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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Oakland, Garrett County 21550
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Oakland, Garrett County 21550
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    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
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | 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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    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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    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
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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 / 19
    6 Bedrooms, 7 Bathrooms, Sleeps 25 | Quick View
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    Oakland, Garrett County 21550
    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Oakland, Garrett County 21550
    1 / 19
    1 Bedroom, 1 Bathroom, Sleeps 5 | 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
    1 / 24
    3 Bedrooms, 1 Bathroom, Sleeps 8 | 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
    1 / 24
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | 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
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    1 / 18
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    All About the View is a remarkable lakefront home that encompasses all the qualities that make a vacation truly great. Its unique design, desirable amenities and ideal location combine to create the perfect venue for a vacation with family and friends. Gathering together in the Great Room will... View all property information
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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 
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    5 Bedrooms, 2 Bathrooms, Sleeps 16 | Quick View
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    Oakland, Garrett County 21550
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | 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 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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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 / 24
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | 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 / 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 / 10
    5 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    Oakland, Garrett County 21550
    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | 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 / 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 / 7
    1 Bedroom, 1 Bathroom, Sleeps 4 | 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 / 16
    6 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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    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 / 24
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | 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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    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
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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 / 23
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • x
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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
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    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
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    Oakland, Garrett County 21550
    1 / 26
    8 Bedrooms, 7 Bathrooms, Sleeps 26 | Quick View
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    • x
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    • x
    About this property
    Reserve Today for a Fall Getaway and receive a 3rd Night FREE through December 15, 2016! This Spectacular Lake Front Chalet is Waiting for Your Deep Creek Lake Getaway! Blueberry Hill is under NEW Ownership and Numerous UPDATES are in Progress! Have a large group or planning a small family... View all property information
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    Oakland, Garrett County 21550
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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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!... View all property information
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    Oakland, Garrett County 21550
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    4 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Enjoy Deep Creek Lake in this Original Bungalow Nestled between Towering Pines and Lush Rhododendrons with an Amazing Deck Space, Stone Fireplace, WiFi, and a Boat Slip! Home Layout: Main Level: * Living Room with Fireplace * Kitchen with Breakfast Bar * Dining Area * Bedroom - Queen Bed *... View all property information
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    Oakland, Garrett County 21550
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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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
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    Oakland, Garrett County 21550
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Oakland, Garrett County 21550
    Oakland Flight and Weather Info
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