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Search results; 781 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
13–18 Sept
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4.99 out of 5 average rating, 148 reviews
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Home in Smiths Grove
Vineyard House At Bluegrass Vineyard & Winery
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.94 out of 5 average rating, 399 reviews
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Top guest favourite
Home in Smiths Grove
Smith's Station
2 bedrooms, 3 beds, 1.5 bathrooms
15–20 Sept
4.85 out of 5 average rating, 178 reviews
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Top 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
5.0 out of 5 average rating, 29 reviews
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Home in Bowling Green
Jenny’s Southland Homestead, LLC
5 bedrooms, 5 beds, 4.5 bathrooms
7–12 Oct
4.87 out of 5 average rating, 47 reviews
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Farm stay in Smiths Grove
The Maples
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.97 out of 5 average rating, 444 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
1–6 Sept
4.9 out of 5 average rating, 29 reviews
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Guest favourite
Home in Smiths Grove
Texie’s Treasure on the Hill
3 bedrooms, 3 queen beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 101 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
13–18 Sept
4.97 out of 5 average rating, 235 reviews
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Home in Smiths Grove
Country setting near Mammoth cave , Barren River
2 bedrooms, 5 beds, 1 bathroom
18–23 Sept
4.93 out of 5 average rating, 371 reviews
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Home in Bowling Green
Cottage At Sunnyside/Private/Wooded 5 Acres/Garage
1 bedroom, 2 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 51 reviews
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Home in Oakland
A beautiful Victorian house
2 bedrooms, 2 beds, 1 bathroom
1–6 Sept
4.72 out of 5 average rating, 25 reviews
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Home in Bowling Green
6 bedroom 5 bath Dream Escape
6 bedrooms, 8 beds, 3 bathrooms
5–10 Oct
4.51 out of 5 average rating, 61 reviews
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Guest favourite
Home in Bowling Green
Riverside Retreat
3 bedrooms, 3 king beds, 2 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Farm stay in Smiths Grove
Cute Farmhouse close to Mammoth Cave/Bowling Green
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 191 reviews
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Home in Bowling Green
The Plum Springs House
3 bedrooms, 5 beds, 2 bathrooms
5–10 Oct
4.91 out of 5 average rating, 70 reviews
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Cabin in Smiths Grove
Gorgeous Log Cabin close to Cave and Lakes!!
3 bedrooms, 3 beds, 2 bathrooms
17–22 Sept
4.91 out of 5 average rating, 231 reviews
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Home in Bowling Green
Riverwood Retreat-Comfortable & Centrally Located
3 bedrooms, 4 beds, 1 bathroom
1–6 Sept
4.98 out of 5 average rating, 91 reviews
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Bungalow in Bowling Green
Bungalow In The River Bend
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 411 reviews