Berryville Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Berryville Holiday
Our pick of the best Berryville Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
NZ$259
1 Nov - 2 Nov
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"rooms are clean, spacious, and serviced everyday. Good breakfast on offer and the Bar is good too. Greal location and good parking. Staff very helpful and knowledgeable about the area. Shenandoah mountains are wonderful. Lots of wineries and farmers market near by"
Reviewed on 21 Oct 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
NZ$137
1 Nov - 2 Nov
includes taxes & fees
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
Fully refundableReserve now, pay when you stay
NZ$162
22 Nov - 23 Nov
includes taxes & fees
9.2/10 Wonderful! (1,435 reviews)
"The room was just ok; not any room in the bathroom to put anything so I had to store items on top of the toilet; breakfast was just mediocre."
Reviewed on 23 Oct 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.
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. Savour 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. Savour guided tastings of Cabernet Franc and Riesling while enjoying the serene 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.
Barns of Rose Hill
This renovated dairy barn duo now serves as a vibrant cultural centre with exceptional acoustics. Enjoy intimate concerts, art exhibitions, and workshops in a historic Shenandoah Valley setting.
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.
Frequently asked questions
How much does a Berryville holiday 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 holiday 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 holiday packages? Avoid visiting during public holidays and any major events.
How many days is enough for Berryville?
With a well-organised 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 holiday for longer.
Is it worth booking a holiday package to Berryville?
From leading attractions such as The Fire House Gallery and Barns of Rose Hill to its epic history, a Berryville holiday offers a vibrant mix of experiences. With so much to do and see, find out for yourself why Berryville is such a good holiday 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 customise your search by "Property class," "Number of bedrooms," "Traveller 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 travelling on a weekday, when prices are often lower.
Is it cheaper to book a Berryville holiday as a package?
Expedia holiday 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 customised Berryville holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday 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?
- 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.
- 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.
- 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.
- Bundle your airfare and accommodation: Once you've settled on your travel dates and duration, book the right Berryville holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
