Vacation rentals in Simpsonville, KY

63 available vacation rental offers

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Best vacation rentals and Airbnb offers in Simpsonville, KY

Boulevard Stays Tranquil 1BR Getaway - Simpsonville, KY

Boulevard Stays Tranquil 1BR Getaway

Apartment, Simpsonville

Boulevard Stays Tranquil 1BR Getaway is a apartment in Simpsonville, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Boulevard Stays Tranquil 1BR Getaway

Boulevard Stays Tranquil 1BR Getaway is a apartment in Simpsonville, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $753.

From$108/night
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Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi - Simpsonville, KY

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Apartment, Simpsonville

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi is a apartment in Simpsonville, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi is a apartment in Simpsonville, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $775.

From$111/night
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Unique Downtown Studio with an Industrial Vibe - Simpsonville, KY

Unique Downtown Studio with an Industrial Vibe

Apartment, Simpsonville

Unique Downtown Studio with an Industrial Vibe is a apartment in Simpsonville, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe is a apartment in Simpsonville, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $809.

From$116/night
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Boulevard Stays Comfy 1BR Haven Pool, Free Parking & Cozy Details - Simpsonville, KY

Boulevard Stays Comfy 1BR Haven Pool, Free Parking & Cozy Details

Apartment, Simpsonville

Boulevard Stays Comfy 1BR Haven Pool, Free Parking & Cozy Details is a apartment in Simpsonville, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable…

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About Boulevard Stays Comfy 1BR Haven Pool, Free Parking & Cozy Details

Boulevard Stays Comfy 1BR Haven Pool, Free Parking & Cozy Details is a apartment in Simpsonville, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $842.

From$120/night
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Vacation rentals with a pool in Simpsonville, KY

Add a pool to the search when you want an easy place to cool off between outings.

King Suite | Perfect for Business Travelers - Simpsonville, KY

King Suite | Perfect for Business Travelers

Condo, Simpsonville

King Suite · Perfect for Business Travelers is a condo in Simpsonville, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About King Suite | Perfect for Business Travelers

King Suite · Perfect for Business Travelers is a condo in Simpsonville, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,120.

From$160/night
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Comfortable Suite in Louisville! Free Breakfast Buffet + Shared Outdoor Pool | Great for Business Travelers! - Simpsonville, KY

Comfortable Suite in Louisville! Free Breakfast Buffet + Shared Outdoor Pool | Great for Business Travelers!

Condo, Simpsonville

Comfortable Suite in Louisville! Free Breakfast Buffet + Shared Outdoor Pool · Great for Business Travelers! is a condo in Simpsonville, with pool access, parking, and kitchen access. This…

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About Comfortable Suite in Louisville! Free Breakfast Buffet + Shared Outdoor Pool | Great for Business Travelers!

Comfortable Suite in Louisville! Free Breakfast Buffet + Shared Outdoor Pool · Great for Business Travelers! is a condo in Simpsonville, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,185.

From$169/night
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Comfortable Suite! Free Breakfast Buffet + Shared Outdoor Pool. Close to Ford Motor Company! - Simpsonville, KY

Comfortable Suite! Free Breakfast Buffet + Shared Outdoor Pool. Close to Ford Motor Company!

Condo, Simpsonville

Comfortable Suite! Free Breakfast Buffet + Shared Outdoor Pool. Close to Ford Motor Company! is a condo in Simpsonville, with pool access and kitchen access. This stay gives travelers a…

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About Comfortable Suite! Free Breakfast Buffet + Shared Outdoor Pool. Close to Ford Motor Company!

Comfortable Suite! Free Breakfast Buffet + Shared Outdoor Pool. Close to Ford Motor Company! is a condo in Simpsonville, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,201.

From$172/night
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Pool | Golf Simulator | Hot Tub | 10 Acres | Horse Barn - Simpsonville, KY

Pool | Golf Simulator | Hot Tub | 10 Acres | Horse Barn

Holiday Home, Simpsonville

Pool · Golf Simulator · Hot Tub · 10 Acres · Horse Barn is a holiday home in Simpsonville, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Pool | Golf Simulator | Hot Tub | 10 Acres | Horse Barn

Pool · Golf Simulator · Hot Tub · 10 Acres · Horse Barn is a holiday home in Simpsonville, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,753.

From$1,250/night
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Vacation rentals with parking in Simpsonville, KY

Find vacation rentals that make arriving by car easier.

Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE - Simpsonville, KY

Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE

Holiday Home, Simpsonville

Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE is a holiday home in Simpsonville, with parking and kitchen access. This stay gives travelers a comfortable…

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About Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE

Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE is a holiday home in Simpsonville, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,806.

From$258/night
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3-bedroom cabin just 30 minutes from The Outlet Shoppes of the Bluegrass - Simpsonville, KY

3-bedroom cabin just 30 minutes from The Outlet Shoppes of the Bluegrass

Cabin, Simpsonville

3-bedroom cabin just 30 minutes from The Outlet Shoppes of the Bluegrass is a cabin in Simpsonville, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About 3-bedroom cabin just 30 minutes from The Outlet Shoppes of the Bluegrass

3-bedroom cabin just 30 minutes from The Outlet Shoppes of the Bluegrass is a cabin in Simpsonville, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,937.

From$277/night
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Blessings Private Home - Simpsonville, KY

Blessings Private Home

B & B, Simpsonville

Blessings Private Home is a b & b in Simpsonville, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family…

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About Blessings Private Home

Blessings Private Home is a b & b in Simpsonville, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,299.

From$287/night
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Peace and Quiet Close to Louisville - 80+ Acres - Simpsonville, KY

Peace and Quiet Close to Louisville - 80+ Acres

Country House, Simpsonville

Peace and Quiet Close to Louisville - 80+ Acres is a country house in Simpsonville, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Peace and Quiet Close to Louisville - 80+ Acres

Peace and Quiet Close to Louisville - 80+ Acres is a country house in Simpsonville, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and onsite parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,447.

From$350/night
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Pet-friendly vacation rentals in Simpsonville, KY

Bring your pet along with stays that welcome four-legged travelers.

Boulevard Stays Charming 2BR Retreat Pool, Parking, Gym - Simpsonville, KY

Boulevard Stays Charming 2BR Retreat Pool, Parking, Gym

Apartment, Simpsonville

Boulevard Stays Charming 2BR Retreat Pool, Parking, Gym is a apartment in Simpsonville, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for…

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About Boulevard Stays Charming 2BR Retreat Pool, Parking, Gym

Boulevard Stays Charming 2BR Retreat Pool, Parking, Gym is a apartment in Simpsonville, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,189.

From$170/night
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Boulevard Stays Stylish 3BR Getaway Pool, Gym Access & Free Parking - Simpsonville, KY

Boulevard Stays Stylish 3BR Getaway Pool, Gym Access & Free Parking

Apartment, Simpsonville

Boulevard Stays Stylish 3BR Getaway Pool, Gym Access & Free Parking is a apartment in Simpsonville, with pet-friendly space, pool access, and parking. This stay gives travelers a…

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About Boulevard Stays Stylish 3BR Getaway Pool, Gym Access & Free Parking

Boulevard Stays Stylish 3BR Getaway Pool, Gym Access & Free Parking is a apartment in Simpsonville, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,272.

From$182/night
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Historic home freshly renovated on the Bourbon Trail - Simpsonville, KY

Historic home freshly renovated on the Bourbon Trail

Holiday Home, Simpsonville

Historic home freshly renovated on the Bourbon Trail is a holiday home in Simpsonville, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Historic home freshly renovated on the Bourbon Trail

Historic home freshly renovated on the Bourbon Trail is a holiday home in Simpsonville, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,646.

From$235/night
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Shelbyville, KY - Bourbon Trail, Horse Country and more. A modern, spacious gem. - Simpsonville, KY

Shelbyville, KY - Bourbon Trail, Horse Country and more. A modern, spacious gem.

Holiday Home, Simpsonville

Shelbyville, KY - Bourbon Trail, Horse Country and more. A modern, spacious gem. is a holiday home in Simpsonville, with pet-friendly space and kitchen access. This stay gives travelers a…

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About Shelbyville, KY - Bourbon Trail, Horse Country and more. A modern, spacious gem.

Shelbyville, KY - Bourbon Trail, Horse Country and more. A modern, spacious gem. is a holiday home in Simpsonville, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,869.

From$267/night
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Vacation rentals with a kitchen in Simpsonville, KY

Compare stays with kitchen access for longer trips and easier meals.

Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance - Simpsonville, KY

Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

Cabin, Simpsonville

Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance is a cabin in Simpsonville, with kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance is a cabin in Simpsonville, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,842.

From$263/night
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The Horse & Hound Bourbon Trail Retreat at Chickapoo Farm - Simpsonville, KY

The Horse & Hound Bourbon Trail Retreat at Chickapoo Farm

Country House, Simpsonville

The Horse & Hound Bourbon Trail Retreat at Chickapoo Farm is a country house in Simpsonville, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for…

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About The Horse & Hound Bourbon Trail Retreat at Chickapoo Farm

The Horse & Hound Bourbon Trail Retreat at Chickapoo Farm is a country house in Simpsonville, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,078.

From$297/night
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Stylish Home on water, minutes from downtown. Secluded and Convenient to it all! - Simpsonville, KY

Stylish Home on water, minutes from downtown. Secluded and Convenient to it all!

Holiday Home, Simpsonville

Stylish Home on water, minutes from downtown. Secluded and Convenient to it all! is a holiday home in Simpsonville, with parking and kitchen access. This stay gives travelers a comfortable…

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About Stylish Home on water, minutes from downtown. Secluded and Convenient to it all!

Stylish Home on water, minutes from downtown. Secluded and Convenient to it all! is a holiday home in Simpsonville, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,632.

From$376/night
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Bourbon Country Escape! Spacious Home w/ Fire Pit - Simpsonville, KY

Bourbon Country Escape! Spacious Home w/ Fire Pit

Holiday Home, Simpsonville

Bourbon Country Escape! Spacious Home w/ Fire Pit is a holiday home in Simpsonville, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Bourbon Country Escape! Spacious Home w/ Fire Pit

Bourbon Country Escape! Spacious Home w/ Fire Pit is a holiday home in Simpsonville, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,671.

From$382/night
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Family-friendly vacation rentals in Simpsonville, KY

Plan a trip with stays that give families more room to spread out.

Hygge Creek Cottage near Bourbon Trail, Taylorsville Lake, Derby & Kayaking - Simpsonville, KY

Hygge Creek Cottage near Bourbon Trail, Taylorsville Lake, Derby & Kayaking

Cottage, Simpsonville

Hygge Creek Cottage near Bourbon Trail, Taylorsville Lake, Derby & Kayaking is a cottage in Simpsonville, with kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Hygge Creek Cottage near Bourbon Trail, Taylorsville Lake, Derby & Kayaking

Hygge Creek Cottage near Bourbon Trail, Taylorsville Lake, Derby & Kayaking is a cottage in Simpsonville, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,840.

From$263/night
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Valhalla View Home-Minutes to Golf Course-Perfect for Golfers, Horses, Trailers - Simpsonville, KY

Valhalla View Home-Minutes to Golf Course-Perfect for Golfers, Horses, Trailers

Holiday Home, Simpsonville

Valhalla View Home-Minutes to Golf Course-Perfect for Golfers, Horses, Trailers is a holiday home in Simpsonville, with kitchen access. This stay gives travelers a comfortable base for…

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About Valhalla View Home-Minutes to Golf Course-Perfect for Golfers, Horses, Trailers

Valhalla View Home-Minutes to Golf Course-Perfect for Golfers, Horses, Trailers is a holiday home in Simpsonville, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,856.

From$265/night
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2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub - Simpsonville, KY

2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub

Cottage, Simpsonville

2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub is a cottage in Simpsonville, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About 2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub

2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub is a cottage in Simpsonville, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,111.

From$302/night
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Beautiful restored Victorian farmhouse - Simpsonville, KY

Beautiful restored Victorian farmhouse

Cottage, Simpsonville

Beautiful restored Victorian farmhouse is a cottage in Simpsonville, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse is a cottage in Simpsonville, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,139.

From$306/night
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