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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Villas in Berryville and around

Private10000sf Retreat GuitarPool Hottub-Wine Area
Outdoor pool, a heated pool

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
Exterior

Events and Concierge! 6BR Heated Pool Near Wineries

Events and Concierge! 6BR Heated Pool Near Wineries
Amazing Lagoon, Beach, Cross Fit Gym, Fishing
Terrace/patio

Amazing Lagoon, Beach, Cross Fit Gym, Fishing

10.0 out of 10, Exceptional, (10)
"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
Exterior

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
Terrace/patio

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
Exterior

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!
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 Berryville Hotel Reviews

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"staff was amazing and room was great "
Michael 1-night trip
Posted 1 day ago
Comfort Inn & Suites Winchester

Frequently asked questions

Why book your villa in Berryville with Expedia?
We think holiday time shouldn't be hard, so if you're looking for villas at an affordable price, Expedia can help. Keep costs down and opt for an all-inclusive stay, or splurge on a luxury villa to spoil your loved ones. Use our search filters to find a retreat in Berryville that matches your needs.
How can I find cheap villas in Berryville?
Expedia can help you look for cheap villas in Berryville. Use our filter tool to select budget, amenities and star rating to refine your search and find the perfect stay in a couple of clicks.
What is there to do near my villa in Berryville?
Berryville has enough sights and experiences to entertain you for weeks, starting with The Fire House Gallery. Barns of Rose Hill, Watermelon Park Campground and Mackintosh Fruit Farm are other well-known attractions. If you're in town a while, Holy Cross Abbey and 612 Vineyard are worthwhile additions to your itinerary.