Old Town Winchester Vacations from $318
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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.
Phoenix Park Hotel
Northwest
$560
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (2,172 reviews)
Site was excellent with room being super comfortable. Staff willingly helped us with a few items that were special asks. The only issue was the sound of sirens throughout the night.
Reviewed on Aug 30, 2026
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
$450
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,253 reviews)
Muy bien ubicado. Solamente la cafetera del cuarto no funcionaba o muy difícil de prender.
Reviewed on Aug 29, 2026
Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
$122 nightly
$138 total
Sep 7 - Sep 8
Total with taxes and fees
Nostalgia Lane in the heart of the city
Winchester VA
$295 nightly
$334 total
Aug 31 - Sep 1
Total with taxes and fees
9.2/10 Wonderful! (18 reviews)
"Perfect location for exploring Winchester. Beautiful rooms. Clean and comfortable."
Reviewed on Jul 27, 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
$77 nightly
$87 total
Sep 28 - Sep 29
Total with taxes and fees
9.2/10 Wonderful! (1,004 reviews)
"Having Breakfast is a plus. Clean and quiet = Good"
Reviewed on Aug 29, 2026
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 Old Town Winchester attractions
Shenandoah Valley Discovery Museum
8.6/10 (78 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.
Bright Box Theater
7.8/10 (18 reviews)
Enjoy a show at Bright Box Theater, a storied theater in Winchester. While in this walkable area, you can savor the top-notch restaurants.
Handley Regional Library
9.6/10 (4 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.
George Washington's Office
8.0/10 (1 review)
You can learn about the history of Winchester when you stop by George Washington's Office. While in this walkable area, you can savor the top-notch restaurants.
Old Court House Civil War Museum
8.0/10 (1 review)
You can study the exhibits at Old Court House Civil War Museum, a museum with a story of its own, during your trip to Winchester. While in this walkable area, you can savor the top-notch restaurants.
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- George Washington's Office
- Shen-Val Farm Market
- Museum of the Shenandoah Valley
- Bright Box Theater
- Rocking S Ranch
- Belle Grove Plantation
- Shenandoah University
- Stonewall Jackson's Headquarters
- Cedar Creek and Belle Grove National Historical Park
- Patsy Cline Historic House
- Holy Cross Abbey
- Watermelon Park Campground
- Abram's Delight
- Virginia River Trips
- Mackintosh Fruit Farm
- Valerie Hill Winery
- Jim Barnett Park
- Dinosaur Land
- Shenandoah Valley Discovery Museum
- Rock Harbor Golf Course
- Berryville Vacations
- Hupp's Hill Civil War Park
- Jackson's Chase Golf Course
- Visit Old Town Winchester
- Veramar Vineyard
- Mt Hebron Cemetery
- Appleland Sports Center
- Visit Winchester
- Nalls Farm Market
- Great Falls Park
- 612 Vineyard
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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.