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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.
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    5 of 5 bubbles (24) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    4 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
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    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
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    Oakland, Garrett County 21550
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Oakland, Garrett County 21550
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Oakland, Garrett County 21550
    1 / 52
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Nestled among the trees in this quiet cul-de-sac, you'll find this beautifully decorated and spacious home which is part of the Mountainside Resort and Marine Club subdivision. Have complete access to tennis, basketball and volleyball courts found in a gorgeous mountain setting. Delight in filtered... View all property information
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    Oakland, Garrett County 21541
    1 / 19
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    Oakland, Garrett County 21550
    1 / 14
    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    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 / 23
    3 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Oakland, Garrett County 21550
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    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Luxury awaits you in this 3 level, 3,000 square foot, lakefront townhome in the heart of Deep Creek Lake with a Great Location!! * Wisp Ski & Golf Resort is just a short drive away for 4-season fun! * Arrowhead Market, Honi Honi Bar & Garrett 8 Cinemas are conveniently within walking distance!... 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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    Oakland, Garrett County 21550
    1 / 23
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Oakland, Garrett County 21550
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Oakland, Garrett County 21550
    1 / 24
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    Oakland, Garrett County 21550
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Oakland, Garrett County 21550
    1 / 19
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Oakland, Garrett County 21550
    1 / 24
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Oakland, Garrett County 21550
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    Oakland, Garrett County 21550
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Oakland, Garrett County 21550
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    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Oakland, Garrett County 21550
    1 / 24
    9 Bedrooms, 9 Bathrooms, Sleeps 26 | Quick View
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    Oakland, Garrett County 21550
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    This Lovely Split Lake Front Home with Numerous Spaces for Everyone and Nice Outdoor Amenities with a Private Dock is Waiting for You! This unique and recently updated home has two levels both with a kitchen, dining area, gathering room, full bath, and sleeping spaces. Two homes in one and... View all property information
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    Oakland, Garrett County 21550
    1 / 7
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Oakland, Garrett County 21550
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    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
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    Oakland, Garrett County 21550
    1 / 24
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Oakland, Garrett County 21550 
    1 / 12
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Oakland, Garrett County 21550
    1 / 24
    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
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    Oakland, Garrett County 21550
    1 / 24
    10 Bedrooms, 11 Bathrooms, Sleeps 34 | Quick View
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    Oakland, Garrett County 21550
    1 / 24
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    Oakland, Garrett County 21550
    1 / 22
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    Oakland, Garrett County 21550
    1 / 16
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Oakland, Garrett County 21550
    1 / 24
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    Oakland, Garrett County 21550
    1 / 24
    9 Bedrooms, 7 Bathrooms, Sleeps 28 | Quick View
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    Oakland, Garrett County 21550
    1 / 19
    5 Bedrooms, 2 Bathrooms, Sleeps 16 | Quick View
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    Oakland, Garrett County 21550
    1 / 14
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Oakland, Garrett County 21550
    1 / 23
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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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 / 24
    8 Bedrooms, 7 Bathrooms, Sleeps 24 | Quick View
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    Oakland, Garrett County 21550 
    1 / 24
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Oakland, Garrett County 21550
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Oakland, Garrett County 21550
    1 / 19
    6 Bedrooms, 7 Bathrooms, Sleeps 25 | Quick View
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    Oakland, Garrett County 21550
    1 / 13
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Oakland, Garrett County 21550
    1 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    If you are looking for a home that goes “Above and Beyond”, this 4 bedroom mountain home is the ideal choice for you and your family! Located on top of a quiet mountaintop, here you will find the privacy you need but still relish the close proximity to all area shopping, dining, and state parks!... View all property information
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    Oakland, Garrett County 21550
    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
    About this property
    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
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Oakland, Garrett County 21550
    1 / 10
    5 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    Oakland, Garrett County 21550
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    6 Bedrooms, 6 Bathrooms, Sleeps 20 | Quick View
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    Oakland, Garrett County 21550
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Oakland, Garrett County 21550
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Oakland, Garrett County 21550
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