Oakland: Vacation Rental By Owner

Showing 20 Of 401 Vacation Rentals
  • Property-1 Image 1
    Cabin $327 / Nightly
    • 2 Bed
    • 1 Baths
    • (36)
    Oakland, MD

    We would love to host you at The Love Shack, our cozy cabin in the woods, located in Deep Creek Lake’s quaint Yellowstone Village. Let the amazing ambiance and... ...more

  • Property-2 Image 1
    House $364 / Nightly
    • 4 Bed
    • 3 Baths
    • (71)
    Oakland, MD

    Original Deep Creek Lake stone cottage completely restored and updated. This 4 bedroom cottage is a great place to get away and unwind from the "real world". All... ...more

  • Property-3 Image 1
    House Select Dates for Price
    • 1 Bed
    • 1 Baths
    • (1) Exceptional
    Oakland, MD

    Located on a beautiful 65 acre farm, Haley Farm offers a chance to experience the beauty and tranquility of a farm while staying in comfort. Your suite is... ...more

  • Property-4 Image 1
    Condo $208 / Nightly
    • 1 Bed
    • 1 Baths
    OAKLAND, MD

    These two level units come with a full kitchen, living and dining area also comes with a great fireplace and scenic balcony all on the main level. The upper level... ...more

  • Property-5 Image 1
    Condo Select Dates for Price
    • 1 Bed
    • 1 Baths
    OAKLAND, MD

    These units have a full kitchen, living and dining areas, 1 Queen bed in the bedroom, and bath all on one level. You can gather around the fireplaces located in... ...more

  • Property-6 Image 1
    House Select Dates for Price
    • 5 Bed
    • 3 Baths
    Oakland, MD

    Parking limit 5 vehicles. Please note that this home has exterior security cameras. Head to Lakeside Paradise for an unforgettable vacation throughout all four... ...more

  • Property-7 Image 1
    House Select Dates for Price
    • 4 Bed
    • 3 Baths
    • (2)
    Oakland, MD

    Parking for 4 vehicles only. Relaxation Ridge is a place where you can kick-back, relax and experience a truly memorable Deep Creek Lake vacation! The convenient... ...more

  • Property-8 Image 1
    House Select Dates for Price
    • 4 Bed
    • 3 Baths
    Oakland, MD

    Paradise Found is truly life in paradise! Located along the shores of Deep Creek Lake, this stunning lakefront home is the ideal place to gather with family and... ...more

  • Property-9 Image 1
    House Select Dates for Price
    • 4 Bed
    • 4 Baths
    • (3) Exceptional
    Oakland, MD

    Brimming with charm, Picture Perfect offers you all the comforts of home plus a lot more! The central location and well-chosen décor make it the ideal starting... ...more

  • Property-10 Image 1
    House Select Dates for Price
    • 3 Bed
    • 2 Baths
    • (1) Exceptional
    Oakland, MD

    Parking limit 3 vehicles. Please note that this home has exterior security cameras. Perched on a hillside, Howling Wolf Den is the ultimate vacation spot for... ...more

  • Property-11 Image 1
    House Select Dates for Price
    • 5 Bed
    • 5 Baths
    • (2) Exceptional
    Oakland, MD

    Parking limit 5 vehicles. If you want to experience the best of Deep Creek Lake, look no further than Inn 2 Deep, a well-appointed vacation home with the perfect... ...more

  • Property-12 Image 1
    House Select Dates for Price
    • 3 Bed
    • 4 Baths
    • (7)
    Oakland, MD

    If your definition of the perfect vacation retreat includes a convenient location, multiple master suites, and great outdoor space, it is time to experience... ...more

  • Property-13 Image 1
    House $381 / Nightly
    • 3 Bed
    • 2 Baths
    • (41) Wonderful
    Oakland, MD

    Welcome to a truly special lakefront experience on the shores of Deep Creek Lake. Located in a private community on a peninsula at the Northern end of the lake,... ...more

  • Property-14 Image 1
    House Select Dates for Price
    • 5 Bed
    • 3 Baths
    Oakland, MD

    Situated in the heart of Deep Creek Lake, Canoe Cottage offers you amazing lake views, spectacular sunrises and easy access to favorite activities! Upon... ...more

  • Property-15 Image 1
    House Select Dates for Price
    • 4 Bed
    • 5 Baths
    • (13) Very Good
    Oakland, MD

    Get away from it all at this lovely home with multiple master suites and beautiful views! Nestled on a wooded hillside, you will love the feeling of seclusion... ...more

  • Property-16 Image 1
    Cabin $476 / Nightly
    • 4 Bed
    • 4 Baths
    • (18) Exceptional
    Oakland, MD

    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... ...more

  • Property-17 Image 1
    House $333 / Nightly
    • 4 Bed
    • 3 Baths
    • (1) Exceptional
    Oakland, MD

    Laurel Grove is a large chalet situated on a beautiful mountain site with western exposures for perfect sunsets! Inside you will enjoy a warm and inviting... ...more

  • Property-18 Image 1
    House Select Dates for Price
    • 6 Bed
    • 5 Baths
    • (5) Excellent
    Oakland, MD

    At Last promises amazing lake views, fun adventures and treasured memories for your next Deep Creek Lake vacation! Conveniently located, this elegant log home is... ...more

  • Property-19 Image 1
    House Select Dates for Price
    • 5 Bed
    • 5 Baths
    • (36) Very Good
    Oakland, MD

    Logxurious is the ideal name for this 5 bedroom lakefront log home that exemplifies the definition of luxury living. Inside the lodge, guests are treated to a... ...more

  • Property-20 Image 1
    House Select Dates for Price
    • 7 Bed
    • 6 Baths
    • (4)
    Oakland, MD

    Parking limit 7 vehicles. Please note this home has an exterior security camera. Discover Paradise at Deep Creek! This well-appointed chalet offers a level lake... ...more

loader

Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Oakland. Many accommodations in Oakland provide "Non Smoking Only", there are 390, or there are 387 of Vacation Rentals in Oakland with a "Children Welcome", there are also 322 with "Pool - Spa", which is another great reason to visit Oakland.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Oakland. The most expensive month of the next 12 months is in July, where prices hit an average of $64 a night. In June, prices will hit an average low of $351 per night.