Name: Holiday Inn Winchester Se-Historic Gateway by IHG
Price range: CA $121

Your Millwood Vacation

Come and experience this captivating city for yourself with a Millwood vacation package. Consider basing yourself in the neighborhood of Old Town Winchester, which is great for cafes and history, and your time here is sure to be unforgettable. Fill your itinerary with visits to Dinosaur Land, Watermelon Park Campground and Burwell-Morgan Mill, some of the things you just have to see during a trip to Millwood. That dream Millwood vacation is a few clicks away. Search hotels, airfares and more on Expedia for a getaway that's tailored to suit your style.

Top Millwood Vacation Deals

Price found within the past 48 hours. Click for updated prices.

Hotel Arboretum

Northeast

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

The St. Gregory Hotel

Downtown Washington D.C.

CA $667

per person

Oct 3 - Oct 6

found 19 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

SIXTY DC

Downtown Washington D.C.

CA $612

per person

Oct 4 - Oct 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) 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 Watergate Hotel

Northwest

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

Kellogg Conference Hotel at Gallaudet University

Northeast

CA $593

per person

Oct 11 - Oct 13

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Washington (WAS)

8.2/10 Very Good! (1,001 reviews)

Beautiful place! Amazing staff!

Reviewed on Aug. 21, 2025

Ready to book your vacation to Millwood?

Choose your dates

Millwood Hotel Deals

La Quinta Inn & Suites by Wyndham Winchester

1055 Millwood Pike, Route 50 East, Winchester, VA

Fully refundableReserve now, pay when you stay

CA $141

CA $153 total

Sep 1 - Sep 2

includes taxes & fees

Holiday Inn Winchester Se-Historic Gateway by IHG

333 Front Royal Pike, Winchester, VA

Fully refundable

CA $121

CA $136 total

Sep 15 - Sep 16

includes taxes & fees

Salamander Resort And Spa

500 North Pendleton Street, Middleburg, VA

Fully refundableReserve now, pay when you stay

CA $736

CA $910 total

Sep 1 - Sep 2

includes taxes & fees

See all 526 properties in Millwood

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.