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Family friendly Hotels in Winchester, Virginia

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Check availability on Winchester Family friendly Hotels

Tonight
Oct 4 - Oct 5
Tomorrow
Oct 5 - Oct 6
Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

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 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.
A hotel room with two beds, a desk, a chair, a desk lamp, a window with curtains, a bathroom with a mirror and sink.

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.
P5,755
P6,405 total
includes taxes & fees
Nov 1 - Nov 2
Microtel Inn & Suites by Wyndham Winchester
A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.
An indoor swimming pool with clear water, blue lounge chairs, and a wooden ceiling.
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.

2. La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
Winchester
P6,756
P7,519 total
includes taxes & fees
Oct 25 - Oct 26
La Quinta 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 bathroom with a toilet, two sinks, a large mirror, and a shower area.
A hotel dining area with multiple tables and chairs, large windows, and a television screen.
Lobby

3. Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
Winchester
P6,168
P6,865 total
includes taxes & fees
Oct 11 - Oct 12
Comfort Inn & Suites 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 living room with a fireplace, leather sofa, armchairs, and a large painting.

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.
P8,156
P9,240 total
includes taxes & fees
Oct 11 - Oct 12
The George Washington Hotel, A Wyndham Grand Hotel
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.

5. 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.
P5,844
P6,622 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Winchester-University/Mall Area
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 bathroom with a shower, bathtub, sink, and towel rack.
A hotel lobby with a blue sofa, red chairs, a patterned rug, and artwork on the walls.

6. Quality Inn Winchester

Quality Inn Winchester
Winchester
  • Splash into family fun at this Winchester hotel with seasonal outdoor pool, breakfast, and kid-friendly accommodations.
P5,264
P5,859 total
includes taxes & fees
Oct 25 - Oct 26
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 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.

7. 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.
P5,610
P6,244 total
includes taxes & fees
Oct 25 - Oct 26
Country Inn & Suites by Radisson, Winchester, VA
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.
A swimming pool with lounge chairs and a changing room.
A spacious lobby with a checkered floor, a reception desk, and a seating area with a sofa and chairs.
A hotel room with a bed, a desk with a computer, a chair, and a TV.

8. 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.
P6,193
P7,080 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Winchester Se-Historic Gateway by IHG
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 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.

9. Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
Winchester
P4,441
P4,898 total
includes taxes & fees
Oct 11 - Oct 12
Travelodge by Wyndham Winchester
A modern dining area with a large white table, blue chairs, and a flat-screen TV mounted on the wall.
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.
An indoor swimming pool with a lifeguard chair, a pool lift, and a window.

10. Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG
Winchester
P7,381
P8,215 total
includes taxes & fees
Nov 4 - Nov 5
Holiday Inn Express Hotel & Suites Winchester 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 hotel lobby with a reception desk, seating area, and a large window providing natural light.
A hotel room with a large bed, a bedside table with a lamp, a small desk, and a kitchenette area.
A lobby with yellow patterned chairs, a round table, a TV on the wall, and a patterned rug.
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
P6,617
P7,497 total
includes taxes & fees
Oct 11 - Oct 12
Hampton Inn Winchester N/Conference Center, 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 hotel lobby with a blue sofa, red chairs, a patterned rug, and artwork on the walls.
A hotel room with two beds, a mounted painting, a nightstand with a phone, and a window with curtains.

Quality Inn Winchester

Quality Inn Winchester
Winchester
P5,264
P5,859 total
includes taxes & fees
Oct 25 - Oct 26
Quality Inn 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 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.

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
Winchester
P5,755
P6,405 total
includes taxes & fees
Nov 1 - Nov 2
Microtel Inn & Suites by Wyndham 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 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.

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
Winchester
P5,610
P6,244 total
includes taxes & fees
Oct 25 - Oct 26
Country Inn & Suites by Radisson, Winchester, VA
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.
A swimming pool with lounge chairs and a changing room.
A spacious lobby with a checkered floor, a reception desk, and a seating area with a sofa and chairs.
A hotel room with a bed, a desk with a computer, a chair, and a TV.

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
Winchester
P6,193
P7,080 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Winchester Se-Historic Gateway by IHG
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.
An indoor swimming pool with clear signage, a lifeguard duty sign, and a pool lift.
A Sleep Inn hotel with a stone facade, multiple balconies, and a parking lot with several cars.

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
Winchester
P4,466
P4,971 total
includes taxes & fees
Oct 25 - Oct 26
Sleep Inn & Suites Winchester near University
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 indoor pool area with multiple seating areas and a clear view of the outdoors through large windows.

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
Winchester
P7,284
P8,252 total
includes taxes & fees
Oct 12 - Oct 13
Hilton Garden Inn Winchester
A modern dining area with a large white table, blue chairs, and a flat-screen TV mounted on the wall.
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.
An indoor swimming pool with a lifeguard chair, a pool lift, and a window.

Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG
Winchester
P7,381
P8,215 total
includes taxes & fees
Nov 4 - Nov 5
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 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 chairs and a lamp, a sign indicating continental breakfast hours, and a door with a small window.
A hotel with a registration sign, a parking lot, and a tree in front.

Days Inn by Wyndham Winchester

Days Inn by Wyndham Winchester
Winchester
P3,941
P4,386 total
includes taxes & fees
Oct 6 - Oct 7
Days Inn by Wyndham Winchester
A restaurant interior with a bar area, seating, and artwork on the walls.
A spacious lobby with a stone fireplace, blue upholstered sofas, and a chandelier.
A spacious lobby with a reception desk, seating area with sofas, and a chandelier.
A hotel lobby with a reception desk, a minibar, a seating area, and a clothing rack.

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
Front Royal
P7,284
P8,034 total
includes taxes & fees
Nov 1 - Nov 2
DoubleTree by Hilton Front Royal Blue Ridge Shadows
View all properties

Family-friendly hotels with pools in Winchester

A modern hotel lobby with a reception desk, seating area, and a large window providing natural light.
A hotel room with a large bed, a bedside table with a lamp, a small desk, and a kitchenette area.
A lobby with yellow patterned chairs, a round table, a TV on the wall, and a patterned rug.
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
P6,617
P7,497 total
includes taxes & fees
Oct 11 - Oct 12
Hampton Inn Winchester N/Conference Center, 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 hotel lobby with a blue sofa, red chairs, a patterned rug, and artwork on the walls.
A hotel room with two beds, a mounted painting, a nightstand with a phone, and a window with curtains.

Quality Inn Winchester

Quality Inn Winchester
Winchester
P5,264
P5,859 total
includes taxes & fees
Oct 25 - Oct 26
Quality Inn 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 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.

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
Winchester
P5,755
P6,405 total
includes taxes & fees
Nov 1 - Nov 2
Microtel Inn & Suites by Wyndham Winchester
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.
A swimming pool with lounge chairs and a changing room.
A spacious lobby with a checkered floor, a reception desk, and a seating area with a sofa and chairs.
A hotel room with a bed, a desk with a computer, a chair, and a TV.

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
Winchester
P6,193
P7,080 total
includes taxes & fees
Nov 2 - Nov 3
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 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.

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
Winchester
P5,610
P6,244 total
includes taxes & fees
Oct 25 - Oct 26
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 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.
An indoor swimming pool with a lifeguard chair, a pool lift, and a window.

Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG
Winchester
P7,381
P8,215 total
includes taxes & fees
Nov 4 - Nov 5
Holiday Inn Express Hotel & Suites Winchester by IHG
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.
An indoor swimming pool with clear signage, a lifeguard duty sign, and a pool lift.
A Sleep Inn hotel with a stone facade, multiple balconies, and a parking lot with several cars.

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
Winchester
P4,466
P4,971 total
includes taxes & fees
Oct 25 - Oct 26
Sleep Inn & Suites Winchester near University
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 indoor pool area with multiple seating areas and a clear view of the outdoors through large windows.

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
Winchester
P7,284
P8,252 total
includes taxes & fees
Oct 12 - Oct 13
Hilton Garden Inn Winchester
A restaurant interior with a bar area, seating, and artwork on the walls.
A spacious lobby with a stone fireplace, blue upholstered sofas, and a chandelier.
A spacious lobby with a reception desk, seating area with sofas, and a chandelier.
A hotel lobby with a reception desk, a minibar, a seating area, and a clothing rack.

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
Front Royal
P7,284
P8,034 total
includes taxes & fees
Nov 1 - Nov 2
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 Baymont Inn & Suites reception desk with a blue wall, two overhead lights, and a Dell computer.
A breakfast counter with various food items and a coffee machine.
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.

Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park
Front Royal
P3,669
P4,083 total
includes taxes & fees
Nov 2 - Nov 3
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.
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Top Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"The bed was amazingly comfortable and the room was very clean."
Cindy 1-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham Winchester
Quality Inn Winchester

Quality Inn Winchester

8/10 Good
"Great staff Very helpful,friendly Place is quite spartan but well kept Close to highway Great bargain"
Jeffrey 1-night trip
Posted 2 hours ago
Quality Inn Winchester
Days Inn by Wyndham Winchester

Days Inn by Wyndham Winchester

10/10 Excellent
"Staff are friendly and helpful, price is best in the area, the area behind the Dennys has a large number of friendly Groundhogs that the dog really appreciated. Easy access to the north-South skirmish Association's Ft. Shenandoah."
Dan 2-night trip
Posted 5 hours ago
Days Inn by Wyndham Winchester
Lansdowne Resort and Spa

Lansdowne Resort and Spa

8/10 Good
"It was a very busy weekend. Room service was unfortunately backed up and basically unavailable by phone."
Michael 2-night trip
Posted 5 hours ago
Lansdowne Resort and Spa
Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America

10/10 Excellent
"Great food in both of the restaurants! Bed was comfy and great service overall."
Jonathan 2-night trip
Posted 6 hours ago
Mimslyn Inn Historic Hotels Of America
Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG

10/10 Excellent
"Nice place to stay. Convenient for our travels."
marilyn 1-night trip
Posted 1 day ago
Candlewood Suites Winchester by IHG
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent
"For the price we could not ask for more......well run hotel.....thanks!"
Jeffrey 1-night trip
Posted 1 day ago
Holiday Inn Winchester Se-Historic Gateway by IHG
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

8/10 Good
"The staff is very friendly. The room was clean, comfortable beds. The breakfast could be updated with better pantries. I would stay there again."
Mary Jo 1-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Winchester, VA

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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