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Check prices for these dates

Tonight
12 Nov - 13 Nov
Tomorrow
13 Nov - 14 Nov
This weekend
13 Nov - 15 Nov
Next weekend
20 Nov - 22 Nov

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.

1. Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,451 reviews)
  • cleanliness
    A kid-friendly getaway with indoor pool and free breakfast, just minutes from the Shenandoah Valley Discovery Museum.
The price is AED 291
AED 324 total
includes taxes & fees
15 Nov - 16 Nov
Microtel Inn & Suites by Wyndham Winchester
A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.

2. La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (2,267 reviews)
The price is AED 340
AED 379 total
includes taxes & fees
29 Nov - 30 Nov
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.

3. Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,153 reviews)
The price is AED 320
AED 356 total
includes taxes & fees
2 Dec - 3 Dec
Comfort Inn & Suites Winchester
A spacious living room with a fireplace, wooden staircase, and a bookshelf.

4. Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
Winchester
8.8 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Family-friendly fun at this Winchester inn begins with an indoor pool, complimentary breakfast, and premium entertainment options.
The price is AED 309
AED 343 total
includes taxes & fees
2 Dec - 3 Dec
Country Inn & Suites by Radisson, Winchester, VA
A spacious lobby with a checkered floor, yellow chairs, a green carpet, and a wall with the text "It only takes a spark".

5. Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Experience kid-friendly adventures with premium TV channels and cribs, just minutes from Shenandoah Valley Discovery Museum.
The price is AED 238
AED 270 total
includes taxes & fees
29 Nov - 30 Nov
Spark by Hilton Winchester
A hotel room with two beds, a mounted painting, a nightstand with a phone, and a window with curtains.

6. Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,003 reviews)
  • cleanliness
    Splash into family fun at this Winchester hotel with seasonal outdoor pool, breakfast, and kid-friendly accommodations.
The price is AED 265
AED 295 total
includes taxes & fees
18 Nov - 19 Nov
Quality Inn Winchester
A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.

7. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (975 reviews)
The price is AED 340
AED 379 total
includes taxes & fees
15 Nov - 16 Nov
Fairfield Inn & Suites by Marriott Winchester
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.

8. Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Child-friendly indoor pool and activities make this hotel a perfect Winchester family retreat with premium entertainment extras.
The price is AED 364
AED 416 total
includes taxes & fees
10 Dec - 11 Dec
Holiday Inn Winchester Se-Historic Gateway by IHG
A buffet with multiple self-service stations, including omelets and other prepared foods.

9. Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG
2.5 star property
Winchester
9.0 out of 10, Wonderful, (871 reviews)
The price is AED 400
AED 446 total
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn Express Hotel & Suites Winchester by IHG
A snack and beverage display area with shelves stocked with various snacks and a refrigerated section with beverages.

10. Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area
2.5 star property
Winchester
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Family-friendly fun with outdoor pool and fitness center, steps from Shenandoah University makes vacation dreams a reality.
The price is AED 337
AED 382 total
includes taxes & fees
6 Dec - 7 Dec
Hampton Inn Winchester-University/Mall Area
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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Choose what matters most at family-friendly hotels in Winchester

Breakfast included
Pool

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.
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1451)
The price is AED 291
AED 324 total
includes taxes & fees
15 Nov - 16 Nov
Microtel Inn & Suites by Wyndham Winchester
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.
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1451)
The price is AED 291
AED 324 total
includes taxes & fees
15 Nov - 16 Nov
Microtel Inn & Suites by Wyndham 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

An outdoor seating area with a fire feature, wicker furniture, and a building with multiple windows.
TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
Front Royal

10/10 Excellent

Staff was great. Room was nice. Never felt so safe in my life. U.S. customs and border protection was house there. Thank them for what they do. God Bless.
United States
Joseph
Reviewed November 12, 2026
TownePlace Suites by Marriott Front Royal

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.