Old Town Winchester Vacations from $281
Book a Hotel + Flight or Car together to unlock savings
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
Save 100% on your flight
Price was $515, price is now $281 per person
$281
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
9.4/10 Exceptional! (1,010 reviews)
Only complaint is the room only had one tea/coffee cup. Called for service and was only given paper cups.
Reviewed on Sep 29, 2025
Kellogg Conference Hotel at Gallaudet University
Northeast
Save 100% on your flight
Price was $608, price is now $346 per person
$346
per person
Dec 5 - Dec 10
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.2/10 Very Good! (1,002 reviews)
This was a great option with the hotel on the college campus for convenience to visit with grandkids but also walking distance for great restaurants. Very clean, friendly and accommodating staff. Highly recommend it.
Reviewed on Sep 11, 2025
SIXTY DC
Downtown Washington D.C.
Save 100% on your flight
Price was $1,083, price is now $630 per person
$630
per person
Nov 3 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
9.8/10 Exceptional! (55 reviews)
Details. This place had high end features.
Reviewed on Sep 12, 2025
Hotel Arboretum
Northeast
Save 100% on your flight
Price was $548, price is now $340 per person
$340
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
8/10 Very Good! (1,015 reviews)
Very pleasant stay. Not memorable for any positives or negatives.
Reviewed on Oct 1, 2025
Hilton Alexandria Old Town
Old Town Alexandria
Save 100% on your flight
Price was $644, price is now $405 per person
$405
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,004 reviews)
Room was clean, staff was professional.
Reviewed on Sep 18, 2025
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
$127 nightly
The price is $144 total per night from Oct 9 to Oct 10
$144 total
Oct 9 - Oct 10
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
"The beauty of the property to begin with. Old world charm but modernized without detracting from the original character. The grand mailbox, each floor having a mailbox which directly connects with and is fed by gravity to the “grand” collection box on the ground floor! Beautiful! The basement pool ..."
Reviewed on Sep 24, 2025
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $118 total per night from Nov 2 to Nov 3
$118 total
Nov 2 - Nov 3
Total with taxes and fees
9.2/10 Wonderful! (2,158 reviews)
"Convenient off I-81, clean, quiet,nice warm breakfast, even great dark roast coffee. Will definitely make this a stop on our way south annually"
Reviewed on Oct 1, 2025
Hampton Inn Winchester-University/Mall Area
640 East Jubal Early Drive, Winchester, VA
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $120 total per night from Oct 13 to Oct 14
$120 total
Oct 13 - Oct 14
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
"It to it out travel plans"
Reviewed on Oct 1, 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.
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- Winchester Hotels
- Cheap Hotels in Winchester
- Pet-friendly Hotels in Winchester
- Motels in Winchester
- Luxury Hotels in Winchester
- Cabin Rentals in Winchester
- Extended Stay Hotels in Winchester
- B&B in Winchester
- Hotels with an Indoor Pool in Winchester
- Resorts & Hotels with Spas in Winchester
- Best Western Hotels in Winchester
- Hotels with Restaurants in Winchester
- Hotels with Hot Tubs in Winchester
- Hotels with Kitchenettes in Winchester
- 5 Star Hotels in Winchester
- Winery Hotels in Winchester
- Hotels with Bars in Winchester
- Honeymoon Resorts & in Winchester
- Hotel Wedding Venues Hotels in Winchester
- Hotels with an Outdoor Pool in Winchester
- 4 Star Hotels in Winchester
- Historic Hotels in Winchester
- Hotels with Balconies in Winchester
- Hotels with Free Breakfast in Winchester
- Romantic Hotels in Winchester
- Boutique Hotels in Winchester
- Apartments in Winchester
- Hotels with smoking rooms in Winchester
- Hotels with Early Check-in in Winchester
- Family Hotels in Winchester
- Cottages in Winchester
- Golf Hotels in Winchester
- Casino Hotels in Winchester
- Hotels with a View in Winchester
- Hotels with Room Service in Winchester
- Hotels with a Pool in Winchester
- Hotels with Suites in Winchester
- Gay friendly Hotels in Winchester
- 3 Star Hotels in Winchester
- Hotels with Laundry Facilities in Winchester
- Beach Hotels in Winchester
- Non-Smoking Hotels in Winchester
- Hotels with Fireplaces in Winchester
- Villas in Winchester
- Hotels with a Gym in Winchester
- Ski Hotels in Winchester
- Hotels with Free Parking in Winchester
- Quiet Resorts & in Winchester
- Lodges in Winchester
- Vacation Homes in Winchester
- Hotels with Tennis Courts in Winchester
- Hotels with Connecting Rooms in Winchester
- Hotels near Bright Box Theater
- Hotels near Old Court House Civil War Museum
- Frederick County Hotels
- Hotels near Shenandoah Valley Discovery Museum
- Hotels near George Washington's Office
- Hotels near Handley Regional Library
- Hotels near Mt Hebron Cemetery
- Hotels near Winchester Little Theater
- Hotels near Stonewall Jackson's Headquarters
- Hotels near Patsy Cline Historic House
- Hotels near Museum of the Shenandoah Valley
- Hotels near Jim Barnett Park
- Hotels near Abram's Delight
- Hotels near Winchester-Frederick County Convention & Visitors Bureau
- Hotels near Shenandoah University
- Car rentals near Winchester
- Enterprise Rental Cars in Winchester
- Hertz Rental Cars in Winchester
- Thrifty Car Rental Rental Cars in Winchester
- Budget Rental Cars in Winchester
- Rent A Wreck Rental Cars in Winchester
- Avis Rental Cars in Winchester
- Alamo Rent A Car Rental Cars in Winchester
- Convertible Car Rentals in Winchester
- Minivan Car Rentals in Winchester
- Luxury Car Rentals in Winchester
- Sportscar Car Rentals in Winchester
- National Car Rental Rental Cars in Winchester
- Car rentals near Patsy Cline Historic House
- Car rentals near Nalls Farm Market
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.