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Search results; Over 1,000 places in Upperville

Superhost
Cottage in Upperville
Cottage on Pantherskin Creek - Upperville
1 queen bed
Apr 1 – 6
4.87 out of 5 average rating, 111 reviews
Guest favorite
Cottage in Upperville
Lanham House - Fully Restored Upperville Gem
3 beds
Apr 8 – 13
5.0 out of 5 average rating, 77 reviews
Guest favorite
Home in Upperville
Peaceful Country Retreat
3 beds
Apr 1 – 6
4.95 out of 5 average rating, 41 reviews
Guest favorite
Guest suite in Middleburg
Serene retreat in the heart of wine country
1 queen bed
Apr 1 – 6
4.92 out of 5 average rating, 72 reviews
Guest favorite
Home in Upperville
Upperville Hunt Country Cottage
5 beds
Apr 1 – 6
4.91 out of 5 average rating, 161 reviews
Guest favorite
Home in Upperville
Raspberry Repose
9 beds
Apr 7 – 12
5.0 out of 5 average rating, 18 reviews
Guest favorite
Cabin in Upperville
Island cabin
1 queen bed
Apr 6 – 11
4.93 out of 5 average rating, 122 reviews
Apartment in Middleburg
Magnificent Middleburg Getaway
2 beds
Apr 1 – 6
Guest favorite
Guesthouse in Middleburg
18th Century Middleburg Cottage
1 queen bed
Jun 9 – 14
5.0 out of 5 average rating, 39 reviews
Guest favorite
Cottage in Middleburg
Waterfront Cottage at Goose Creek
2 beds
Apr 21 – 26
4.95 out of 5 average rating, 161 reviews
Guest favorite
Farm stay in Upperville
The Ark in Upperville
1 queen bed
Apr 1 – 6
4.99 out of 5 average rating, 67 reviews
Superhost
Home in Upperville
The Upperville Academy
5 beds
Apr 7 – 12
4.95 out of 5 average rating, 44 reviews
Superhost
Home in Middleburg
The Coach Stop at White Hall
4 queen beds
Apr 1 – 6
4.94 out of 5 average rating, 132 reviews
Guest favorite
Cottage in Middleburg
Cottage at Finnway Farm in Middleburg, VA
4 beds
Apr 1 – 6
5.0 out of 5 average rating, 17 reviews
Guest favorite
Cottage in Upperville
Meticulous Hunt Country 2BR 1BA Upperville Cottage
2 beds
Apr 1 – 6
4.94 out of 5 average rating, 88 reviews
Guest favorite
Home in Upperville
Reynard's Retreat in Upperville
3 beds
Apr 4 – 9
5.0 out of 5 average rating, 5 reviews
Guest favorite
Cottage in Delaplane
Seaton Place House
3 beds
Apr 2 – 7
5.0 out of 5 average rating, 24 reviews
Guest favorite
Home in Middleburg
Stone Cottage, Comfort, Peace and Nature.
4 beds
Apr 1 – 6
4.95 out of 5 average rating, 41 reviews