Find Family-Friendly Hotels in Winchester, IN

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
8 Nov - 9 Nov
Tomorrow
9 Nov - 10 Nov
Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov

Our top choices for Winchester family-friendly hotels

A golf course with a pond, trees, and a clear sky.

1. Randolph Inn and Suites

Randolph Inn and Suites
2.5 star property
Winchester
8.8 out of 10, Excellent, (289 reviews)
The price is £82
includes taxes & fees
9 Nov - 10 Nov
Randolph Inn and Suites
A buffet with various food items, including omelets and other dishes, served in metal containers.

2. Holiday Inn Express & Suites Portland by IHG

Holiday Inn Express & Suites Portland by IHG
2.5 star property
Portland
9.2 out of 10, Wonderful, (397 reviews)
  • cleanliness
    Portland family getaway offers indoor pool, free cots, rollaway beds, and hot breakfast daily.
The price is £92
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express & Suites Portland by IHG
A hotel room with two beds, a desk with a TV, a dresser, and a window with curtains.

3. Motel 6 Portland, IN

Motel 6 Portland, IN
2.0 star property
Portland
7.2 out of 10, Good, (129 reviews)
The price is £53
includes taxes & fees
10 Nov - 11 Nov
Motel 6 Portland, IN
A hotel room with a large bed, a desk with a computer, a chair, and a TV.

4. Baymont by Wyndham Richmond I-70

Baymont by Wyndham Richmond I-70
2.5 star property
Richmond
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Family fun awaits with indoor pool adventures, a relaxing hot tub, and a kid-friendly haven just minutes from Middlefork Reservoir Park.
The price is £70
includes taxes & fees
10 Nov - 11 Nov
Baymont by Wyndham Richmond I-70
A bathroom with a toilet, a bathtub, and a shower curtain.

5. Hoosier Inn

Hoosier Inn
2.5 star property
Portland
8.8 out of 10, Excellent, (147 reviews)
The price is £67
includes taxes & fees
9 Nov - 10 Nov
Hoosier Inn
A hotel room with a large bathtub, a double bed, a desk, and a chair.

6. Quality Inn Greenville North

Quality Inn Greenville North
2.5 star property
Greenville
8.2 out of 10, Very good, (391 reviews)
The price is £76
includes taxes & fees
29 Nov - 30 Nov
Quality Inn Greenville North
A room with multiple wooden tables and benches, a pool table, and a green arcade machine.

7. Surestay By Best Western Greenville

Surestay By Best Western Greenville
2.5 star property
Greenville
7.8 out of 10, Good, (459 reviews)
  • cleanliness
    Family escape with a difference: bowl, sail, or canoe at this friendly hotel where kids thrive in active fun.
The price is £78
includes taxes & fees
15 Nov - 16 Nov
Surestay By Best Western Greenville
Living area

8. Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
Economy
6.0 out of 10, (2 reviews)
The price is £236
includes taxes & fees
9 Nov - 10 Nov
Pets Welcome! Quiet Economy Home w/ Spacious Yard
A building with a stone facade, a glass entrance, and a 'Lobby' sign.

9. Red Roof Inn Richmond, IN

Red Roof Inn Richmond, IN
2.0 star property
Richmond
7.0 out of 10, Good, (982 reviews)
The price is £39
includes taxes & fees
1 Dec - 2 Dec
Red Roof Inn Richmond, IN
A hotel room with three beds, a desk, and a chair. There are paintings on the walls and a window with curtains.

10. Super 8 by Wyndham Centerville-Richmond

Super 8 by Wyndham Centerville-Richmond
2.0 star property
Centerville
6.2 out of 10, (373 reviews)
The price is £44
includes taxes & fees
15 Nov - 16 Nov
Super 8 by Wyndham Centerville-Richmond
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

Choose what matters most at family-friendly hotels in Winchester

Breakfast included
Pool

Top Winchester Hotel Reviews

A golf course with a pond, trees, and a clear sky.
Randolph Inn and Suites

Randolph Inn and Suites

Randolph Inn and Suites
Winchester

10/10 Excellent

Ideally located for racing at Eldora and Winchester Speedways. Hope to visit again.
United Kingdom
David
Reviewed July 22, 2024
Randolph Inn and Suites

Find out more about Winchester

Family friendly things to do in Winchester

Winchester, Indiana, offers a delightful array of family-friendly activities that cater to both children and adults. Begin your adventure at the Winchester Speedway, where the roaring engines and exhilarating races provide an electrifying experience for the whole family. If your little ones are keen on the outdoors, the picturesque Winchester Parks offer ample space to play, picnic, and explore nature trails, making it a perfect spot for a family day out. For a taste of history, visit the historic Winchester Courthouse, where engaging tours reveal fascinating stories from the past. Arts enthusiasts will appreciate the Winchester Art Gallery, which often hosts family-friendly workshops, allowing children to unleash their creativity while parents relax in a vibrant setting. Finally, don’t miss the chance to explore the nearby Deer Creek Reservoir, where fishing and recreational activities , ensuring a fun-filled day on the water. Families will find a variety of comfortable hotels in the downtown area that provide convenient access to these attractions, coupled with attentive service and amenities designed for younger guests, such as spacious family rooms and complimentary breakfasts, making your stay both enjoyable and straightforward.

Frequently Asked Questions

Which area of Winchester, Indiana, United States of America is best to stay in for families?

For families, the northwest part of Winchester offers an excellent balance of safety and comfort. Residents consistently rate this area as the safest in the city, providing peace of mind for parents.


If convenience and family-friendly amenities are your priority, the area around City Park and the historic Main Street District is an ideal choice. Here, you'll find hotels boasting spacious rooms, refreshing pools, and complimentary breakfast, all within easy reach of downtown activities.


Should a quieter, more suburban atmosphere be what you seek, Meadowbranch presents a wonderful option.

Can I cancel my family hotel reservation on Expedia?

Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right family-friendly hotel in Winchester for you.

How can I save on a family-friendly hotel in Winchester with Expedia?

There are plenty of ways to save on a family-friendly hotel in Winchester. Join One Key™, our free travel rewards programme, to unlock instant discounts with Member Prices across a range of hotels. Typically, booking in advance will help you save on your family hotel booking.

How much does a family hotel in Winchester cost?

Travellers can find great deals on family-friendly Winchester hotels from £38 with Expedia. You may find hotels in Winchester that let kids stay for free, which can help you save. There are plenty of factors that can impact the price of family hotels, including location, amenities and the time of year. Sort Winchester hotels on Expedia by price to see our cheapest prices first.

Explore a world of travel with Expedia