Find Family Hotels in Old Town Winchester, VA
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on Old Town Winchester Family Hotels
Our top choices for Old Town Winchester family-friendly hotels
DoubleTree by Hilton Front Royal Blue Ridge Shadows
DoubleTree by Hilton Front Royal Blue Ridge ShadowsFront Royal
9.0 out of 10, Wonderful, (1003)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
Dorothy
The price is NT$3,078
NT$3,395 total
includes taxes & fees
Dec 30 - Dec 31
7.6 out of 10, Good, (1001)
"The staff was friendly and attentive.
The room was clean.
The breakfast was good, with pancakes, toast, cereal, juice, and coffee.
Good location for visiting Shenandoah National Park."
Teresa
The price is NT$1,955
NT$2,177 total
includes taxes & fees
Dec 23 - Dec 24
The price is NT$2,271
NT$2,820 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Winchester Se-Historic Gateway by IHG
Holiday Inn Winchester Se-Historic Gateway by IHGWinchester
9.0 out of 10, Wonderful, (1002)
"Great room cozy bed fabulous restaurant great staff on property"
joyce
The price is NT$2,586
NT$2,908 total
includes taxes & fees
Dec 24 - Dec 25
Country Inn & Suites by Radisson, Winchester, VA
Country Inn & Suites by Radisson, Winchester, VAWinchester
8.8 out of 10, Excellent, (1001)
"Have stayed here multiple times -always good"
Robert
The price is NT$2,607
NT$2,836 total
includes taxes & fees
Jan 11 - 2026/1/12
9.2 out of 10, Wonderful, (1392)
"Clean room great helpful staff good breakfast"
Loretta
The price is NT$2,347
NT$2,553 total
includes taxes & fees
Jan 4 - 2026/1/5
9.2 out of 10, Wonderful, (1003)
"Great stay"
Jaron
The price is NT$2,386
NT$2,596 total
includes taxes & fees
Jan 4 - 2026/1/5
8.8 out of 10, Excellent, (510)
"Great hotel"
DONNA D
The price is NT$3,181
NT$3,605 total
includes taxes & fees
Dec 25 - Dec 26
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.
Top Old Town Winchester Hotel Reviews
Quality Inn Winchester
10/10 Excellent
Frequently asked questions
Explore a world of travel with Expedia
- Cottages in Frederick County
- Strasburg Hotels
- Hotels near Dinosaur Land
- Beach Hotels in Old Town Winchester
- Casino Hotels in Old Town Winchester
- Rv Parks in Warren County
- Hotels with Hot Tubs in Strasburg
- Hotels with an Indoor Pool in Woodstock
- Destination Hotels in Bluemont
- Cabin Rentals in Front Royal
- Family Hotels in Strasburg
- 5 Star Hotels in Front Royal
- Pet-Friendly Hotels in Winchester
- Hotel Wedding Venues Hotels in Winchester
- Hotels near Blue Ridge Shadows Golf Club
- Rv Parks in Brucetown
- Hotels with smoking rooms in Front Royal
- Hotels with a Pool in Strasburg
- Rv Parks in White Post
- Historic Hotels in Front Royal
- Family Hotels in Woodstock
- Apartments in Winchester
- Hotels with an Indoor Pool in Middletown
- Hotels with Bars in Front Royal
- Casino Hotels in Winchester
- Hotels near Jim Barnett Park
- 5 Star Hotels in Linden
- Gay friendly Hotels in Winchester
- Hotels with an Indoor Pool in Front Royal
- Middletown Hotels
- Historic Hotels in Purcellville
- Hotels with an Indoor Pool in Winchester
- 5 Star Hotels in Berryville
- Hotels with a Pool in Winchester
- Cheap Hotels in Stephens City
- 4 Star Hotels in Front Royal
- Historic Hotels in Stephens City
- Cheap Hotels in Woodstock
- Resorts & Hotels with Spas in Old Town Winchester
- Hotels near Patsy Cline Historic House
- Apartments in Gore
- Hotels with an Indoor Pool in Strasburg
- Hotels near Wayside Theater
- Hotels near Winchester Medical Center
- Motels in Gore
- Resorts & Hotels with Spas in Winchester
- Hotels near Sky Meadows State Park
- Berryville Hotels
- Romantic Hotels in Winchester
- Hotels near Front Royal - Warren County
- Hotel Wedding Venues Hotels in Front Royal
- 4 Star Hotels in Gore
- Ski Hotels in Middletown
- Adventure Hotels in Lovettsville
- Hotels with Bars in Woodstock
- Flights from Chicago (ORD) to Front Royal (FRR)
- Flights from Baltimore (BWI) to Winchester (WGO)
- Flights from Chicago (ORD) to Winchester (WGO)
- Flights to Millwood
- Flights from Washington (DCA) to Winchester (WGO)
- Flights from Rochester (ROC) to Winchester (WGO)
- Flights to Stephens City
- Flights from Huntsville (HSV) to Winchester (WGO)
- Flights from Atlanta (ATL) to Winchester (WGO)
- Flights from Flint (FNT) to Winchester (WGO)
- Flights from Grand Rapids (GRR) to Winchester (WGO)
- Flights from Baltimore (BWI) to Front Royal (FRR)
- Flights from Mexico City (MEX) to Winchester (WGO)
- Flights from Gothenburg (GOT) to Winchester (WGO)
- Flights from Stephens City
- Flights from Cross Junction
- Flights from Punta Gorda Airport (PGD) to Winchester (WGO)
- Flights from Front Royal
- Flights from Birmingham (BHM) to Winchester (WGO)
- Flights to Star Tannery
- Flights from Blacksburg (BCB) to Winchester (WGO)
- Bluemont Vineyard
- Nalls Farm Market
- Patsy Cline Historic House
- Front Royal Entrance Shenandoah National Park
- Appleland Sports Center
- Visit Millwood
- Boyce Vacations
- Visit Berryville
- Visit Strasburg
- Belle Grove Plantation
- Visit Gore
- Front Royal Visitor's Center
- State Arboretum of Virginia
- Sky Meadows State Park
- Shenandoah River
- Holy Cross Abbey
- Jim Barnett Park
- Rock Harbor Golf Course