Old Town Winchester Vacations from $203
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Your Old Town Winchester Vacation
Book a customized vacation package to Old Town Winchester and experience the wonders of this neighborhood from sunup to sundown. From its cafes and history to its distinct personality and vibe, there are loads of good reasons to visit Old Town Winchester. Hoping to sightsee during your trip to Old Town Winchester? Don't miss nearby attractions like Shenandoah University, Museum of the Shenandoah Valley and Apple Blossom Mall. Stop daydreaming and start doing. When it's time to book your ideal vacation to Old Town Winchester, Expedia will help get you there.
The Latest Old Town Winchester Vacation Packages
Price found within the past 48 hours. Click for updated prices.
InterContinental Washington D.C. - The Wharf by IHG
The Wharf
Price was $515, price is now $203 per person
$203
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,010 reviews)
So much fun! Great Location! lots of thing to do ! The drinks at the restaurant oh boy!
Reviewed on Oct 13, 2025
Park Hyatt Washington
Northwest
Price was $3,246, price is now $971 per person
$971
per person
Dec 4 - Dec 7
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (876 reviews)
Staff at the front desk greeted me warmly. When I shared that it was my first time staying at the hotel (and I visit Washington DC about 12 times a year), I received an automatic upgrade! Free Peleton in the room allowed me to workout in the morning before a full day of meeting. the coffee in the room was SUPERB! Can't tell you how relaxing it is to have a cup of fresh brewed decaf - so delicious - before rest! I can't wait to bring my husband!
Reviewed on Sep 28, 2025
SIXTY DC
Downtown Washington D.C.
Price was $839, price is now $381 per person
$381
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.8/10 Exceptional! (55 reviews)
The room was small and limited in space to move around. Staff were easy to talk to and receive support. Overall, the location provided many options for walking to historic locations or to take a short uber drive to the Capital, White House or many other areas of interest.
Reviewed on Oct 10, 2025
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
Save 100% on your flight
Price was $673, price is now $381 per person
$381
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,044 reviews)
The happy hour is fantastic, and the location is excellent. The staff is friendly, especially the overnight valet.specially the overnight valet.
Reviewed on Oct 14, 2025
Kellogg Conference Hotel at Gallaudet University
Northeast
Save 100% on your flight
Price was $570, price is now $330 per person
$330
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.2/10 Very Good! (1,002 reviews)
Bathroom was outdated and bathtub was poorly kept. Staff was pleasant overall and the property itself was decent.
Reviewed on Oct 10, 2025
Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St, Winchester, VA
$127 nightly
The price is $144 total per night from Oct 26 to Oct 27
$144 total
Oct 26 - Oct 27
Total with taxes and fees
9.2/10 Wonderful! (1,010 reviews)
"I’d return for sure. Our room was wonderful."
Reviewed on Oct 10, 2025
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $112 total per night from Nov 2 to Nov 3
$112 total
Nov 2 - Nov 3
Total with taxes and fees
9.2/10 Wonderful! (2,184 reviews)
"Was just one night with group of friends. Location was great, easy check in and out, good breakfast and comfy beds. Would highly recommend."
Reviewed on Oct 12, 2025
Hampton Inn Winchester-University/Mall Area
640 East Jubal Early Drive, Winchester, VA
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $129 total per night from Nov 2 to Nov 3
$129 total
Nov 2 - Nov 3
Total with taxes and fees
9/10 Wonderful! (1,019 reviews)
"Great stay! Would definitely would stay again!"
Reviewed on Oct 10, 2025
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.
Discover the most popular places to visit in Old Town Winchester
Handley Regional Library
5/5(2 reviews)
After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
Museum of the Shenandoah Valley
5/5(19 reviews)
You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
Shenandoah Valley Discovery Museum
4.5/5(11 reviews)
You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savor the top-notch restaurants.
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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.