Vacation rentals in Winchester, KY

Best vacation rentals and Airbnb offers in Winchester, KY

2 Full Beds | Non-Smoking, Micfridge

Apartment, Winchester

2 Full Beds · Non-Smoking, Micfridge is a apartment in Winchester, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About 2 Full Beds | Non-Smoking, Micfridge

2 Full Beds · Non-Smoking, Micfridge is a apartment in Winchester, with pet-friendly space. 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, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $432.

From$62/night

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1 King Bed | Non-Smoking, Micfridge

Apartment, Winchester

1 King Bed · Non-Smoking, Micfridge is a apartment in Winchester, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About 1 King Bed | Non-Smoking, Micfridge

1 King Bed · Non-Smoking, Micfridge is a apartment in Winchester, with pet-friendly space. 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, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $467.

From$67/night

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Cozy, Bright Home in Historic Downtown

Holiday Home, Winchester

Cozy, Bright Home in Historic Downtown is a holiday home in Winchester, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Cozy, Bright Home in Historic Downtown

Cozy, Bright Home in Historic Downtown is a holiday home in Winchester, 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 gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $596.

From$85/night

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Cozy 1-bedroom apartment in charming Richmond close to EKU, free WiFi

Apartment, Winchester

Cozy 1-bedroom apartment in charming Richmond close to EKU, free WiFi is a apartment in Winchester, with pet-friendly space, parking, and room for a group. This stay gives travelers a…

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About Cozy 1-bedroom apartment in charming Richmond close to EKU, free WiFi

Cozy 1-bedroom apartment in charming Richmond close to EKU, free WiFi is a apartment in Winchester, with pet-friendly space, parking, 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, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $762.

From$109/night

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Vacation rentals with a pool in Winchester, KY

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

1791 Cabin on Historic Horse Farm

Holiday Home, Winchester

1791 Cabin on Historic Horse Farm is a holiday home in Winchester, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About 1791 Cabin on Historic Horse Farm

1791 Cabin on Historic Horse Farm is a holiday home in Winchester, 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 $1,115.

From$159/night

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Historical 4-bedroom farmhouse in serene Sharpsburg with AC.

Country House, Winchester

Historical 4-bedroom farmhouse in serene Sharpsburg with AC. is a country house in Winchester, with pool access, kitchen access, and room for a group. This stay gives travelers a…

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About Historical 4-bedroom farmhouse in serene Sharpsburg with AC.

Historical 4-bedroom farmhouse in serene Sharpsburg with AC. is a country house in Winchester, with pool access, 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, pool, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,084.

From$298/night

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Guest Home on Historic Horse Farm

Country House, Winchester

Guest Home on Historic Horse Farm is a country house in Winchester, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Guest Home on Historic Horse Farm

Guest Home on Historic Horse Farm is a country house in Winchester, 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 $2,280.

From$326/night

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Traditional Bed & Breakfast in Irvine KY with Swimming pool, Wi-Fi Room 2

B & B, Winchester

Traditional Bed & Breakfast in Irvine KY with Swimming pool, Wi-Fi Room 2 is a b & b in Winchester, with pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Traditional Bed & Breakfast in Irvine KY with Swimming pool, Wi-Fi Room 2

Traditional Bed & Breakfast in Irvine KY with Swimming pool, Wi-Fi Room 2 is a b & b in Winchester, with pool 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, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,587.

From$227/night

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Vacation rentals with parking in Winchester, KY

Find vacation rentals that make arriving by car easier.

Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington

Apartment, Winchester

Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington is a apartment in Winchester, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington

Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington is a apartment in Winchester, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $788.

From$113/night

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Bourbon Trail - Loft in Downtown Lexington

Apartment, Winchester

Bourbon Trail - Loft in Downtown Lexington is a apartment in Winchester, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Bourbon Trail - Loft in Downtown Lexington

Bourbon Trail - Loft in Downtown Lexington is a apartment in Winchester, 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 $871.

From$124/night

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2BR Central Loft w/ Garage, near NCR & Downtown

Holiday Home, Winchester

2BR Central Loft w/ Garage, near NCR & Downtown is a holiday home in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About 2BR Central Loft w/ Garage, near NCR & Downtown

2BR Central Loft w/ Garage, near NCR & Downtown is a holiday home in Winchester, with pet-friendly space, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $998.

From$143/night

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Historic Log Cabin - Farm - Near RRG and Lex. Winter retreat rates available

Cabin, Winchester

Historic Log Cabin - Farm - Near RRG and Lex. Winter retreat rates available is a cabin in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Historic Log Cabin - Farm - Near RRG and Lex. Winter retreat rates available

Historic Log Cabin - Farm - Near RRG and Lex. Winter retreat rates available is a cabin in Winchester, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,419.

From$203/night

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Pet-friendly vacation rentals in Winchester, KY

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

Westfield Gold

Apartment, Winchester

Westfield Gold is a apartment in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Westfield Gold

Westfield Gold is a apartment in Winchester, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $776.

From$111/night

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Richmond Retreat by Raydarr Properties, LLC

Holiday Home, Winchester

Richmond Retreat by Raydarr Properties, LLC is a holiday home in Winchester, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Richmond Retreat by Raydarr Properties, LLC

Richmond Retreat by Raydarr Properties, LLC is a holiday home in Winchester, with pet-friendly space, 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, pet friendly, pets friendly, and kitchen.

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

From$115/night

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Morning Glory - Cozy Apt in Downtown Lexington

Apartment, Winchester

Morning Glory - Cozy Apt in Downtown Lexington is a apartment in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Morning Glory - Cozy Apt in Downtown Lexington

Morning Glory - Cozy Apt in Downtown Lexington is a apartment in Winchester, 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 $895.

From$116/night

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Seabiscuit Loft - Studio Stay in Downtown Lexington

Apartment, Winchester

Seabiscuit Loft - Studio Stay in Downtown Lexington is a apartment in Winchester, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Seabiscuit Loft - Studio Stay in Downtown Lexington

Seabiscuit Loft - Studio Stay in Downtown Lexington is a apartment in Winchester, 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 $867.

From$124/night

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Vacation rentals with a kitchen in Winchester, KY

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

Westfield Blue

Apartment, Winchester

Westfield Blue is a apartment in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Westfield Blue

Westfield Blue is a apartment in Winchester, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

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

From$120/night

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Modern Studio - Stylish Apartment in Downtown Lexington

Apartment, Winchester

Modern Studio - Stylish Apartment in Downtown Lexington is a apartment in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Modern Studio - Stylish Apartment in Downtown Lexington

Modern Studio - Stylish Apartment in Downtown Lexington is a apartment in Winchester, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $938.

From$134/night

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Big Blue - Stylish Studio in Downtown Lexington

Apartment, Winchester

Big Blue - Stylish Studio in Downtown Lexington is a apartment in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Big Blue - Stylish Studio in Downtown Lexington

Big Blue - Stylish Studio in Downtown Lexington is a apartment in Winchester, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $948.

From$135/night

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Cozy 2-bedroom condo with WiFi, AC in marvelous Lexington

Condo, Winchester

Cozy 2-bedroom condo with WiFi, AC in marvelous Lexington is a condo in Winchester, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Cozy 2-bedroom condo with WiFi, AC in marvelous Lexington

Cozy 2-bedroom condo with WiFi, AC in marvelous Lexington is a condo in Winchester, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,119.

From$160/night

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Family-friendly vacation rentals in Winchester, KY

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

175 LEX - Loft in Downtown Lexington, Rupp Arena

Condo, Winchester

175 LEX - Loft in Downtown Lexington, Rupp Arena is a condo in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About 175 LEX - Loft in Downtown Lexington, Rupp Arena

175 LEX - Loft in Downtown Lexington, Rupp Arena is a condo in Winchester, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,020.

From$146/night

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175 LEX - Walk to Rupp Arena Downtown Top Floor

Condo, Winchester

175 LEX - Walk to Rupp Arena Downtown Top Floor is a condo in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About 175 LEX - Walk to Rupp Arena Downtown Top Floor

175 LEX - Walk to Rupp Arena Downtown Top Floor is a condo in Winchester, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,020.

From$146/night

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175 LEX - Walkable Loft to Rupp Arena & Downtown!

Condo, Winchester

175 LEX - Walkable Loft to Rupp Arena & Downtown! is a condo in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About 175 LEX - Walkable Loft to Rupp Arena & Downtown!

175 LEX - Walkable Loft to Rupp Arena & Downtown! is a condo in Winchester, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,020.

From$146/night

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Peaceful Mt Sterling Cabin: Deck & Fire Pit!

Cottage, Winchester

Peaceful Mt Sterling Cabin: Deck & Fire Pit! is a cottage in Winchester, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

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About Peaceful Mt Sterling Cabin: Deck & Fire Pit!

Peaceful Mt Sterling Cabin: Deck & Fire Pit! is a cottage in Winchester, with pet-friendly space, outdoor 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 $1,618.

From$181/night

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