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Oakland: Vacation Rental By Owner

Search result 1 to 20 Of 374
  • Property-1 Image 1
    Cottage Select Dates for Price
    • 4Bed
    • 3Baths
    • (2) Exceptional
    Oakland, MD

    Free yourself from the burdens of the day-to-day and prepare for adventure at this Deep Creek Lake vacation rental! This 4-bedroom, 3-bathroom cottage provides... ...more

  • Property-2 Image 1
    Cabin $383 / Nightly
    • 3Bed
    • 2Baths
    • (88)
    Oakland, MD

    Our cabin is a charming retreat in a native woodland setting. It's in the heart of Deep Creek Lake, offering recreational activities year round. Wisp Ski Resort... ...more

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

    Property Location With a stay at this vacation home in Oakland (Blakeslee), you'll be within a 15-minute drive of Deep Creek Lake and Deep Creek Lake State... ...more

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

    Property Location With a stay at this vacation home in Oakland, you'll be a 1-minute drive from Deep Creek Lake and 6 minutes from Wisp Resort. This vacation... ...more

  • Property-5 Image 1
    House Select Dates for Price
    • 4Bed
    • 3Baths
    Oakland, MD

    Property Location When you stay at this vacation home in Oakland, you'll be 1 minutes by foot from Deep Creek Lake. This vacation home is 7.4 mi (11.9 km) from... ...more

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

    Property Location With a stay at this vacation home in Oakland, you'll be within a 15-minute drive of Deep Creek Lake and Deep Creek Lake State Park. This... ...more

  • Property-7 Image 1
    House Select Dates for Price
    • 5Bed
    • 4Baths
    Oakland, MD

    Property Location With a stay at this vacation home in Oakland (Blakeslee), you'll be 3 minutes by foot from Deep Creek Lake. This vacation home is 7.4 mi (11.9... ...more

  • Property-8 Image 1
    House Select Dates for Price
    • 5Bed
    • 3Baths
    Oakland, MD

    Property Location With a stay at this vacation home in Oakland, you'll be within a 15-minute drive of Deep Creek Lake and Lodestone Golf Club. This 4-star... ...more

  • Property-9 Image 1
    House Select Dates for Price
    • 5Bed
    • 6Baths
    Oakland, MD

    Property Location With a stay at this vacation home in Oakland (Mountainside), you'll be a 4-minute drive from Deep Creek Lake and 10 minutes from Wisp Resort.... ...more

  • Property-10 Image 1
    House Select Dates for Price
    • 4Bed
    • 6Baths
    Oakland, MD

    Property Location With a stay at this vacation home in Oakland, you'll be a 1-minute drive from Deep Creek Lake and 8 minutes from Deep Creek Lake State Park.... ...more

  • Property-11 Image 1
    House Select Dates for Price
    • 5Bed
    • 4Baths
    Oakland, MD

    Property Location With a stay at this vacation home in Oakland, you'll be a 1-minute drive from Deep Creek Lake and 7 minutes from Deep Creek Lake State Park.... ...more

  • Property-12 Image 1
    Condo Select Dates for Price
    • 3Bed
    • 2Baths
    Oakland, MD

    Property Location Located in Oakland, this condo is within a 15-minute drive of Deep Creek Lake and Deep Creek Lake State Park. This condo is 10.6 mi (17.1 km)... ...more

  • Property-13 Image 1
    House Select Dates for Price
    • 4Bed
    • 4Baths
    Oakland, MD

    Property Location With a stay at this vacation home in Oakland, you'll be a 1-minute drive from Deep Creek Lake and 9 minutes from Deep Creek Lake State Park.... ...more

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

    Property Location With a stay at this vacation home in Oakland, you'll be a 1-minute drive from Deep Creek Lake and 9 minutes from Wisp Resort. This vacation... ...more

  • Property-15 Image 1
    House Select Dates for Price
    • 5Bed
    • 3Baths
    Oakland, MD

    Property Location With a stay at this vacation home in Oakland (Blakeslee), you'll be within a 15-minute drive of Deep Creek Lake and Deep Creek Lake State... ...more

  • Property-16 Image 1
    House Select Dates for Price
    • 3Bed
    • 4Baths
    Oakland, MD

    Property Location With a stay at this vacation home in Oakland, you'll be a 1-minute drive from Deep Creek Lake and 6 minutes from Wisp Resort. This vacation... ...more

  • Property-17 Image 1
    House Select Dates for Price
    • 5Bed
    • 4Baths
    Oakland, MD

    Property Location With a stay at this vacation home in Oakland, you'll be a 1-minute drive from Deep Creek Lake and 7 minutes from Deep Creek Lake State Park.... ...more

  • Property-18 Image 1
    House Select Dates for Price
    • 3Bed
    • 2Baths
    Oakland, MD

    Property Location Located in Oakland, this vacation home is within a 15-minute drive of Deep Creek Lake and Deep Creek Lake State Park. This vacation home is... ...more

  • Property-19 Image 1
    House Select Dates for Price
    • 5Bed
    • 5Baths
    Oakland, MD

    Property Location With a stay at this vacation home in Oakland, you'll be a 1-minute drive from Deep Creek Lake and 8 minutes from Deep Creek Lake State Park.... ...more

  • Property-20 Image 1
    House Select Dates for Price
    • 2Bed
    • 1Baths
    Oakland, MD

    Property Location With a stay at this vacation home in Oakland, you'll be within a 10-minute drive of Deep Creek Lake and Wisp Resort. This vacation home is... ...more

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 January, where prices hit an average of $11 a night. In December, prices will hit an average low of $0 per night.