Round Hill Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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

Hotel Arboretum

2 out of 5
Northeast
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Washington (WAS)
8/10 Very Good! (968 reviews)
Good location. Clean Room. Breakfast average. Laundry facility.

Reviewed on Aug. 13, 2025

The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Washington (DCA)
8.6/10 Excellent! (1,005 reviews)
Good location, friendly staff, great breakfast, clean and quiet rooms, best sleep in a week

Reviewed on Aug. 12, 2025

Hampton Inn & Suites Washington DC-Navy Yard

Hampton Inn & Suites Washington DC-Navy Yard

3 out of 5
Navy Yard
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Washington (WAS)
8.8/10 Excellent! (1,003 reviews)
Great hotel. Always our go to location when attending a Nationals game. Suite was wonderful. Great view of the stadium and the water.

Reviewed on Aug. 3, 2025

YOTEL Washington DC

YOTEL Washington DC

4 out of 5
Northwest
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Washington (WAS)
8.2/10 Very Good! (2,041 reviews)
After driving eight hours to Washington, I was looking forward to relaxing at the hotel. Check-in itself went smoothly, but the lobby was extremely crowded with people in swimsuits, smoking, drinking, and laughing loudly. We were told there was a private pool party that would be over by 9 p.m. Unfortunately, the noise continued well into the night. At around 3 a.m., I had to call the reception to complain. I was told that this kind of disturbance had been happening for a while, which was very disappointing to hear. The next day, we checked out without being able to enjoy the pool or get much rest. I cannot recommend this hotel, especially when private events like this are held without proper consideration for other guests.

Reviewed on Aug. 13, 2025

Holiday Inn Alexandria at Carlyle by IHG

Holiday Inn Alexandria at Carlyle by IHG

3 out of 5
Eisenhower East
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Washington (WAS)
8/10 Very Good! (1,003 reviews)
Close to the metro, safe walking back to the hotel at nighttime. Rooms were clean

Reviewed on Aug. 12, 2025

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
See all 797 properties in Round Hill
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

What to do in Round Hill

Harpers Ferry Tour

Harpers Ferry Tour

CA $177
per traveller
Harpers Ferry Tour
See all activities 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.