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Top Winchester hotels

Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy

Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy

Fort recovery
This vacation home features a gym and a hot tub. Families will appreciate the playground and onsite laundry facilities. A garden and barbecue grills are also ...
"We had a wonderful time staying here. The pool and gym were amazing!"

Reviewed on Jul 16, 2025

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Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!

Winchester
A water park and an indoor pool are featured at this smoke-free vacation home. There's fun for all ages with a playground and an arcade/game room, and barbecue ...
Very roomy and family friendly home
"Our immediate family of 12 adults and 9 kids stayed at this home. It had enough bedrooms and bathrooms to make our experience very relaxing. The pool was a big hit for everyone. It rained at times but having the pool inside didn’t hinder our fun. Lots of outside space for baseball and kickball and ..."

Reviewed on Jul 14, 2025

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Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Comfort Suites

Comfort Suites

2.5 out of 5
421 Commerce Road, Richmond, IN
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $107 total per night from Aug 3 to Aug 4
$107 total
Aug 3 - Aug 4
Total includes taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will ...
"Great place! Clean, comfortable, and safe"

Reviewed on Jul 22, 2025

Comfort Suites
Home2 Suites by Hilton Richmond

Home2 Suites by Hilton Richmond

3 out of 5
5950 National Rd E, Richmond, IN
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $142 total per night from Aug 3 to Aug 4
$142 total
Aug 3 - Aug 4
Total includes taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests ...
"I always stay at Homes2Suite Richmond, IN when I visit family. From the moment I arrive to when I leave, everything is great! The front desk and breakfast staff are always so helpful and accommodating to our needs! The only thing, my husband says the water pressure in the shower needs work! Lol"

Reviewed on Jul 21, 2025

Home2 Suites by Hilton Richmond
Randolph Inn and Suites

Randolph Inn and Suites

2.5 out of 5
890 E Washington, Winchester, IN
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $121 total per night from Jul 27 to Jul 28
$121 total
Jul 27 - Jul 28
Total includes taxes and fees
This hotel features an indoor pool and a gym. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. ...
"It was very clean and the staff was very accommodating. It was close to the Walmart for anything that you would need and restaurants."

Reviewed on Jul 20, 2025

Randolph Inn and Suites
Baymont by Wyndham Richmond I-70

Baymont by Wyndham Richmond I-70

2.5 out of 5
912 Mendleson Dr, Richmond, IN
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $85 total per night from Aug 10 to Aug 11
$85 total
Aug 10 - Aug 11
Total includes taxes and fees
This inn features an indoor pool and a 24-hour gym. Enjoy the hot tub and free perks like self-serve breakfast and free self parking. A business center, free ...
"Nice place to stay! Loved the pool and hot tub!"

Reviewed on Jul 23, 2025

Baymont by Wyndham Richmond I-70
Super 8 by Wyndham Muncie/Ball St. College Area

Super 8 by Wyndham Muncie/Ball St. College Area

2 out of 5
3601 W Fox Ridge Ln, Muncie, IN
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $73 total per night from Jul 30 to Jul 31
$73 total
Jul 30 - Jul 31
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the ...
"All good"

Reviewed on Jul 18, 2025

Super 8 by Wyndham Muncie/Ball St. College Area
Days Inn by Wyndham Muncie -Ball State University

Days Inn by Wyndham Muncie -Ball State University

2 out of 5
3509 N Everbrook Ln, Muncie, IN
Fully refundableReserve now, pay when you stay
$59 nightly
The price is $66 total per night from Jul 27 to Jul 28
$66 total
Jul 27 - Jul 28
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the ...
"Everything was super clean and neat."

Reviewed on Jul 21, 2025

Days Inn by Wyndham Muncie -Ball State University
Baymont by Wyndham Muncie Near Ball State University

Baymont by Wyndham Muncie Near Ball State University

2.5 out of 5
3400 North Chadam Lane, Muncie, IN
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $83 total per night from Jul 30 to Jul 31
$83 total
Jul 30 - Jul 31
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the ...
"The only thing we did not like is that the room seem to be extremely humid and carpet was Sticky like it was holding a lot of moisture, and there was a bit of an odor when we walked in of a little bit musty otherwise the place was very clean"

Reviewed on Jul 18, 2025

Baymont by Wyndham Muncie Near Ball State University
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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.

Winchester Hotel & Travel Guide

While you won't find any Travelocity-registered accommodations in Winchester there is one an easy drive away.

About 40 miles (60 kilometers) outside Winchester is Anderson which hosts a selection of places to stay, such as the Holiday Inn Express Hotel & Suites ANDERSON NORTH and Hampton Inn Anderson.

After you have spent some time in Winchester, put aside some time to check out the other great attractions Central Indiana has to offer. Central Indiana boasts rural landscapes, and commonly visited tourist attractions are history museums. Visitors and locals alike in this part of United States of America often love cycling and shore fishing.

Located 40 miles (60 kilometers) to the west of Winchester is Anderson, which has a number of hotels and apartments. The Best Western Plus Anderson and Quality Inn And Suites are a selection of the establishments here.

Ensure a sports fix by making a voyage to Fraze Pavillion, which is located 55 miles (86 kilometers) to the southeast of Winchester. Book Travelocity-listed accommodation in the middle of the action at the Marriott at the University of Dayton or the Courtyard by Marriott Dayton-University of Dayton.

James M. Cox Dayton International Airport is a closeby airport, and is found 45 miles (70 kilometers) from Winchester's center. Hotels that are nearby include Super 8 Vandalia / Dayton International Airport and Airport Inn and Parking/Dayton International Airport.

Top reasons for your vacation to Winchester

  • Adventure Parks: Winchester, Indiana offers nearby adventure parks, providing thrilling activities such as hiking, biking, and exploring nature trails.
  • Golf Courses: Golf enthusiasts can enjoy the beautiful landscapes and challenging holes at the local golf courses in Winchester.
  • Historic Shopping District: Explore the historic shopping district of Winchester, where you can browse through unique shops and boutiques.
  • Rich History: Winchester offers opportunities to learn about its rich past, with historical attractions and sites to explore.
  • Standardbred Racetrack: Experience the excitement of horse racing at Winchester's standardbred racetrack.

Find your favorite hotels in Winchester

If you're planning a sports vacation in Winchester, Indiana, you'll find a range of hotel accommodations to suit your needs. From affordable options to luxurious hotels, there is something for every budget. You can browse through hotel reviews to find the best fit for your family. Whether you're looking for a top hotel with excellent amenities or a cheap hotel that offers value for money, you'll have plenty of options to choose from in Winchester.

Hotel nameTypeStarsDescription
Randolph Inn and SuitesHotel2.5This 2.5-star rated hotel is a great option for your sports vacation in Winchester, Indiana. Located close to an indoor pool, countryside, golf courses, and recreational areas, it offers convenient access to sports facilities. Whether you're traveling for business or leisure, this hotel provides a range of amenities including a swimming pool, family-friendly environment, and a no-smoking policy. Each room is equipped with a microwave, ensuring your comfort during your stay. With its proximity to sports and leisure activities, Randolph Inn and Suites is an excellent choice for your sports vacation.

Explore the best activities and sights in Winchester

Winchester, Indiana offers a range of activities for a sports vacation with your family. Nearby attractions include adventure parks and golf courses, perfect for outdoor enthusiasts. For those interested in history, Winchester offers opportunities to explore its historic shopping district and learn about the town's rich past. Additionally, the standardbred racetrack provides thrilling horse racing experiences. Located in the beautiful Shenandoah Valley, Winchester offers a variety of options to keep your family engaged and entertained during your sports vacation.

  1. Winchester Speedway: Winchester Speedway is a thrilling motor racing destination that offers an exhilarating experience. Feel the adrenaline rush as you watch fast-paced races and witness the skillful maneuvers of the drivers. The Speedway's vibrant atmosphere and the roar of the engines create an electrifying ambiance. Whether you're a racing enthusiast or just looking for an exciting adventure, Winchester Speedway guarantees an unforgettable experience.
  2. Winchester Golf Club: Nestled in picturesque surroundings, Winchester Golf Club is a golfer's paradise. This stunning golf course provides a unique outdoor experience with its lush green fairways and meticulously designed holes. Enjoy a leisurely game of golf while taking in the breathtaking views of the surrounding countryside. Whether you're a seasoned golfer or a beginner, Winchester Golf Club caters to players of all levels. Immerse yourself in the tranquility of nature and challenge yourself on this remarkable course.
  3. Historic Shopping & Dining District of Winchester, Indiana: Step back in time as you explore the charming Historic Shopping & Dining District of Winchester, Indiana. This vibrant street is lined with beautifully preserved historical buildings, offering a glimpse into the city's rich heritage. Stroll along the sidewalks and discover a diverse range of shops, boutiques, and restaurants. Indulge in delectable cuisine and browse unique, locally crafted goods. The district's captivating architecture and quaint atmosphere make it the perfect place for a city adventure. Experience the charm of Winchester's past and create lasting memories in this enchanting district.

Where to stay in Winchester

Winchester, Indiana offers a range of exciting sports activities for your vacation. Start by exploring the close proximity to adventure, with opportunities for hiking, biking, and exploring nature trails in the surrounding area. Golf enthusiasts can enjoy a round or two at the local golf courses, known for their beautiful landscapes and challenging holes. For a taste of history, visit the historic shopping district, where you can browse through unique shops and boutiques. Don't miss the nearby town of New Paris, which offers a charming small-town atmosphere. Research by neighborhood and discover the hidden gems of Jefferson Township. Winchester has something for everyone on your sports vacation!

  1. Muncie: Muncie is a vibrant city located 21.5 miles away from Winchester. It offers a range of unique experiences for sports vacations with your family. The city is known for its thriving art scene, with galleries and studios showcasing local talent. Muncie is also home to a renowned university, providing opportunities for educational exploration. Sports enthusiasts can catch football games and enjoy various sporting activities. Families can visit museums to learn about the city's history and culture. Muncie is family-friendly, with attractions such as shopping centers and a casino for entertainment. The city's beautiful flower gardens create a tranquil atmosphere, and the dining options cater to diverse tastes.
  2. Richmond: Located 24.2 miles from Winchester, Richmond is a city that offers a rich blend of historical charm and modern attractions. Families can immerse themselves in vibrant festivals that celebrate the city's culture. The university in Richmond provides opportunities for educational experiences. Art and sports enthusiasts can explore museums and enjoy various sporting events. The city is family-friendly, with activities suitable for all ages. The architecture and monuments add to the city's character, and the beautiful flower displays create a picturesque atmosphere. Richmond is a destination that offers a diverse range of experiences for a sports vacation with your family.
  3. New Weston: New Weston is a popular city located 20.5 miles away from Winchester. While it may be smaller than Muncie and Richmond, New Weston offers a peaceful and laid-back atmosphere. Families can enjoy the scenic surroundings and engage in outdoor activities such as hiking and picnicking. The city provides a break from the bustling urban environment, allowing you to connect with nature. Although New Weston may not have as many attractions as the larger cities, it offers a charming retreat for families seeking a quieter sports vacation experience.

Best times to go to Winchester

The travel seasons of Winchester

Trips to Winchester show no change in popularity throughout the year. The peak season to visit is from July to September, with July being the highest month. Off-peak season starts from November to January, and December sees the least travelers.

Winchester has something in store for you whenever you visit. January is the coldest month of the year, while July is hottest, with average temperatures up to 72.9 degrees Fahrenheit. The wettest month in Winchester is May, so pack accordingly.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationcloud iconCloudiness
January26.8°F (-2.9°C)Light RainMostly Cloudy
February29.7°F (-1.3°C)Light RainMostly Cloudy
March40.5°F (4.7°C)Light RainMostly Cloudy
April50.7°F (10.4°C)Light RainMostly Sunny
May61.9°F (16.6°C)Light RainMostly Sunny
June69.8°F (21.0°C)Light RainMostly Sunny
July72.9°F (22.7°C)Light RainMostly Sunny
August71.1°F (21.7°C)Light RainMostly Sunny
September65.5°F (18.6°C)Light RainMostly Sunny
October54.1°F (12.3°C)Light RainMostly Sunny
November41.7°F (5.4°C)Light RainMostly Sunny
December33.4°F (0.8°C)Light RainMostly Cloudy

Food and dining in Winchester

Winchester, Indiana is a haven for food enthusiasts, with plenty of restaurants offering a diverse range of cuisines. One highly popular dining place is Casey's, a pizzeria known for its mouthwatering pizzas. For a taste of Latin American and Mexican flavors, El Carreton is a top-rated choice. Their menu is filled with delicious dishes that will satisfy your cravings. If you're in the mood for North American cuisine, Arby's is a moderately rated but highly popular restaurant. Don't forget to try the famous Wick's pies, a local specialty that you can find in several restaurants in Winchester. Enjoy exploring the vibrant dining district of Winchester!

How do I find a great hotel with Travelocity?

Ensure your entire crew enjoys an unforgettable vacation. Utilize our family-friendly badge to find hotels that offer extra amenities for children. Our custom filters assist in narrowing down hotels based on proximity to popular attractions, enhanced cleaning protocols, and affordability.

Why should I book with Travelocity?

Conference calls, to-do lists and, of course, football practice. Busy lives and packed schedules call for trips that are hassle-free. Our aim is to provide stress-free travel every time you and your family book with us so that you can spend less time worrying and more time creating lasting memories. In pursuit of this, we will assist you in finding and planning your ideal trip, while offering transparent pricing and verifiable reviews, as well as 24/7 guaranteed customer support before, during, and after your vacation.

How can I save money on my trip to Winchester?

Avoid the peak season from July to September when planning your trip to Winchester. The less popular season from November to January offers more affordable rates. To save money, consider combining your flights, hotel, and car bookings as a bundle at a discounted price. In Winchester, you can explore inexpensive local attractions such as hiking trails in the nearby state parks, visiting the Winchester Speedway for races, and taking a self-guided tour of the historic homes and buildings in the downtown area.

Frequently asked questions

What are the top kid-friendly hotels in Winchester?
From carefully considered amenities to bigger rooms, kid-friendly hotels come with features that can help transform a great family vacation into an incredible one. These Winchester options make vacationing with young ones a cinch: Your gang will enjoy their time at Randolph Inn and Suites. Complimentary breakfast and a swimming pool are just a couple of the things that help make this place an attractive option. Also consider staying at Holiday Inn Express & Suites Portland, an IHG Hotel. It offers a swimming pool, complimentary breakfast and lots of opportunities to hang out together.
Where can I find cheap hotels in Winchester?
At Travelocity you'll find really nice hotels in Winchester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Winchester rather than in Winchester. We may find you even better rates, too.
How do I find the best Winchester hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Winchester then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Winchester?
The cheapest hotel in Winchester is $66. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Winchester?
There are 112 hotels in Winchester on Travelocity.
What are the best hotels in Winchester?
Winchester has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Winchester for you!
When is the best time to visit Winchester?
If you want the joy of a fun-filled trip in peak season, visit Winchester during December, January and February. If you'd prefer the peace of off-season, book a stay during quieter months, such as June, July and November.
When is the cheapest time to stay in Winchester?
Based on historic data is usually the cheapest month to visit Winchester. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Winchester?
There are multiple hotels in Winchester that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Winchester. We have plenty of kid-friendly hotels in Winchester to choose from on Travelocity!
Why book a hotel in Winchester through Travelocity?
Because we have the top hotels in Winchester! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Winchester on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Winchester hotel reviews by fellow wanderers

Comfort Suites

Comfort Suites

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Great place! Clean, comfortable, and safe "
A verified traveler stayed at Comfort Suites
Comfort Suites
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