Berryville Vacations
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Your Berryville Vacation
Let our vacation packages to Berryville inspire your next great escape. You'll find a whole lot to love about this captivating city, starting with the neighborhood of Old Town Winchester, which is good for cafes and history. A trip to Berryville is a wonderful opportunity to do a bit of sightseeing. Check out well-known attractions like Mackintosh Fruit Farm, Veramar Vineyard and Barns of Rose Hill. Stop dreaming and start doing. Check out the broad range of options on Expedia today and put your Berryville vacation plans into motion!
Stay near popular Berryville attractions
Watermelon Park Campground
Nestled along the Shenandoah River since 1939, this family-owned campground offers a peaceful escape for outdoor enthusiasts. Enjoy tubing, kayaking, and fishing while surrounded by the stunning Blue Ridge Mountains.
Mackintosh Fruit Farm
10.0/10 (2 reviews)
Harvest your own seasonal bounty at this sustainable family farm nestled in Virginia's countryside. Savor farm-to-table meals from the kitchen while exploring the market's locally-sourced treasures.
Veramar Vineyard
This family-owned vineyard crafts award-winning wines amid stunning Blue Ridge Mountain views. Savor guided tastings of Cabernet Franc and Riesling while enjoying the serene Shenandoah Valley setting.
Barns of Rose Hill
This renovated dairy barn duo now serves as a vibrant cultural center with exceptional acoustics. Enjoy intimate concerts, art exhibitions, and workshops in a historic Shenandoah Valley setting.
Holy Cross Abbey
10.0/10 (2 reviews)
Holy Cross Abbey offers a serene Trappist monastery retreat along the Shenandoah River. Visitors can join monastic services, browse monk-made goods in the gift shop, and absorb the peaceful countryside views.
612 Vineyard
This intimate Shenandoah Valley winery offers locally-crafted wines in a picturesque Blue Ridge Mountain setting. Enjoy tastings with live weekend music on the stone patio or in the spacious indoor tasting room.
Cool Spring
This Civil War battlefield site shares grounds with Holy Cross Abbey, a working Trappist monastery. Walk the historic fields where soldiers clashed, then find moments of reflection amid the monks' peaceful sanctuary.
Berryville Hotel Deals
Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
Fully refundableReserve now, pay when you stay
$612 nightly
$697 total
Sep 8 - Sep 9
Total with taxes and fees
9.2/10 Wonderful! (410 reviews)
"The property and staff are amazing. Lots to do if you bring the kiddos, the kids camp let's adults relax and enjoy amenities. The one thing the property can work on is the food menu; more variety is needed. The Red Horse Tavern is a 5-minute walk into town and has the best food!!"
Reviewed on Jul 21, 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
$77 nightly
$87 total
Aug 30 - Aug 31
Total with taxes and fees
9.2/10 Wonderful! (1,010 reviews)
"Very good for the price"
Reviewed on Aug 8, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
Fully refundable
$94 nightly
$104 total
Aug 12 - Aug 13
Total with taxes and fees
9/10 Wonderful! (1,015 reviews)
"no phone cord for the hotel phone so I couldn't call room to room and there were only 3 bath towels for 4 people but both were easy fixes. But my reservation said free breakfast and they wanted $10 for 2 people, so not sure what that was about"
Reviewed on Aug 7, 2026
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.
Find the Best Berryville Vacation Packages
Berryville Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 4,300 |
Max Temp Winter | 40ºF |
Max Temp Summer | 85ºF |
Top Sights | Bluemont Vineyard, Dinosaur Land and Twin Oaks Tavern Winery |
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Frequently asked questions
How much does a Berryville vacation package cost?
You'll find cheap prices on Expedia for your Berryville break. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Berryville costs.
What are the cheapest months to go to Berryville?
You can typically find lower prices and greater availability in January, May and July. Browse our cheap Berryville vacation packages and you could land some excellent off-season deals.
How many days is enough for Berryville?
The ideal length of your Berryville vacation depends on what you'd like to see. Usually, a handful of days to a week will give you enough time to go to all the main sights and explore some hidden treasures along the way.
Is it worth booking a vacation package to Berryville?
Well known for its history and home to popular attractions like The Fire House Gallery, a Berryville vacation is sure to leave an impression. Another top sight to check out? Don't miss Barns of Rose Hill.
How to find the best Berryville package deals?
Finding a cheap Berryville package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can customize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Berryville package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Berryville vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component separately. And you'll still have the flexibility to create a customized Berryville vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Berryville?
If you're planning a spur-of-the-moment Berryville getaway, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find terrific deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Berryville vacation packages?
Set off on your ideal getaway to Berryville with help from Expedia's Book Now, Pay Later vacations. There's no need to save up or hold off until the next payday — we've partnered with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to budget for your trip and snap up travel deals before they sell out.
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- Appleland Sports Center
- Holy Cross Abbey
- Shenandoah Valley Discovery Museum
- Great Falls Park
- Bright Box Theater
- Sky Meadows State Park
- Stoneleigh Golf and Country Club
- Shenandoah University
- Watermelon Park Campground
- Visit Berryville
- Virginia River Trips
- Abram's Delight
- 868 Estate Vineyards
- K & S Pewter
- Veramar Vineyard
- Paris Barns
- Mackintosh Fruit Farm
- Mt Hebron Cemetery
- Patsy Cline Historic House
- 612 Vineyard
- Shen-Val Farm Market
- Bluemont Vineyard
- Rock Harbor Golf Course
- Museum of the Shenandoah Valley
- Nalls Farm Market
- George Washington's Office
- Jim Barnett Park
- Visit Winchester
- Stonewall Jackson's Headquarters
- Round Hill Vacations
- Dinosaur Land
- Winchester Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
