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Check availability on Winchester Family-Friendly Hotels

Tonight
9 Sept - 10 Sept
Tomorrow
10 Sept - 11 Sept
This weekend
11 Sept - 13 Sept
Next weekend
18 Sept - 20 Sept

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 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.

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.
₹8,193
₹9,119 total
includes taxes & fees
13 Sept - 14 Sept
Microtel Inn & Suites by Wyndham 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 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.

2. Quality Inn Winchester

Quality Inn Winchester
Winchester
  • Splash into family fun at this Winchester hotel with seasonal outdoor pool, breakfast, and kid-friendly accommodation.
₹7,577
₹8,433 total
includes taxes & fees
16 Sept - 17 Sept
Quality Inn Winchester
A modern hotel lobby with a reception desk, seating area, and a large window providing natural light.
A hotel lobby with a reception desk, refrigerated display cases, shelves with snacks, and a trash bin.
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.

3. Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
Winchester
₹10,031
₹11,365 total
includes taxes & fees
16 Sept - 17 Sept
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 bar area with a counter, multiple bar stools, and a television screen.
A swimming pool with lounge chairs and a changing room.

4. 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.
₹9,922
₹11,326 total
includes taxes & fees
20 Sept - 21 Sept
Holiday Inn Winchester Se-Historic Gateway by IHG
A modern interior with a geometric ceiling design, recessed lighting, and hanging pendant lights.
A spacious indoor pool area with multiple seating areas and a clear view of the outdoors through large windows.
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.

5. 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.
₹11,041
₹12,510 total
includes taxes & fees
20 Sept - 21 Sept
Hilton Garden 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 poolside area with lounge chairs and a stack of towels on a table.
A woman using a stationary bike in a gym with red walls and multiple exercise machines.

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.
₹9,600
₹10,685 total
includes taxes & fees
4 Oct - 5 Oct
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.
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.

7. Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG
Winchester
₹11,569
₹12,876 total
includes taxes & fees
13 Sept - 14 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 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.
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.
₹5,974
₹6,649 total
includes taxes & fees
13 Sept - 14 Sept
Days Inn by Wyndham Winchester
A lobby with a green wall, a reception desk, and seating area with sofas and armchairs.
An indoor swimming pool with clear signage, a lifeguard duty sign, and a pool lift.
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 modern hotel lobby with a reception desk, a coffee station, and a seating area.

9. 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.
₹7,722
₹8,594 total
includes taxes & fees
30 Sept - 1 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.

10. Motel 6 Winchester, VA

Motel 6 Winchester, VA
Winchester
₹6,825
₹7,733 total
includes taxes & fees
23 Sept - 24 Sept
Motel 6 Winchester, VA
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 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
₹8,193
₹9,119 total
includes taxes & fees
13 Sept - 14 Sept
Microtel Inn & Suites by Wyndham 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 swimming pool with a metal railing, surrounded by lounge chairs and an umbrella.
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
₹7,577
₹8,433 total
includes taxes & fees
16 Sept - 17 Sept
Quality Inn Winchester
A modern hotel lobby with a reception desk, seating area, and a large window providing natural light.
A hotel lobby with a reception desk, refrigerated display cases, shelves with snacks, and a trash bin.
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.

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
Winchester
₹10,031
₹11,365 total
includes taxes & fees
16 Sept - 17 Sept
Hampton Inn Winchester N/Conference Center, VA
A modern interior with a geometric ceiling design, recessed lighting, and hanging pendant lights.
A spacious indoor pool area with multiple seating areas and a clear view of the outdoors through large windows.
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
₹11,041
₹12,510 total
includes taxes & fees
20 Sept - 21 Sept
Hilton Garden Inn Winchester
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 bar area with a counter, multiple bar stools, and a television screen.
A swimming pool with lounge chairs and a changing room.

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
Winchester
₹9,922
₹11,326 total
includes taxes & fees
20 Sept - 21 Sept
Holiday Inn Winchester Se-Historic Gateway by IHG
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 poolside area with lounge chairs and a stack of towels on a table.
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
₹9,600
₹10,685 total
includes taxes & fees
4 Oct - 5 Oct
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.
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
₹11,569
₹12,876 total
includes taxes & fees
13 Sept - 14 Sept
Holiday Inn Express Hotel & Suites Winchester by IHG
A lobby with a green wall, a reception desk, and seating area with sofas and armchairs.
An indoor swimming pool with clear signage, a lifeguard duty sign, and a pool lift.
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 modern hotel lobby with a reception desk, a coffee station, and a seating area.

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
Winchester
₹7,722
₹8,594 total
includes taxes & fees
30 Sept - 1 Oct
Sleep Inn & Suites Winchester near University
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 seating area with two blue leather chairs and a beverage vending machine.
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
₹5,974
₹6,649 total
includes taxes & fees
13 Sept - 14 Sept
Days Inn by Wyndham Winchester
A restaurant interior with a bar area, seating, and artwork on the walls.
A hotel lobby with a reception desk, a minibar, a seating area, and a clothing rack.
An indoor swimming pool with a hot tub, lounge chairs, and a view of the outdoors.
A spacious lobby with a stone fireplace, blue upholstered sofas, and a chandelier.

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
Front Royal
₹11,586
₹12,779 total
includes taxes & fees
27 Sept - 28 Sept
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 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
₹8,193
₹9,119 total
includes taxes & fees
13 Sept - 14 Sept
Microtel Inn & Suites by Wyndham 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 swimming pool with a metal railing, surrounded by lounge chairs and an umbrella.
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
₹7,577
₹8,433 total
includes taxes & fees
16 Sept - 17 Sept
Quality Inn Winchester
A modern interior with a geometric ceiling design, recessed lighting, and hanging pendant lights.
A spacious indoor pool area with multiple seating areas and a clear view of the outdoors through large windows.
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
₹11,041
₹12,510 total
includes taxes & fees
20 Sept - 21 Sept
Hilton Garden Inn Winchester
A modern hotel lobby with a reception desk, seating area, and a large window providing natural light.
A hotel lobby with a reception desk, refrigerated display cases, shelves with snacks, and a trash bin.
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.

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
Winchester
₹10,031
₹11,365 total
includes taxes & fees
16 Sept - 17 Sept
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 bar area with a counter, multiple bar stools, and a television screen.
A swimming pool with lounge chairs and a changing room.

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
Winchester
₹9,922
₹11,326 total
includes taxes & fees
20 Sept - 21 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
₹11,569
₹12,876 total
includes taxes & fees
13 Sept - 14 Sept
Holiday Inn Express Hotel & Suites Winchester by IHG
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 poolside area with lounge chairs and a stack of towels on a table.
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
₹9,600
₹10,685 total
includes taxes & fees
4 Oct - 5 Oct
Country Inn & Suites by Radisson, Winchester, VA
A lobby with a green wall, a reception desk, and seating area with sofas and armchairs.
An indoor swimming pool with clear signage, a lifeguard duty sign, and a pool lift.
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 modern hotel lobby with a reception desk, a coffee station, and a seating area.

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
Winchester
₹7,722
₹8,594 total
includes taxes & fees
30 Sept - 1 Oct
Sleep Inn & Suites Winchester near University
A restaurant interior with a bar area, seating, and artwork on the walls.
A hotel lobby with a reception desk, a minibar, a seating area, and a clothing rack.
An indoor swimming pool with a hot tub, lounge chairs, and a view of the outdoors.
A spacious lobby with a stone fireplace, blue upholstered sofas, and a chandelier.

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
Front Royal
₹11,586
₹12,779 total
includes taxes & fees
27 Sept - 28 Sept
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 breakfast counter with various food items and a coffee machine.

Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park
Front Royal
₹5,884
₹6,549 total
includes taxes & fees
4 Oct - 5 Oct
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

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent
"The breakfast was great and lots of food variety. The oatmeal was yummy. The ladies who worked during breakfast, were so helpful and kind, made our visit that much better!!!"
Maura 2-night trip
Posted less than an hour ago
Fairfield Inn & Suites by Marriott Winchester
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

10/10 Excellent
"This minimalist motel is reasonably priced. I found my room very comfortable. It was immaculate, nice TV, bed comfortable and clean, the AC was very good. The AM breakfast is minimal but very nice and well attended to by pleasant staff. Parking was free and plentiful. No noise on halls or from the highway. The staff was professional, helpful and attentive. I will be staying here again!"
Mike 3-night trip
Posted 1 hour ago
Travelodge by Wyndham Winchester
Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"We enjoyed the stay. It is located in a great location right off hwy 81, and very clean. The customer service was very friendly and helpful. We would stay there again."
PIMPORN 1-night trip
Posted 2 hours ago
Quality Inn Winchester
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"1000 percent stay here!"
William 1-night trip
Posted 3 hours ago
The George Washington Hotel, A Wyndham Grand Hotel
Spark by Hilton Winchester

Spark by Hilton Winchester

8/10 Good
"This hotel is very satisfactory other than the soft water. Please add less water softener!"
Sean 2-night trip
Posted 5 hours ago
Spark by Hilton Winchester
Lansdowne Resort and Spa

Lansdowne Resort and Spa

10/10 Excellent
"A lovely place to spend a weekend. Staff was helpful and friendly. Everything was great"
Donald 1-night trip
Posted 4 days ago
Lansdowne Resort and Spa
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 9 days ago
Days Inn by Wyndham 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?
Holiday Inn Winchester Se-Historic Gateway by IHG is a hotel with an indoor pool and a restaurant, and it's a top choice on Expedia for families. Other good options for your stay with the children include Quality Inn Winchester and Microtel Inn & Suites by Wyndham Winchester.
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 Apple Blossom Mall, Bright Box Theater and Winchester Little Theater. Make sure that you have lots of time for activities such as Rocking S Ranch and Handley Regional Library.

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