Vacation rentals in Upperville, VA

Best vacation rentals and Airbnb offers in Upperville, VA

Apple Mountain Retreat

Apartment, Upperville

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

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About Apple Mountain Retreat

Apple Mountain Retreat is a apartment in Upperville, 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 $1,064.

From$152/night

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Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Apartment, Upperville

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries. is a apartment in Upperville, with pet-friendly space and parking. This stay gives travelers a comfortable…

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About Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries. is a apartment in Upperville, 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 $1,180.

From$169/night

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NEW! Historic Schoolhouse HotTub+FirePit+Wineries

Apartment, Upperville

NEW! Historic Schoolhouse HotTub+FirePit+Wineries is a apartment in Upperville, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About NEW! Historic Schoolhouse HotTub+FirePit+Wineries

NEW! Historic Schoolhouse HotTub+FirePit+Wineries is a apartment in Upperville, 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 $1,184.

From$169/night

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Middleburg address - Charming Cottage with super location in country setting

Cottage, Upperville

Middleburg address - Charming Cottage with super location in country setting is a cottage in Upperville, with pet-friendly space and kitchen access. This stay gives travelers a comfortable…

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About Middleburg address - Charming Cottage with super location in country setting

Middleburg address - Charming Cottage with super location in country setting is a cottage in Upperville, 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 $1,243.

From$178/night

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Vacation rentals with a pool in Upperville, VA

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

Romantic African-Inspired Studio on Alpaca Farm – Under the Stars

Apartment, Upperville

Romantic African-Inspired Studio on Alpaca Farm – Under the Stars is a apartment in Upperville, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a…

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About Romantic African-Inspired Studio on Alpaca Farm – Under the Stars

Romantic African-Inspired Studio on Alpaca Farm – Under the Stars is a apartment in Upperville, with pet-friendly space, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,289.

From$327/night

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The Van Gogh Room in Villa

B & B, Upperville

The Van Gogh Room in Villa is a b & b in Upperville, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About The Van Gogh Room in Villa

The Van Gogh Room in Villa is a b & b in Upperville, with 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: pool, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,323.

From$332/night

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2 minutes to the Upperville Horse Show

Holiday Home, Upperville

2 minutes to the Upperville Horse Show is a holiday home in Upperville, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 2 minutes to the Upperville Horse Show

2 minutes to the Upperville Horse Show is a holiday home in Upperville, 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 $8,435.

From$1,205/night

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Tyrolean Garden Suite w/pool/private entrance n patio

B & B, Upperville

Tyrolean Garden Suite w/pool/private entrance n patio is a b & b in Upperville, with pool access, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the…

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About Tyrolean Garden Suite w/pool/private entrance n patio

Tyrolean Garden Suite w/pool/private entrance n patio is a b & b in Upperville, with pool access, 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: pool, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,698.

From$243/night

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Vacation rentals with parking in Upperville, VA

Find vacation rentals that make arriving by car easier.

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

Cabin, Upperville

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub is a cabin in Upperville, 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 Upperville, 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 $1,589.

From$227/night

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Whiskey Hill Cabin a mountain escape in Virginia wine country

Cabin, Upperville

Whiskey Hill Cabin a mountain escape in Virginia wine country is a cabin in Upperville, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Whiskey Hill Cabin a mountain escape in Virginia wine country

Whiskey Hill Cabin a mountain escape in Virginia wine country is a cabin in Upperville, 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 $1,624.

From$232/night

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Skycrest Cabin • Mountain View • Hot Tub & Sauna

Cabin, Upperville

Skycrest Cabin · Mountain View · Hot Tub & Sauna is a cabin in Upperville, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Skycrest Cabin • Mountain View • Hot Tub & Sauna

Skycrest Cabin · Mountain View · Hot Tub & Sauna is a cabin in Upperville, 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: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,761.

From$252/night

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Villa Maud

Villa, Upperville

Villa Maud is a villa in Upperville, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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About Villa Maud

Villa Maud is a villa in Upperville, 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: hot tub, free wifi, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,314.

From$263/night

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Pet-friendly vacation rentals in Upperville, VA

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

The Grape Escape - A-Frame Cabin

Cabin, Upperville

The Grape Escape - A-Frame Cabin is a cabin in Upperville, 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 The Grape Escape - A-Frame Cabin

The Grape Escape - A-Frame Cabin is a cabin in Upperville, 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 $1,325.

From$189/night

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The Outpost Suite 3 - Whimsical Farmhouse Retreat

Apartment, Upperville

The Outpost Suite 3 - Whimsical Farmhouse Retreat is a apartment in Upperville, 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 Upperville, 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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Blue Mountain Cabin, secluded, perfect for couples, near main road

Cabin, Upperville

Blue Mountain Cabin, secluded, perfect for couples, near main road is a cabin in Upperville, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain Cabin, secluded, perfect for couples, near main road is a cabin in Upperville, 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 $1,519.

From$217/night

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Quiet Virginia Wine Country Retreat

Holiday Home, Upperville

Quiet Virginia Wine Country Retreat is a holiday home in Upperville, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Quiet Virginia Wine Country Retreat

Quiet Virginia Wine Country Retreat is a holiday home in Upperville, 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 $2,029.

From$290/night

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Vacation rentals with a kitchen in Upperville, VA

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

Mountain cabin near national park & wineries

Cabin, Upperville

Mountain cabin near national park & wineries is a cabin in Upperville, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Mountain cabin near national park & wineries

Mountain cabin near national park & wineries is a cabin in Upperville, 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 $1,662.

From$237/night

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Cedarbank • Cabin in Virginia Wine Country

Cabin, Upperville

Cedarbank · Cabin in Virginia Wine Country is a cabin in Upperville, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cedarbank • Cabin in Virginia Wine Country

Cedarbank · Cabin in Virginia Wine Country is a cabin in Upperville, 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 $1,843.

From$263/night

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Blue Mountain Getaway: Hot tub, Winery, Game Room

Holiday Home, Upperville

Blue Mountain Getaway: Hot tub, Winery, Game Room is a holiday home in Upperville, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Blue Mountain Getaway: Hot tub, Winery, Game Room

Blue Mountain Getaway: Hot tub, Winery, Game Room is a holiday home in Upperville, 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 $1,991.

From$284/night

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Mont Bleu, A-Frame Cabin w/ Hot Tub & Scenic Views

Holiday Home, Upperville

Mont Bleu, A-Frame Cabin w/ Hot Tub & Scenic Views is a holiday home in Upperville, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Mont Bleu, A-Frame Cabin w/ Hot Tub & Scenic Views

Mont Bleu, A-Frame Cabin w/ Hot Tub & Scenic Views is a holiday home in Upperville, 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 $2,009.

From$287/night

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Family-friendly vacation rentals in Upperville, VA

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

Suite 4: Outpost · Gorgeous Farm Carriage House Loft

Country House, Upperville

Suite 4: Outpost · Gorgeous Farm Carriage House Loft is a country house in Upperville, 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 Upperville, 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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super cosy cottage with high speed internet!

Holiday Home, Upperville

super cosy cottage with high speed internet! is a holiday home in Upperville, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About super cosy cottage with high speed internet!

super cosy cottage with high speed internet! is a holiday home in Upperville, 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 $1,483.

From$212/night

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

Cottage, Upperville

Charming 2-bedroom cottage with WiFi, AC in delightful Boyce is a cottage in Upperville, 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 Upperville, 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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Lovely Guest House 2.5 miles from downtown Middleburg

Cottage, Upperville

Lovely Guest House 2.5 miles from downtown Middleburg is a cottage in Upperville, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Lovely Guest House 2.5 miles from downtown Middleburg

Lovely Guest House 2.5 miles from downtown Middleburg is a cottage in Upperville, 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 $2,412.

From$345/night

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