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Vacation Rentals near Prairie Berry Winery

23837 Highway 385, Hill City, South Dakota 57745-6517
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    Travelers to Hill City are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    All 154 Rentals in Hill City
    0.1 miles from Prairie Berry Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Family Friendly Vacation Home Near Hill City1 / 21
    (92)Excellent
    5.1 miles from Prairie Berry Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    The Hynes Cabin- 1925 Renovated Classic with Stunning Views1 / 20
    (81)Excellent
    3.1 miles from Prairie Berry Winery
    1 Bedroom, 2 Bathrooms, Sleeps 7 Quick View
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    Rail house 3 bedroom, 2 bath, 2 story house. Lots parking Downtown Hill City, SD1 / 23
    (6)Excellent
    2.9 miles from Prairie Berry Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    Hill City, South Dakota
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 11
    Quaint Cabin in the Heart of the Black Hills1 / 18
    (3)Excellent
    2.5 miles from Prairie Berry Winery
    1 Bedroom, 1 Bathroom, Sleeps 8 Quick View
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    Reviewed June 24, 2017
    This small house is owned by a lady from Texas. It was her Grandmother's home, and she rents it out in the summer. There is a master bedroom with a queen bed, and queen bed in...
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    Hill City, South Dakota
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 8
    1.5 miles from Prairie Berry Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Hill City, South Dakota
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Spring Creek Splendor. The Perfect Location. Private Lower Level Apartment. Fun!1 / 30
    (116)Excellent
    5.0 miles from Prairie Berry Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Hill City, South Dakota
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Enjoy the peace & quiet of the Hills. This unit is located west of Hill City.1 / 30
    (5)Excellent
    10.1 miles from Prairie Berry Winery
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Hill City, South Dakota
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
    Dads Two Bedroom 1 Bath home and1 car garage. Walk to downtown Hill City, SD1 / 17
    (40)Very good
    2.5 miles from Prairie Berry Winery
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Hill City, South Dakota
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 7
    Spacious McCaskell Cabin- Nestled out in the countryside.  Home away from Home.1 / 30
    (55)Excellent
    5.4 miles from Prairie Berry Winery
    7 Bedrooms, 3 Bathrooms, Sleeps 17 Quick View
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    Hill City, South Dakota
    Rental Home - 7 Bedrooms, 3 Bathrooms, Sleeps 17
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    Deluxe Accommodations In The Heart Of The Black Hills!1 / 21
    (82)Excellent
    5.2 miles from Prairie Berry Winery
    6 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
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    Hill City, South Dakota
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 18
    Cottage at Storm Mountain #71 / 18
    (1)Excellent
    1.5 miles from Prairie Berry Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Hill City, South Dakota
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Best Of The Black Hills Lake Side Property—Fun, Relaxation, And Excitement1 / 30
    (59)Excellent
    10.1 miles from Prairie Berry Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Hill City, South Dakota
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    2 Bedroom Log Cabin Located in Heart of Black Hills1 / 20
    (160)Excellent
    1.5 miles from Prairie Berry Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Hill City, South Dakota
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Hill City's Finest! Cabin by the Mickelson Trail.1 / 30
    (87)Excellent
    5.2 miles from Prairie Berry Winery
    6 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    • Grill
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    Reviewed November 12, 2021
    A roaring fire in the gas fireplace and bubbling hot tub greeted us when we arrived at this location, followed shortly by a quick visit from the very friendly son of the owner...
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    Hill City, South Dakota
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 18
    Tranquil Creekside Cottage in the Heart of the Beautiful Black Hills1 / 30
    (228)Excellent
    1.5 miles from Prairie Berry Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Hill City, South Dakota
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Centrally located to all Black Hills attractions! Best views of Hill City.1 / 17
    (3)Excellent
    2.7 miles from Prairie Berry Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Hill City, South Dakota
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Black Hills Forest Edge Cabin1 / 13
    (18)Excellent
    10.6 miles from Prairie Berry Winery
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Hill City, South Dakota
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 6
    0.5 miles from Prairie Berry Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Hill City, South Dakota
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 12
    Barnestone....luxury in the Heart of the Hills1 / 12
    (4)Excellent
    1.9 miles from Prairie Berry Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Hill City, South Dakota
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.6 miles from Prairie Berry Winery
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Hill City, South Dakota
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    BEAUTIFUL TOWNHOME OVERLOOKING HISTORIC MAIN STREET1 / 14
    (4)Excellent
    2.7 miles from Prairie Berry Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Hill City, South Dakota
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    3.1 miles from Prairie Berry Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Hill City, South Dakota
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Cozy cabin with a great fire pit area.1 / 9
    (7)Excellent
    0.7 miles from Prairie Berry Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Hill City, South Dakota
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Black Hills Vacation in comfort at Bighorn Vista!1 / 8
    (8)Excellent
    1.1 miles from Prairie Berry Winery
    1 Bedroom, 2 Bathrooms, Sleeps 12 Quick View
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    Hill City, South Dakota
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 12
    3.0 miles from Prairie Berry Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Hill City, South Dakota
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    2.9 miles from Prairie Berry Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Hill City, South Dakota
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Great value! Great location! Located walking distance to downtown Hill City!1 / 17
    (16)Excellent
    2.8 miles from Prairie Berry Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Hill City, South Dakota
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Mountain Peaks Inn, OLD BALDY MTN SUITE, Hill City, SD, near Mount Rushmore1 / 13
    (9)Excellent
    2.7 miles from Prairie Berry Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Hill City, South Dakota
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    2.2 miles from Prairie Berry Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Hill City, South Dakota
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Available YEAR 'ROUND!  Centrally located!!  A Perfect Place to Stay!!1 / 28
    (9)Excellent
    2.7 miles from Prairie Berry Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Hill City, South Dakota
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2.4 miles from Prairie Berry Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Hill City, South Dakota
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    12.4 miles from Prairie Berry Winery
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Hill City, South Dakota
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    A Black Hills Vacation in Comfort at Elk Hollow Cabin!1 / 6
    (7)Excellent
    0.8 miles from Prairie Berry Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Hill City, South Dakota
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 12
    Super cute little cabin!1 / 7
    (4)Excellent
    0.7 miles from Prairie Berry Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Hill City, South Dakota
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    2.4 miles from Prairie Berry Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Hill City, South Dakota
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    2.4 miles from Prairie Berry Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Hill City, South Dakota
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Mountain Peaks Inn, BEAR MOUNTAIN SUITE, Hill City, SD, near Mt. Rushmore1 / 21
    (9)Excellent
    2.7 miles from Prairie Berry Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Hill City, South Dakota
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.7 miles from Prairie Berry Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Hill City, South Dakota
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    0.6 miles from Prairie Berry Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Hill City, South Dakota
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Very nice, new cabin with 2 bedrooms.1 / 16
    (13)Excellent
    0.7 miles from Prairie Berry Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Hill City, South Dakota
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    2.3 miles from Prairie Berry Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Hill City, South Dakota
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Black Hills Vacation in Comfort at Buck Haven!1 / 8
    (5)Excellent
    1.1 miles from Prairie Berry Winery
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Hill City, South Dakota
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 6
    3.1 miles from Prairie Berry Winery
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Hill City, South Dakota
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 8
    Whistle Stop Cabin with Meadow View1 / 30
    (18)Very good
    1.9 miles from Prairie Berry Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Hill City, South Dakota
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    2.9 miles from Prairie Berry Winery
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Hill City, South Dakota
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Cozy cabin for the family!1 / 12
    (6)Excellent
    0.7 miles from Prairie Berry Winery
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Grill
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    • Patio
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    Location Information
    Hill City, South Dakota
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 6
    3.1 miles from Prairie Berry Winery
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Air Conditioning
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    Smoking allowed
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    Location Information
    Hill City, South Dakota
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 8
    3.0 miles from Prairie Berry Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Terrace
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Hill City, South Dakota
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    2.9 miles from Prairie Berry Winery
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Hill City, South Dakota
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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