Vacation rentals in Winchester, VA

29 available vacation rental offers

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Best vacation rentals and Airbnb offers in Winchester, VA

Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed - Winchester, VA

Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed

Guest House, Winchester

Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed is a guest house in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed

Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed is a guest house in Winchester, 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, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $772.

From$110/night
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The Stock Exchange downtown 3rd floor studio apt - Winchester, VA

The Stock Exchange downtown 3rd floor studio apt

Apartment, Winchester

The Stock Exchange downtown 3rd floor studio apt is a apartment in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt is a apartment in Winchester, 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 $773.

From$110/night
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Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything! - Winchester, VA

Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

Apartment, Winchester

Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything! is a apartment in Winchester, with parking and room for a group. This stay gives travelers a comfortable base for…

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About Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything! is a apartment in Winchester, with 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, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $819.

From$117/night
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Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly - Winchester, VA

Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly

Apartment, Winchester

Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly is a apartment in Winchester, with pet-friendly space and room for a group. This stay gives travelers a…

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About Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly

Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly is a apartment in Winchester, with pet-friendly space 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, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $821.

From$117/night
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Vacation rentals with parking in Winchester, VA

Find vacation rentals that make arriving by car easier.

Modern Log House First Level Primary - Winchester, VA

Modern Log House First Level Primary

Holiday Home, Winchester

Modern Log House First Level Primary is a holiday home in Winchester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Modern Log House First Level Primary

Modern Log House First Level Primary is a holiday home in Winchester, 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, paid parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,266.

From$148/night
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Charming 3-bedroom house with porch and yard in Winchester - Winchester, VA

Charming 3-bedroom house with porch and yard in Winchester

Holiday Home, Winchester

Charming 3-bedroom house with porch and yard in Winchester is a holiday home in Winchester, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Charming 3-bedroom house with porch and yard in Winchester

Charming 3-bedroom house with porch and yard in Winchester is a holiday home 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 $1,432.

From$205/night
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Cabin on a farm stay with roaming peecocks - Winchester, VA

Cabin on a farm stay with roaming peecocks

Holiday Home, Winchester

Cabin on a farm stay with roaming peecocks is a holiday home in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cabin on a farm stay with roaming peecocks

Cabin on a farm stay with roaming peecocks is a holiday home in Winchester, 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 $1,631.

From$233/night
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Pet-friendly vacation rentals in Winchester, VA

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

7 acre Farm in Strasburg, Virginia - Winchester, VA

7 acre Farm in Strasburg, Virginia

Holiday Home, Winchester

7 acre Farm in Strasburg, Virginia is a holiday home in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 7 acre Farm in Strasburg, Virginia

7 acre Farm in Strasburg, Virginia is a holiday home 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $802.

From$115/night
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Stunning Mountain Top 1 Bedroom Apartment - Walk-out Basement - Winchester, VA

Stunning Mountain Top 1 Bedroom Apartment - Walk-out Basement

Apartment, Winchester

Stunning Mountain Top 1 Bedroom Apartment - Walk-out Basement is a apartment in Winchester, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a…

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About Stunning Mountain Top 1 Bedroom Apartment - Walk-out Basement

Stunning Mountain Top 1 Bedroom Apartment - Walk-out Basement is a apartment in Winchester, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,137.

From$162/night
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The Overlook - Winchester, VA

The Overlook

Cabin, Winchester

The Overlook is a cabin in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About The Overlook

The Overlook is a cabin 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,293.

From$185/night
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WonderClock House downtown vintage duplex w/ porches, steps to Handley Library - Winchester, VA

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

Apartment, Winchester

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library is a apartment in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers…

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About WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library 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 $1,404.

From$201/night
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Vacation rentals with a kitchen in Winchester, VA

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

The Outpost Suite 3 - Whimsical Farmhouse Retreat - Winchester, VA

The Outpost Suite 3 - Whimsical Farmhouse Retreat

Apartment, Winchester

The Outpost Suite 3 - Whimsical Farmhouse Retreat is a apartment in Winchester, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base…

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About The Outpost Suite 3 - Whimsical Farmhouse Retreat

The Outpost Suite 3 - Whimsical Farmhouse Retreat is a apartment 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,330.

From$190/night
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Modern 3BR Farmhouse in the Country - Winchester, VA

Modern 3BR Farmhouse in the Country

Country House, Winchester

Modern 3BR Farmhouse in the Country is a country house in Winchester, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Modern 3BR Farmhouse in the Country

Modern 3BR Farmhouse in the Country is a country house in Winchester, with 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 gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,568.

From$224/night
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Family Retreat w/ Deck Near Appalachian Trail! - Winchester, VA

Family Retreat w/ Deck Near Appalachian Trail!

Cottage, Winchester

Family Retreat w/ Deck Near Appalachian Trail! 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 Family Retreat w/ Deck Near Appalachian Trail!

Family Retreat w/ Deck Near Appalachian Trail! 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 $3,489.

From$421/night
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Family Retreat w/ Deck Near Appalachian Trail! - Winchester, VA

Family Retreat w/ Deck Near Appalachian Trail!

Holiday Home, Winchester

Family Retreat w/ Deck Near Appalachian Trail! is a holiday home in Winchester, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

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About Family Retreat w/ Deck Near Appalachian Trail!

Family Retreat w/ Deck Near Appalachian Trail! is a holiday home 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,062.

From$437/night
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Family-friendly vacation rentals in Winchester, VA

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

Suite 4: Outpost · Gorgeous Farm Carriage House Loft - Winchester, VA

Suite 4: Outpost · Gorgeous Farm Carriage House Loft

Country House, Winchester

Suite 4: Outpost · Gorgeous Farm Carriage House Loft is a country house in Winchester, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring…

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About Suite 4: Outpost · Gorgeous Farm Carriage House Loft

Suite 4: Outpost · Gorgeous Farm Carriage House Loft is a country house in Winchester, with 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, family friendly, and kids toys.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,441.

From$206/night
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Charming 2-bedroom cottage with WiFi, AC in delightful Boyce - Winchester, VA

Charming 2-bedroom cottage with WiFi, AC in delightful Boyce

Cottage, Winchester

Charming 2-bedroom cottage with WiFi, AC in delightful Boyce is a cottage in Winchester, with room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Charming 2-bedroom cottage with WiFi, AC in delightful Boyce

Charming 2-bedroom cottage with WiFi, AC in delightful Boyce is a cottage in Winchester, with 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, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,642.

From$235/night
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19th Century Renovated Church Building. A spacious sanctuary retreat. - Winchester, VA

19th Century Renovated Church Building. A spacious sanctuary retreat.

Holiday Home, Winchester

19th Century Renovated Church Building. A spacious sanctuary retreat. is a holiday home in Winchester, with kitchen access and a quieter setting. This stay gives travelers a comfortable…

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About 19th Century Renovated Church Building. A spacious sanctuary retreat.

19th Century Renovated Church Building. A spacious sanctuary retreat. is a holiday home in Winchester, 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 kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,946.

From$278/night
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Family Retreat w/ Deck Near Appalachian Trail! - Winchester, VA

Family Retreat w/ Deck Near Appalachian Trail!

Holiday Home, Winchester

Family Retreat w/ Deck Near Appalachian Trail! is a holiday home in Winchester, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for…

Read more

About Family Retreat w/ Deck Near Appalachian Trail!

Family Retreat w/ Deck Near Appalachian Trail! is a holiday home in Winchester, with pet-friendly space, outdoor 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 wifi, pet friendly, pets friendly, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,362.

From$379/night
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