Berryville Vacations

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Find the Best Berryville Vacation Packages

Berryville Hotel Deals

Salamander Resort And Spa

Salamander Resort And Spa

500 North Pendleton Street Middleburg VA
Fully refundableReserve now, pay when you stay
NT$21,903
NT$26,749 total
Sep 7 - Sep 8
includes taxes & fees
Salamander Resort And Spa
Spark by Hilton Winchester

Spark by Hilton Winchester

150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
NT$2,510
NT$2,844 total
Sep 14 - Sep 15
includes taxes & fees
Spark by Hilton Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

333 Front Royal Pike Winchester VA
Fully refundable
NT$2,963
NT$3,393 total
Aug 30 - Aug 31
includes taxes & fees
9/10 Wonderful! (1,022 reviews)
"We were warmly greeted by Ellie. She really made us feel welcome. A very welcome experience. Our room is fantastic. The bed is comfortable. room spacious and well furnished. The amenities are numerous. The room was clean, spacious and comfortable. The only "complaint" is the towels were thin and ..."

Reviewed on 2026/8/22

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 938 properties in Berryville
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.

Stay near popular Berryville attractions

A camping scene by a lake with tents and a table with food.

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.
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A close-up of red apples on a tree branch with green leaves.

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.
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A vineyard with metal gates and a clear blue sky.

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.
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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.
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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.
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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.
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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.
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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?
The off-season is the best time to head to Berryville if you're hoping to keep costs down. Another tip for finding cheap Berryville vacation packages? Avoid visiting during public holidays and any major events.
How many days is enough for Berryville?
With a well-organized schedule, you can easily hit the most popular Berryville sights in a few days. But if you prefer to explore off the beaten track or go on day trips, think about booking your Berryville vacation for longer.
Is it worth booking a vacation package to Berryville?
From leading attractions such as The Fire House Gallery and Barns of Rose Hill to its epic history, a Berryville vacation offers a vibrant mix of experiences. With so much to do and see, find out for yourself why Berryville is such a good vacation destination.
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.
How to plan a trip to Berryville?
  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to Berryville.
  2. Budget wisely: In addition to the cost of your stay, you'll need to consider other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that may arise during your trip to Berryville.
  3. Work out your trip length: Think about how long you want to spend exploring Berryville. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Bundle your airfare and accommodations: Once you've settled on your travel dates and duration, book the right Berryville vacation package for you.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.