A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

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Check availability on Winchester Family friendly Hotels

Tonight
11 Oct - 12 Oct
Tomorrow
12 Oct - 13 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

Our top choices for Winchester family-friendly hotels

A Comfort Inn & Suites building with a modern design, featuring a prominent logo on the facade, a covered entrance, and multiple windows.
A hotel dining area with multiple tables and chairs, large windows, and a television screen.
A hotel room with two beds, a desk with a TV, a lamp, and a view of the outdoors.
A bathroom with a toilet, two sinks, a large mirror, and a shower area.

1. Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
Winchester
S$142
includes taxes & fees
18 Oct - 19 Oct
Comfort Inn & Suites Winchester
A courtyard with a fountain, tables with white tablecloths, and brick buildings.
A spacious lobby with a round table, chairs, a chandelier, and an American flag.
A bar area with a piano, seating, and a bar counter with bottles.
A large brick building with a classic facade, a central entrance with a decorative arch, and a sign reading "The George Washington Hotel."

2. The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
Old Town Winchester
  • Georgian hotel offers family fun with indoor pool, spa, and prime location near Shenandoah Valley Discovery Museum.
S$189
includes taxes & fees
28 Oct - 29 Oct
The George Washington Hotel, A Wyndham Grand Hotel
A spacious lobby with a checkered floor, yellow chairs, a green carpet, and a wall with the text "It only takes a spark".
A modern indoor space with a long wooden table and benches, surrounded by chairs and a green carpet.
An indoor swimming pool with clear glass walls, a tiled floor, and a few lounge chairs.
A modern hotel room with a bed, sofa, and a small table. There are two doors, one blue and one white, and a small table with chairs.

3. Spark by Hilton Winchester

Spark by Hilton Winchester
Winchester
  • Experience kid-friendly adventures with premium TV channels and cots, just minutes from Shenandoah Valley Discovery Museum.
S$111
includes taxes & fees
18 Oct - 19 Oct
Spark by Hilton Winchester
A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.
A coffee station with multiple coffee dispensers and a sign above.
A swimming pool with a tiled deck, lounge chairs, and a sunshade.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.

4. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
Winchester
S$132
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Winchester
A modern lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.
A modern Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.
A hotel room with two beds, a desk, a chair, a desk lamp, a window with curtains, a bathroom with a mirror and sink.
A modern lounge area with seating, a TV, and a children's play area.

5. Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
Winchester
  • A kid-friendly getaway with indoor pool and free breakfast, just minutes from the Shenandoah Valley Discovery Museum.
S$123
includes taxes & fees
8 Nov - 9 Nov
Microtel Inn & Suites by Wyndham Winchester
A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.
A modern hotel with a flat facade, multiple windows, and a well-lit entrance.
A modern lounge area with a sofa, chairs, and tables, featuring a patterned carpet and a decorative ceiling light.
A modern bathroom with a glass-enclosed shower, a vanity with a large mirror, and a built-in dishwasher.

6. La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
Winchester
S$154
includes taxes & fees
18 Oct - 19 Oct
La Quinta Inn & Suites by Wyndham Winchester
A hotel room with two beds, a mounted painting, a nightstand with a phone, and a window with curtains.
A hotel reception area with a black counter, coffee dispensers, a juice dispenser, and a small refrigerator.
A swimming pool with a metal railing, surrounded by lounge chairs and an umbrella.
A bathroom with a shower, bathtub, sink, and towel rack.

7. Quality Inn Winchester

Quality Inn Winchester
Winchester
  • Splash into family fun at this Winchester hotel with seasonal outdoor pool, breakfast, and kid-friendly accommodation.
S$117
includes taxes & fees
8 Nov - 9 Nov
Quality Inn Winchester
A spacious living room with a fireplace, wooden staircase, and a bookshelf.
A woman using a stationary bike in a gym with red walls and multiple exercise machines.
A poolside area with lounge chairs and a stack of towels on a table.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.

8. Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
Winchester
  • Family-friendly fun at this Winchester inn begins with an indoor pool, complimentary breakfast, and premium entertainment options.
S$126
includes taxes & fees
8 Nov - 9 Nov
Country Inn & Suites by Radisson, Winchester, VA
A hotel room with two beds, a desk, a TV, and a window with a view.
A spacious lobby with a seating area featuring yellow patterned chairs, a flat-screen TV mounted on the wall, and a large window providing natural light.
A kitchen with a microwave, refrigerator, sink, and wooden cabinets.
A modern bathroom with a sink, mirror, and toilet.

9. Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
Winchester
S$153
includes taxes & fees
18 Oct - 19 Oct
Hampton Inn Winchester N/Conference Center, VA
A Courtyard by Marriott hotel with a covered entrance, multiple floors, and a brick facade.
A bar area with a display case of baked goods, a fruit basket, and a television screen displaying news.
A modern hotel lobby with a curved sofa, a glass coffee table, and a flat-screen TV mounted on the wall.
An outdoor seating area with wicker furniture and a small table, surrounded by greenery and a building in the background.

10. Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
Winchester
S$144
includes taxes & fees
18 Oct - 19 Oct
Courtyard by Marriott Winchester
View all properties

Choose what matters most at family-friendly hotels in Winchester

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Family-friendly hotels with free breakfast in Winchester

A Comfort Inn & Suites building with a modern design, featuring a prominent logo on the facade, a covered entrance, and multiple windows.
A hotel dining area with multiple tables and chairs, large windows, and a television screen.
A hotel room with two beds, a desk with a TV, a lamp, and a view of the outdoors.
A hotel room with a television, desk, chair, sofa, and kitchenette.

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
Winchester
S$142
includes taxes & fees
18 Oct - 19 Oct
Comfort Inn & Suites Winchester
A spacious lobby with a checkered floor, yellow chairs, a green carpet, and a wall with the text "It only takes a spark".
A modern indoor space with a long wooden table and benches, surrounded by chairs and a green carpet.
An indoor swimming pool with clear glass walls, a tiled floor, and a few lounge chairs.
A modern hotel room with a bed, sofa, and a small table. There are two doors, one blue and one white, and a small table with chairs.

Spark by Hilton Winchester

Spark by Hilton Winchester
Winchester
S$111
includes taxes & fees
18 Oct - 19 Oct
Spark by Hilton Winchester
A courtyard with a fountain, tables with white tablecloths, and brick buildings.
A spacious lobby with a round table, chairs, a chandelier, and an American flag.
A bar area with a piano, seating, and a bar counter with bottles.
A large brick building with a classic facade, a central entrance with a decorative arch, and a sign reading "The George Washington Hotel."

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
Old Town Winchester
S$189
includes taxes & fees
28 Oct - 29 Oct
The George Washington Hotel, A Wyndham Grand Hotel
A modern lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.
A modern Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.
A hotel room with two beds, a desk, a chair, a desk lamp, a window with curtains, a bathroom with a mirror and sink.
A modern lounge area with seating, a TV, and a children's play area.

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
Winchester
S$123
includes taxes & fees
8 Nov - 9 Nov
Microtel Inn & Suites by Wyndham Winchester
A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.
A modern hotel with a flat facade, multiple windows, and a well-lit entrance.
A gym with treadmills, elliptical machines, and dumbbells.
An indoor swimming pool with clear water, blue lounge chairs, and a wooden ceiling.

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
Winchester
S$154
includes taxes & fees
18 Oct - 19 Oct
La Quinta Inn & Suites by Wyndham Winchester
A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.
A coffee station with multiple coffee dispensers and a sign above.
A modern restaurant interior with wooden tables and chairs, a green booth area, and artwork on the walls.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
Winchester
S$132
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Winchester
A modern hotel with a covered outdoor area, landscaped gardens, and a parking lot.
A hotel reception area with a black counter, coffee dispensers, a juice dispenser, and a small refrigerator.
A swimming pool with a metal railing, surrounded by lounge chairs and an umbrella.
A hotel lobby with a blue sofa, red chairs, a patterned rug, and artwork on the walls.

Quality Inn Winchester

Quality Inn Winchester
Winchester
S$117
includes taxes & fees
8 Nov - 9 Nov
Quality Inn Winchester
A spacious living room with a fireplace, wooden staircase, and a bookshelf.
A woman using a stationary bike in a gym with red walls and multiple exercise machines.
A poolside area with lounge chairs and a stack of towels on a table.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
Winchester
S$126
includes taxes & fees
8 Nov - 9 Nov
Country Inn & Suites by Radisson, Winchester, VA
A modern living room with a sofa, armchair, dining table, and chairs. There is a TV mounted on the wall and a small table with a lamp.
A hotel reception area with a stone counter, a chandelier, a desk with a computer, and a seating area with chairs and a table.
A spacious indoor area with a long table and chairs, a statue, and a large window.
A hotel room with a sofa, a desk, a TV, a dresser, and a bed.

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
Winchester
S$100
includes taxes & fees
25 Oct - 26 Oct
Travelodge by Wyndham Winchester
A hotel room with two beds, a desk, a TV, and a window with a view.
A kitchen with a microwave, refrigerator, sink, and wooden cabinets.
A gym with various exercise equipment, a mirror, and a door to another room.
A spacious lobby with a seating area featuring yellow patterned chairs, a flat-screen TV mounted on the wall, and a large window providing natural light.

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
Winchester
S$153
includes taxes & fees
18 Oct - 19 Oct
Hampton Inn Winchester N/Conference Center, VA
View all properties

Family-friendly hotels with pools in Winchester

A modern lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.
A modern Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.
A hotel room with two beds, a desk, a chair, a desk lamp, a window with curtains, a bathroom with a mirror and sink.
A modern lounge area with seating, a TV, and a children's play area.

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
Winchester
S$123
includes taxes & fees
8 Nov - 9 Nov
Microtel Inn & Suites by Wyndham Winchester
A courtyard with a fountain, tables with white tablecloths, and brick buildings.
A spacious lobby with a round table, chairs, a chandelier, and an American flag.
A bar area with a piano, seating, and a bar counter with bottles.
A large brick building with a classic facade, a central entrance with a decorative arch, and a sign reading "The George Washington Hotel."

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
Old Town Winchester
S$189
includes taxes & fees
28 Oct - 29 Oct
The George Washington Hotel, A Wyndham Grand Hotel
A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.
A modern hotel with a flat facade, multiple windows, and a well-lit entrance.
A gym with treadmills, elliptical machines, and dumbbells.
An indoor swimming pool with clear water, blue lounge chairs, and a wooden ceiling.

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
Winchester
S$154
includes taxes & fees
18 Oct - 19 Oct
La Quinta Inn & Suites by Wyndham Winchester
A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.
A coffee station with multiple coffee dispensers and a sign above.
A modern restaurant interior with wooden tables and chairs, a green booth area, and artwork on the walls.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
Winchester
S$132
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Winchester
A spacious living room with a fireplace, wooden staircase, and a bookshelf.
A woman using a stationary bike in a gym with red walls and multiple exercise machines.
A poolside area with lounge chairs and a stack of towels on a table.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
Winchester
S$126
includes taxes & fees
8 Nov - 9 Nov
Country Inn & Suites by Radisson, Winchester, VA
A modern hotel with a covered outdoor area, landscaped gardens, and a parking lot.
A hotel reception area with a black counter, coffee dispensers, a juice dispenser, and a small refrigerator.
A swimming pool with a metal railing, surrounded by lounge chairs and an umbrella.
A hotel lobby with a blue sofa, red chairs, a patterned rug, and artwork on the walls.

Quality Inn Winchester

Quality Inn Winchester
Winchester
S$117
includes taxes & fees
8 Nov - 9 Nov
Quality Inn Winchester
A Courtyard by Marriott hotel with a covered entrance, multiple floors, and a brick facade.
A bar area with a display case of baked goods, a fruit basket, and a television screen displaying news.
A modern hotel lobby with a curved sofa, a glass coffee table, and a flat-screen TV mounted on the wall.
An outdoor seating area with wicker furniture and a small table, surrounded by greenery and a building in the background.

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
Winchester
S$144
includes taxes & fees
18 Oct - 19 Oct
Courtyard by Marriott Winchester
An outdoor patio with a fire feature, seating, and a covered area.
A hotel room with two beds, a desk, a chair, and a large window.
An indoor swimming pool with clear water, metal railings, and lounge chairs.
A modern hotel with a covered entrance, a sign reading "SPRINGHILL SUITES BY MARRIOTT," and a landscaped area with plants.

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
Winchester
S$162
includes taxes & fees
8 Nov - 9 Nov
SpringHill Suites by Marriott Winchester
A hotel room with two beds, a desk, a TV, and a window with a view.
A kitchen with a microwave, refrigerator, sink, and wooden cabinets.
A gym with various exercise equipment, a mirror, and a door to another room.
A spacious lobby with a seating area featuring yellow patterned chairs, a flat-screen TV mounted on the wall, and a large window providing natural light.

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
Winchester
S$153
includes taxes & fees
18 Oct - 19 Oct
Hampton Inn Winchester N/Conference Center, VA
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.
A bar area with a counter, multiple bar stools, and a television screen.
A spacious lobby with a checkered floor, a reception desk, and a seating area with a sofa and chairs.
A swimming pool with lounge chairs and a changing room.

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
Winchester
S$139
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Winchester Se-Historic Gateway by IHG
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

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

8/10 Good
"Good stay. Crowded breakfast room"
Stephen 1-night trip
Posted less than an hour ago
Country Inn & Suites by Radisson, Winchester, VA
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

8/10 Good
"The staff was very welcoming and friendly. The room was big, nice and clean. The towels were not clean. There were visible stains. The shower never got warm."
Yolanda 1-night trip
Posted 3 hours ago
Holiday Inn Winchester Se-Historic Gateway by IHG
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

10/10 Excellent
"Nice property."
Dale 1-night trip
Posted 5 hours ago
Travelodge by Wyndham Winchester
Lansdowne Resort and Spa

Lansdowne Resort and Spa

10/10 Excellent
"I always enjoy my stay. Very customer service oriented and friendly staff. I love Spa Mineral!"
Estrellita 1-night trip
Posted 11 hours ago
Lansdowne Resort and Spa
Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"The room was clean and updated. The only minor complaint is the shower didn't get as hot as I am used too. It was in a good neighborhood with lots of options for eating."
Nicholas 1-night trip
Posted 15 hours ago
Quality Inn Winchester
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

8/10 Good
"Nice clean hotel."
Eric 5-night trip
Posted 20 hours ago
Courtyard by Marriott Winchester
Days Inn by Wyndham Winchester

Days Inn by Wyndham Winchester

8/10 Good
"Friendly staff. My only complaint was there was no coffeemaker in the room as most hotels/motels now have."
Marsha 1-night trip
Posted 21 hours ago
Days Inn by Wyndham Winchester
Skyland

Skyland

10/10 Excellent
"We enjoyed our stay- the property is right on Skyline Drive- so convenient! The room was clean and very basic- nothing fancy or upscale about this property- something you would expect from a lodge within the Shenandoah National Park"
Geoffrey 1-night trip
Posted 1 day ago
Skyland
Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America

10/10 Excellent
"Great place to stay in Luray."
Eric 1-night trip
Posted 3 days ago
Mimslyn Inn Historic Hotels Of America

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?
Quality Inn Winchester is a hotel with a restaurant and free parking, 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 Holiday Inn Winchester Se-Historic Gateway by IHG.
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 Handley Regional Library. Make sure that you have lots of time for activities such as Rocking S Ranch and Winchester Little Theater.

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