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Holiday Rentals near Circle R Ranch

4151 Sand Flat Rd, Oakland, Maryland 21550-7039
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    100 Matching Rentals in the Oakland AreaView all 119 rentals
    Red Run Cabin1 / 22
    (29)Excellent
    Oakland
    3.3 kilometres from Circle R Ranch
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    At Last1 / 55
    (5)Excellent
    Oakland
    3.6 kilometres from Circle R Ranch
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Oh, give me a home with room there to roam! Home on the Ridge is a sweet and sp1 / 42
    (1)Excellent
    Oakland
    2.2 kilometres from Circle R Ranch
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    A304- Studio & Loft suite w/ standard view, has fireplace & private balcony!1 / 22
    (1)Excellent
    Oakland
    3.6 kilometres from Circle R Ranch
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Oakland, Garrett County
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
    Split Lakefront Home w/Dock Slip, Hot Tub, Fire Pit, & Gazebo!1 / 38
    (8)Very good
    Oakland
    2.7 kilometres from Circle R Ranch
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Oakland
    3.6 kilometres from Circle R Ranch
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Lake Access Home w/Hot Tub, Central A/C, & 2 Gas Fireplaces!1 / 45
    (1)Excellent
    Oakland
    2.5 kilometres from Circle R Ranch
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Oakland
    3.6 kilometres from Circle R Ranch
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Oakland, Garrett County
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Oakland
    3.9 kilometres from Circle R Ranch
    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
    Oakland
    5.3 kilometres from Circle R Ranch
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    Oakland
    4.0 kilometres from Circle R Ranch
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Location Information
    Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Oakland
    4.0 kilometres from Circle R Ranch
    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
    Oakland
    5.3 kilometres from Circle R Ranch
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
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    Bobsled Townhouse #102 Make the most of your family trip to Park City at Bobsled Townhome and create wonderful and wholesome memories that will last a lifetime! Turn on the fireplace to warm the living room while watching your favorite movie on the flatscreen TV. The kitchen is fully equipped to...
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    Oakland, Garrett County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Lakefront, dog-friendly home w/ hot tubs, game room, dock & space for 25!1 / 47
    (59)Excellent
    Oakland
    3.9 kilometres from Circle R Ranch
    6 Bedrooms, 7 Bathrooms, Sleeps 25 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 25
    Lakefront on Deep Creek Lake -- walkout to water!1 / 13
    (13)Excellent
    Oakland
    3.6 kilometres from Circle R Ranch
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    Oakland, Garrett County
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
    Lovely lakefront cabin w/amenities, private dock & water views - so much to see!1 / 50
    (5)Excellent
    Oakland
    4.1 kilometres from Circle R Ranch
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
    Lake access chalet-style home w/ 2 furnished patios, & private hot tub - dogs OK1 / 50
    (19)Excellent
    Oakland
    2.2 kilometres from Circle R Ranch
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    DOGS WELCOME! Lakefront Home w/Private Dock, Hot Tub, & Lake Views!1 / 31
    (4)Very good
    Oakland
    4.1 kilometres from Circle R Ranch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Traditional with a twist! Tolson Cabin is a beautifully crafted home boasting a1 / 32
    (3)Very good
    Oakland
    3.5 kilometres from Circle R Ranch
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    The possibilities are endless at Awesome View! The grandeur of this spacious la1 / 50
    (2)Very good
    Oakland
    3.5 kilometres from Circle R Ranch
    8 Bedrooms, 7 Bathrooms, Sleeps 24 Quick View
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    • DVD Player
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    • Shared Indoor Pool
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    • Sauna
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    Oakland, Garrett County
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 24
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    Tranquil home w/ private hot tub & game room - close to lake access1 / 50
    (17)Very good
    Oakland
    3.8 kilometres from Circle R Ranch
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
    Perfect for a romantic getaway or intimate family gathering, Swallow Falls Inn1 / 10
    (1)Very good
    Oakland
    5.9 kilometres 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
    Charming lake house w/ private hot tub & great views from the deck - dogs OK!1 / 42
    (20)Very good
    Oakland
    5.0 kilometres 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
    Where can you go to tuck away from the hustle and bustle of town, yet remain ju1 / 49
    (2)Excellent
    Oakland
    4.2 kilometres from Circle R Ranch
    7 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 20
    OWLS NEST,Cozy Romantic, Cabin w HotTub,Premiere Lake Waterfront, private dock1 / 50
    (81)Excellent
    Oakland
    4.7 kilometres from Circle R Ranch
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    A114- 1 bedroom suite w/ standard view, private bedroom, and fireplace!1 / 17
    (2)Excellent
    Oakland
    3.6 kilometres from Circle R Ranch
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Oakland, Garrett County
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Bring on Summer! Boat Slip, Fire Pits, Hot Tub, Wifi, Dog Friendly, Private Road1 / 33
    (53)Excellent
    Oakland
    3.7 kilometres 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
    If you're looking to retreat to the privacy of the woods, Blue Spruce is perfec1 / 29
    (6)Excellent
    Oakland
    3.4 kilometres 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
    Lovin Life Deep Creek 5 Bedroom Luxury Log Home w/ Pool Table & Hot Tub1 / 23
    (19)Excellent
    Oakland
    3.8 kilometres 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
    DOGS WELCOME! Lake Access Home w/Hot Tub, Fire Pit, Pool Table, & 2 Fireplaces!1 / 36
    (58)Excellent
    Oakland
    1.9 kilometres 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
    Bold and beautiful, Lake's End is a dream come true. Bring all your favorite pe1 / 50
    (3)Excellent
    Oakland
    3.6 kilometres from Circle R Ranch
    8 Bedrooms, 6 Bathrooms, Sleeps 22 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 22
    Wooded Lake Area Home w/Jetted Tub, Wood Fireplace, & Basketball Hoop!1 / 49
    (1)Excellent
    Oakland
    4.0 kilometres from Circle R Ranch
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    DOGS WELCOME! Lakefront Home w/Indoor Pool, Private Dock, & Home Theater!1 / 43
    (9)Very good
    Oakland
    2.9 kilometres from Circle R Ranch
    6 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 20
    Lakefront home w/ lake view, private hot tub & dock - dogs OK1 / 50
    (16)Excellent
    Oakland
    5.3 kilometres 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
    Lake Access Chalet-NO “OWNER FEES”, Indoor Pool, Home Theater, BoatDock, Firepit1 / 36
    (59)Excellent
    Oakland
    3.6 kilometres from Circle R Ranch
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    Lake Front 1st Floor Walk Out Luxury Condo w/ Private Deck1 / 7
    (22)Excellent
    Oakland
    3.6 kilometres from Circle R Ranch
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Oakland, Garrett County
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Dolce Vita Offers a private hot tub, walking path, central Resort location1 / 40
    (3)Excellent
    Oakland
    3.1 kilometres 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
    Family- and dog-friendly home w/ deck, forest view - close to lake & ski slopes1 / 32
    (48)Excellent
    Oakland
    3.6 kilometres 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
    DOGS WELCOME! Lake Access Home w/Dock Slip, Hot Tub, & MANY Community Amenities!1 / 50
    (34)Very good
    Oakland
    3.3 kilometres 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
    Dog-friendly country cabin w/ deck, firepit & air hockey - close to Yough River!1 / 45
    (42)Excellent
    Oakland
    5.8 kilometres from Circle R Ranch
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    FIVE STAR REVIEWS!  Book Ski weekends! Wisp has amazing snow making equipment!1 / 50
    (25)Excellent
    Oakland
    4.0 kilometres 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
    Oakland
    4.5 kilometres 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
    State Park And Swallow Falls Only 5 - 10 Minutes Away, Walking Distance To JG’S1 / 32
    (47)Excellent
    Oakland
    1.6 kilometres 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
    Unwind in Unreel! From summertime friends, to a family of skiers, to fishermen1 / 50
    (3)Average
    Oakland
    4.7 kilometres 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
    Indoor pleasure combines with outdoor excitement at Sundance. The relaxed inter1 / 50
    (7)Very good
    Oakland
    4.1 kilometres from Circle R Ranch
    7 Bedrooms, 7 Bathrooms, Sleeps 22 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 22
    Dog-friendly cabin in the woods with hot tub, furnished deck, & pool table1 / 35
    (29)Very good
    Oakland
    3.1 kilometres from Circle R Ranch
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Peppered with warm mountain ambiance and delightful accents, Little Bear’s Den1 / 26
    (9)Very good
    Oakland
    4.0 kilometres 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
    5 bedroom, 5 full bathroom suites, minutes from WISP mountain and the lake1 / 24
    (13)Excellent
    Oakland
    6.3 kilometres from Circle R Ranch
    5 Bedrooms, 7 Bathrooms, Sleeps 15 Quick View
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    Oakland, Garrett County
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 15
    5BR lakefront Cottage.  Almost Heaven offers a true family retreat at Deep Creek1 / 41
    (11)Very good
    Oakland
    4.9 kilometres 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
    Dog-friendly, lakefront log home on a quiet cove w/ a front deck & private dock1 / 41
    (37)Very good
    Oakland
    3.6 kilometres from Circle R Ranch
    2 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Location Information
    Oakland, Garrett County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 10
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