Round Hill Packages (Flight + Hotel)

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Top hotels in Round Hill

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 ฿6,458 per night from 5 Aug to 6 Aug
฿6,458
฿8,733 total
5 Aug - 6 Aug
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"It’s a beautiful place but the rooms were fairly average. Nothing special. The shower was the worst part, it was either super hot or cold. Went to a trickle on medium. Couldn’t wash my hair! Also the breakfast buffet was $30 per person and not that great either. If you’re a golfer, you’d love it. ..."

Reviewed on 3 Jul 2026

Lansdowne Resort and Spa
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
The price is ฿2,693 per night from 19 Jul to 20 Jul
฿2,693
฿2,998 total
19 Jul - 20 Jul
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
"Good location but floor was sticky in room and no closets, just open hooks."

Reviewed on 4 Jul 2026

TRU By Hilton Winchester
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is ฿2,557 per night from 20 Jul to 21 Jul
฿2,557
฿2,897 total
20 Jul - 21 Jul
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"This newly renovated, squeaky clean hotel is a favorite of ours as a stop off on our I-81 journeys. It is at an excellent location, quiet, clean, and the rooms are spacious. Hotel gym, breakfast, and pool are excellent additions to our stay here. They are also pet friendly and have a nice spot to ..."

Reviewed on 28 Jun 2026

Spark by Hilton Winchester
See all 860 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.

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

฿3,942
per adult
3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade
Exclusive Virginia Wine Country Day Trip Tour

Private Virginia Wine Country Tour

฿16,360
per traveller
Private Virginia Wine Country Tour
See all activities in Round Hill

Frequently asked questions

How much does a Round Hill holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday 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?
Plan your getaway for the off-peak season and you're likely to score cheap Round Hill holiday packages. Remember that school holiday periods and major local events can impact prices, so do your research before booking.
How many days is enough for Round Hill?
With a well-organised itinerary, you can easily visit the most popular Round Hill attractions in a few days. But if you'd like to discover hidden spots or go on day trips, consider booking your Round Hill holiday for longer.
Is it worth booking a holiday package to Round Hill?
It's no wonder a Round Hill holiday is on the to-do list of many travellers. Top attractions like Round Hill Arts Centre are just the start of things to see and do here.
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 holiday as a package?
Expedia holiday 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 holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday 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 when to travel: Check your schedule and pack your bags. Your preferred time of year and the type of activities on offer will also help you decide when to escape to Round Hill.
  2. Budget wisely: On top of the cost of your accommodation, you'll need to factor in other expenses. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may come up during your trip to Round Hill.
  3. Decide how long to go away for: Now that you're up to speed on Round Hill, you can work out the right length of your holiday. Pull together a draft plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your accommodation and airfare: Once you've nailed down your dates and duration, book the right Round Hill holiday package for you.

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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.