We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Oakland Holiday Vacation with Pools

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    $630 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travellers to Oakland are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    7 Matching Rentals in OaklandView all 269 rentals
    Sort by:
    Default
    Attractive & Inviting 4 Bedroom home with hot tub in prestigious community!1 / 36
    (11)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    8 Bedrooms, 8 Bathrooms, Sleeps 26 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Hot Tub
    • Cable/satellite TV
    • DVD Player
    • Private Indoor Pool
    • Sauna
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and stay at Deep Creek's premier lakefront property where dreams do come true, and the fun begins at this exquisite eight bedroom home known as Celebration at Deep Creek. From the moment that you step inside this luxurious mountain home you will be in awe. Walking through the foyer, you will...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 26
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Parking
    • Grill
    • Hot Tub
    • Waterfront
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise is a spectacular 4 bedroom lakefront home that will quickly become host to your family’s favorite Deep Creek memories. From the moment that you begin pulling up to the home, you will embrace the charm of the serene tree lined drive. Offering over 4 acres of private lawn, outdoor enthusiasts...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    Make Enquiry
    5 Bedroom Immaculate Chalet with Dock Slip and Community Indoor Pool1 / 31
    (37)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • DVD Player
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2015
    We stayed at this location with 10 adults (5 couples) and it was perfect. For a group who loves to cook the kitchen was stocked with everything that was needed. The home felt...
    See all reviews
    About this property
    American Pride is an inviting 5 bedroom 3 bath chalet nestled among the trees in one of the most requested communities in Deep Creek Lake. A few steps into the home and you will find yourself entering into the elegantly decorated Great Room which features large cathedral ceilings, a massive stone...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Red Run 1A3 is an alluring 3 bedroom condominium located in the desirable Red Run Community. Summer days don't get better than this as you and your guests relish time spent swimming & playing from the nearby beach area or lounging lazily around the outdoor community swimming pool. Winter evenings...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Save time - get the best Oakland rentals sent straight to your email!
    Get the List
    List your property
    Owner log in