
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.

Hotel Arboretum
Northeast
Price was CA $671, price is now CA $459 per person
CA $459
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (WAS)
8/10 Very Good! (1,012 reviews)
We were told when we checked in around 3pm that the hotel main entrance will be locked at 11pm.
Reviewed on Aug. 30, 2025

SIXTY DC
Downtown Washington D.C.
Price was CA $1,859, price is now CA $1,110 per person
CA $1,110
per person
Nov 3 - Nov 8
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Washington (WAS)
9.8/10 Exceptional! (45 reviews)
The staff is extremely friend, adn the foods in the restaurant are wonderful
Reviewed on Aug. 26, 2025

The St. Gregory Hotel
Downtown Washington D.C.
Price was CA $1,015, price is now CA $667 per person
CA $667
per person
Oct 3 - Oct 6
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Washington (WAS)
8.6/10 Excellent! (1,008 reviews)
Nicely renovated and great staff
Reviewed on Aug. 28, 2025

DoubleTree by Hilton Hotel Laurel
West Laurel
Price was CA $999, price is now CA $679 per person
CA $679
per person
Nov 3 - Nov 8
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Baltimore (BWI)
8.2/10 Very Good! (1,006 reviews)
I had a medical procedure in the Baltimore area, with a 5 AM call time to arrive at the facility. The staff was wonderful, accommodating my late check-in, and I was able to have a successful procedure that morning.
Reviewed on Aug. 30, 2025

The Watergate Hotel
Northwest
Price was CA $1,011, price is now CA $713 per person
CA $713
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (WAS)
8.8/10 Excellent! (1,006 reviews)
Only first day I noticed after showering that the water started leaking out of the shower causing a pool a of water. I notified the front desk immediately who then contacted maintenance to fix the shower leak. 24 hours later my shower was not fixed. I had to contact the front again to ask what is going on. They sent maintenance up to my room again to look at the leak. He came to look and didn’t return for an hour. I contacted the front again to ask what is going on which is when they offered to move me. I had to repack my things and move to another room which had a smell of mildew. I bought my own air freshener and left the patio door open because I was so tired of moving around. I was not compensated for the inconvenience at all. It was almost as if they just said ok well things happen which I totally understand but at the same time it’s about giving people outstanding customer service when running a business.
Reviewed on Aug. 28, 2025
Round Hill Hotel Deals

La Quinta Inn & Suites by Wyndham Winchester
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 $153 total
Sep 1 - Sep 2
includes taxes & fees

Quality Inn
25 Union St, Harpers Ferry, WV
Fully refundableReserve now, pay when you stay
The price is CA $112 per night from Sep 7 to Sep 8
CA $112
CA $126 total
Sep 7 - Sep 8
includes taxes & fees

Lansdowne Resort and Spa
44050 Woodridge Pkwy, Leesburg, VA
Fully refundableReserve now, pay when you stay
The price is CA $256 per night from Sep 1 to Sep 2
CA $256
CA $343 total
Sep 1 - Sep 2
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.
What to do in Round Hill
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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.