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Check availability on Winchester Family-Friendly Hotels

Tonight
22 Sep - 23 Sep
Tomorrow
23 Sep - 24 Sep
This weekend
25 Sep - 27 Sep
Next weekend
2 Oct - 4 Oct

Our top choices for Winchester family-friendly hotels

A modern lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.
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.
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 Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.

1. 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.
฿3,108
฿3,459 total
includes taxes & fees
24 Sept - 25 Sept
Microtel Inn & Suites by Wyndham Winchester
A modern hotel lobby with a reception desk, seating area, and a large window providing natural light.
A lobby with yellow patterned chairs, a round table, a TV on the wall, and a patterned rug.
A hotel room with a large bed, a bedside table with a lamp, a small desk, and a kitchenette area.
A modern kitchen with wooden cabinets, a countertop, and a window with a view.

2. Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
Winchester
฿3,516
฿3,984 total
includes taxes & fees
29 Sept - 30 Sept
Hampton Inn Winchester N/Conference Center, VA
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.
A hotel room with a bed, a desk with a computer, a chair, and a TV.
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.

3. 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.
฿3,490
฿3,984 total
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Winchester Se-Historic Gateway by IHG
A modern dining area with a large white table, blue chairs, and a flat-screen TV mounted on the wall.
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.
A hotel room with a bed, a desk, a chair, a window with a view, and a TV on the wall.

4. Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG
Winchester
฿4,065
฿4,524 total
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Express Hotel & Suites Winchester by IHG
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.

5. Quality Inn Winchester

Quality Inn Winchester
Winchester
  • Splash into family fun at this Winchester hotel with seasonal outdoor pool, breakfast, and kid-friendly accommodation.
฿3,080
฿3,427 total
includes taxes & fees
29 Sept - 30 Sept
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 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.

6. 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.
฿3,292
฿3,664 total
includes taxes & fees
19 Oct - 20 Oct
Country Inn & Suites by Radisson, Winchester, VA
A modern interior with a geometric ceiling design, recessed lighting, and hanging pendant lights.
A modern kitchen with a long counter, built-in bar, and seating area.
A reception area with a wooden reception desk, a wine cooler, and a microwave.
A bar area with a long counter, bar stools, and shelves with bottles.

7. Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
Winchester
  • Family-friendly indoor pool oasis with premium amenities makes Winchester stays delightful for visitors of all ages.
฿3,870
฿4,385 total
includes taxes & fees
5 Oct - 6 Oct
Hilton Garden Inn Winchester
A lobby with a green wall, a reception desk, and seating area with sofas and armchairs.
A living room with a brown sofa, two armchairs, a coffee table, and two lamps. There are two windows with blinds, and a wall with a leaf pattern.
A Sleep Inn hotel with a stone facade, multiple balconies, and a parking lot with several cars.
An indoor swimming pool with clear signage, a lifeguard duty sign, and a pool lift.

8. Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
Winchester
  • Family-friendly hotel with spacious rooms offers premium entertainment and free perks near Shenandoah Valley Discovery Museum.
฿2,692
฿2,997 total
includes taxes & fees
12 Oct - 13 Oct
Sleep Inn & Suites Winchester near University
A bathroom with a sink, mirror, and shower.
A room with a wooden wall, a blue door, a wall-mounted soap and bleach dispenser, and a small table with chairs.
A modern interior with a reception desk, seating area, and large windows offering a view of the street.
A reception area with a white reception desk, a grey carpet, and a view of the street outside.

9. Motel 6 Winchester, VA

Motel 6 Winchester, VA
Winchester
฿2,393
฿2,711 total
includes taxes & fees
29 Sept - 30 Sept
Motel 6 Winchester, VA
A hotel room with two beds, a blue armchair, a nightstand with a lamp, and a wall-mounted painting.
A laundry area with stacked washers and dryers, a window with a view of a tree and gravel path, and visible plumbing.
A hotel with a registration sign, a parking lot, and a tree in front.
A seating area with two blue leather chairs and a beverage vending machine.

10. Days Inn by Wyndham Winchester

Days Inn by Wyndham Winchester
Winchester
  • Friendly Winchester escape where kids enjoy complimentary breakfast and convenient amenities near family attractions.
฿2,154
฿2,397 total
includes taxes & fees
23 Sept - 24 Sept
Days Inn by Wyndham 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 modern lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.
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.
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 Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
Winchester
฿3,108
฿3,459 total
includes taxes & fees
24 Sept - 25 Sept
Microtel Inn & Suites by Wyndham 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
฿3,080
฿3,427 total
includes taxes & fees
29 Sept - 30 Sept
Quality Inn Winchester
A modern hotel lobby with a reception desk, seating area, and a large window providing natural light.
A lobby with yellow patterned chairs, a round table, a TV on the wall, and a patterned rug.
A hotel room with a large bed, a bedside table with a lamp, a small desk, and a kitchenette area.
A modern kitchen with wooden cabinets, a countertop, and a window with a view.

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
Winchester
฿3,516
฿3,984 total
includes taxes & fees
29 Sept - 30 Sept
Hampton Inn Winchester N/Conference Center, VA
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 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.

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
Winchester
฿3,292
฿3,664 total
includes taxes & fees
19 Oct - 20 Oct
Country Inn & Suites by Radisson, Winchester, VA
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.
A hotel room with a bed, a desk with a computer, a chair, and a TV.
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.

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
Winchester
฿3,490
฿3,984 total
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Winchester Se-Historic Gateway by IHG
A modern dining area with a large white table, blue chairs, and a flat-screen TV mounted on the wall.
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.
A hotel room with a bed, a desk, a chair, a window with a view, and a TV on the wall.

Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG
Winchester
฿4,065
฿4,524 total
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Express Hotel & Suites Winchester by IHG
A hotel room with two beds, a blue armchair, a nightstand with a lamp, and a wall-mounted painting.
A seating area with two chairs and a lamp, a sign indicating continental breakfast hours, and a door with a small window.
A laundry area with stacked washers and dryers, a window with a view of a tree and gravel path, and visible plumbing.
A seating area with two blue leather chairs and a beverage vending machine.

Days Inn by Wyndham Winchester

Days Inn by Wyndham Winchester
Winchester
฿2,154
฿2,397 total
includes taxes & fees
23 Sept - 24 Sept
Days Inn by Wyndham Winchester
A modern interior with a geometric ceiling design, recessed lighting, and hanging pendant lights.
A modern kitchen with a long counter, built-in bar, and seating area.
A reception area with a wooden reception desk, a wine cooler, and a microwave.
A spacious kitchen area with a central island, a waffle maker, and a coffee station.

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
Winchester
฿3,870
฿4,385 total
includes taxes & fees
5 Oct - 6 Oct
Hilton Garden Inn Winchester
A lobby with a green wall, a reception desk, and seating area with sofas and armchairs.
A living room with a brown sofa, two armchairs, a coffee table, and two lamps. There are two windows with blinds, and a wall with a leaf pattern.
A Sleep Inn hotel with a stone facade, multiple balconies, and a parking lot with several cars.
An indoor swimming pool with clear signage, a lifeguard duty sign, and a pool lift.

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
Winchester
฿2,692
฿2,997 total
includes taxes & fees
12 Oct - 13 Oct
Sleep Inn & Suites Winchester near University
A restaurant interior with a bar area, seating, and artwork on the walls.
A spacious lobby with a reception desk, seating area with sofas, and a chandelier.
A spacious lobby with a stone fireplace, blue upholstered sofas, and a chandelier.
An indoor swimming pool with a hot tub, lounge chairs, and a view of the outdoors.

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
Front Royal
฿4,062
฿4,480 total
includes taxes & fees
12 Oct - 13 Oct
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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 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.
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 Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
Winchester
฿3,108
฿3,459 total
includes taxes & fees
24 Sept - 25 Sept
Microtel Inn & Suites by Wyndham 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
฿3,080
฿3,427 total
includes taxes & fees
29 Sept - 30 Sept
Quality Inn Winchester
A modern hotel lobby with a reception desk, seating area, and a large window providing natural light.
A lobby with yellow patterned chairs, a round table, a TV on the wall, and a patterned rug.
A hotel room with a large bed, a bedside table with a lamp, a small desk, and a kitchenette area.
A modern kitchen with wooden cabinets, a countertop, and a window with a view.

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
Winchester
฿3,516
฿3,984 total
includes taxes & fees
29 Sept - 30 Sept
Hampton Inn Winchester N/Conference Center, VA
A modern dining area with a large white table, blue chairs, and a flat-screen TV mounted on the wall.
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.
A hotel room with a bed, a desk, a chair, a window with a view, and a TV on the wall.

Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG
Winchester
฿4,065
฿4,524 total
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Express Hotel & Suites Winchester by IHG
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.
A hotel room with a bed, a desk with a computer, a chair, and a TV.
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.

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
Winchester
฿3,490
฿3,984 total
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Winchester Se-Historic Gateway by IHG
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 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.

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
Winchester
฿3,292
฿3,664 total
includes taxes & fees
19 Oct - 20 Oct
Country Inn & Suites by Radisson, Winchester, VA
A modern interior with a geometric ceiling design, recessed lighting, and hanging pendant lights.
A modern kitchen with a long counter, built-in bar, and seating area.
A reception area with a wooden reception desk, a wine cooler, and a microwave.
A spacious kitchen area with a central island, a waffle maker, and a coffee station.

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
Winchester
฿3,870
฿4,385 total
includes taxes & fees
5 Oct - 6 Oct
Hilton Garden Inn Winchester
A lobby with a green wall, a reception desk, and seating area with sofas and armchairs.
A living room with a brown sofa, two armchairs, a coffee table, and two lamps. There are two windows with blinds, and a wall with a leaf pattern.
A Sleep Inn hotel with a stone facade, multiple balconies, and a parking lot with several cars.
An indoor swimming pool with clear signage, a lifeguard duty sign, and a pool lift.

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
Winchester
฿2,692
฿2,997 total
includes taxes & fees
12 Oct - 13 Oct
Sleep Inn & Suites Winchester near University
A restaurant interior with a bar area, seating, and artwork on the walls.
A spacious lobby with a reception desk, seating area with sofas, and a chandelier.
A spacious lobby with a stone fireplace, blue upholstered sofas, and a chandelier.
An indoor swimming pool with a hot tub, lounge chairs, and a view of the outdoors.

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
Front Royal
฿4,062
฿4,480 total
includes taxes & fees
12 Oct - 13 Oct
DoubleTree by Hilton Front Royal Blue Ridge Shadows
A hotel room with a large bed, a bathroom with a bathtub, and a framed picture on the wall.
A multi-story hotel with a courtyard, outdoor seating, and a guest parking area.
A room with two grey armchairs, a small table with a vase of flowers, a television mounted on the wall, and a desk with a computer.
A Baymont Inn & Suites reception desk with a blue wall, two overhead lights, and a Dell computer.

Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park
Front Royal
฿2,096
฿2,333 total
includes taxes & fees
28 Sept - 29 Sept
Baymont by Wyndham Front Royal Near Shenandoah National Park
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

Skyland

Skyland

8/10 Good
"Beautiful!"
Nathaniel 2-night trip
Posted 4 hours ago
Skyland
Spark by Hilton Winchester

Spark by Hilton Winchester

8/10 Good
"Clean room and quiet"
Stephanie 1-night trip
Posted 18 hours ago
Spark by Hilton Winchester
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Friendly, clean, what more can you ask?!"
Mitzi 1-night trip
Posted 18 hours ago
La Quinta Inn & Suites by Wyndham Winchester
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"Nice area. Very clean. Delicious and hot breakfast."
Rebekah 1-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Winchester, VA
Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"Very comfortable conditions and friendly staff."
Michael 1-night trip
Posted 2 days ago
Quality Inn Winchester
Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG

8/10 Good
"Friendly young man at front desk. Clean hotel, very comfy beds and pillows and a lot of water pressure. Large room with kitchen and large fridge with a freezer."
Kimberley 1-night trip
Posted 3 days ago
Candlewood Suites Winchester by IHG
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

8/10 Good
"We stayed for 1 on night on our way back home. Comfortable beds, clean room & friendly staff. Breakfast had a lot of options, just the eggs looked water and rubbery. Wasn't hard to find something else to eat instead. We didn't use the pool and the rooster behind the building confused me when loading our items back into our truck in the morning, thought I was loosing my mind till I walked over a bit and seen him staring at me. Gave me a good chuckle. We would 100% stay here again."
Patti 1-night trip
Posted 4 days ago
Fairfield Inn & Suites by Marriott Winchester

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 Rocking S Ranch. Make sure that you have lots of time for activities such as Handley Regional Library and Winchester Little Theater.

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