Berryville Vacation Packages
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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!
Ready to book your vacation to Berryville?
Berryville Hotel Deals
Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
Fully refundableReserve now, pay when you stay
CA $999
CA $1,217 total
Aug 31 - Sep 1
includes taxes & fees
9.2/10 Wonderful! (411 reviews)
"A really luxe resort. Outside pool area super good fun and great for kids and adults alike with separate areas. Well staffed in all areas of the hotel"
Reviewed on Aug 18, 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
CA $111
CA $126 total
Sep 17 - Sep 18
includes taxes & fees
9.2/10 Wonderful! (1,015 reviews)
"Very clean and lovely. We enjoyed it"
Reviewed on Aug 20, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
Fully refundable
CA $128
CA $147 total
Aug 30 - Aug 31
includes taxes & fees
9/10 Wonderful! (1,017 reviews)
"Room was clean, roomy and comfy. Comfy chair with ottoman was a plus. Air conditioner was noisy. Breakfast is what you get at other hotels for free. $15 here. Bench out front really needs to be cleaned. Covered with bird poop. Friendly and helpful staff"
Reviewed on Aug 20, 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
You can take time to visit Watermelon Park Campground during your travels to Berryville. While in this trendy area, you can savor the wineries and coffeehouses.
Mackintosh Fruit Farm
10.0/10 (2 reviews)
Commune with nature and explore the great outdoors at Mackintosh Fruit Farm during your travels in Berryville. While in this family-friendly area, you can savor the top-notch restaurants.
Veramar Vineyard
You can enjoy a tasting or tour at Veramar Vineyard during your travels to Berryville. You can enjoy the wineries while in the area.
Holy Cross Abbey
10.0/10 (2 reviews)
Learn about the local history of Berryville when you spend time at Holy Cross Abbey. While you're in the area, find time to visit its casinos.
Barns of Rose Hill
Enjoy an outing to Barns of Rose Hill during your stay in Berryville. While you're here, you can savor the top-notch restaurants.
612 Vineyard
You can enjoy a tasting or tour at 612 Vineyard during your travels to Berryville. While you're in the area, find time to visit its casinos.
Cool Spring
Commune with nature and explore the great outdoors at Cool Spring during your travels in Berryville. Take in the art scene and sunsets in the area.
Frequently asked questions
How much does a Berryville vacation package cost?
You can grab a vacation package to this top destination on Expedia. However, how much your vacation to Berryville costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Berryville?
Plan your getaway for the low season and you're likely to find cheap Berryville vacation packages. Remember that school vacation periods and major festivals and events can have an impact on prices, so do some research before you go.
How many days is enough for Berryville?
The ideal duration of your Berryville vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you enough time to visit all the top sights and discover some hidden gems along the way.
Is it worth booking a vacation package to Berryville?
From attractions such as The Fire House Gallery and Barns of Rose Hill to its excellent history, a Berryville vacation delivers big on experiences. With so much to see and do, it's time to find out for yourself why Berryville is such a good vacation destination.
How to find the best Berryville package deals?
Bagging a cheap Berryville package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, add a couple of filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most economical Berryville package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Berryville vacation as a package?
You can enjoy significant savings on your Berryville escape by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Berryville?
Enjoy incredible bargains by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Berryville adventure.
How to plan a trip to Berryville?
- Choose the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Berryville.
- Plan your budget wisely: In addition to the cost of your hotel, you'll need to consider other expenses. These include transportation, flights and food. Also, set aside a little extra for unexpected expenses that could arise during your trip to Berryville.
- Decide how long to go away for: Now that you know more about Berryville, you can figure out the ideal length of your vacation. Pull together a draft itinerary and give yourself enough time to cover everything you want to do.
- Combine your airfare and accommodations: After you've settled on your travel dates and duration, lock in the ideal Berryville vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
