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Check availability on Winchester Family Hotels

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

Our top choices for Winchester family-friendly hotels

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.
An indoor swimming pool with clear water, blue lounge chairs, and a wooden ceiling.
A modern lounge area with a sofa, chairs, and tables, featuring a patterned carpet and a decorative ceiling light.

1. La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
Winchester
NT$3,448
NT$3,838 total
includes taxes & fees
Oct 18 - Oct 19
La Quinta Inn & Suites by Wyndham 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 hotel reception area with a wooden reception desk, two computers, a map of the USA on the wall, and a small plant on the desk.

2. 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.
NT$2,758
NT$3,070 total
includes taxes & fees
Nov 8 - Nov 9
Microtel Inn & Suites by Wyndham 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.
Lobby
A bathroom with a toilet, two sinks, a large mirror, and a shower area.

3. Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
Winchester
NT$3,175
NT$3,534 total
includes taxes & fees
Oct 18 - Oct 19
Comfort Inn & Suites Winchester
A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
A coffee station with multiple coffee dispensers and a sign above.
A Fairfield by Marriott hotel with a modern entrance, stone pillars, and a well-lit facade.

4. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
Winchester
NT$2,958
NT$3,292 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Winchester
A courtyard with a fountain, tables with white tablecloths, and brick buildings.
A large brick building with a classic facade, a central entrance with a decorative arch, and a sign reading "The George Washington Hotel."
A bar area with a piano, seating, and a bar counter with bottles.
A spacious lobby with a round table, chairs, a chandelier, and an American flag.

5. 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.
NT$4,163
NT$4,716 total
includes taxes & fees
Oct 28 - Oct 29
The George Washington Hotel, A Wyndham Grand Hotel
An outdoor patio with a fire feature, seating, and a covered area.
A modern hotel lobby with a large dining area, wooden accents, and contemporary lighting fixtures.
A modern hotel with a covered entrance, a sign reading "SPRINGHILL SUITES BY MARRIOTT," and a landscaped area with plants.
An indoor swimming pool with clear water, metal railings, and lounge chairs.

6. SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
Winchester
NT$3,624
NT$4,034 total
includes taxes & fees
Nov 8 - Nov 9
SpringHill Suites by Marriott Winchester
A gym with treadmills, exercise balls, and a mirrored wall.
A Hampton Inn hotel with a modern facade, a covered entrance, and a landscaped front yard.
A hotel room with a wooden floor, a round table, and two chairs. There is a lamp on a side table and a large window with curtains.
A modern living room with a sofa, chairs, a coffee table, and a TV mounted on the wall.

7. Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area
Winchester
  • Family-friendly fun with outdoor pool and fitness center, steps from Shenandoah University makes vacation dreams a reality.
NT$3,094
NT$3,505 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Winchester-University/Mall Area
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 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.
An indoor swimming pool with clear glass walls, a tiled floor, and a few lounge chairs.
A hotel with a modern design, featuring a prominent 'spark by Hilton' sign, a well-lit entrance, and a landscaped front yard.

8. Spark by Hilton Winchester

Spark by Hilton Winchester
Winchester
  • Experience kid-friendly adventures with premium TV channels and cribs, just minutes from Shenandoah Valley Discovery Museum.
NT$2,431
NT$2,755 total
includes taxes & fees
Oct 18 - Oct 19
Spark by Hilton Winchester
A hotel room with two beds, a mounted painting, a nightstand with a phone, and a window with curtains.
A bathroom with a shower, bathtub, sink, and towel rack.
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.

9. Quality Inn Winchester

Quality Inn Winchester
Winchester
  • Splash into family fun at this Winchester hotel with seasonal outdoor pool, breakfast, and kid-friendly accommodations.
NT$2,565
NT$2,854 total
includes taxes & fees
Nov 8 - Nov 9
Quality Inn Winchester
A spacious living room with a fireplace, wooden staircase, and a bookshelf.
A Country Inn & Suites by Radisson building with a covered entrance and multiple windows.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
A poolside area with lounge chairs and a stack of towels on a table.

10. 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.
NT$2,820
NT$3,138 total
includes taxes & fees
Nov 8 - Nov 9
Country Inn & Suites by Radisson, Winchester, VA
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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.
Lobby
A hotel room with a television, desk, chair, sofa, and kitchenette.

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
Winchester
NT$3,175
NT$3,534 total
includes taxes & fees
Oct 18 - Oct 19
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 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.
An indoor swimming pool with clear glass walls, a tiled floor, and a few lounge chairs.
A hotel with a modern design, featuring a prominent 'spark by Hilton' sign, a well-lit entrance, and a landscaped front yard.

Spark by Hilton Winchester

Spark by Hilton Winchester
Winchester
NT$2,431
NT$2,755 total
includes taxes & fees
Oct 18 - Oct 19
Spark by Hilton Winchester
A courtyard with a fountain, tables with white tablecloths, and brick buildings.
A large brick building with a classic facade, a central entrance with a decorative arch, and a sign reading "The George Washington Hotel."
A bar area with a piano, seating, and a bar counter with bottles.
A spacious lobby with a round table, chairs, a chandelier, and an American flag.

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
Old Town Winchester
NT$4,163
NT$4,716 total
includes taxes & fees
Oct 28 - Oct 29
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 hotel reception area with a wooden reception desk, two computers, a map of the USA on the wall, and a small plant on the desk.

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
Winchester
NT$2,758
NT$3,070 total
includes taxes & fees
Nov 8 - Nov 9
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 gym with treadmills, elliptical machines, and dumbbells.

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
Winchester
NT$3,448
NT$3,838 total
includes taxes & fees
Oct 18 - Oct 19
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 hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
A coffee station with multiple coffee dispensers and a sign above.
A Fairfield by Marriott hotel with a modern entrance, stone pillars, and a well-lit facade.

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
Winchester
NT$2,958
NT$3,292 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Winchester
A modern hotel with a covered outdoor area, landscaped gardens, and a parking lot.
A hotel lobby with a blue sofa, red chairs, a patterned rug, and artwork on the walls.
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.

Quality Inn Winchester

Quality Inn Winchester
Winchester
NT$2,565
NT$2,854 total
includes taxes & fees
Nov 8 - Nov 9
Quality Inn Winchester
A wooden desk with a black office chair, a framed plant, and a desk lamp.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
A poolside area with lounge chairs and a stack of towels on a table.
A spacious living room with a fireplace, wooden staircase, and a bookshelf.

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
Winchester
NT$2,820
NT$3,138 total
includes taxes & fees
Nov 8 - Nov 9
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 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.
A hotel room with two beds, a wooden headboard, a nightstand with lamps, and a view of the outdoors through the window.

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
Winchester
NT$2,267
NT$2,500 total
includes taxes & fees
Oct 25 - Oct 26
Travelodge by Wyndham Winchester
A hotel room with two beds, a desk, a TV, and a window with a view.
A gym with various exercise equipment, a mirror, and a door to another room.
A vending area with snacks, drinks, and a beverage fridge.
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
NT$3,377
NT$3,826 total
includes taxes & fees
Oct 18 - Oct 19
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 hotel reception area with a wooden reception desk, two computers, a map of the USA on the wall, and a small plant on the desk.

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
Winchester
NT$2,758
NT$3,070 total
includes taxes & fees
Nov 8 - Nov 9
Microtel Inn & Suites by Wyndham Winchester
A courtyard with a fountain, tables with white tablecloths, and brick buildings.
A large brick building with a classic facade, a central entrance with a decorative arch, and a sign reading "The George Washington Hotel."
A bar area with a piano, seating, and a bar counter with bottles.
A spacious lobby with a round table, chairs, a chandelier, and an American flag.

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
Old Town Winchester
NT$4,163
NT$4,716 total
includes taxes & fees
Oct 28 - Oct 29
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 modern lounge area with a sofa, chairs, and tables, featuring a patterned carpet and a decorative ceiling light.
A gym with treadmills, elliptical machines, and dumbbells.

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
Winchester
NT$3,448
NT$3,838 total
includes taxes & fees
Oct 18 - Oct 19
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 hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
A coffee station with multiple coffee dispensers and a sign above.
A Fairfield by Marriott hotel with a modern entrance, stone pillars, and a well-lit facade.

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
Winchester
NT$2,958
NT$3,292 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Winchester
A wooden desk with a black office chair, a framed plant, and a desk lamp.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
A poolside area with lounge chairs and a stack of towels on a table.
A spacious living room with a fireplace, wooden staircase, and a bookshelf.

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
Winchester
NT$2,820
NT$3,138 total
includes taxes & fees
Nov 8 - Nov 9
Country Inn & Suites by Radisson, Winchester, VA
A modern hotel with a covered outdoor area, landscaped gardens, and a parking lot.
A hotel lobby with a blue sofa, red chairs, a patterned rug, and artwork on the walls.
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.

Quality Inn Winchester

Quality Inn Winchester
Winchester
NT$2,565
NT$2,854 total
includes taxes & fees
Nov 8 - Nov 9
Quality Inn Winchester
A Courtyard by Marriott hotel with a covered entrance, multiple floors, and a brick facade.
An outdoor seating area with wicker furniture and a small table, surrounded by greenery and a building in the background.
A hotel room with two beds, a desk, a chair, a desk lamp, and a large window with curtains.
A bar area with a display case of baked goods, a fruit basket, and a television screen displaying news.

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
Winchester
NT$3,229
NT$3,594 total
includes taxes & fees
Oct 18 - Oct 19
Courtyard by Marriott Winchester
An outdoor patio with a fire feature, seating, and a covered area.
A modern hotel lobby with a large dining area, wooden accents, and contemporary lighting fixtures.
A modern hotel with a covered entrance, a sign reading "SPRINGHILL SUITES BY MARRIOTT," and a landscaped area with plants.
An indoor swimming pool with clear water, metal railings, and lounge chairs.

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
Winchester
NT$3,624
NT$4,034 total
includes taxes & fees
Nov 8 - Nov 9
SpringHill Suites by Marriott Winchester
A hotel room with two beds, a desk, a TV, and a window with a view.
A gym with various exercise equipment, a mirror, and a door to another room.
A vending area with snacks, drinks, and a beverage fridge.
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
NT$3,377
NT$3,826 total
includes taxes & fees
Oct 18 - Oct 19
Hampton Inn Winchester N/Conference Center, VA
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.
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.
A bar area with a counter, multiple bar stools, and a television screen.

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
Winchester
NT$3,161
NT$3,614 total
includes taxes & fees
Nov 9 - Nov 10
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

Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America

10/10 Excellent
"Very nice."
David 1-night trip
Posted 1 hour ago
Mimslyn Inn Historic Hotels Of America
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

8/10 Good
"Add some protein to the breakfast please. Otherwise, our stay was excellent!"
John 1-night trip
Posted 2 hours ago
Travelodge by Wyndham Winchester
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 7 hours 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 10 hours ago
Holiday Inn Winchester Se-Historic Gateway by IHG
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 18 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 23 hours ago
Quality Inn Winchester
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

8/10 Good
"Nice clean hotel."
Eric 5-night trip
Posted 1 day 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 1 day 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

Frequently asked questions

What's Winchester like for family-friendly vacations?
The historic destination of Winchester is a good choice if you've been thinking about a trip with your kids. The entertainment, soaring skyscrapers, and theaters are just a few things that make this an attractive family vacation spot. Arrange a flight into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) from the city center.
What's the best hotel for a family vacation to 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 choices for your stay with the kids include Microtel Inn & Suites by Wyndham Winchester and Holiday Inn Winchester Se-Historic Gateway by IHG.
How many family-friendly hotels should I expect to find in Winchester?
Expedia has 10 family-friendly hotels and other accommodations in Winchester.
When's the best time to book a family-friendly vacation in Winchester?
The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Winchester is 46 inches.
What's there to see and do with your family in Winchester?
While you are visiting Winchester, you and the family might want to check out some interesting spots such as Bright Box Theater, Apple Blossom Mall, and Handley Regional Library. Make sure you have lots of time for activities like Rocking S Ranch and Winchester Little Theater.

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