Round Hill Holidays

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Top hotels in Round Hill

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 S$131 per night from 26 Jul to 27 Jul
S$131
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,030 reviews)
"Everything was great except for the fact the shower was terrible. It felt like it took me an hour just to rinse the sham out of my hair because the water was coming out in a slow trickle. It was so bad I thought I would have to just rinse my head under the sink!"

Reviewed on 10 Jul, 2026

TRU By Hilton Winchester
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 S$352 per night from 5 Aug to 6 Aug
S$352
5 Aug - 6 Aug
includes taxes & fees
8.8/10 Excellent! (1,009 reviews)
"My daughter and I stayed at Landdown resort for 2 nights. We used the pools and ate in 2 of the restaurants. Coton and Rye was hit and miss. Our first meal was great, but the second dinner was not. To be fair, tbe resrt did comp my meal and I was grateful. The pools were adequate, but could do with ..."

Reviewed on 11 Jul, 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
The price is S$101 per night from 29 Jul to 30 Jul
S$101
29 Jul - 30 Jul
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"Great staff, clean rooms and delightful breakfast. I'll be back!"

Reviewed on 5 Jul, 2026

Spark by Hilton Winchester
See all 861 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

S$155
per adult
3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade
Exclusive Virginia Wine Country Day Trip Tour

Private Virginia Wine Country Tour

S$644
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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.