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 Hotels

Tonight
Oct 15 - Oct 16
Tomorrow
Oct 16 - Oct 17
This weekend
Oct 16 - Oct 18
Next weekend
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.
A modern bathroom with a glass-enclosed shower, a vanity with a large mirror, and a built-in dishwasher.
An indoor swimming pool with clear water, blue lounge chairs, and a wooden ceiling.

1. La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
Winchester
₩131,822
₩146,717 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 lounge area with seating, a TV, and a children's play area.
A modern Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.
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.
₩112,783
₩125,526 total
includes taxes & fees
Nov 15 - Nov 16
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
₩134,265
₩149,437 total
includes taxes & fees
Nov 5 - Nov 6
Comfort Inn & Suites Winchester
A courtyard with a fountain, tables with white tablecloths, and brick buildings.
A spacious living room with a fireplace, leather sofa, armchairs, and a large painting.
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.

4. 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.
₩175,055
₩198,337 total
includes taxes & fees
Oct 28 - Oct 29
The George Washington Hotel, A Wyndham Grand Hotel
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 hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
A swimming pool with a tiled deck, lounge chairs, and a sunshade.

5. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
Winchester
₩124,397
₩138,454 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Winchester
A gym with treadmills, exercise balls, and a mirrored wall.
A kitchenette with a coffee machine, toaster, and a display case with pastries.
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.

6. 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.
₩130,103
₩147,407 total
includes taxes & fees
Nov 8 - Nov 9
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".
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.
A modern indoor space with a long wooden table and benches, surrounded by chairs and a green carpet.

7. 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.
₩103,491
₩117,255 total
includes taxes & fees
Nov 2 - Nov 3
Spark by Hilton Winchester
A hotel room with two beds, a mounted painting, a nightstand with a phone, and a window with curtains.
A hotel lobby with a blue sofa, red chairs, a patterned rug, and artwork on the walls.
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.

8. Quality Inn Winchester

Quality Inn Winchester
Winchester
  • Splash into family fun at this Winchester hotel with seasonal outdoor pool, breakfast, and kid-friendly accommodations.
₩106,486
₩118,520 total
includes taxes & fees
Nov 15 - Nov 16
Quality Inn 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 lobby with a large dining area, wooden accents, and contemporary lighting fixtures.

9. SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
Winchester
₩152,418
₩169,641 total
includes taxes & fees
Nov 8 - Nov 9
SpringHill Suites by Marriott Winchester
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 hotel room with a bed, a desk with a computer, a chair, and a TV.
A spacious lobby with a checkered floor, a reception desk, and a seating area with a sofa and chairs.

10. Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
Winchester
  • Child-friendly indoor pool and activities make this hotel a perfect Winchester family retreat with premium entertainment extras.
₩132,922
₩151,970 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Winchester Se-Historic Gateway by IHG
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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 modern lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.
A modern lounge area with seating, a TV, and a children's play area.
A modern Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.
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
₩112,783
₩125,526 total
includes taxes & fees
Nov 15 - Nov 16
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.
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.

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
Winchester
₩131,822
₩146,717 total
includes taxes & fees
Oct 18 - Oct 19
La Quinta Inn & Suites by Wyndham Winchester
A spacious lobby with a checkered floor, yellow chairs, a green carpet, and a wall with the text "It only takes a spark".
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.
A modern indoor space with a long wooden table and benches, surrounded by chairs and a green carpet.

Spark by Hilton Winchester

Spark by Hilton Winchester
Winchester
₩103,491
₩117,255 total
includes taxes & fees
Nov 2 - Nov 3
Spark by Hilton 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
₩134,265
₩149,437 total
includes taxes & fees
Nov 5 - Nov 6
Comfort Inn & Suites 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 hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
A modern restaurant interior with wooden tables and chairs, a green booth area, and artwork on the walls.

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
Winchester
₩124,397
₩138,454 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 room with two beds, a mounted painting, a nightstand with a phone, and a window with curtains.
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.

Quality Inn Winchester

Quality Inn Winchester
Winchester
₩106,486
₩118,520 total
includes taxes & fees
Nov 15 - Nov 16
Quality Inn Winchester
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 reception area with a stone counter, a chandelier, a desk with a computer, and a seating area with chairs and a table.
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
₩95,328
₩105,143 total
includes taxes & fees
Nov 10 - Nov 11
Travelodge by Wyndham Winchester
A spacious living room with a fireplace, wooden staircase, and a bookshelf.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
A Country Inn & Suites by Radisson building with a covered entrance and multiple windows.
A woman using a stationary bike in a gym with red walls and multiple exercise machines.

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
Winchester
₩118,475
₩131,864 total
includes taxes & fees
Nov 8 - Nov 9
Country Inn & Suites by Radisson, Winchester, VA
A gym with treadmills, exercise balls, and a mirrored wall.
A kitchenette with a coffee machine, toaster, and a display case with pastries.
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.

Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area
Winchester
₩130,103
₩147,407 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn Winchester-University/Mall Area
A courtyard with a fountain, tables with white tablecloths, and brick buildings.
A spacious living room with a fireplace, leather sofa, armchairs, and a large painting.
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.

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
Old Town Winchester
₩175,055
₩198,337 total
includes taxes & fees
Oct 28 - Oct 29
The George Washington Hotel, A Wyndham Grand Hotel
View all properties

Family-friendly hotels with pools in 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.
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.

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
Winchester
₩131,822
₩146,717 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 lounge area with seating, a TV, and a children's play area.
A modern Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.
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
₩112,783
₩125,526 total
includes taxes & fees
Nov 15 - Nov 16
Microtel 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 hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
A modern restaurant interior with wooden tables and chairs, a green booth area, and artwork on the walls.

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
Winchester
₩124,397
₩138,454 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 room with two beds, a mounted painting, a nightstand with a phone, and a window with curtains.
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.

Quality Inn Winchester

Quality Inn Winchester
Winchester
₩106,486
₩118,520 total
includes taxes & fees
Nov 15 - Nov 16
Quality Inn Winchester
A courtyard with a fountain, tables with white tablecloths, and brick buildings.
A spacious living room with a fireplace, leather sofa, armchairs, and a large painting.
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.

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
Old Town Winchester
₩175,055
₩198,337 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 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 lobby with a large dining area, wooden accents, and contemporary lighting fixtures.

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
Winchester
₩152,418
₩169,641 total
includes taxes & fees
Nov 8 - Nov 9
SpringHill Suites by Marriott Winchester
A gym with treadmills, exercise balls, and a mirrored wall.
A kitchenette with a coffee machine, toaster, and a display case with pastries.
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.

Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area
Winchester
₩130,103
₩147,407 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn Winchester-University/Mall Area
A spacious living room with a fireplace, wooden staircase, and a bookshelf.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
A Country Inn & Suites by Radisson building with a covered entrance and multiple windows.
A woman using a stationary bike in a gym with red walls and multiple exercise machines.

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
Winchester
₩118,475
₩131,864 total
includes taxes & fees
Nov 8 - Nov 9
Country Inn & Suites by Radisson, Winchester, VA
A modern dining area with a large white table, blue chairs, and a flat-screen TV mounted on the wall.
A hotel reception area with a modern design, featuring a blue geometric wall pattern, a reception desk, and a snack shelf with various packaged goods.
An indoor swimming pool with a lifeguard chair, a pool lift, and a window.
A Holiday Inn Express & Suites building with a covered entrance, large windows, and a fire lane.

Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG
Winchester
₩147,692
₩164,381 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Hotel & Suites Winchester by IHG
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.
An outdoor seating area with wicker furniture and a small table, surrounded by greenery and a building in the background.
A modern hotel lobby with a curved sofa, a glass coffee table, and a flat-screen TV mounted on the wall.

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
Winchester
₩143,798
₩160,047 total
includes taxes & fees
Oct 22 - Oct 23
Courtyard by Marriott Winchester
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

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent
"Very clean and comfortable. The front desk staff were friendly. We would stay again."
David 1-night trip
Posted 9 hours ago
Holiday Inn Winchester Se-Historic Gateway by IHG
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"We had a great stay and the staff was super friendly"
Natalie 2-night trip
Posted 19 hours ago
Country Inn & Suites by Radisson, Winchester, VA
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Super clean hotel. Extremely friendly and welcoming staff. Very comfortable rooms and beds! Highly recommend!"
Melissa 1-night trip
Posted 20 hours ago
La Quinta Inn & Suites by Wyndham Winchester
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Friendly, professional staff. Most helpful with an issue I had with my car. Could not have been nicer and understanding."
DOUGLAS 2-night trip
Posted 1 day ago
The George Washington Hotel, A Wyndham Grand Hotel
Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America

8/10 Good
"Restaurant was closed on Sunday night our only night we stayed. The Speakeasy bar downstairs takes on the restaurant dining when restaurant is closed. Speakeasy was nice but not what one would expect because it was not secluded and secretly as they should be. But all that being said it’s a beautiful property and very welcoming"
William 1-night trip
Posted 2 days ago
Mimslyn Inn Historic Hotels Of America
Days Inn by Wyndham Winchester

Days Inn by Wyndham Winchester

10/10 Excellent
"The room was clean. The breakfast is good. Staff is nice. Safe lighted parking."
Mary 1-night trip
Posted 2 days ago
Days Inn by Wyndham Winchester
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

8/10 Good
"Clean place and nice for the price!"
Daniel 1-night trip
Posted 2 days ago
Travelodge by Wyndham Winchester
Lansdowne Resort and Spa

Lansdowne Resort and Spa

10/10 Excellent
"It’s a good place to attend weddings."
Umamaheshwar 1-night trip
Posted 2 days ago
Lansdowne Resort and Spa

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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