Round Hill Vacation Packages

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Your Round Hill Vacation

Our Round Hill vacation packages give you the power to customize your own adventure. Tailor your getaway to your interests and style and make every moment count in this wonderful city. Fill up your itinerary with visits to Bluemont Vineyard, Doukenie Winery and Twin Oaks Tavern Winery, some of the top attractions you simply have to see during a trip to Round Hill. Don't put off your visit to this city any longer. Your perfect Round Hill vacation is just a few clicks away with Expedia.

Top Round Hill Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Arboretum
The St. Gregory Hotel
Hampton Inn & Suites Washington DC-Navy Yard
YOTEL Washington DC
Holiday Inn Alexandria at Carlyle by IHG

Ready to book your vacation to Round Hill?

 

Choose your dates

Round Hill Hotel Deals

Lansdowne Resort and Spa

Lansdowne Resort and Spa

4 out of 5
44050 Woodridge Pkwy, Leesburg, VA
Fully refundableReserve now, pay when you stay
The price is CA $279 per night from Sep 1 to Sep 2
CA $279
CA $370 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Excellent couples getaway for Fourth of July, including great fireworks display. The pools and spa/fitness amenities are top notch and charming historic Leesburg is a 10-minute drive from the property."

Reviewed on Aug. 11, 2025

Lansdowne Resort and Spa
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from Sep 1 to Sep 2
CA $141
CA $154 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (2,121 reviews)
"Pet friendly, wonderful breakfast, clean, and great staff."

Reviewed on Aug. 13, 2025

La Quinta Inn & Suites by Wyndham Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike, Winchester, VA
Fully refundable
The price is CA $118 per night from Aug 17 to Aug 18
CA $118
CA $133 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Bed comfort"

Reviewed on Aug. 12, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
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.

What to do in Round Hill

Frequently asked questions

How much does a Round Hill vacation package cost?
Offering excellent value package deals from CA $771 on Expedia, you'll be pleasantly surprised at how much a vacation to Round Hill costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Round Hill?
To score cheap Round Hill vacation packages, organize your trip outside of busy periods like public holidays and major events. You'll typically find lower prices and better availability when it's less busy.
How many days is enough for Round Hill?
When planning your Round Hill vacation, a few days will be enough to tour the best spots. Be sure to stop by Twin Oaks Tavern Winery — it's one of the main attractions in this destination. If you're after more activities, consider basing yourself here and venturing off on some tours from Round Hill.
Is it worth booking a vacation package to Round Hill?
Round Hill is a good vacation destination with attractions like Round Hill Arts Centre among the many things to keep you busy. Whether you're heading away with the family or getting away with friends, a Round Hill vacation promises a good time for everyone.
How to find the best Round Hill package deals?
Landing a cheap Round Hill package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most economical Round Hill package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Round Hill vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still have the flexibility to create a personalized Round Hill vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Round Hill?
If you have your Round Hill travel dates finalized, book as early as you can to score some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Round Hill?

  1. Choose your travel dates: What you want to do in Round Hill and your preferred season will help you decide when to travel.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and dining out to airfares and activities. Your hotel will probably be the biggest expense during your trip to Round Hill.
  3. Work out your trip length: Consider how long you'd like to spend exploring Round Hill. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a personalized Round Hill vacation package.

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