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.
Lord Baltimore Hotel
Downtown Baltimore
CA $1,088
per person
Oct 2 - Oct 5
found 12 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.4/10 Very good! (3,089 reviews)
Front desk- miserable old bald man running the front desk.hardly spoke-not helpful.
Valet literally missing for almost 1/2 hour when we checked in..NOT busy..just not around.
Bed was hard Queen-no decent blanket
Food was excellent.
I was robbed of a $300 package in the lobby-no one cared to help-1 shadey security guard said he looked at the camera but didn't see anything.
Very disappointed..this was the 3rd time I stayed there and it was the last.
Reviewed on Aug 8, 2026
The Westin Annapolis
CA $1,389
per person
Oct 2 - Oct 5
found 13 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.8/10 Excellent! (1,000 reviews)
Nice clean hotel rooms very nice comfortable bed, loved the pillows close to everything Miss Shirley’s restaurant was very good food
Reviewed on Aug 7, 2026
Ready to book your vacation to Round Hill?
Round Hill Hotel Deals
Lansdowne Resort and Spa
44050 Woodridge Pkwy Leesburg VA
Fully refundableReserve now, pay when you stay
CA $287
CA $385 total
Aug 18 - Aug 19
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
"I liked this place. It's not stellar, but it is full-service and pleasant. Plenty of things to do and the staff is competent."
Reviewed on Aug 5, 2026
Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
Fully refundableReserve now, pay when you stay
CA $734
CA $914 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (410 reviews)
"The property and staff are amazing. Lots to do if you bring the kiddos, the kids camp let's adults relax and enjoy amenities. The one thing the property can work on is the food menu; more variety is needed. The Red Horse Tavern is a 5-minute walk into town and has the best food!!"
Reviewed on Jul 21, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
Fully refundable
CA $130
CA $148 total
Aug 13 - Aug 14
includes taxes & fees
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
Enjoy a round of golf in Round Hill at Stoneleigh Golf and Country Club. While you're in the area, find time to visit its casinos.
Bogati Bodega & Winery
You can enjoy a tasting or tour at Bogati Bodega & Winery during your travels to Round Hill. While you're in the area, find time to visit its casinos.
K & S Pewter
Enjoy a stop at K & S Pewter, an entertaining place to visit in Round Hill. While you're in the area, find time to visit its casinos.
Hill High Country Store
Enjoy a stop at Hill High Country Store, an entertaining place to visit in Round Hill. While you're in the area, find time to visit its casinos.
Round Hill Arts Center
Enjoy a stop at Round Hill Arts Center, an entertaining place to visit in Round Hill. While you're in the area, find time to visit its casinos.
Franklin Park
Franklin Park is just one of the places to see in Round Hill, so why not enjoy the other things to explore during your travels? Take in the art scene while you're in the area.
Round Hill Town Park
Round Hill Town Park is just one of the places to see in Round Hill, so why not enjoy the other things to explore during your travels? Take in the art scene while you're in the area.
B-Chord Brewery
You can take time to visit B-Chord Brewery during your travels to Round Hill. Take in the art scene while you're in the area.
What to do in Round Hill
3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade
CA $169
per adult
Frequently asked questions
How much does a Round Hill vacation package cost?
Offering excellent value package deals from CA $974 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?
- Choose your travel dates: What you want to do in Round Hill and your preferred season will help you decide when to travel.
- 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.
- 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.
- 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.
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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.
