Find hotels in Winchester, IN from $49

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.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	26.8°F (-2.9°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
February	29.7°F (-1.3°C)	Light Rain	Mostly Cloudy	Average	Average
March	40.5°F (4.7°C)	Light Rain	Mostly Cloudy	Average	Average
April	50.7°F (10.4°C)	Light Rain	Mostly Sunny	Average	Average
May	61.9°F (16.6°C)	Light Rain	Mostly Sunny	Average	Slightly High
June	69.8°F (21.0°C)	Light Rain	Mostly Sunny	Average	Average
July	72.9°F (22.7°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	71.1°F (21.7°C)	Light Rain	Mostly Sunny	Slightly High	Average
September	65.5°F (18.6°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
October	54.1°F (12.3°C)	Light Rain	Mostly Sunny	Average	Average
November	41.7°F (5.4°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
December	33.4°F (0.8°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly 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.