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Holiday Rentals near Circle R Ranch

4151 Sand Flat Rd, Oakland, Maryland 21550-7039
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    Travellers to Oakland are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    All 134 Rentals in Oakland
    Red Run Cabin1 / 30
    (30)Excellent
    2.0 miles from Circle R Ranch
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Mystic Haven: Lake Area, Hot Tub, Fire Pit, Pool Table, Fireplace!1 / 30
    (5)Average
    1.8 miles from Circle R Ranch
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    2.9 miles from Circle R Ranch
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    2.5 miles from Circle R Ranch
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
    5.7 miles from Circle R Ranch
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Say goodbye to ordinary and hello to extraordinary at Telstar.gon! Let the brig1 / 30
    (5)Average
    1.9 miles from Circle R Ranch
    6 Bedrooms, 6 Bathrooms, Sleeps 15 Quick View
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    • Skiing: Property Is In A Ski Resort
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    Oakland, Garrett County
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 15
    2.9 miles from Circle R Ranch
    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 14
    Lake Area Home w/Hot Tub, Fire Pit, Pool Table, & Wood Fireplace!1 / 30
    (5)Very good
    2.0 miles from Circle R Ranch
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
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    Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Bear Foot Cove: Split Lakefront, Dock Slip, Fire Pit, Hot Tub!1 / 30
    (3)Very good
    1.7 miles from Circle R Ranch
    5 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 14
    2.5 miles from Circle R Ranch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    Oakland, Garrett County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Where can you go to tuck away from the hustle and bustle of town, yet remain ju1 / 30
    (4)Excellent
    2.5 miles from Circle R Ranch
    7 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    • Hot Tub
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    • Sauna
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    Oakland, Garrett County
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 20
    2.1 miles from Circle R Ranch
    4 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 10
    Copper Canoe: Lakefront, Indoor Pool, Home Theater, Dock!1 / 30
    (8)Very good
    1.8 miles from Circle R Ranch
    6 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Waterfront
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    Oakland, Garrett County
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 20
    3.2 miles from Circle R Ranch
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
    2.5 miles from Circle R Ranch
    7 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Hot Tub
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    Oakland, Garrett County
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 20
    Tranquil Dreams: Lake Access, Hot Tub, Pool Table, Fire Pit, Fireplace1 / 30
    (3)Very good
    2.8 miles from Circle R Ranch
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Treat yourself to a stay at The Herrington and let the endless amenities of thi1 / 30
    (8)Very good
    5.1 miles from Circle R Ranch
    10 Bedrooms, 14 Bathrooms, Sleeps 34 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 10 Bedrooms, 14 Bathrooms, Sleeps 34
    Peaceful Lakefront !/Free WIFI/Wonderful Hot Tub!1 / 24
    (75)Excellent
    2.9 miles from Circle R Ranch
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2.8 miles from Circle R Ranch
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
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    Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    2.5 miles from Circle R Ranch
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Patio
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    Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    2.5 miles from Circle R Ranch
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Waterfront
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    Oakland, Garrett County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
    1.8 miles from Circle R Ranch
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
    OWLS NEST,Lakefront,Waterfront,Dock,HotTub,Kayaks,Paddleboards, Romantic Getaway1 / 30
    (182)Excellent
    2.9 miles from Circle R Ranch
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
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    Oakland, Garrett County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Dog-Friendly Country Cabin with Deck, Firepit & Air Hockey - Close to Yough1 / 30
    (66)Very good
    3.6 miles from Circle R Ranch
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Timroc II, FIVE STAR REVIEWS!  LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!1 / 30
    (4)Excellent
    2.5 miles from Circle R Ranch
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Grill
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    Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
    2.2 miles from Circle R Ranch
    2 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 10
    Divided Sky: Lake Area, Dogs Welcome, Hot Tub, Pool Table!1 / 30
    (9)Very good
    5.2 miles from Circle R Ranch
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Grill
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    Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
    Quiet, cozy, comfortable home at Deep Creek, Maryland1 / 14
    (4)Excellent
    1.9 miles from Circle R Ranch
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Quaint retreat w/ firepit, fully equipped kitchen, & easy access to trails!1 / 30
    (9)Very good
    3.6 miles from Circle R Ranch
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3.3 miles from Circle R Ranch
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    3.7 miles from Circle R Ranch
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Terrace
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    Oakland, Garrett County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Cedar Ridge: Conveniently located chalet w/ private outdoor hot tub1 / 30
    (57)Very good
    3.1 miles from Circle R Ranch
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Serenity Chalet: Dog Friendly Getaway Close to Activities1 / 30
    (5)Very good
    1.3 miles from Circle R Ranch
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Lakefront, Wooded, & Secluded Home - Family Dogs Welcome.1 / 30
    (10)Excellent
    2.8 miles from Circle R Ranch
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    2.0 miles from Circle R Ranch
    6 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 16
    Life Is Good: Lakefront, Private Dock, Hot Tub, A/C!1 / 30
    (1)Very good
    1.9 miles from Circle R Ranch
    4 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 14
    Spacious Chalet with Sunset Lake Views1 / 30
    (9)Excellent
    2.7 miles from Circle R Ranch
    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
    Private Retreat By Lake & Wisp-Firewood & CARC-Deck Firepl. & Hot Tub- FIVE STAR1 / 30
    (95)Excellent
    3.0 miles from Circle R Ranch
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
    Incredible Lakefront w/Spacious Deck1 / 30
    (57)Very good
    3.4 miles from Circle R Ranch
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
    Glistening Waters: Lakefront, Dock Slip, Hot Tub, Grill, Fire Pit!1 / 30
    (1)Very good
    2.7 miles from Circle R Ranch
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    1.9 miles from Circle R Ranch
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Scenic Deep Creek Getaway Cabin-RICK'S RETREAT1 / 30
    (1)Average
    1.0 miles from Circle R Ranch
    4 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 13
    2.6 miles from Circle R Ranch
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    2.7 miles from Circle R Ranch
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Location Information
    Oakland, Garrett County
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
    Spacious 4 bedroom home with phenomenal lakefront!1 / 30
    (35)Excellent
    1.8 miles from Circle R Ranch
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Location Information
    Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Getaway with 3 Master Suites & Covered Deck 5 Minutes from Activities!1 / 30
    (10)Very good
    1.8 miles from Circle R Ranch
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Location Information
    Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
    4.8 miles from Circle R Ranch
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Location Information
    Oakland, Garrett County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3.9 miles from Circle R Ranch
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Location Information
    Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    2.0 miles from Circle R Ranch
    5 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Location Information
    Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 14
    Spacious home with private dock close to Swallow Falls State Park1 / 30
    (8)Excellent
    2.4 miles from Circle R Ranch
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Location Information
    Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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