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Oakland Cheap Vacation Rental Deals

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    Travellers to Oakland are booking September dates now. Secure your vacation rental today, and have the perfect trip.
    25 Matching Rentals in OaklandView all 100 rentals
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    Mountaineer1 / 20
    (6)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Linwood1 / 18
    (7)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lakeshore Breeze1 / 29
    (1)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Papa Bear1 / 11
    (11)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Pet friendly
    Kid friendly
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    About this property
    Colorful walls and accents prevail at Papa Bear- a cute home situated in central Deep Creek! Papa Bear is one enchanting cottage! With bright and cheerful interior stylings, nearby lake access, and charming decorative touches, this home will make you want to stay forever! You will love relaxing...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    Triple-T Lodge1 / 10
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Triple-T Lodge feels just like home, located a short distance from all of Deep Creek's hot spots! Triple-T Lodge offers everything you need for a picture-perfect Deep Creek Lake vacation! Located in the charming Silver Ridge Community, this home is located in central Deep Creek, making it easy to...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Dream On1 / 12
    (10)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Reviewed March 12, 2018
    This home hosted a annual visit to the Deep Creek lake area for the last 6 years. There were 5 couples 40 and over. On initial glimpse all looked nice. The cushions on both...
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    Dream On is rich with contemporary charm! This newly built duplex is a vacationer's haven! A real crowd pleaser, Dream On is a modern duplex that creates a unique vacation haven for any gathering. Professional décor, warm earth tone stylings, a gourmet kitchen and 7 flat screen TV's are just a few...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Bella Vista1 / 17
    (3)Average
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    About this property
    Gorgeous lake views, private dock, and central location: it doesn't get better than Bella Vista! The newly updated Bella Vista is the ideal 5-bedroom vacation destination. Offering an exclusive view of picturesque Deep Creek Lake from the two-level deck, this custom-built lakefront cabin allows...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    About this property
    Lake It Easy! Updated and spacious, this charming home boasts a great central location at the lake! This beautiful townhome will make your next Deep Creek Lake getaway a memorable one! The comfortable furnishings and stylish decor fuse to create a ‘home away from home' with three levels of...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    Hemlock Chalet1 / 15
    (5)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    About this property
    At shaded and secluded Hemlock Chalet, you'll find a perfect fusion of nature and homey comforts! Hemlock Chalet is a hit! Located in the prestigious Blakeslee community, this marvelous chalet offers your favorite amenities and all the little luxuries you are looking for in a vacation retreat....
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    Oakland, Garrett County 21550 
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 12
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    Just Breathe Inn1 / 18
    (2)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    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...
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    Location Information
    Oakland, Garrett County 21550 
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Harmony1 / 35
    (6)Average
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    At Harmony, the cozy comforts, lake views, and spacious rooms make it easy to find your zen! This lakefront home is something special! Complete with elegant furnishings and décor- along with picture perfect lake views- Harmony provides indoor comforts and outdoor delights. Come together in the...
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    Location Information
    Oakland, Garrett County 21550 
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Tranquil Dreams1 / 17
    (4)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
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    About this property
    With natural foliage all around, Tranquil Dreams is a rustic delight with super close lake access! You can rest easy knowing that vacation perfection is assured at Tranquil Dreams! Your stay is destined to be restful at this four-bedroom chalet, situated along a quiet wooded finger of the lake....
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    Location Information
    Oakland, Garrett County 21550 
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Wispering Ridge1 / 8
    (4)Average
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Reviewed January 3, 2017
    We stayed at Wispering Ridge in Oakland Maryland for our annual NYE trip to Deep Creek Lake. We had a group of 6 so we needed a smaller place. Pros:- Gorgeous view- Well...
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    About this property
    When you come to stay at Wispering Ridge, you get the best in both convenience and comfort! Come away to a quiet retreat! Wispering Ridge is the perfect getaway for your small family getaway or a reunion among close friends. This duplex proves that you don't have to be large to have an...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Willow Point1 / 14
    (11)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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 May 27, 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...
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    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...
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    Location Information
    Oakland, Garrett County 21550 
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Baldwins Domain1 / 12
    (3)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    With community perks and tranquil wooded setting, serenity can always be found at Baldwin's Domain! Pure mountain air mixes with comforting home-style touches at Baldwin's Domain to create an appealing signature aesthetic. Catch the view from the sunny living room and stay warm beside the home's...
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    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Edgewater1 / 17
    (8)Average
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Pet friendly
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    About this property
    Edgewater is your own private oasis! You'll love the hot tub overlooking quiet cove waters! For lakefront living full of perks, look no further than Edgewater. When you book a stay at this three-level family home, you get five bedrooms, four bathrooms, and the home's peaceful wooded setting all to...
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    Location Information
    Oakland, Garrett County 21550 
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Cedar Lodge1 / 20
    (15)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    Reviewed February 26, 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 August 15, 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...
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    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...
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    Location Information
    Oakland, Garrett County 21550 
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Crosswinds1 / 12
    (9)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Pet friendly
    Kid friendly
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    Reviewed February 25, 2016
    I stayed at Crosswinds for two nights this month with a group of 10 people. The house was very nice, cozy but not small, and had all the amenities as advertised. The kitchen was...
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    About this property
    Crosswinds combines an ideal location with the right blend of comfort, style, and convenience! Outside or in, Crosswinds is the ideal choice for your next Deep Creek Lake vacation! Within a short walk from the home's front door, you'll have easy access to the home's lake access point - including a...
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    Location Information
    Oakland, Garrett County 21550 
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Glistening Waters1 / 14
    (3)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    About this property
    Where can you revel in the ambiance of wood fires and water views? Glistening Waters, that's where! Tucked away along a quiet corner of the lake, Glistening Waters is everything you would expect- and more! The lake is never brighter and more beautiful than from the shores of this charming lake...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Bunbury Cottage1 / 35
    (3)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    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...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Arctic Retreat1 / 13
    (5)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Arctic Retreat is one tranquil oasis! Embrace the wild and restless energy of this wooded retreat! Perched quietly along the back deck of Arctic Retreat, watch as the splendor of nature comes to life with an early dawn. See the deer trailing along the fringes of the forest, wild turkey, rabbits,...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Hilltop Happy Hour1 / 23
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Reviewed November 9, 2016
    This house is wonderful, very spacious with a lovely lake view. The photos in the listing don't do it justice. It has three living/sleeping levels, plus a loft, which was...
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    Raise a glass to Hilltop Happy Hour and its splendid views, modern upgrades, and convenient location! Convenience and luxury converge at Hilltop Happy Hour! The bright and spacious interior provides a comfortable oasis to rest the head and mend the spirit, readying you for all the action and...
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Home on the Ridge is a sweet and spacious dwelling with breathtaking mountain-lake views! Looking for a comfortable roost to rest the head? Someplace bright and cheery where relaxation and rejuvenation can take hold? Look no further than Home on the Ridge! Perched atop a quiet wooded community,...
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Log Heaven1 / 12
    (1)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Log Heaven was crafted for comfort! This ‘mountain chic' hideaway is rich with rustic-style warmth! Looking for a quiet wooded retreat? Log Heaven wraps you in nature's comforting embrace with the rich and rustic charm found throughout the space. One master suite and 3 additional bedrooms give...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Paradise Lodge1 / 22
    (4)Average
    5 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
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    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,...
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    Oakland, Garrett County 21550 
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 15
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