Find hotels in Winchester, IN from $48

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Compare 132 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Randolph Inn and Suites

2.5 star property
Winchester
9.0 out of 10, Wonderful, (243)
"Nice hotel"
United States
William
$108 nightly
The price is $121
Dec 12 - Dec 13
Total with taxes and fees
Randolph Inn and Suites

Baymont by Wyndham Richmond I-70

2.5 star property
Richmond
8.4 out of 10, Very Good, (1002)
"Good motel "
United States
Parth
$67 nightly
The price is $75
Dec 12 - Dec 13
Total with taxes and fees
Baymont by Wyndham Richmond I-70

Fairfield Inn by Marriott Richmond

2.5 star property
New Paris
9.0 out of 10, Wonderful, (517)
"The room was clean, the staff was polite and friendly. "
United States
Leslie
$101 nightly
The price is $114
Dec 13 - Dec 14
Total with taxes and fees
Fairfield Inn by Marriott Richmond

Comfort Inn & Suites Muncie Near University

2.5 star property
Muncie
8.4 out of 10, Very Good, (718)
"We had a good stay"
United States
Rodney
$86 nightly
The price is $96
Dec 26 - Dec 27
Total with taxes and fees
Comfort Inn & Suites Muncie Near University

Super 8 by Wyndham Muncie/Ball St. College Area

2.0 star property
Muncie
8.0 out of 10, Very Good, (1001)
"Very nice stay for the price. "
United States
Bart
$60 nightly
The price is $67
Dec 28 - Dec 29
Total with taxes and fees
Super 8 by Wyndham Muncie/Ball St. College Area

Quality Inn Greenville North

2.5 star property
Greenville
8.2 out of 10, Very Good, (342)
"Our stay at the Quality Inn was good, it was clean, smelled clean, and the Breakfast options were very good, and at night it was quiet. "
United States
Gregg A
$106 nightly
The price is $120
Dec 23 - Dec 24
Total with taxes and fees
Quality Inn Greenville North

Holiday Inn Express Hotel & Suites Greenville by IHG

2.5 star property
Greenville
8.6 out of 10, Excellent, (302)
"Everything was very nice at this location. Before I found this location I was staying in Richmond to be at a Hilton property. Now that there is something clean and kept I will continue to stay here. "
United States
Janice
$120 nightly
The price is $136
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn Express Hotel & Suites Greenville by IHG

Best Western Plus Richmond Indiana I-70

2.5 star property
Richmond
8.4 out of 10, Very Good, (1003)
"New facility, best hotel I’ve stayed in recently!"
United States
Antonia
$93 nightly
The price is $105
Dec 16 - Dec 17
Total with taxes and fees
Best Western Plus Richmond Indiana I-70

Motel 6 Portland, IN

2.0 star property
Portland
6.8 out of 10, (78)
"clean"
United States
Shane
$75 nightly
The price is $84
Dec 10 - Dec 11
Total with taxes and fees
Motel 6 Portland, IN

Comfort Suites

2.5 star property
Richmond
9.4 out of 10, Exceptional, (650)
"Room was clean, front desk was friendly. "
United States
Susan
$95 nightly
The price is $107
Dec 21 - Dec 22
Total with taxes and fees
Comfort Suites

Best Western Muncie

2.5 star property
Muncie
7.6 out of 10, Good, (839)
"Perfect location for Ball state activities"
United States
Patricia
$85 nightly
The price is $95
Dec 21 - Dec 22
Total with taxes and fees
Best Western Muncie

Hampton Inn & Suites Muncie

2.5 star property
Muncie
8.8 out of 10, Excellent, (879)
"The staff at check in was phenomenal. Very friendly. Very accommodating and very helpful!"
United States
Dyanne
$103 nightly
The price is $116
Dec 27 - Dec 28
Total with taxes and fees
Hampton Inn & Suites Muncie

Courtyard Muncie at Horizon Convention Center

3.0 star property
Muncie
9.0 out of 10, Wonderful, (862)
"Clean room, nice staff, easy to find and get in and aorund. Would stay again"
United States
Samuel
$118 nightly
The price is $132
Dec 21 - Dec 22
Total with taxes and fees
Courtyard Muncie at Horizon Convention Center

Quality Inn and Conference Center

2.5 star property
Richmond
6.8 out of 10, (1004)
"nice place to stay"
United States
Onda
$43 nightly
The price is $48
Dec 21 - Dec 22
Total with taxes and fees
Quality Inn and Conference Center

Holiday Inn Express Richmond by IHG

3.0 star property
Richmond
8.4 out of 10, Very Good, (771)
"It was great."
United States
Chris
$100 nightly
The price is $112
Dec 21 - Dec 22
Total with taxes and fees
Holiday Inn Express Richmond by IHG

Holiday Inn Express & Suites Portland by IHG

2.5 star property
Portland
9.2 out of 10, Wonderful, (354)
"Excellent stay every time we are there friendly staff all around awesome stay"
United States
Rebecca
$97 nightly
The price is $109
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn Express & Suites Portland by IHG

Cozy Garden Inn By OYO Hwy 40 Richmond

2.5 star property
Richmond
6.8 out of 10, (66)
"The location was great and next to Culver's."
United States
Verne
$64 nightly
The price is $71
Dec 15 - Dec 16
Total with taxes and fees
Cozy Garden Inn By OYO Hwy 40 Richmond

Home2 Suites by Hilton Richmond

3.0 star property
Richmond
9.2 out of 10, Wonderful, (401)
"Very spacious room, great amenities, and delicious breakfast every morning!"
United States
Kiana
$108 nightly
The price is $121
Dec 21 - Dec 22
Total with taxes and fees
Home2 Suites by Hilton Richmond

Hampton Inn & Suites Richmond, IN

2.5 star property
Richmond
9.2 out of 10, Wonderful, (939)
"The breakfast service was excellent tasty and well presented "
United States
Terence
$95 nightly
The price is $107
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hampton Inn & Suites Richmond, IN

The Golden Inn

2.5 star property
New Paris
9.2 out of 10, Wonderful, (432)
"Wonderful place to stay, clean rooms and quiet, very comfortable, would stay here again so nice."
United States
Renee
$79 nightly
The price is $89
Dec 10 - Dec 11
Total with taxes and fees
The Golden Inn
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.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Winchester attractions

Top Winchester Hotel Reviews

More cheap stays in Winchester

Hotels in Winchester with star-rating

Find out more about Winchester

Top reasons to visit Winchester

  • Outdoor Adventure: Winchester is a haven for outdoor enthusiasts, with activities like motor racing and exploring scenic parks and nature preserves.
  • Live Music Venues: Experience the vibrant local music scene at various event venues throughout the community.
  • Charming Downtown: Stroll through downtown Winchester, where unique shops and eateries await, all within walking distance.
  • Wine Country: Discover nearby wineries and savor the local flavors in the picturesque wine country.
  • Diverse Accommodations: Enjoy a range of lodging options, from cozy motels to pet-friendly hotels, ensuring a comfortable stay.

Find great hotels in and around Winchester

Discover a variety of lodging options in Winchester, Indiana, perfect for every type of traveler. From cozy motels to welcoming hotels, you'll find pet-friendly accommodations and business-themed facilities that cater to your needs. Whether you're searching for the best hotels, reading reviews, or comparing room rates, Winchester has something for everyone to ensure a comfortable and enjoyable stay.

  • Baymont by Wyndham Greenville OH: A welcoming retreat for families and pet lovers, Baymont by Wyndham Greenville OH is designed to provide a comfortable and inclusive experience. Located 20 miles from Winchester, this hotel stands out for its pet-friendly policies and LGBTQIA-friendly atmosphere. It offers amenities tailored for families, including cribs available for a fee. With a commitment to service, guests can enjoy a hassle-free stay knowing that their furry friends are welcome, making it an ideal choice for travelers seeking a home away from home.
  • Holiday Inn Express & Suites Portland by IHG: Situated 18 miles from Winchester, the Holiday Inn Express & Suites Portland by IHG caters to business travelers with its professional amenities. This hotel features a 24-hour business center and conference space, ensuring you stay productive while on the road. The property is also LGBTQIA welcoming, creating an inclusive environment for all guests. With comfortable accommodations and essential business facilities, it’s the perfect spot for those traveling for work who still want to feel at ease.
  • Randolph Inn and Suites: Located right in Winchester, Randolph Inn and Suites is a cozy option that offers a variety of amenities to enhance your stay. Guests can indulge in a complimentary daily breakfast, including continental options, perfect for starting your day off right. For leisure, the hotel boasts fitness facilities and entertainment features like satellite TV and premium channels. This property provides a homely atmosphere and is ideal for travelers looking for convenience and comfort without compromising on quality.

Where to stay near Winchester

Winchester, Indiana, offers a delightful blend of adventure and history for travelers. Explore the charming downtown area, where friendly locals welcome you to enjoy unique shops and eateries within walking distance. Nearby, discover the scenic wine country, featuring numerous wineries that invite you to savor local flavors. Whether you're seeking outdoor sports or a peaceful retreat, Winchester and its surrounding areas promise an unforgettable vacation experience.

  • Saratoga: Located 6 miles from Winchester, Saratoga is a charming city that attracts visitors year-round, with peak arrivals during the summer months of June to August. Travelers flock here for family-friendly adventures and outdoor experiences. The highlight of Saratoga is its amusement park, which offers thrills and fun for all ages. Additionally, you'll find a nearby theme park that adds to the excitement, making it a great spot for a day trip or a weekend getaway.
  • Farmland: Situated 8 miles away from Winchester, Farmland is known for its seasonal appeal. The city sees a surge in visitors during January, June, August, and October, making it a popular destination for outdoor enthusiasts and families seeking scenic views. Here, you can explore recreational areas and enjoy activities like motor racing and camping. The local attractions, including a picturesque lake and a lively stadium, make Farmland a delightful place to experience the great outdoors and enjoy community events.
  • Ridgeville: Also located 8 miles from Winchester, Ridgeville is a city that welcomes travelers throughout the year, with a peak season from June to August. Visitors come for a mix of city-themed experiences, business opportunities, and family fun. The public market is a highlight, offering a taste of local culture and fresh produce. Outdoor enthusiasts will appreciate the nearby lake and mountain, perfect for hiking and enjoying nature's beauty. Ridgeville offers a balanced blend of urban convenience and natural exploration.

Things to do in and around Winchester

Winchester, Indiana, is perfect for adventure seekers and outdoor enthusiasts. Enjoy thrilling activities like motor racing and explore the local campground and recreational areas. Don't miss the chance to experience live music at various event venues, play a round of golf, and relax in outdoor seating. Be sure to visit the beautiful waterfall for a picturesque escape that adds to the charm of this vibrant community.

Shopping

Winchester offers a charming shopping experience with local gems. For unique gifts, visit Warm Glow Candle Company, located 22 miles away. If you're up for a drive, Richmond Mall (25 miles away) provides a larger shopping environment, while Southway Centre Shopping Center (21 miles away) has a variety of family-friendly options.

Recreation

Experience a round of golf at Winchester Golf Club, where you can enjoy the outdoors and the sport. For a serene escape, visit Prairie Creek Reservoir and Campground, perfect for relaxation and wellness activities. Cardinal Hills Golf Course, located nearby, also offers a fantastic golfing experience amidst nature.

Adventure

Experience the thrill at Winchester Speedway with exciting motor racing events right in town, perfect for adrenaline junkies. For more racing action, head 21 miles to Eldora Speedway, renowned for its vibrant sports atmosphere. Enjoy a more leisurely adventure 23 miles away at Cardinal Creek Tennis Center for tennis fun.

Nightlife

For a vibrant nightlife, catch a show at Muncie Civic Theatre, just 21 miles away, offering a mix of culture and family entertainment. Alternatively, enjoy Richmond Civic Theatre, 24 miles away, where you can immerse yourself in romance and engaging performances for the whole family.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Winchester

To save money on your trip to Winchester, consider visiting between November and January when hotel prices are lower, especially on Mondays. Use Expedia's search tool to find budget-friendly accommodations, and sort options from lowest to highest price. Look for package deals that combine flights and hotels for added savings. Join Expedia's One Key membership for exclusive discounts and earn OneKeyCash for future stays. Explore free activities in the area and utilize local public transport to keep costs down while enjoying your visit.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winchester are November to January, where the prices are slightly lower. This is in comparison to May, July and September, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Winchester is Monday. The most expensive day to stay in Winchester is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia’s search tool to narrow down your options based on your budget, desired location, and preferred hotel style. To find the best prices and deals, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Winchester with your flights and activities through an Expedia package deal.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions in and around Winchester

Winchester, Indiana, offers a perfect getaway for adventure and outdoor enthusiasts. Visitors can explore local attractions such as the fairgroundShowGround, urban parks, and nature preserves. These points of interest provide a blend of cultural experiences and family-friendly activities, making it an ideal destination for travelers seeking sports and outdoor fun. Whether you're enjoying a day at the park or participating in local events, Winchester has something for everyone.

  • Randolph County Courthouse: This historic building is an architectural gem located in the heart of Winchester, showcasing beautiful design and rich local culture. It's a great spot for photography and learning about the area's history.
  • Levi Coffin House: Located 15 miles from Winchester, this historic house is known as the Grand Central Station of the Underground Railroad. Visitors can explore its fascinating history and learn about the abolitionist movement.
  • Historic Shopping & Dining District of Winchester, Indiana: This charming street offers a delightful mix of unique shops and local dining options, perfect for experiencing the vibrant city atmosphere and supporting local businesses.

Best time to go to Winchester

The best time to visit Winchester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.8°F (-2.9°C)Light RainMostly CloudySlightly LowSlightly Low
February29.7°F (-1.3°C)Light RainMostly CloudyAverageAverage
March40.5°F (4.7°C)Light RainMostly CloudyAverageAverage
April50.7°F (10.4°C)Light RainMostly SunnyAverageAverage
May61.9°F (16.6°C)Light RainMostly SunnyAverageSlightly High
June69.8°F (21.0°C)Light RainMostly SunnyAverageAverage
July72.9°F (22.7°C)Light RainMostly SunnySlightly HighSlightly High
August71.1°F (21.7°C)Light RainMostly SunnySlightly HighAverage
September65.5°F (18.6°C)Light RainMostly SunnySlightly HighSlightly High
October54.1°F (12.3°C)Light RainMostly SunnyAverageAverage
November41.7°F (5.4°C)Light RainMostly SunnySlightly LowSlightly Low
December33.4°F (0.8°C)Light RainMostly CloudySlightly LowSlightly Low

The nearest major airports for your trip to Winchester

To visit Winchester, Indiana, you can fly into several nearby airports. Dayton International Airport (DAY) is located 44 miles away, with hotels such as Wingate by Wyndham Dayton North, 4 miles from the airport, and Holiday Inn Dayton/Fairborn Interstate 675, 12 miles away. Fort Wayne International Airport (FWA) is 57 miles from Winchester, offering options like The Bradley Hotel and Hilton Fort Wayne, both 7 miles from the airport. Muncie’s Delaware County Airport (MIE) is the closest at 22 miles, with nearby hotels including Courtyard Muncie and Best Western, both 2-3 miles away. Each airport provides various transportation services to ensure a smooth journey.

Frequently asked questions

What are the best budget hotels in Winchester?
Randolph Inn and Suites in Winchester, Indiana, is a highly-rated budget hotel with an excellent review score of 9.0, making it a reliable choice for travelers seeking comfort and value. This inviting property offers a range of amenities designed for a stress-free stay, including complimentary breakfast and free WiFi, ensuring you can stay connected and fueled for your adventures. View all budget hotels in Winchester.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Winchester.
How can I save on a Winchester hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Winchester hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Winchester hotel?
Prices for hotels in Winchester often vary, but you can find a great deal from $48 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

Explore a world of travel with Expedia