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Search results; Over 1,000 homes in Upperville

Top guest favourite

Cottage in Upperville

Cozy Country Getaway in the Heart of Upperville

2 bedrooms, 3 beds, 2 private bathrooms

2–7 Aug

$2,011 SGD for 5 nights

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4.9 out of 5 average rating, 108 reviews

Guest favourite

Home in Upperville

Upperville Hunt Country Cottage

3 bedrooms, 5 beds, 2 bathrooms

3–8 Aug

$2,570 SGD for 5 nights

4.91 out of 5 average rating, 207 reviews

Top guest favourite

Cottage in Upperville

Green Acre - A Hunt Country Retreat

2 bedrooms, 3 beds, 2 bathrooms

10–15 Aug

$2,504 SGD for 5 nights

4.95 out of 5 average rating, 37 reviews

Home in Upperville

Virginia Horse and Wine Country Farm Stay

3 bedrooms, 4 beds, 1 bathroom

3–8 Aug

$1,724 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Guest favourite

Cottage in Upperville

Meticulous Hunt Country 2BR 1BA Upperville Cottage

2 bedrooms, 2 beds, 1 bathroom

2–7 Aug

$2,872 SGD for 5 nights

4.93 out of 5 average rating, 102 reviews

Guest favourite

Home in Upperville

Reynard's Retreat in Upperville

3 bedrooms, 3 beds, 2 bathrooms

3–8 Aug

$3,091 SGD for 5 nights

4.95 out of 5 average rating, 22 reviews

Guest favourite

Guest suite in Middleburg

Middleburg Sunset Private Guest Suite

1 bedroom, 2 beds, 1 bathroom

5–10 Aug

$1,332 SGD for 5 nights

4.9 out of 5 average rating, 20 reviews

Top guest favourite

Guest house in Round Hill

Private Carriage House

1 bedroom, 1 queen bed, 1 bathroom

22–27 Aug

$1,081 SGD for 5 nights

4.97 out of 5 average rating, 506 reviews

Guest favourite

Cabin in Upperville

Island cabin

1 bedroom, 1 queen bed, 1 bathroom

2–7 Aug

$1,988 SGD for 5 nights

4.94 out of 5 average rating, 180 reviews

Top guest favourite

Guest suite in Bluemont

Blueridge Mountain Retreat Apartment

1 bedroom, 2 beds, 1 bathroom

17–22 Aug

$859 SGD for 5 nights

4.93 out of 5 average rating, 660 reviews

Home in Upperville

Upperville Farm Cottage

2 bedrooms, 2 beds, 2 bathrooms

2–7 Aug

4.67 out of 5 average rating, 3 reviews

Top guest favourite

Cottage in Middleburg

Middleburg Bliss!

3 bedrooms, 5 beds, 2 bathrooms

19–24 Aug

$2,054 SGD for 5 nights

5.0 out of 5 average rating, 86 reviews

Top guest favourite

Guest house in Middleburg

18th Century Middleburg Cottage

1 bedroom, 1 queen bed, 1 bathroom

21–26 Aug

$1,987 SGD for 5 nights

5.0 out of 5 average rating, 132 reviews

Guest favourite

Room in Bluemont

A Castle in the Woods at Bluemont VIrginia

5 beds, 1.5 bathrooms

22–27 Aug

$605 SGD for 5 nights

4.91 out of 5 average rating, 376 reviews

Top guest favourite

Loft in Purcellville

Saddle Tree at Akeley Wood Farm

1 bedroom, 1 king bed, 1 bathroom

3–8 Aug

$1,227 SGD for 5 nights

4.97 out of 5 average rating, 94 reviews

Top guest favourite

Flat in Middleburg

Middleburg Carriage House Studio - The Loft

1 bedroom, 1 queen bed, 1 bathroom

14–19 Aug

$1,844 SGD for 5 nights

5.0 out of 5 average rating, 23 reviews

Top guest favourite

Home in Boyce

Cottage on the Shenandoah

3 bedrooms, 3 beds, 2 bathrooms

2–7 Aug

$1,667 SGD for 5 nights

4.99 out of 5 average rating, 81 reviews

Guest favourite

Cottage in Paris

Luxe Mountain Escape Near Upperville + Middleburg

1 bedroom, 1 queen bed, 1 bathroom

10–15 Aug

$2,411 SGD for 5 nights

4.97 out of 5 average rating, 357 reviews

Top guest favourite

Farm stay in Upperville

Farmhouse, pond & paddock views

4 bedrooms, 5 beds, 3 bathrooms

4–9 Aug

$4,770 SGD for 5 nights

5.0 out of 5 average rating, 14 reviews