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Search results; Over 1,000 homes in Upperville

Guest favourite

Cabin in Upperville

Island cabin

1 bedroom, 1 bed, 1 private bathroom

2–7 Aug

$2,004 SGD for 5 nights

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4.94 out of 5 average rating, 180 reviews

Top guest favourite

Cottage in Upperville

Cozy Country Getaway in the Heart of Upperville

2 bedrooms, 3 beds, 2 bathrooms

1–6 Aug

$2,026 SGD for 5 nights

4.9 out of 5 average rating, 108 reviews

Top guest favourite

Cottage in Upperville

Green Acre - A Hunt Country Retreat

2 bedrooms, 3 beds, 2 bathrooms

10–15 Aug

$2,525 SGD for 5 nights

4.95 out of 5 average rating, 37 reviews

Guest favourite

Home in Upperville

Upperville Hunt Country Cottage

3 bedrooms, 5 beds, 2 bathrooms

1–6 Aug

$2,591 SGD for 5 nights

4.91 out of 5 average rating, 207 reviews

Top guest favourite

Home in Upperville

Pool|King Bed|Home Theater|Game Room|Wineries

1 bedroom, 1 king bed, 1 bathroom

9–14 Aug

$1,551 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 6 reviews

Top guest favourite

Farm stay in Middleburg

The Blacksmith Cottage

1 bedroom, 1 queen bed, 1 bathroom

1–6 Aug

$1,467 SGD for 5 nights

4.96 out of 5 average rating, 127 reviews

Guest favourite

Cottage in Upperville

Meticulous Hunt Country 2BR 1BA Upperville Cottage

2 bedrooms, 2 beds, 1 bathroom

1–6 Aug

$2,971 SGD for 5 nights

4.93 out of 5 average rating, 102 reviews

Home in Upperville

Virginia Horse and Wine Country Farm Stay

3 bedrooms, 4 beds, 1 bathroom

1–6 Aug

$1,738 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Guest suite in Bluemont

Blueridge Mountain Retreat Apartment

1 bedroom, 2 beds, 1 bathroom

3–8 Aug

$866 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

Guest favourite

Home in Upperville

Reynard's Retreat in Upperville

3 bedrooms, 3 beds, 2 bathrooms

1–6 Aug

$3,116 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

4–9 Aug

$1,254 SGD for 5 nights

4.9 out of 5 average rating, 20 reviews

Guest favourite

Flat in The Plains

Charming barn apartment in horse /wine country

1 bedroom, 1 double bed, 1 bathroom

3–8 Aug

$1,023 SGD for 5 nights

4.96 out of 5 average rating, 23 reviews

Guest favourite

Room in Bluemont

A Castle in the Woods at Bluemont VIrginia

5 beds, 1.5 bathrooms

22–27 Aug

$610 SGD for 5 nights

Free cancellation

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

$1,237 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 94 reviews

Guest favourite

Farm stay in The Plains

Elegant, Country Capsule: Suite and Stone Kitchen

1 bedroom, 1 queen bed, 1 bathroom

1–6 Dec

$701 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Top guest favourite

Farm stay in Marshall

Charming 3BR Farmhouse • Wine Country Getaway

3 bedrooms, 6 beds, 2.5 bathrooms

2–7 Aug

$1,215 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 32 reviews

Top guest favourite

Flat in Middleburg

Middleburg Carriage House Flat Coachman’s Quarters

2 bedrooms, 2 beds, 1 bathroom

9–14 Aug

$2,248 SGD for 5 nights

5.0 out of 5 average rating, 85 reviews

Top guest favourite

Farm stay in Middleburg

Retreat to horse country!

1 bedroom, 1 bed, 1.5 bathrooms

9–14 Aug

$1,709 SGD for 5 nights

4.97 out of 5 average rating, 100 reviews