt. Indoors, you will... View all property information
    Location Information
    Oakland, Garrett County 21550 
    5 of 5 bubbles Reviewed August 15, 2014
    Our family, 2 adults and 3 children (12, 15 and 17) plus Snow Lab, Luie enjoyed this spacious 4 bedroom home. Great hot tub. Saw many deer in the wooded backyard. Short walk to...
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    1 / 24
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    Oakland, Garrett County 21550
    1 / 24
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • DVD Player
    • Grill
    • Balcony
    • Satellite TV
    • Washer
    • Air Conditioning
    • Patio
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
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    Location Information
    Oakland, Garrett County 21550
    1 / 13
    3 of 5 bubbles (7) Average
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Come savor seclusion at charming Creekside Cove. Encircled by an enchanting forest of flowering laurel and scented pines, this comfortable lakefront chalet possesses an aura of tranquility. Pleasantly furnished, you will find a comfortable interior with a lovely stone fireplace and a fun pool table... View all property information
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    Oakland, Garrett County 21550
    1 / 14
    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Air Conditioning
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    • Porch
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    • ?
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    • x
    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... View all property information
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    Oakland, Garrett County 21550
    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Oakland, Garrett County 21550 
    1 / 14
    4.5 of 5 bubbles (4) Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 20 | Quick View
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    About this property
    The discriminating guest will appreciate this luxurious lakefront home. Waterfront Chateau is the ultimate rendezvous for family and friends. Located on a dead end street just 4 miles from Wisp, the setting is tranquil ---away from the hustle and bustle. Enjoy the cool mountain air from the... View all property information
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    Oakland, Garrett County 21550 
    1 / 13
    4.5 of 5 bubbles (18) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    About this property
    It doesn’t get much cuter than this this original stone lakefront cottage loaded with great amenities. This three-bedroom Deep Creek home is quite spacious, and the level lawn leading to the lake and private dock is incredibly picturesque. Large windows in the great room offer spectacular views of... View all property information
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    Oakland, Garrett County 21550 
    1 / 19
    4.5 of 5 bubbles (13) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    What would you say to the perfect lakefront home, in the perfect location, with the perfect list of amenities? You would say “Aah, Chalet!” You can have it all when you stay at this fantastic retreat! Soak in the home’s outdoor hot tub, relax in the loft, or challenge your friends to game of pool... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 10
    3 of 5 bubbles (1) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Come catch a Lakeshore Breeze at this cozy cabin on the waterfront. What a prime location near McHenry Cove on Deep Creek Lake and just a few miles from everything else the lake has to offer?  You may never want to stop soaking in rays of sun on your private dock, but this home also features an... View all property information
    Location Information
    Oakland, Garrett County 21550 
    3 of 5 bubbles Reviewed January 1, 2017
    The house was advertised as sleeping 10, which, while physically possible, would be impracticle. We had a party of 6 and any more would have been a crowd. The house has only one...
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    1 / 7
    3.5 of 5 bubbles (2) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    This cozy chalet with lake access is the perfect escape for couples or a small family. Decorated in a fun western style, guests will enjoy three comfortable bedrooms and two bathrooms. The tranquil wooded setting of this Deep Creek vacation rental will make you feel worlds away from it all, while... View all property information
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    Oakland, Garrett County 21550 
    1 / 21
    4 of 5 bubbles (10) Very good
    9 Bedrooms, 9 Bathrooms, Sleeps 26 | Quick View
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    About this property
    Look beyond the beautiful furnishings and the numerous amenities and you will find peaceful relaxation with incredible panoramic views of Deep Creek Lake and the surrounding mountains. Nestled “Under the Stars” in Mountainside, this recently redecorated chalet is sequestered away from the beaten... View all property information
    Location Information
    Oakland, Garrett County 21550 
    4 of 5 bubbles Reviewed August 5, 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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    1 / 26
    4 of 5 bubbles (1) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    At Sunset Dream you really can have it all!  Thoughtfully situated on a level, 1-acre+, lakefront lot, this well-appointed, 4,500 square foot home sits on a quiet cove in the highly sought, Sandy Beach community. The surrounding tall timbers and natural beauty provide an idyllic lakeside... View all property information
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    Oakland, Garrett County 21550
    1 / 13
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    The tranquil setting of this vacation home make it an ideal getaway any time of year. Grill out on the back deck, unwind in the hot tub, or take on a game of pool, this family friendly retreat has lots to offer. The home is located in a quiet community with lake access and tennis courts close by.... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    • Satellite TV
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    • Grill
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    • Wi-Fi
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    Newer 2200-square-foot, custom, log cabin with three-sided wrap deck nestled on one+ acre in Deerfield off of Mayhew Inn Road. Beautiful trees and ferns with room to breath. Three miles from Swallows Falls, 2 miles to horseback riding stables and 5 miles to State Park Beach which has full water... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 12
    4 of 5 bubbles (9) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • x
    About this property
    Within a short walk you'll have easy access to the Lake - including a picturesque picnic table area for you and your guests - as well as the neighboring Silver Tree marina. Drive just a few miles further to reach state parks, skiing, movie theater, and area shops. The two fireplaces emit a warm... View all property information
    Location Information
    Oakland, Garrett County 21550 
    4 of 5 bubbles Reviewed February 25, 2016
    I stayed at Crosswinds for two nights this month with a group of 10 people. The house was very nice, cozy but not small, and had all the amenities as advertised. The kitchen was...
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    1 / 16
    4.5 of 5 bubbles (4) Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Pine Oasis offers everything one could need for a relaxing Deep Creek Lake vacation. This lakefront home boasts five bedrooms, a lovely kitchen, a game room, and a soaring stacked stone fireplace in the great room. Enjoy an expansive back deck, a cozy screened porch, and a perfectly manicured lawn... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 17
    4 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Providence at Penn Cove will make the perfect destination for an unforgettable Deep Creek getaway! The beautifully landscaped backyard with a small pond and fire pit is a great spot to relax or venture out to the lake access and head out on the water! Inside the home offers comfortable furnishings,... View all property information
    Location Information
    Oakland, Garrett County 21550
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Hot Tub
    • Housekeeping...
    • Grill
    • Patio
    • Satellite TV
    • Internet Access
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    Oakland, Garrett County 21550
    1 / 17
    5 of 5 bubbles (5) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Experience the thrill of lakefront living at this spectacular retreat. Lake Shore Lodge brims with the promise of vacation memories that will last a lifetime. With two fireplaces and an outdoor hot tub, there's definitely no shortage on fun. Just yards from the water's edge, friends and family will... View all property information
    Location Information
    Oakland, Garrett County 21550 
    1 / 10
    5 of 5 bubbles (5) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located in the picturesque Silver Ridge community, this Craftsman style home is the epitome of style. Relax and enjoy the crisp mountain air from the comfort of the wrap around porch as you plan the day's activities. With state parks, skiing, golf and more within a short drive, the opportunities... View all property information
    Location Information
    Oakland, Garrett County 21550 
    1 / 9
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Relax in this peaceful cabin located near Swallow Falls State Park, where you can visit Muddy Creek Falls, one of Deep Creek’s most popular sites. Swimming, fishing, and hiking are all conveniently located just moments away. An updated interior complete with a full kitchen, fireplace, and two... View all property information
    Location Information
    Oakland, Garrett County 21550
    5 of 5 bubbles Reviewed August 15, 2015
    This was a perfect getaway for 2, It was very clean, private, plenty of space for the two of us, and provided everything we needed! We can't wait to make a trip back! Check in and...
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