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Search results; Over 1,000 places in Upperville

Guest favorite
Cottage in Upperville
Lanham House - Fully Restored Upperville Gem
3 beds
Apr 29 – May 4
5.0 out of 5 average rating, 77 reviews
Superhost
Cottage in Upperville
Cottage on Pantherskin Creek - Upperville
1 queen bed
Apr 18 – 23
4.88 out of 5 average rating, 114 reviews
Guest favorite
Cottage in Upperville
Cozy Country Getaway in the Heart of Upperville
3 beds
Apr 21 – 26
4.82 out of 5 average rating, 62 reviews
Guest favorite
Home in Upperville
Upperville Hunt Country Cottage
5 beds
Apr 19 – 24
4.91 out of 5 average rating, 161 reviews
Guest favorite
Home in Upperville
Peaceful Country Retreat
3 beds
May 3 – 8
4.95 out of 5 average rating, 41 reviews
Guest favorite
Farm stay in Middleburg
Self-contained apartment on Organic vegetable farm
2 beds
May 5 – 10
4.9 out of 5 average rating, 91 reviews
Guest favorite
Guest suite in Middleburg
Serene retreat in the heart of wine country
1 queen bed
Apr 25 – 30
4.92 out of 5 average rating, 73 reviews
Guest favorite
Cottage in Middleburg
Waterfront Cottage at Goose Creek
2 beds
Jun 24 – 29
4.95 out of 5 average rating, 163 reviews
Guest favorite
Farm stay in Middleburg
Retreat to horse country!
1 bed
Apr 21 – 26
4.94 out of 5 average rating, 36 reviews
Guest favorite
Cottage in Upperville
Meticulous Hunt Country 2BR 1BA Upperville Cottage
2 beds
Apr 19 – 24
4.94 out of 5 average rating, 88 reviews
Guest favorite
Cottage in Middleburg
Middleburg Bliss
5 beds
Jun 18 – 23
5.0 out of 5 average rating, 12 reviews
Guest favorite
Guesthouse in Middleburg
18th Century Middleburg Cottage
1 queen bed
May 10 – 15
5.0 out of 5 average rating, 40 reviews
Guest favorite
Cabin in Upperville
Island cabin
1 queen bed
Apr 21 – 26
4.93 out of 5 average rating, 124 reviews
Superhost
Home in Middleburg
The Coach Stop at White Hall
4 queen beds
Apr 29 – May 4
4.94 out of 5 average rating, 132 reviews
Guest favorite
Home in Middleburg
Stone Cottage, Comfort, Peace and Nature.
4 beds
Apr 29 – May 4
4.95 out of 5 average rating, 41 reviews
Superhost
Home in Upperville
The Upperville Academy
5 beds
Apr 21 – 26
4.95 out of 5 average rating, 44 reviews
Guest favorite
Barn in Middleburg
Country Bank Barn
5 beds
Apr 21 – 26
4.98 out of 5 average rating, 218 reviews
Guest favorite
Home in Upperville
Raspberry Repose
Apr 21 – 26
4.9 out of 5 average rating, 20 reviews