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Check prices for these dates

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Aug 22 - Aug 24
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Aug 29 - Aug 31
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Sep 12 - Sep 14
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Oct 10 - Oct 12

Browse Select Round Hill Villas

Private10000sf Retreat GuitarPool Hottub-Wine Area
Interior

Private10000sf Retreat GuitarPool Hottub-Wine Area

10.0 out of 10, Exceptional, (26)
"We’ve been twice and hope to return again, the perfect place for a family reunion."
Private10000sf Retreat GuitarPool Hottub-Wine Area
Events and Concierge! 6BR Heated Pool Near Wineries
TV, fireplace, DVD player, stereo

Events and Concierge! 6BR Heated Pool Near Wineries

The price is CA $580
CA $1,939 total
includes taxes & fees
Aug 14 - Aug 15
Events and Concierge! 6BR Heated Pool Near Wineries
Amazing Lagoon, Beach, Cross Fit Gym, Fishing
Property grounds

Amazing Lagoon, Beach, Cross Fit Gym, Fishing

10.0 out of 10, Exceptional, (9)
"Great home on such lovely, large private property. Everything was beautifully decorated and so well thought out. Comfortable beds, well-stocked kitchen, and amazing view from all the rooms. The kids especially loved peddle boating, and walking around the quarry to find hidden treasures. There were just so many things to do! We highly recommend this place, and hope to come back soon."
Amazing Lagoon, Beach, Cross Fit Gym, Fishing
Historic Virginia Wine Country Villa w/ Pool, Yard
Outdoor dining

Historic Virginia Wine Country Villa w/ Pool, Yard

7.6 out of 10, Good, (15)
"We had a great family vacation, everyone lived the pool!!"
Historic Virginia Wine Country Villa w/ Pool, Yard
Highmeadows Estate in the heart of Bluemont Virginia
Interior

Highmeadows Estate in the heart of Bluemont Virginia

Highmeadows Estate in the heart of Bluemont Virginia
Elegant Paris Manor w/ Private Pool!
Villa (6 Bedrooms) | Interior

Elegant Paris Manor w/ Private Pool!

3.0 star property
Elegant Paris Manor w/ Private Pool!
Historic Virginia Wine Country Villa w/ Pool, Yard
TV, fireplace, DVD player, iPod dock

Historic Virginia Wine Country Villa w/ Pool, Yard

3.0 star property
Historic Virginia Wine Country Villa w/ Pool, Yard
Stunning Former Winery w/ Pool & Mtn Views!
Villa (Multiple Bedrooms) | Interior

Stunning Former Winery w/ Pool & Mtn Views!

3.0 star property
Stunning Former Winery w/ Pool & Mtn Views!
Red Cherry Oasis - Charming 2 bedroom villa with AC, WiFi in serene Aldie
Exterior

Red Cherry Oasis - Charming 2 bedroom villa with AC, WiFi in serene Aldie

The price is CA $150
CA $402 total
includes taxes & fees
Sep 2 - Sep 3
Red Cherry Oasis - Charming 2 bedroom villa with AC, WiFi in serene Aldie
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Round Hill Hotel Reviews

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

10/10 Excellent
"Loved it, so neat and clean, and staff super nice, would recommend 👌. "
alejandra 2-night trip
Posted 21 hours ago
SpringHill Suites by Marriott Winchester