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!

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Berryville Hotel Deals

13 BR Boutique in Berryville
13 BR Boutique in Berryville
Berryville
7.4/10 Good! (6 reviews)
In area for family wedding
"This house is a gem in progress. It was very spacious and naturally divided into separate areas so it worked well to group families with small children away from older couples without children. Several issues did develop during our stay which were immediately addressed. The dish washer was repaired ..."

Reviewed on Oct. 13, 2023

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13 BR Boutique in Berryville
Stunning Former Winery w/ Pool & Mtn Views!
Stunning Former Winery w/ Pool & Mtn Views!
Berryville
8.6/10 Excellent! (4 reviews)
Amazing views
"This place was perfect for our family and wedding party to all stay together. There was plenty of room, everyone was comfortable, and the scenery was fabulous!"

Reviewed on Sep. 15, 2024

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Stunning Former Winery w/ Pool & Mtn Views!
La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Apr. 3 to Apr. 4
CA $137
CA $149 total
includes taxes & fees
Apr 3 - Apr 4
9/10 Wonderful! (1,857 reviews)
"Great clean hotel just off the interstate."

Reviewed on Mar. 7, 2025

La Quinta Inn & Suites by Wyndham Winchester
See all 850 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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.

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