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.

Pet Friendly Holiday Rentals in Oakland

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
    R 2 020 Average
    |||
    |||
    R 0R 15 000+
    Suitability
    More filters
    Travellers to Oakland are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    27 Matching Rentals in OaklandView all 100 rentals
    Sort by:
    Default
    Red Run Cabin1 / 44
    (28)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Special Last Minute Summer Rates! Stay At Our Wonderful Upscale Cabin!1 / 14
    (3)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Hemlock Chalet1 / 15
    (5)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Serendipity1 / 46
    (3)Average
    8 Bedrooms, 7 Bathrooms, Sleeps 22 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Serendipity! This splendid lake house showcases a sunlit interior, level lakefront, and large deck! Bursting with promise, Serendipity is a vacation retreat unlike anything you have ever seen! Come in, take a look around, and let amazement take hold; every corner of this magnificent lake estate is...
    View all property information
    Location Information
    21550 , Oakland, Garrett County
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 22
    Make Enquiry
    Linwood1 / 36
    (7)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The traditional comforts and community amenities at Linwood make for proven vacation bliss! Let Linwood take your spirit to a place where everyday concerns are left behind and relaxation and felicity can take hold, unchecked and unencumbered. With tree covered lot, nearby lake access, and...
    View all property information
    Location Information
    21550 , Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Creature Comforts1 / 20
    (9)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The modern and stylish touches of Creature Comforts make this home the envy of all others! Don't miss the comforting splendor of this fabulous lakefront resort home! Creature Comforts promises to provide a series of little luxuries and patent charms guaranteed to make you feel relaxed and warm....
    View all property information
    Location Information
    21550 , Oakland, Garrett County
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 16
    Make Enquiry
    Just Breathe Inn1 / 18
    (2)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Immerse in nature! Life is unspoiled and unforgettable at the lakefront of Just Breathe Inn! Leisure time is perfected at Just Breathe Inn! Spellbinding and spectacular, this lakefront chalet is rich with charm. You'll feel rested and ready for adventure when you take in a morning sunrise from the...
    View all property information
    Location Information
    21550 , Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Making Memories1 / 16
    (1)Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 May 2016
    I stayed here back in January with a group of close friends and family and we were so impressed with this house. It is even more beautiful in person than the photos. The layout...
    See all reviews
    About this property
    Refined elegance meets lakefront living at Making Memories! This exquisite home is a sure thing! This beautiful lake home delivers one warm welcome! From the moment you arrive, this home will surround you in an easy elegance for perfection that feels effortless. With a natural stone fireplace,...
    View all property information
    Location Information
    21550, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
    Make Enquiry
    Willow Point1 / 14
    (11)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Mountain Views
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Waterfront
    • Housekeeping Included
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 May 2014
    The location was great, just what we wanted for our lab puppy. Nice big yard going right to the water. The hot tub was great because it was a bit chilly. The house itself is a...
    See all reviews
    About this property
    You'll love the setting of Willow Point, a cozy cottage with sprawling lakefront and classic appeal! Willow Point is a wonder! Fill your days with soft winds and crystal waters at this charming lakefront stone cottage. The delightful décor and exquisite lakefront add together to build a wonderland...
    View all property information
    Location Information
    21550 , Oakland, Garrett County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Washer
    • Internet Access
    • Grill
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious enough for a family reunion or a truly memorable holiday celebration, this warm and welcoming cabin in the woods comes with a well-appointed deck and a covered patio with a forest view, an outdoor hot tub, wood-burning fireplace, pool table, and a romantic, in-room Jacuzzi. Up to 10 guests...
    View all property information
    Location Information
    21550, Oakland, Garrett County
    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
    LinLaurAl1 / 13
    (4)Average
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    LinLaurAl is a charming and private pastoral oasis that includes a level lakefront among tall trees! LinLaurAl is a five-bedroom Deep Creek vacation rental with something for the whole family! Featuring 600 feet of level lakefront and plenty of privacy, this charming home is the perfect lakefront...
    View all property information
    Location Information
    21550 , Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    Bunbury Cottage1 / 70
    (3)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rustic and warm, Bunbury Cottage is a charming Lincoln-lodge style home with lots to offer! Want to try and solve a vacation riddle? What's charming and irresistible, immensely private, with 2 streams running on either side, and guaranteed to refresh your spirit? Here's a hint: it's tucked away...
    View all property information
    Location Information
    21550, Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Cedar Lodge1 / 20
    (15)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 February 2017
    Very nice Layout!! Big open spaces, kitchen extensively equipped. Great location. Only negatives are the beds (all off them) were quite uncomfortable... we actually all...
    Reviewed 15 August 2014
    Our family, 2 adults and 3 children (12, 15 and 17) plus Snow Lab, Luie enjoyed this spacious 4 bedroom home. Great hot tub. Saw many deer in the wooded backyard. Short walk...
    See all reviews
    About this property
    Community perks- like the tennis courts and community docks- are yours to enjoy at Cedar Lodge! Nestled among the tall oaks and maples of the surrounding forest, Cedar Lodge offers privacy and seclusion along with the fun and excitement of a lake vacation. You'll love the convenience of having the...
    View all property information
    Location Information
    21550 , Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    Amazing Love1 / 12
    (5)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The dramatic wood ceilings and warm décor of Amazing Love make for vacation perfection! Looking for the ultimate vacation experience? Amazing Love has you covered! This five-bedroom vacation rental was recently remodeled and features a host of fantastic amenities, including an air hockey table,...
    View all property information
    Location Information
    21550, Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
    Make Enquiry
    Waterfront Chateau1 / 14
    (4)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront Chateau delights with a tranquil wooded setting, charming lakefront, and sunny interior! The discriminating guest will appreciate this luxurious lakefront home! Waterfront Chateau is the ultimate rendezvous destination for a getaway among family and friends. Located on a dead end street...
    View all property information
    Location Information
    21550 , Oakland, Garrett County
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 20
    Make Enquiry
    6 Bedrooms, 7 Bathrooms, Sleeps 25 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Patio
    • Internet Access
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Hot Tub
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious Oakland home is the perfect choice for your next large family gathering. It accommodates up to 25 guests and offers a high-end yet comfortable home base with amenities like two hot tubs, a game room, a dock with your very own slip, and much more! Come live the good life, and bring...
    View all property information
    Location Information
    21550, Oakland, Garrett County
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 25
    Make Enquiry
    Morning Breeze1 / 21
    (9)Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wide open spaces await you at Morning Breeze! This lakefront home gives you a taste of the good life! Located along the banks of sparkling Deep Creek Lake, Morning Breeze is the perfect spot for your next family vacation! The great room boasts a warm stone fireplace, as well as cathedral ceilings,...
    View all property information
    Location Information
    21550, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Always in Season1 / 13
    (8)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come sun or snow, this home is “Always in Season!” Celebrate the seasons at this lakefront home! The seasons have never been more beautiful than at Always in Season! Sunbathe and water ski in the warm summer months, celebrate fall with a hike through bright leaves, patter gently through pristine...
    View all property information
    Location Information
    21550 , Oakland, Garrett County
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    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
    • Parking
    • Grill
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    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 an...
    View all property information
    Location Information
    21550, Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Patio
    • Parking
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring the whole family together at this chalet-style Oakland home, complete with a game room, two furnished patios, and a private hot tub. The family dogs are also welcome for a small nightly fee! Just up the road, Deep Creek Lake is an exceptional fishing destination, so don't forget your bait...
    View all property information
    Location Information
    21550, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Paradise Lodge1 / 22
    (4)Average
    5 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Some of the best lake views can be found at Paradise Lodge! This home is full of timeless appeal! Enjoy fresh mountain air, tall trees, and stunning lakefront views at Paradise Lodge. This classic lodge-style lake home offers seclusion and privacy, yet boasts a location close to many stores,...
    View all property information
    Location Information
    21550 , Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 15
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Waterfront
    • Patio
    • Washer
    • Internet Access
    • Parking
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tranquil lakes and quiet forests await when you book a stay at this spacious, dog-friendly Deep Creek cabin. Fashioned with a wraparound porch, a private dock, and spectacular lakefront views, this charming home offers a unique sense of seclusion and relaxation. The house is perched on the banks...
    View all property information
    Location Information
    21550, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    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
    • Internet Access
    • Parking
    • Grill
    • Washer
    • Cable/satellite TV
    • Patio
    • Waterfront
    • DVD Player
    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
    21550, Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Awesome View1 / 19
    (11)Average
    8 Bedrooms, 7 Bathrooms, Sleeps 24 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Awesome View is the perfect place to swim, stay, and play! The indoor pool always delights! Get it all at Awesome View! Just beyond the tree line of this magnificent estate, get ready for a very special treat: sweeping, panoramic views of Deep Creek envelop you from the home's private dock. This...
    View all property information
    Location Information
    21550 , Oakland, Garrett County
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 24
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Hot Tub
    • Patio
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With a name that means 'nest' in Farsi, this welcoming and dog-friendly lake house will delight you from the outside in. Marvel at the partial lake views as you cook out on the deck's charcoal grill or soak your cares away in the private hot tub. The whole family is sure to love their stay here!...
    View all property information
    Location Information
    21550, Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • DVD Player
    • Patio
    • Internet Access
    • Hot Tub
    • 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
    21550, Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Washer
    • Air Conditioning
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy your next family vacation near the shore of beautiful Deep Creek Lake at this dog-friendly, well-appointed home in the woods complete with a furnished deck, a gas grill, and plenty of space for up to eight guests. This home is conveniently close to Garrett Highway for easy access to nearby...
    View all property information
    Location Information
    21550, Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    List your property
    Owner log in