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Search results; 799 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, 147 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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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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Top guest favourite
Home in Smiths Grove
Smith's Station
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Sept
4.85 out of 5 average rating, 177 reviews
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Flat in Smiths Grove
The Loft off Main I
1 bedroom, 1 bed, 1 bathroom
6–11 Sept
4.9 out of 5 average rating, 126 reviews
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Top guest favourite
Cottage in Smiths Grove
Cozy Farmhouse Cottage
1 queen bed, 1 bathroom
23–28 Sept
4.94 out of 5 average rating, 500 reviews
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Top guest favourite
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, 370 reviews
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Top guest favourite
Flat in Smiths Grove
The Loft off Main II
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 88 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
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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Guest favourite
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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Superhost
Farm stay in Scottsville
Stylish MidCentury Modern Farmstay on Flower Farm
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Sept
4.97 out of 5 average rating, 131 reviews
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Superhost
Guest suite in Bowling Green
Country farm stay STR # WC0046
2 bedrooms, 3 beds, 1 bathroom
31 Dec – 5 Jan
4.93 out of 5 average rating, 40 reviews
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Top guest favourite
Barn in Smiths Grove
Barefoot
1 bedroom, 3 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 104 reviews
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Superhost
Home in Bowling Green
3BR Retreat by Park & Track – Huge Yard & Trails
3 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 49 reviews
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Guest favourite
Treehouse in Brownsville
The Eagle's Nest Treehouse
2 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.91 out of 5 average rating, 188 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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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
Camper van/Motorhome in Smiths Grove
High Point Grove
2 bedrooms, 5 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 13 reviews