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Oakland Luxury Rentals

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    Travelers to Oakland are booking September dates now. Secure your vacation rental today, and have the perfect trip.
    15 Matching Rentals in OaklandView all 102 rentals
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    Price (High to low)
    Awesome View1 / 19
    (11)Average
    8 Bedrooms, 7 Bathrooms, Sleeps 24 Quick View
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    6 Bedrooms, 7 Bathrooms, Sleeps 25 Quick View
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    Journey's End1 / 36
    (8)Excellent
    8 Bedrooms, 9 Bathrooms, Sleeps 26 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Washer
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newer 2200-square-foot, custom, log cabin with three-sided wrap deck nestled on one+ acre in Deerfield off of Mayhew Inn Road. Beautiful trees and ferns with room to breath. Three miles from Swallows Falls, 2 miles to horseback riding stables and 5 miles to State Park Beach which has full water...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Private Yard
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our 2 year young chalet offers rustic charm, yet decorated for today! Close to docks and lake you will find nature & zen and plenty of land to romp and play. Fully stocked kitchen with linens provided, native stone fireplace, 4 bedrooms and 4 baths. Newly finished basement offers second tv, pool...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    Serendipity1 / 46
    (3)Average
    8 Bedrooms, 7 Bathrooms, Sleeps 22 Quick View
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    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...
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    Oakland, Garrett County 21550 
    Rental Home - 8 Bedrooms, 7 Bathrooms, Sleeps 22
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    Making Memories1 / 16
    (1)Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
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    Reviewed May 10, 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...
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    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,...
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    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    *Secluded & Quiet UNIQUE OUTSIDE FIREPLACE *XL HOT TUB*Pool Table-5 Star QUALITY1 / 56
    (5)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
    other traveler has booked this property
    Even more relaxing was sitting in the hot tub watching snow cover the lush pine trees in the back.
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    Amenities & Details
    • Hot Tub
    • Housekeeping Included
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 17, 2018
    Looking for a weekend getaway with my friends, we stumbled upon this quaint mountain escape. We were all looking forward to weekend where we did not have to leave the house for...
    Reviewed January 1, 2018
    Fabulous accommodation. Has everything - outdoor fireplace, big porches, granite kitchen counters, water filter, sleeps around 12 or so, pool table, heated downstairs floor...
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    About this property
    Architecturally pleasing to the eye and the soul, this UNIQUE AND GORGEOUS 'GREEN HOME' boasts a 31' great room ceiling with 2 INTERIOR and 1 EXTERIOR (on deck) WOOD BURNING STACKED STONE FIREPLACES (also 31' tall) plus LARGE HOT TUB ON DECK and LARGE FIRE PIT in back yard. This serene gem backs to...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Patio
    • Housekeeping Included
    • Central Heating
    • Washer
    • Hot Tub
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your mountain vacation will be filled with magical memories when you choose to stay in this spectacular 3 master suite bedroom log home. You and your guests will immediately feel at home when you step through the front door. Luxurious décor compliments the gorgeous hardwood floors giving the...
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    Oakland, Garrett County 21550
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Waterfront Chateau1 / 14
    (4)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    • Internet Access
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    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...
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    Location Information
    Oakland, Garrett County 21550 
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 20
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • Internet Access
    • Cable/satellite TV
    • Grill
    • Patio
    • Hot Tub
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book your next vacation in Oakland at this gorgeous lakefront condo, featuring a private hot tub overlooking the water and two gas fireplaces. The balcony offers beautiful views of Deep Creek Lake, and there's a dock for easy access to the water. In the evening, gather around the outdoor firepit...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Unreel1 / 55
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unwind in Unreel! This lovely lakefront home boasts the perfect location for four-season fun! A Signature Collection home! This beautiful log chalet offers the charm and aesthetic appeal of yesteryear alongside all the contemporary comforts you'd expect in a luxury lake retreat. Pamper yourself...
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    Location Information
    Oakland, Garrett County 21550 
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    Special Last Minute Summer Rates! Stay At Our Wonderful Upscale Cabin!1 / 14
    (3)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Air Conditioning
    • Mountain Views
    • Washer
    • Hot Tub
    • Cable/satellite TV
    • Porch
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 25, 2017
    Had a great time at the cabin! Very clean, peaceful, and relaxing! We would love to stay again! We are talking about going in the winter when we can use the fireplace. The...
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    About this property
    Our log home is situated on our private 1.5 acre lot so as to capture the best views of farm land and mountains. Enjoy your own peaceful getaway knowing that all lake and sport activities are just minutes away. We designed our cabin with comfort in mind--the first floor includes an inviting great...
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    Location Information
    Oakland, Garrett County 21550
    Cabin - 3 Bedrooms, 4 Bathrooms, Sleeps 9
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    Red Run Cabin1 / 22
    (28)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Great place, nice hot tub!
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    Amenities & Details
    • Washer
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 7, 2018
    Had a wonderful time. Very peaceful and serene. The house is beatifully done and very homey. The pictures dont do it justice. Only downfall was it rained most of our stay...
    Reviewed October 11, 2017
    Great location, fantastic cabin, great weather for our trip - cool nights and mornings - perfect for walking our dog. We had a great time visiting the neighborhood and several...
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    About this property
    Red Run Cabin is a 1 story 3 bedroom cottage with a finished basement on an acre wooded lot near the west end of Deep Creek Lake, accomodating up to 6 people. It has lake access through the Red Run Restaurant property leading to a sandy beach and shallow lake bottom far out into the lake, making...
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    Location Information
    Oakland, Garrett County 21550
    Cabin - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bear Foot Cove1 / 18
    (1)Very good
    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 9, 2015
    Bear Foot Cove is a fairly new rental in Deep Creek Lake. It is an easy drive to the ski slopes that are 9 miles away. The home is layed out well so 12 people had a places to...
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    About this property
    The tall ceilings, modern upgrades, and open layout of Bear Foot Cove make for great gatherings! This new construction will wow you at every turn! Located along a quiet cove, your private dock is just a short walk away; all you have to do is stroll across the street and you're there! Bear Foot...
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    Location Information
    Oakland, Garrett County 21550
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 14
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