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    Travellers to Oakland are booking December dates now. Secure your holiday home today, and have the perfect trip.
    262 Matching Rentals in OaklandView all 337 rentals
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    State Park And Swallow Falls Only 5 - 10 Minutes Away, Walking Distance To JG’S1 / 28
    (43)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lovin Life Deep Creek 5 Bedroom Luxury Log Home w/ Pool Table & Hot Tub1 / 24
    (19)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village1 / 33
    (155)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Peaceful Lakefront !/Free WIFI/Wonderful Hot Tub!1 / 24
    (40)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    OWLS NEST,Cozy Cabin,Premiere Lake Waterfront,private dock,wHotTub&Linens1 / 34
    (64)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    January through April -Early Check In - Late Check out -pets considered1 / 24
    (30)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek1 / 38
    (84)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    5 bedroom, 5 full bathroom suites, minutes from WISP mountain and the lake1 / 24
    (9)Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 15 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 15
    Centrally located Craftsman home close to DCL state park!1 / 26
    (27)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Centrally located, tastefully decorated townhome!1 / 40
    (28)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Luxury log home in a central location!1 / 29
    (25)Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
    Beautiful,  Charming Lakefront Cabin With Stunning Views, Private Dock, Kayaks.1 / 26
    (82)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
    Close to DCL state park, large yard, great outdoor space!1 / 30
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Spacious townhome - 5 minutes from favorite activities & restaurants!1 / 38
    (48)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    If you're looking to retreat to the privacy of the woods, Blue Spruce is perfec1 / 29
    (6)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    5BR - Family-friendly, Wood Fireplace, Dock Slip, Park Pass, Hot Tub, near WISP1 / 38
    (15)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Skiing: Property Is In A Ski Resort
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
    Lakefront home with 5 masters & private dock!1 / 50
    (15)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 18
    Dog-friendly country cabin w/ deck, firepit & air hockey - close to Yough River!1 / 45
    (36)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Family- and dog-friendly home w/ deck, forest view - close to lake & ski slopes1 / 32
    (43)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Astounding & secluded mountain chalet with lake views!1 / 39
    (60)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    5 Bedroom Immaculate Chalet with Dock Slip and Community Indoor Pool1 / 46
    (160)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
    Spacious Chalet with Sunset Lake Views1 / 42
    (18)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
    Brand New Home, 4 Master Suites, Outdoor Kitchen with Pizza Oven!1 / 48
    (6)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
    3 bedroom log home in central DCL, dog friendly, indoor hot tub!1 / 50
    (29)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Combines a central location with stylish decor!1 / 36
    (12)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 14
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Looking for a picture-perfect cabin retreat? Designed with relaxation in mind,1 / 25
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Breath Taking Views, Lake Access, Modern Chalet1 / 28
    (61)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Sisters Treehouse1 / 22
    (24)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
    FIVE STAR REVIEWS! Enjoy the bold colors of FALL! Book Ski weekends!1 / 50
    (25)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    5BR lakefront Cottage.  Almost Heaven offers a true family retreat at Deep Creek1 / 41
    (11)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
    Walking distance to restaurants, 5 minutes from DCL State Park!1 / 36
    (7)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Wonderful 5 Bedroom Lakefront home with outdoor hot tub & private dock!1 / 43
    (55)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
    Adorable Chalet in peaceful setting with multiple game tables!1 / 28
    (46)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Charming, Dog Friendly A-Frame Close to Activities!1 / 38
    (22)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Classic and comfortable, Triple-T Lodge is every bit as welcoming as your own h1 / 32
    (9)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Oakland, Garrett County 21550 
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Peppered with warm mountain ambiance and delightful accents, Little Bear’s Den1 / 26
    (9)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Chalet with Private Dock & Central Location1 / 28
    (11)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
    Warm & Cozy 4 Bedroom Log Home w/ elegant furnishings in private setting!1 / 38
    (86)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Lakefront, dog-friendly home w/ hot tubs, game room, dock & space for 25!1 / 47
    (51)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 25 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 25
    Lake access chalet-style home w/ 2 furnished patios, & private hot tub - dogs OK1 / 50
    (15)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Captivating 2 Bedroom cottage with hot tub offers amazing river access!1 / 35
    (131)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Adorable Pet Friendly Family Home with Hot Tub1 / 42
    (24)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Bearadise: Lake Access Home with Large Yard1 / 33
    (18)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
    Gorgeous 7 Bedroom Central-Lake w/Dock Slip; Beautiful Sunrises from the Deck1 / 48
    (111)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    Oakland, Garrett County 21550
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 18
    Spacious home w/convenient location & hot tub, near lake & dining1 / 49
    (9)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Location Information
    Oakland, Garrett County 21550
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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