Search Family-Friendly Hotels in Winchester

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Check availability on Winchester Family-Friendly Hotels

Tonight
29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Winchester family-friendly hotels

Lobby
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1407)
"Clean room great helpful staff good breakfast"
United States
Loretta
The price is ฿2,458
฿2,674 total
includes taxes & fees
4 Jan - 5 Jan 2026
Microtel Inn & Suites by Wyndham Winchester
Lobby
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
Winchester
8.8 out of 10, Excellent, (1002)
"Have stayed here multiple times -always good"
United States
Robert
The price is ฿2,550
฿2,774 total
includes taxes & fees
25 Jan - 26 Jan 2026
Country Inn & Suites by Radisson, Winchester, VA
Lobby
Quality Inn Winchester

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1001)
"Great stay"
United States
Jaron
The price is ฿2,348
฿2,554 total
includes taxes & fees
5 Jan - 6 Jan 2026
Quality Inn Winchester
Lobby
Super 8 by Wyndham Front Royal

Super 8 by Wyndham Front Royal

Super 8 by Wyndham Front Royal
2.0 star property
Front Royal
7.6 out of 10, Good, (1001)
"Good condition "
United States
Phillip
The price is ฿1,924
฿2,142 total
includes taxes & fees
30 Dec - 31 Dec
Super 8 by Wyndham Front Royal
Bar (on property)
DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
Front Royal
9.0 out of 10, Wonderful, (1002)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is ฿3,028
฿3,340 total
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Free buffet breakfast
Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
2.5 star property
Stephens City
8.2 out of 10, Very good, (807)
"Clean room, nice staff, simple but good breakfast, fresh ground coffee machine was really nice. "
United States
Rose
The price is ฿2,297
฿2,499 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Winchester South-Stephens City by IHG
Exterior
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1002)
"Great room cozy bed fabulous restaurant great staff on property"
United States
joyce
The price is ฿2,421
฿2,727 total
includes taxes & fees
18 Jan - 19 Jan 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
Lobby
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
2.5 star property
Winchester
7.8 out of 10, Good, (1001)
"great stay with breakfast too"
United States
James
The price is ฿1,920
฿2,089 total
includes taxes & fees
25 Jan - 26 Jan 2026
Sleep Inn & Suites Winchester near University
Bar (on property)
Wayside Inn

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (418)
"Historic inn. "
United States
David
The price is ฿2,235
฿2,775 total
includes taxes & fees
30 Dec - 31 Dec
Wayside Inn
Snack bar
Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
2.5 star property
Winchester
9.2 out of 10, Wonderful, (851)
"Super friendly reception and perfectly clean room. "
United States
Dwight
The price is ฿3,283
฿3,720 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Winchester N/Conference Center, VA
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.
View all properties

Top Winchester Hotel Reviews

Lansdowne Resort and Spa

Lansdowne Resort and Spa

10/10 Excellent
"We’ve stayed there multiple times over the years and it seems better than ever. So well kept. We live locally so "
David 1-night trip
Posted 2 weeks ago
Lansdowne Resort and Spa
Salamander Resort And Spa

Salamander Resort And Spa

10/10 Excellent
"."
Ivanti 2-night trip
Posted 3 weeks ago
Salamander Resort And Spa

Frequently asked questions

What's Winchester like for family-friendly holidays?
The historic destination of Winchester is a good choice if you've been thinking about a trip with your children. The entertainment, soaring skyscrapers and theatres are just a few things that make this an attractive family holiday destination. Arrange a flight into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) from the city centre.
What's the best family accommodation in Winchester?
Holiday Inn Winchester Se-Historic Gateway by IHG is a hotel with an indoor pool and a restaurant, and it's a top choice on Expedia for families. Other good options for your stay with the children include Microtel Inn & Suites by Wyndham Winchester and Quality Inn Winchester.
How many family hotels will I be able to find in Winchester?
Expedia has 10 family-friendly hotels and other accommodation options in Winchester.
When's the best time to book a family-friendly holiday in Winchester?
The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Winchester is 1172 mm.
What's there to see and do with your family in Winchester?
While you are visiting Winchester, you and the family may want to explore some interesting spots such as Bright Box Theater, Apple Blossom Mall and Winchester Little Theater. Make sure that you have lots of time for activities such as Winchester Gateway and Rocking S Ranch.