Vacation rentals in Orlean, VA

Best Vacation rentals and Airbnb offers in Orlean, VA

Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper

Holiday Home, Orlean

Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper is a holiday home in Orlean, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper

Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper is a holiday home in Orlean, 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 $851.

From$89/night

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Serene 1-bedroom house in Front Royal perfect for a getaway

Holiday Home, Orlean

Serene 1-bedroom house in Front Royal perfect for a getaway is a holiday home in Orlean, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for…

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About Serene 1-bedroom house in Front Royal perfect for a getaway

Serene 1-bedroom house in Front Royal perfect for a getaway is a holiday home in Orlean, 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, laundry service, and toiletries.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $992.

From$100/night

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Cozy 1BR Apt Minutes From Skyline Drive!!

Apartment, Orlean

Cozy 1BR Apt Minutes From Skyline Drive!! is a apartment in Orlean, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Cozy 1BR Apt Minutes From Skyline Drive!!

Cozy 1BR Apt Minutes From Skyline Drive!! is a apartment in Orlean, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,081.

From$122/night

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Apple Mountain Retreat

Apartment, Orlean

Apple Mountain Retreat is a apartment in Orlean, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Apple Mountain Retreat

Apple Mountain Retreat is a apartment in Orlean, 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 cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,180.

From$128/night

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Best Pet-Friendly Vacation Rentals in Orlean, VA

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

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

Cabin, Orlean

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub is a cabin in Orlean, with pet-friendly space and parking. This stay gives travelers a comfortable base for…

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About A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub is a cabin in Orlean, 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, hot tub, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,753.

From$181/night

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The Serenity Cabin | Firepit | Wineries | Hiking

Cabin, Orlean

The Serenity Cabin · Firepit · Wineries · Hiking is a cabin in Orlean, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About The Serenity Cabin | Firepit | Wineries | Hiking

The Serenity Cabin · Firepit · Wineries · Hiking is a cabin in Orlean, 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 $1,667.

From$184/night

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Hidden Gem on Hidden Valley Lane

Cabin, Orlean

Hidden Gem on Hidden Valley Lane is a cabin in Orlean, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Hidden Gem on Hidden Valley Lane

Hidden Gem on Hidden Valley Lane is a cabin in Orlean, 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 $2,012.

From$208/night

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Our place is dog-friendly, stunning views of Shenandoah Skyline Drive

Country House, Orlean

Our place is dog-friendly, stunning views of Shenandoah Skyline Drive is a country house in Orlean, with pet-friendly space and parking. This stay gives travelers a comfortable base for…

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About Our place is dog-friendly, stunning views of Shenandoah Skyline Drive

Our place is dog-friendly, stunning views of Shenandoah Skyline Drive is a country house in Orlean, 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, parking, free parking, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,106.

From$229/night

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Our Favorite Family-Friendly Vacation Rentals in Orlean, VA

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

New! Modern family cottage oasis with fast WiFi and pet friendly.

Cottage, Orlean

New! Modern family cottage oasis with fast WiFi and pet friendly. is a cottage in Orlean, with pet-friendly space, parking, and room for a group. This stay gives travelers a comfortable…

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About New! Modern family cottage oasis with fast WiFi and pet friendly.

New! Modern family cottage oasis with fast WiFi and pet friendly. is a cottage in Orlean, 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 $1,833.

From$197/night

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Serene Farmhouse and former winery on 44 acres of rolling hills.

Country House, Orlean

Serene Farmhouse and former winery on 44 acres of rolling hills. is a country house in Orlean, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Serene Farmhouse and former winery on 44 acres of rolling hills.

Serene Farmhouse and former winery on 44 acres of rolling hills. is a country house in Orlean, 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,501.

From$525/night

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Secluded Farmhouse Cottage w/Bucolic Setting

Country House, Orlean

Secluded Farmhouse Cottage w/Bucolic Setting is a country house in Orlean, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Secluded Farmhouse Cottage w/Bucolic Setting

Secluded Farmhouse Cottage w/Bucolic Setting is a country house in Orlean, 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 $5,859.

From$650/night

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Luxury Pet + Family Friendly Retreat With Pool, Hot Tub, Fire Pit, Amazing Views

Holiday Home, Orlean

Luxury Pet + Family Friendly Retreat With Pool, Hot Tub, Fire Pit, Amazing Views is a holiday home in Orlean, with pet-friendly space, pool access, and room for a group. This stay gives…

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About Luxury Pet + Family Friendly Retreat With Pool, Hot Tub, Fire Pit, Amazing Views

Luxury Pet + Family Friendly Retreat With Pool, Hot Tub, Fire Pit, Amazing Views is a holiday home in Orlean, with pet-friendly space, pool 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $16,127.

From$1,914/night

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