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Check availability on Winchester Family Hotels

Tonight
Sep 16 - Sep 17
Tomorrow
Sep 17 - Sep 18
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

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 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.
A modern lounge area with seating, a TV, and a children's play area.

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.
₩121,710
₩135,463 total
includes taxes & fees
Sep 20 - Sep 21
Microtel Inn & Suites by Wyndham Winchester
A modern hotel lobby with a reception desk, seating area, and a large window providing natural light.
A modern kitchen with wooden cabinets, a countertop, and a window with a view.
A lobby with yellow patterned chairs, a round table, a TV on the wall, and a patterned rug.
A hotel lobby with a reception desk, refrigerated display cases, shelves with snacks, and a trash bin.

2. Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
Winchester
₩142,417
₩161,358 total
includes taxes & fees
Sep 23 - Sep 24
Hampton Inn Winchester N/Conference Center, VA
A hotel room with two beds, a mounted painting, a nightstand with a phone, and a window with curtains.
A swimming pool with a metal railing, surrounded by lounge chairs and an umbrella.
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.

3. Quality Inn Winchester

Quality Inn Winchester
Winchester
  • Splash into family fun at this Winchester hotel with seasonal outdoor pool, breakfast, and kid-friendly accommodations.
₩113,295
₩126,097 total
includes taxes & fees
Sep 23 - Sep 24
Quality Inn Winchester
A modern interior with a geometric ceiling design, recessed lighting, and hanging pendant lights.
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.
A bar area with a long counter, bar stools, and shelves with bottles.

4. 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.
₩136,361
₩154,497 total
includes taxes & fees
Sep 28 - Sep 29
Hilton Garden Inn 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 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.

5. 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.
₩140,886
₩156,806 total
includes taxes & fees
Oct 11 - Oct 12
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 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.

6. 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.
₩143,121
₩163,383 total
includes taxes & fees
Sep 20 - Sep 21
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.
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.
A Holiday Inn Express & Suites building with a covered entrance, large windows, and a fire lane.

7. Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG
Winchester
₩166,293
₩185,084 total
includes taxes & fees
Sep 27 - Sep 28
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 hotel with a registration sign, a parking lot, and a tree in front.
A bathroom with a bathtub, toilet, sink, and a mirror.

8. 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.
₩87,243
₩97,112 total
includes taxes & fees
Sep 21 - Sep 22
Days Inn by Wyndham Winchester
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
₩96,924
₩109,822 total
includes taxes & fees
Sep 23 - Sep 24
Motel 6 Winchester, VA
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.

10. 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.
₩104,274
₩116,058 total
includes taxes & fees
Oct 12 - Oct 13
Sleep Inn & Suites Winchester near University
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 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.
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
₩121,710
₩135,463 total
includes taxes & fees
Sep 20 - Sep 21
Microtel Inn & Suites by Wyndham Winchester
A modern hotel with a covered outdoor area, landscaped gardens, and a parking lot.
A swimming pool with a metal railing, surrounded by lounge chairs and an umbrella.
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.

Quality Inn Winchester

Quality Inn Winchester
Winchester
₩113,295
₩126,097 total
includes taxes & fees
Sep 23 - Sep 24
Quality Inn Winchester
A modern hotel lobby with a reception desk, seating area, and a large window providing natural light.
A modern kitchen with wooden cabinets, a countertop, and a window with a view.
A lobby with yellow patterned chairs, a round table, a TV on the wall, and a patterned rug.
A hotel lobby with a reception desk, refrigerated display cases, shelves with snacks, and a trash bin.

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
Winchester
₩142,417
₩161,358 total
includes taxes & fees
Sep 23 - Sep 24
Hampton Inn Winchester N/Conference Center, 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 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.

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
Winchester
₩143,121
₩163,383 total
includes taxes & fees
Sep 20 - Sep 21
Holiday Inn Winchester Se-Historic Gateway by IHG
A modern interior with a geometric ceiling design, recessed lighting, and hanging pendant lights.
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.
A spacious kitchen area with a central island, a waffle maker, and a coffee station.

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
Winchester
₩136,361
₩154,497 total
includes taxes & fees
Sep 28 - Sep 29
Hilton Garden Inn 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 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.

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
Winchester
₩140,886
₩156,806 total
includes taxes & fees
Oct 11 - Oct 12
Country Inn & Suites by Radisson, Winchester, VA
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 hotel with a registration sign, a parking lot, and a tree in front.

Days Inn by Wyndham Winchester

Days Inn by Wyndham Winchester
Winchester
₩87,243
₩97,112 total
includes taxes & fees
Sep 21 - Sep 22
Days Inn by Wyndham Winchester
A modern dining area with a large white table, blue chairs, and a flat-screen TV mounted on the wall.
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.
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
₩166,293
₩185,084 total
includes taxes & fees
Sep 27 - Sep 28
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.
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
₩104,274
₩116,058 total
includes taxes & fees
Oct 12 - Oct 13
Sleep Inn & Suites Winchester near University
A restaurant interior with a bar area, seating, and artwork on the walls.
An indoor swimming pool with a hot tub, lounge chairs, and a view of the outdoors.
A hotel lobby with a reception desk, a minibar, a seating area, and a clothing rack.
A spacious lobby with a reception desk, seating area with sofas, and a chandelier.

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
Front Royal
₩166,539
₩183,691 total
includes taxes & fees
Sep 24 - Sep 25
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 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.
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
₩121,710
₩135,463 total
includes taxes & fees
Sep 20 - Sep 21
Microtel Inn & Suites by Wyndham Winchester
A modern hotel with a covered outdoor area, landscaped gardens, and a parking lot.
A swimming pool with a metal railing, surrounded by lounge chairs and an umbrella.
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.

Quality Inn Winchester

Quality Inn Winchester
Winchester
₩113,295
₩126,097 total
includes taxes & fees
Sep 23 - Sep 24
Quality Inn Winchester
A modern hotel lobby with a reception desk, seating area, and a large window providing natural light.
A modern kitchen with wooden cabinets, a countertop, and a window with a view.
A lobby with yellow patterned chairs, a round table, a TV on the wall, and a patterned rug.
A hotel lobby with a reception desk, refrigerated display cases, shelves with snacks, and a trash bin.

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
Winchester
₩142,417
₩161,358 total
includes taxes & fees
Sep 23 - Sep 24
Hampton Inn Winchester N/Conference Center, 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 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.

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
Winchester
₩143,121
₩163,383 total
includes taxes & fees
Sep 20 - Sep 21
Holiday Inn Winchester Se-Historic Gateway by IHG
A modern interior with a geometric ceiling design, recessed lighting, and hanging pendant lights.
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.
A spacious kitchen area with a central island, a waffle maker, and a coffee station.

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
Winchester
₩136,361
₩154,497 total
includes taxes & fees
Sep 28 - Sep 29
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 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.
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
₩166,293
₩185,084 total
includes taxes & fees
Sep 27 - Sep 28
Holiday Inn Express Hotel & Suites Winchester by IHG
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 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.

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
Winchester
₩140,886
₩156,806 total
includes taxes & fees
Oct 11 - Oct 12
Country Inn & Suites by Radisson, Winchester, VA
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
₩104,274
₩116,058 total
includes taxes & fees
Oct 12 - Oct 13
Sleep Inn & Suites Winchester near University
A restaurant interior with a bar area, seating, and artwork on the walls.
An indoor swimming pool with a hot tub, lounge chairs, and a view of the outdoors.
A hotel lobby with a reception desk, a minibar, a seating area, and a clothing rack.
A spacious lobby with a reception desk, seating area with sofas, and a chandelier.

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
Front Royal
₩166,539
₩183,691 total
includes taxes & fees
Sep 24 - Sep 25
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 breakfast counter with various food items and a coffee machine.
A Baymont Inn & Suites reception desk with a blue wall, two overhead lights, and a Dell computer.
A multi-story hotel with a courtyard, outdoor seating, and a guest parking area.

Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park
Front Royal
₩85,830
₩95,529 total
includes taxes & fees
Sep 28 - Sep 29
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

Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"Excellent room! The room was equipped with everything we needed. Very comfortable bed. Impressed with the wonderful breakfast provided. Will definitely be staying on each of our trips north and on our way back home . Want to compliment the young lady taking care of the breakfast area. She was so very pleasant and kept the area clean and well stocked."
Robert 1-night trip
Posted 9 hours ago
Quality Inn Winchester
Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG

10/10 Excellent
"Had an amazing experience at candle wood very clean very nice and peaceful i look forward to staying again"
Latasha 1-night trip
Posted 12 hours ago
Candlewood Suites Winchester by IHG
Skyland

Skyland

10/10 Excellent
"The rooms were very comfortable and clean. Area around was safe. Staff was very helpful and welcoming."
Larry 2-night trip
Posted 17 hours ago
Skyland
Spark by Hilton Winchester

Spark by Hilton Winchester

10/10 Excellent
"One of the cleanest hotels I’ve stayed in."
Kaitlyn 2-night trip
Posted 21 hours ago
Spark by Hilton Winchester
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"The room was very clean. The bed was comfortable. The bathroom was immaculate and it was a great breakfast. I enjoyed my stay thank you very much."
Chris 1-night trip
Posted 22 hours ago
Country Inn & Suites by Radisson, Winchester, VA
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

10/10 Excellent
"We stay here a couple of times a year. Always super clean. Great place for the $. Breakfast is not as good as it used to be. Instant coffee. A lot of carbs c"
Lynda 1-night trip
Posted 2 days ago
Travelodge by Wyndham Winchester
Quality Inn Harpers Ferry - Charles Town

Quality Inn Harpers Ferry - Charles Town

8/10 Good
"."
Shenandoah 1-night trip
Posted 3 days ago
Quality Inn Harpers Ferry - Charles Town
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent
"Highly recommend"
Mary 1-night trip
Posted 6 days ago
Fairfield Inn & Suites by Marriott Winchester
Days Inn by Wyndham Winchester

Days Inn by Wyndham Winchester

8/10 Good
"Not too shabby. I would stay again"
Jeannie 1-night trip
Posted 2 weeks ago
Days Inn by Wyndham Winchester

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

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