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 Cheap Vacation Rental Deals

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
    Location
    Any Distance
    from
    Price
    per night
    C$176 Average
    |||
    |||
    C$0C$1,000+
    Suitability
    More filters
    Travellers to Oakland are booking February dates now. Secure your vacation rental today, and have the perfect trip.
    32 Matching Rentals in OaklandView all 129 rentals
    Sort by:
    Price (Low to high)
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Known for its spacious common areas, sandy beach and quiet cove location, Four Hooppole is a favorite lakefront community that offers ten acres of level manicured lawn and a fantastic swimming area. The main level of this well-appointed townhome features a spacious great room with lake views and...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get the much deserved break that you crave when you stay at Bear Paws. This charming log cabin pairs total comfort with a convenient location! Featuring an open floorplan, the spacious main level is highlighted by vaulted ceilings and polished hardwood floors. Bear themed décor adds a playful...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Check out this really cool townhome at Four Hooppole on the shores of Deep Creek Lake! The community offers around 10 acres of level manicured yard, community tennis court, community basketball court, playground, and one of the only sandy beaches with a roped off swimming area for your safety and...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Washer
    • DVD Player
    • Central Heating
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the pleasures of country living at this three-bedroom Oakland home, a dog-friendly Maryland escape with a private deck and firepit, its very own air hockey table, and a wondrous location close to Swallow Falls, the Yough River, and Deep Creek Lake. This two-level cabin is located on...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Home Sweet Cabin is a charismatic mountain home that rests in a quiet, peaceful cove. Expansive wooden cathedral ceilings highlight the stone fireplace and gives promises of nights spent bonding with family and friends. The open floor plan allows you to entertain your guests while preparing the...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore, relax and take a well-deserved break at Deep Breath! Convenient to area activities and attractions, it is the perfect home base for your Deep Creek Lake vacation. The spacious interior of this Craftsman-style home is brimming with attention to detail. Upon entering, a dual sided gas...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Prepare to be swept away by the majesty that is Overlook Point. Creature comforts surround you in the Great Room with expansive cathedral ceilings, bright open window and lustrous hardwood floors. Add in the addition of a cozy stone, gas fireplace, plush leather furnishings and a large flat screen...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Save time - get the best Oakland rentals sent straight to your email!
    Get the List
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A lifetime of family memories is just a phone call away when you choose to stay in the lovely 3 bedroom chalet known as Timber Trails. Truly a get away from it all home, you will love the private and peaceful setting while cherishing your close proximity to Oakland, Wisp Resort, and area shopping...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let the adventure begin! Sunset Reflections is a cheerful 3 bedroom lakefront home that will allow you to experience a true Deep Creek getaway! The beautifully decorated Great Room is enhanced with cathedral style ceilings, an impressive stacked stone fireplace and floor to ceiling windows which...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brimming with charm, By the Stream is Deep Creek Lake area vacation home that is ready to host your next getaway! So close to it all, yet just far enough away, you will love the wooded location that's just around the corner from Wisp Resort. Enter the roomy main level to discover lots of living...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome Home Friends! Paradise at Penn Cove is a captivating 3 bedroom chalet that rests on quiet road overlooking Penn Cove. Upon entrance you will immediately feel the warm and cozy atmosphere of the Great Room. Expansive vaulted ceilings, floor to ceiling windows, and an immense stone stacked...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Prepare yourself for a relaxing getaway when choose Bear Feet as your vacation getaway. Exploding with charm, this 3 bedroom townhome will easily beckon you to return time and time again. Step inside and appreciate the open floor plan and the wall of windows that boast extraordinary lake views....
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Conveniently located, yet off the beaten path, these Yellowstone Log Cabins (Property #s 359, 360, 365, and 367) offer cozy, quaint, and comfortable accommodations! All cabins are situated closely enough to one another for ideal couple retreats or single family getaways while offering a quiet...
    View all property information
    Location Information
    Oakland, Garrett County 21541
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you want a classic Deep Creek Lake vacation with convenient lake access, look no further than Lakeview Cottage. This A-frame style home is ideal for a family getaway or a couples' trip. Wood-lined walls create a warm ambiance in the great room, and a wall of windows lets in lots of natural light...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hidden from view, a true Treasure of the mountains awaits. This charming cabin is nestled amongst a soaring canopy of trees at Deep Creek Lake. Hidden Treasure features cozy comfort with all the extra amenities. As an added bonus, you can bring your dog on vacation too! Relax in the great room by...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Dog-friendly, lakefront log home on a quiet cove - front deck & shared dock1 / 41
    (1)Terrible
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Grill
    • Patio
    • DVD Player
    • Waterfront
    • Washer
    • Central Heating
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Head to Deep Creek Lake for a quiet vacation with family and friends, complete with all the conveniences that comes with being close to town. Your group will have ready access to the lake and the slopes, as well as in-town convenience. And to make your getaway complete, you can bring the family dog...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Ski Solitude1 / 30
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Parking
    • Grill
    • Central Heating
    • Cable/satellite TV
    • Patio
    • Mountain Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 12, 2018
    Had a very good stay in Captivating Cabin. My two concerns with any rental were swiftly taken care of, comfortable sofas and comfortable bed! Kitchen had good cookware and a...
    Reviewed August 7, 2018
    Cabin was very relaxing and comfortable. The grandchildren enjoyed the fire pit making smores. It was fully stocked with everything you would need.
    See all reviews
    About this property
    Classic lake cabin totally updated 2017! three bedroom two bath cabin that sits back from the road with plenty of parking . Cabin is situated on one acre of wooded grounds surrounded by large boulders and a pond. The stately stone fireplace is the centerpiece of this home. The soaring ceiling in...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the beauty of Deep Creek Lake at Fox Den, a charming A-frame cottage that offers a treasured chance to unwind. Both romance-seekers and those in pursuit of inner peace will relish time spent at this classic mountain getaway. Highlighted by a wall of windows, wood accents, tasteful decor...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Craftsman-style details, tasteful décor and a central location make Just Relax the perfect choice when you want to unwind at Deep Creek Lake. Step inside, and the first thing you will notice is the open floorplan that is ideal for entertaining. Natural light reflects off of gleaming hardwood floors...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in the woods, Hideaway is an adorable A-frame mountain chalet that is the perfect getaway for a small family or a couple's retreat. Recently renovated, this home offers a cozy Great Room with stylish furnishing and glistening hardwood floors. Family time will be spent watching your favorite...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of it all, Arrowhead 15 is the perfect choice for a family vacation or a Deep Creek Lake getaway with friends. You will love being able to walk to restaurants, a full-service market, the movie theater and nightlife! Easy lake access and lots of community outdoor space is a true...
    View all property information
    Location Information
    Oakland, Garrett County 21565
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The woodsy charms of Western Maryland are all around you at this three-bedroom, 1,100 sq. ft., Oakland cabin, an atmospheric escape on the shores of Deep Creek Lake with a waterfront dock and firepit, an expansive deck, and a private hot tub for soothing soaks among the trees. This cabin sits...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Changed to: 'Canaima' is the name of the friendly spirit of the jungles of Venezuela and Brazil. It is also the site of the novel 'The Lost World' by Arthur Conan Doyle and the location of the 'Green Mansions', the place where Rima lived, in the beloved novel of William Hudson. Our cabin carries...
    View all property information
    Location Information
    Oakland, Garrett County 21541
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Once starting your vacation at Beardise, you will want time to stand still to enjoy the many pleasures at Deep Creek Lake along with the view. This home offers the ultimate peaceful, easy feeling that will your stress from scheduled living to surrender! The only schedule needed is enjoying your...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tucked among towering trees, Knotty Pines offers you a classic mountain getaway with lots of opportunities to make lasting memories with your favorite people. Tastefully decorated, the great room will be a popular place to gather whether you are curling up on the sectional sofa to watch TV or...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the popular Blakeslee Community, Blue Waters is the perfect starting point for a great Deep Creek Lake vacation! Surrounded by a level lawn that is dotted with trees, you will love having outdoor space where the kids can run and play while staying within your sight as you relax on the...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Conveniently located, yet off the beaten path, these Yellowstone Log Cabins offer cozy, quaint, and comfortable accommodations! All cabins are situated closely enough to one another for ideal couple retreats or single family getaways while offering a quiet wooded setting. Lured Away offers an...
    View all property information
    Location Information
    Oakland, Garrett County 21541
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Washer
    • DVD Player
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make this lovely, lakefront rental your home away from home when you come to Deep Creek Lake and enjoy amenities like a hot tub, a dock with your own assigned slip, and shared tennis. You'll have the best of both worlds with easy access to the slopes and in-town conveniences. The family dog is also...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Memory Lane is a home designed to bring friends and family together for fun and laughter. Tucked among gracious, blossomed trees with a meticulously maintained lawn, you will truly feel like you have discovered your mountain oasis. Gather with loved ones in the Great Room where you can enjoy your...
    View all property information
    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Make Enquiry
    List your property
    Owner log in