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upperville va
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Search results; Over 1,000 rooms in Upperville
Over 1,000 rooms in Upperville
Superhost
Superhost
Cottage in Upperville
Cottage on Pantherskin Creek - Upperville
1 queen bed
1 queen bed
Apr 20 – 25
Apr 20 – 25
R4,347 ZAR
night
R4,347 ZAR per night
4.88 out of 5 average rating, 114 reviews
4.88 (114)
Guest favorite
Guest favorite
Cottage in Upperville
Lanham House - Fully Restored Upperville Gem
3 beds
3 beds
Apr 29 – May 4
Apr 29 – May 4
R5,955 ZAR
night
R5,955 ZAR per night
5.0 out of 5 average rating, 77 reviews
5.0 (77)
Guest favorite
Guest favorite
Home in Upperville
Upperville Hunt Country Cottage
5 beds
5 beds
Apr 21 – 26
Apr 21 – 26
R7,274 ZAR
night
R7,274 ZAR per night
4.91 out of 5 average rating, 161 reviews
4.91 (161)
Guest favorite
Guest favorite
Cottage in Upperville
Cozy Country Getaway in the Heart of Upperville
3 beds
3 beds
Apr 21 – 26
Apr 21 – 26
R5,717 ZAR
night
R5,717 ZAR per night
4.82 out of 5 average rating, 62 reviews
4.82 (62)
Guest favorite
Guest favorite
Place to stay in Middleburg
Old Historic Charm on a Lovely 66 acre Farm
1 queen bed
1 queen bed
May 6 – 11
May 6 – 11
R3,520 ZAR
night
R3,520 ZAR per night
4.95 out of 5 average rating, 43 reviews
4.95 (43)
Guest favorite
Guest favorite
Home in Upperville
Peaceful Country Retreat
3 beds
3 beds
May 3 – 8
May 3 – 8
R6,476 ZAR
night
R6,476 ZAR per night
4.95 out of 5 average rating, 41 reviews
4.95 (41)
Superhost
Superhost
Home in Upperville
The Upperville Academy
5 beds
5 beds
Apr 21 – 26
Apr 21 – 26
R14,199 ZAR
night
R14,199 ZAR per night
4.95 out of 5 average rating, 44 reviews
4.95 (44)
Guest favorite
Guest favorite
Farm stay in Middleburg
Self-contained apartment on Organic vegetable farm
2 beds
2 beds
May 5 – 10
May 5 – 10
R3,138 ZAR
night
R3,138 ZAR per night
4.9 out of 5 average rating, 91 reviews
4.9 (91)
Guest favorite
Guest favorite
Farm stay in Middleburg
Retreat to horse country!
1 bed
1 bed
Apr 21 – 26
Apr 21 – 26
R4,763 ZAR
night
R4,763 ZAR per night
4.94 out of 5 average rating, 36 reviews
4.94 (36)
Guest favorite
Guest favorite
Cottage in Middleburg
Middleburg Bliss
5 beds
5 beds
Jun 18 – 23
Jun 18 – 23
R6,173 ZAR
night
R6,173 ZAR per night
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Guest favorite
Guest favorite
Cabin in Upperville
Island cabin
1 queen bed
1 queen bed
Apr 21 – 26
Apr 21 – 26
R5,622 ZAR
night
R5,622 ZAR per night
4.93 out of 5 average rating, 124 reviews
4.93 (124)
Guest favorite
Guest favorite
Home in Upperville
Raspberry Repose
Apr 21 – 26
Apr 21 – 26
R7,881 ZAR
R5,961 ZAR
night
R5,961 ZAR per night, originally R7,881 ZAR
4.9 out of 5 average rating, 20 reviews
4.9 (20)
Guest favorite
Guest favorite
Guesthouse in Middleburg
18th Century Middleburg Cottage
1 queen bed
1 queen bed
May 12 – 17
May 12 – 17
R5,435 ZAR
night
R5,435 ZAR per night
5.0 out of 5 average rating, 40 reviews
5.0 (40)
Guest favorite
Guest favorite
Cottage in Upperville
Meticulous Hunt Country 2BR 1BA Upperville Cottage
2 beds
2 beds
Apr 20 – 25
Apr 20 – 25
R8,099 ZAR
night
R8,099 ZAR per night
4.94 out of 5 average rating, 88 reviews
4.94 (88)
Guest favorite
Guest favorite
Home in Middleburg
The Old Post Office
2 beds
2 beds
May 13 – 18
May 13 – 18
R5,171 ZAR
night
R5,171 ZAR per night
4.86 out of 5 average rating, 7 reviews
4.86 (7)
Guest favorite
Guest favorite
Cottage in Middleburg
Waterfront Cottage at Goose Creek
2 beds
2 beds
Jun 24 – 29
Jun 24 – 29
R5,651 ZAR
night
R5,651 ZAR per night
4.95 out of 5 average rating, 163 reviews
4.95 (163)
Guest favorite
Guest favorite
Home in Middleburg
Littlefield Cottage
4 beds
4 beds
Apr 21 – 26
Apr 21 – 26
R8,130 ZAR
R6,265 ZAR
night
R6,265 ZAR per night, originally R8,130 ZAR
5.0 out of 5 average rating, 139 reviews
5.0 (139)
Guest favorite
Guest favorite
Guest suite in Middleburg
Serene retreat in the heart of wine country
1 queen bed
1 queen bed
Apr 25 – 30
Apr 25 – 30
R3,326 ZAR
night
R3,326 ZAR per night
4.92 out of 5 average rating, 73 reviews
4.92 (73)
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