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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

1–6 Aug

$2,020 SGD for 5 nights

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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

1–6 Aug

$2,523 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

$2,589 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

$1,550 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

$1,461 SGD for 5 nights

4.96 out of 5 average rating, 127 reviews

Home in Upperville

Virginia Horse and Wine Country Farm Stay

3 bedrooms, 4 beds, 1 bathroom

1–6 Aug

$1,736 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

1–6 Aug

$2,969 SGD for 5 nights

4.93 out of 5 average rating, 102 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, 659 reviews

Top guest favourite

Home in Middleburg

English Cottage/Main House

2 bedrooms, 2 beds, 2 bathrooms

1–6 Aug

$2,062 SGD for 5 nights

5.0 out of 5 average rating, 55 reviews

Guest favourite

Guest suite in Middleburg

Middleburg Sunset Private Guest Suite

1 bedroom, 2 beds, 1 bathroom

4–9 Aug

$1,253 SGD for 5 nights

4.9 out of 5 average rating, 20 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

Guest favourite

Cabin in Upperville

Island cabin

1 bedroom, 1 queen bed, 1 bathroom

2–7 Aug

$2,015 SGD for 5 nights

4.94 out of 5 average rating, 180 reviews

Home in Upperville

Upperville Farm Cottage

2 bedrooms, 2 beds, 2 bathrooms

1–6 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

$3,114 SGD for 5 nights

4.95 out of 5 average rating, 22 reviews

Top guest favourite

Loft in Purcellville

Saddle Tree at Akeley Wood Farm

1 bedroom, 1 king bed, 1 bathroom

3–8 Aug

$1,236 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 94 reviews

Guest favourite

Cabin in Purcellville

The 1744 Custom Cabin

1 bedroom, 1 queen bed, 1 bathroom

3–8 Aug

$1,163 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 25 reviews

Guest favourite

Home in Marshall

Middleburg Wine Country Retreat on 135 Acres

3 bedrooms, 3 beds, 2 bathrooms

5–10 Aug

$2,071 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 10 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

Guest favourite

Home in Bluemont

The Country French Cottage at High Meadows Estate

2 bedrooms, 2 beds, 1 bathroom

2–7 Aug

$1,350 SGD for 5 nights

4.9 out of 5 average rating, 260 reviews