Round Hill Vacations from $236

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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.

The Latest Round Hill vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Columbia East-Jessup by IHG

Holiday Inn Columbia East-Jessup by IHG

3 out of 5
Save 100% on your flight
Price was $353, price is now $236 per person
$236
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (1,011 reviews)
The staff were friendly and helpful. The room was clean and comfortable. There were lots of restaurants and stores near by. Check out was quick and easy.

Reviewed on Jun 24, 2026

Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Save 100% on your flight
Price was $1,586, price is now $946 per person
$946
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Baltimore (BWI)
9.6/10 Exceptional! (75 reviews)
Loved our time here - will definitely be coming back

Reviewed on Jun 22, 2026

Residence Inn by Marriott Washington, DC National Mall

Residence Inn by Marriott Washington, DC National Mall

3 out of 5
Southwest
Save 100% on your flight
Price was $1,216, price is now $730 per person
$730
per person
Jul 27 - Jul 30
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,000 reviews)
Clean, safe, walkable, helpful and friendly staff. Very nice, spacious one bedroom suite. The free breakfast is one of the best I've ever seen.

Reviewed on Jun 25, 2026

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $634, price is now $402 per person
$402
per person
Aug 20 - Aug 24
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,022 reviews)
This is a safe, nice hotel on a college campus in a great location of DC. The staff was friendly and professional. The only thing we had an issue is with allergies. Seemed like a dust issue as the rooms all have the air conditioning with recycled air. Overall great property.

Reviewed on Jun 15, 2026

Convention Center PH Free indoor parking

Convention Center PH Free indoor parking

4 out of 5
Downtown Baltimore
Save 100% on your flight
Price was $555, price is now $359 per person
$359
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
6/10 (1 review)
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Stay near popular Round Hill attractions

Stoneleigh Golf and Country Club

Nestled against the Blue Ridge Mountains, this 18-hole course features historic stone walls and a manor house. Members enjoy uncrowded fairways with strategic elevation changes and scenic natural features.
See properties

What to do in Round Hill

Luxe Day Trip: 3 VA Wineries & Optional Tasting-Inclusive Upgrade

3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade

$120
per adult
3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade
Exclusive Virginia Wine Country Day Trip Tour

Private Virginia Wine Country Tour

$498
per traveler
Private Virginia Wine Country Tour
See all activities in Round Hill

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
$275 nightly
The price is $314 total per night from Jul 7 to Jul 8
$314 total
Jul 7 - Jul 8
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
"The resort was gorgeous and well maintained. The proximity to various vineyards was perfect."

Reviewed on Jun 22, 2026

Lansdowne Resort and Spa
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $87 total per night from Jul 20 to Jul 21
$87 total
Jul 20 - Jul 21
Total with taxes and fees
9/10 Wonderful! (1,007 reviews)
"Overall great experience - with that said their computer system wasnt working right. I was charged for the room twice (over and above the already charged payment from Expedia) and also a $100 security deposit. I brought it up the next day and it was immediately corrected. Nice hotel, good local, ..."

Reviewed on Jun 24, 2026

Spark by Hilton Winchester
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $83 total per night from Jul 5 to Jul 6
$83 total
Jul 5 - Jul 6
Total with taxes and fees
9.2/10 Wonderful! (985 reviews)
"Great overnight stay with the family. The rooms were clean and comfortable, and the kids absolutely loved the breakfast spread. I would recommend staying here if you're in the area or just passing through."

Reviewed on Jun 26, 2026

TRU By Hilton Winchester
See all 858 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.

Find the Best Round Hill Vacation Packages

Round Hill Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Washington Dulles Intl. Airport (IAD)
Population
640
Top Sights
Greenhill Winery & Vineyards, Cana Vineyards and Winery and Bogati Bodega & Winery

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Frequently asked questions

How much does a Round Hill vacation package cost?
Offering great value package deals from $236 on Expedia, you'll be thrilled with how little a vacation to Round Hill costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Round Hill?
November, December and January are the best times to search for cheap Round Hill vacation packages. Opting to travel in less busy periods means you can typically find reduced prices on flights and hotels.
How many days is enough for Round Hill?
You can explore all the leading sights in Round Hill within a few days, including the must-see Round Hill Arts Center. If you're after a longer Round Hill vacation, look at what sort of day trips and activities are available nearby.
Is it worth booking a vacation package to Round Hill?
Round Hill has everything you need for a wonderful trip. Get your Round Hill vacation off to a flying start by checking out popular attractions like Round Hill Arts Center.
How to find the best Round Hill package deals?
Start your search for a Round Hill package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Round Hill package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Round Hill getaway off to a flying start.
Is it cheaper to book a Round Hill vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component individually. And you'll still have the flexibility to create a tailored Round Hill vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Round Hill?
If you're planning a spontaneous Round Hill trip, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Round Hill?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Round Hill.
  2. Set a budget: Consider costs such as flights, meals and transportation when working out how much to save for your trip to Round Hill. Then, pick a property that suits your budget, whether that's an economical stay or a lavish retreat.
  3. Discover Round Hill with Expedia's trip planning tool: Gain insights into the most popular attractions and best stays for your trip to Round Hill. You can also save your favorite locations, collaborate with family and friends and organize all your plans in one place.
  4. Set the duration of your trip: Start by compiling a list of the attractions you want to get to in Round Hill. Then, estimate how long you'll need for each, along with any travel time.
  5. Combine your airfare and accommodations: After you've nailed down your travel dates and duration, book the perfect Round Hill vacation package for you.
  6. Book experiences or activities ahead of time: Whether it's a ticket to a big attraction or a walking tour, you won't have to worry about missing out on the best Round Hill has to offer. Find all the exciting things to do in Round Hill with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Round Hill vacation packages?
If you're like us, you love traveling the world but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Round Hill vacation across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you see them.

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