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Holiday Rentals and Homes in Oakland, MD

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    All 210 Rentals in Oakland
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    Travellers to Oakland are booking August dates now. Secure your holiday rental today, and have the perfect trip.
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    From
    €495
    / Night
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    1 / 11
    4.5 of 5 stars (5) Very good
    6 Bedrooms / 5 Bathrooms / Sleeps 14
    Overview Reviews (5) Make Enquiry
    From
    €1,265
    / Night
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    1 / 23
    5 of 5 stars (1) Excellent
    8 Bedrooms / 8 Bathrooms / Sleeps 26
    Overview Reviews (1) Make Enquiry
    From
    €425
    / Night
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    1 / 18
    4.5 of 5 stars (7) Very good
    5 Bedrooms / 5 Bathrooms / Sleeps 12
    Overview Reviews (7) Make Enquiry
    From
    €305
    / Night
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    1 / 17
    4.5 of 5 stars (2) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 12
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • DVD Player
    • Water Views
    • TV
    • Grill
    • Parking
    • Hot Tub
    • Fireplace
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Bedding: King, Queen, Queen, 2 Bunks with Twin Trundles Let the adventure begin! Mother Nature will astound when you choose to stay in the captivating lakefront home known as Summer Haven! Imagine relaxing on the expansive wraparound deck as you take in the phenomenal lake views! Amenities abound... View all property information
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    Location Information
    Oakland, Garrett County 21550
    From
    €350
    / Night
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    1 / 20
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • TV
    • Water Views
    • DVD Player
    • Fireplace
    • Grill
    • Hot Tub
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Bedding: Queen, King, Queen, 2 Twins, Queen Air Mattress Clear View is a spectacular 4 bedroom lakefront home that could easily be described as a “vacationer’s dream”. Showcasing 350 feet of phenomenal lakefront, you and your guests will be thrilled with all that this home has to offer. Gleaming... View all property information
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    Location Information
    Oakland, Garrett County 21550
    From
    €396
    / Night
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    1 / 16
    3.5 of 5 stars (2) Average
    5 Bedrooms / 4 Bathrooms / Sleeps 14
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • TV
    • Fireplace
    • Air Conditioning
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Bedding: King, King, King, Duobunk and Bunk, Duobunk and bunk, Queen Spectacular plush country views will mesmerize you with their splendor when you stay in the magnificent log home known as Log Mahal. This custom crafted 5 bedroom home will quickly win you over with it's unique style and decor.... View all property information
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    Location Information
    Oakland, Garrett County 21550
    From
    €269
    / Night
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    1 / 6
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Hot Tub
    • Parking
    • TV
    • Grill
    • Fireplace
    • DVD Player
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Bedding: King; Double; Double, 2 Twin Rollaways 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... View all property information
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    Location Information
    Oakland, Garrett County 21550
    From
    €282
    / Night
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    1 / 18
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Parking
    • Water Views
    • Fireplace
    • Grill
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Community: Stockslager Bedding: King, King, Queen, Queen Sleeper Sofa, 2 Twin Rollaways Prepare to be dazzled by the sophistication and grandeur that is Cedar Ridge. This alluring 3 bedroom split level lakefront is the perfect choice for the small family escape or for the couple’s retreat. Located... View all property information
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    Location Information
    Oakland, Garrett County 21550
    From
    €269
    / Night
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    1 / 12
    5 Bedrooms / 6 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Water Views
    • TV
    • Grill
    • Fireplace
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Community: Roman Ridge Bedding: King, King, Queen, 2 Doubles, Double, Double Futon Perched on a hillside overlooking Deep Creek Lake, this well-appointed home is the perfect starting point for a great vacation. Tasteful décor and a spacious layout create comfortable surroundings for your gathering... View all property information
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    Location Information
    Oakland, Garrett County 21550
    From
    €169
    / Night
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    1 / 8
    5 of 5 stars (4) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • TV
    • Grill
    • DVD Player
    • Fireplace
    • Shared Outdoor Pool...
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Community: Red Run Bedding: King, Queen, Bunk & Bunk Tucked in the western end of the lake, off a quiet cove, sits the Red Run Condominiums. This condo is equipped with a flat screen TV, a fully stocked kitchen, wood fireplace, and lake access with a dock slip. Not to mention the community access... View all property information
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    Location Information
    Oakland, Garrett County 21550
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