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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

23–28 Aug

$1,997 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

19–24 Aug

$2,563 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

11–16 Aug

$2,588 SGD for 5 nights

4.95 out of 5 average rating, 38 reviews

Top guest favourite

Guest house in Middleburg

18th Century Middleburg Cottage

1 bedroom, 1 queen bed

22–27 Aug

$1,962 SGD for 5 nights

5.0 out of 5 average rating, 134 reviews

Top guest favourite

Farm stay in Upperville

Farmhouse, pond & paddock views

4 bedrooms, 5 beds

10–15 Aug

$4,541 SGD for 5 nights

5.0 out of 5 average rating, 14 reviews

Top guest favourite

Cottage in Middleburg

Middleburg Bliss!

3 bedrooms, 5 beds

19–24 Aug

$1,990 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 87 reviews

Guest favourite

Home in Upperville

Reynard's Retreat in Upperville

3 bedrooms, 3 beds

19–24 Aug

$3,083 SGD for 5 nights

Pay $0 today

Free cancellation

4.95 out of 5 average rating, 22 reviews

Top guest favourite

Barn in Middleburg

The Hayloft

2 bedrooms, 4 beds

23–28 Aug

$4,950 SGD for 5 nights

5.0 out of 5 average rating, 76 reviews

Guest favourite

Home in Upperville

Horse Country | Pool | MNT Views | Full Kitchen

6 bedrooms, 8 beds

13–18 Sept

Pay $0 today

Free cancellation

4.9 out of 5 average rating, 20 reviews

Guest favourite

Home in Middleburg

Grand 9BR Manor Ideal for Weddings & Gatherings

9 bedrooms, 9 beds

21–26 Aug

$10,888 SGD for 5 nights

5.0 out of 5 average rating, 7 reviews

Home in Upperville

Virginia Horse and Wine Country Farm Stay

3 bedrooms, 4 beds

15–20 Aug

$1,719 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 4 reviews

Guest favourite

Cabin in Upperville

Island cabin

1 bedroom, 1 queen bed

30 Aug – 4 Sept

$1,993 SGD for 5 nights

4.94 out of 5 average rating, 180 reviews

Top guest favourite

Home in Middleburg

English Cottage/Main House

2 bedrooms, 2 beds

9–14 Aug

$2,086 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 56 reviews

Top guest favourite

Cabin in Marshall

The Serenity Cabin | Firepit | Wineries | Hiking

1 bedroom, 2 beds

8–13 Aug

Pay $0 today

Free cancellation

4.96 out of 5 average rating, 70 reviews

Guest favourite

Home in Marshall

Atoka Cottage

3 bedrooms, 3 beds

16–21 Aug

$2,224 SGD for 5 nights

Pay $0 today

Free cancellation

4.89 out of 5 average rating, 28 reviews

Top guest favourite

Cabin in Linden

Chipmunk Hollow | Hot Tub, Grill & Fire Table

3 bedrooms, 4 beds

16–21 Aug

Extended stay discount

4.97 out of 5 average rating, 69 reviews

Guest favourite

Cottage in Middleburg

Waterfront Cottage at Goose Creek

1 bedroom, 2 beds

2–7 Nov

$2,020 SGD for 5 nights

Pay $0 today

Free cancellation

4.94 out of 5 average rating, 235 reviews

Guest favourite

Guest suite in Middleburg

Middleburg Sunset Private Guest Suite

1 bedroom, 2 beds

11–16 Aug

$1,647 SGD for 5 nights

4.9 out of 5 average rating, 21 reviews

Top guest favourite

Barn in Middleburg

The Studio

1 bedroom, 1 king bed

18–23 Aug

$3,026 SGD for 5 nights

Pay $0 today

Free cancellation

4.98 out of 5 average rating, 107 reviews