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Search results; 788 homes in Oakland

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Top guest favourite
Barn in Oakland
Nonna’s Place Pole Barn Dwelling Near Mammoth Cave
2 bedrooms, 3 beds, 1 private bathroom
19–24 Oct
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4.99 out of 5 average rating, 149 reviews
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Home in Bowling Green
Jenny’s Southland Homestead, LLC
5 bedrooms, 5 beds, 4.5 bathrooms
7–12 Oct
4.86 out of 5 average rating, 49 reviews
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Home in Smiths Grove
Texie’s Treasure on the Hill
3 bedrooms, 3 queen beds, 2 bathrooms
11–16 Oct
4.93 out of 5 average rating, 106 reviews
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Guest favourite
Home in Smiths Grove
Vineyard House At Bluegrass Vineyard & Winery
3 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.94 out of 5 average rating, 401 reviews
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Home in Smiths Grove
Smith's Station
2 bedrooms, 3 beds, 1.5 bathrooms
12–17 Oct
4.86 out of 5 average rating, 181 reviews
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Guest favourite
Home in Bowling Green
Loving Union Stay at Sunnyside/5 bdrm 3.5 bath
5 bedrooms, 6 beds, 3.5 bathrooms
5–10 Oct
4.97 out of 5 average rating, 32 reviews
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Farm stay in Smiths Grove
The Maples
3 bedrooms, 3 beds, 2 bathrooms
24–29 Oct
4.97 out of 5 average rating, 445 reviews
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Home in Bowling Green
Cottage At Sunnyside/Private/Wooded 5 Acres/Garage
1 bedroom, 2 beds, 1.5 bathrooms
5–10 Oct
5.0 out of 5 average rating, 54 reviews
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Guest favourite
Home in Bowling Green
Jenny's Southland Homestead, LLC - Guest House
2 bedrooms, 2 queen beds, 1 bathroom
5–10 Oct
4.9 out of 5 average rating, 30 reviews
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Top guest favourite
Cottage in Smiths Grove
Cozy Farmhouse Cottage
1 queen bed, 1 bathroom
1–6 Oct
4.94 out of 5 average rating, 500 reviews
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Home in Smiths Grove
Country setting near Mammoth cave , Barren River
2 bedrooms, 5 beds, 1 bathroom
1–6 Oct
4.93 out of 5 average rating, 376 reviews
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Home in Bowling Green
6 bedroom 5 bath Dream Escape
6 bedrooms, 8 beds, 3 bathrooms
5–10 Oct
4.52 out of 5 average rating, 63 reviews
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Top guest favourite
Home in Brownsville
The Cave Retreat - 4 Minutes from Mammoth Cave!
3 bedrooms, 4 beds, 1 bathroom
22–27 Oct
4.99 out of 5 average rating, 207 reviews
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Farm stay in Smiths Grove
Cute Farmhouse close to Mammoth Cave/Bowling Green
2 bedrooms, 3 beds, 2 bathrooms
18–23 Oct
4.96 out of 5 average rating, 192 reviews
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Guest favourite
Cabin in Smiths Grove
Gorgeous Log Cabin close to Cave and Lakes!!
3 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
4.92 out of 5 average rating, 232 reviews
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Top guest favourite
Cabin in Smiths Grove
1830s Log Cabin • 5 Acres Near Mammoth Cave
2 bedrooms, 4 beds, 1 bathroom
30 Oct – 4 Nov
4.97 out of 5 average rating, 238 reviews
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Top guest favourite
Home in Alvaton
Country Living~ Horses & Wildlife
3 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
4.97 out of 5 average rating, 33 reviews
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Home in Bowling Green
Riverwood Retreat-Comfortable & Centrally Located
3 bedrooms, 4 beds, 1 bathroom
15–20 Oct
4.98 out of 5 average rating, 93 reviews
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Guest favourite
Home in Bowling Green
Corvettes, TransPark & more
2 bedrooms, 3 beds, 1 bathroom
19–24 Oct
4.92 out of 5 average rating, 24 reviews