Find hotels in Winchester, KY from $57

Top reasons to visit Winchester

• Outdoor Adventures: Winchester, Kentucky, is a haven for outdoor enthusiasts, featuring stunning parks, scenic hiking trails, and beautiful campgrounds.
• Charming Downtown: Stroll through the quaint downtown area, known for its friendly atmosphere and picturesque Kentucky hills.
• Rich History: Explore antique shops that reflect the area’s rich heritage and invite visitors to uncover local stories.
• Family-Friendly Activities: Enjoy a variety of cultural experiences and family-friendly activities in national and urban parks.
• Diverse Accommodations: Choose from a range of comfortable lodging options, including pet-friendly and business-themed properties.

Find great hotels near Winchester

Explore a variety of comfortable lodging options in Winchester, Kentucky, including hotels and agritourism properties. Whether you're seeking pet-friendly accommodations, business-themed services, or an LGBTQIA welcoming environment, you'll find the perfect fit for your vacation. Discover the best hotels in Winchester, including Wyndham options, and read reviews to ensure a delightful stay in this charming city.

• WoodSpring Suites Lexington: Ideal for business travelers and pet owners, WoodSpring Suites Lexington offers a practical, pet-friendly atmosphere just 15 miles from Winchester. The hotel is designed with convenience in mind, featuring a Business District with essential amenities tailored for corporate guests. Enjoy the flexibility of pet policies that welcome dogs while providing necessary restrictions. With a focus on a comfortable stay, this hotel ensures you have everything you need for a productive getaway.
• GuestHouse Lexington: Located 14 miles from Winchester, GuestHouse Lexington combines a family-friendly environment with essential business amenities. This hotel caters to those traveling with children, offering safety measures like window guards and access to cribs for a comfortable stay. The on-site Business Center is perfect for professionals needing a productive space. With a welcoming atmosphere, this hotel is an excellent choice for families looking for a blend of work and leisure during their vacation.
• Hyatt Place Lexington: A 3-star hotel situated 13 miles from Winchester, Hyatt Place Lexington is perfect for families and business travelers seeking a pet-friendly experience. The hotel boasts multiple meeting rooms, a 24-hour accessible Business Center, and a welcoming environment for children, with complimentary cribs available. Pets are welcome with specific policies in place, making it easy for you to bring your furry friend along. With a focus on comfort and convenience, Hyatt Place Lexington is an excellent choice for a memorable stay.

Where to stay in Winchester

Winchester, Kentucky, offers a delightful blend of outdoor adventures and scenic beauty, perfect for any traveler. Explore the charming downtown area with its friendly atmosphere, enjoy low crowds, and take in the picturesque hills of Kentucky. Nearby Clark County invites families and adventurers alike to embark on memorable excursions, making it a favorite destination for those seeking a relaxing yet active vacation experience.

• Lexington: A vibrant metropolis, Lexington is a hub of activity that perfectly complements your visit to Winchester. As the second-largest city in Kentucky, it offers a diverse range of outdoor adventures and family-friendly experiences. Visitors can explore numerous parks, national state parks, and hiking trails, making it ideal for nature enthusiasts. The city also boasts a lively atmosphere with recreational areas and campgrounds, making it a great place for those seeking adventure. Don’t miss local landmarks such as the iconic stadiums and beautifully maintained parks that enhance the city’s charm.
• Clintonville: Located a mere 8 miles from Winchester, Clintonville is a quaint village that provides a picturesque escape for travelers. Known for its stunning scenery and outdoor adventures, visitors can enjoy activities such as golfing and hiking along scenic trails. The village's proximity to national state parks and canyon gorges offers breathtaking views and opportunities for exploration. Clintonville's laid-back atmosphere and beautiful parks make it a perfect spot for relaxation and immersion in nature, ensuring a delightful experience during your vacation.
• North Middletown: Just 11 miles away from Winchester, North Middletown is a charming village that offers a unique blend of sports and cultural experiences. This family-friendly destination is home to various educational facilities and sports facilities, making it an excellent choice for those interested in community activities. Visitors can engage in local sports events or enjoy the resources of the modern college university nearby. The village's welcoming environment and cultural undertones provide an enriching experience for all ages, making it a worthwhile stop on your journey.

Things to do in and around Winchester

Winchester, Kentucky, is perfect for outdoor enthusiasts and adventure seekers, featuring beautiful recreational areas, campgrounds, and scenic hiking trails. Visitors can enjoy picnic areas for a relaxing day outdoors, as well as explore charming antique shops that showcase the area's rich history. Whether you're looking to hike, camp, or shop, Winchester offers a delightful blend of activities for a memorable vacation.

Shopping

For a great shopping experience in Winchester, visit Hamburg Pavilion, a vibrant shopping center offering entertainment and family-friendly options, located 13 miles away. If you're up for a drive, Hamburg Place is another excellent destination, 14 miles from Winchester, featuring similar city vibes and activities.

Recreation

Enjoy a round of golf at Southwind Golf Course, where you can appreciate the beautiful outdoor scenery while perfecting your swing. For a fun adventure, head to Lexington Ice Center for exciting ice skating just 15 miles away, or catch a game at Applebee's Park, located 17 miles from Winchester.

Adventure

Explore the Legacy Trail, an 18-mile hiking trail perfect for adventure seekers, offering beautiful outdoor scenery. Additionally, visit the Shillito Park Tennis Center, located 19 miles away, where you can enjoy a spirited game of tennis in a vibrant and adventurous atmosphere.

Nightlife

Experience the vibrant nightlife in Winchester by visiting the Lyric Theatre and Cultural Arts Center for a romantic show, catch a film at the Kentucky Theater, or explore the stars at Hummel Planetarium. Each venue offers unique entertainment perfect for a memorable evening out.

Booking tips and Expedia advantages for Winchester

To save money on your trip to Winchester, Kentucky, consider visiting from December to February when prices are lower. Monday is the best day to check into hotels, while Saturday tends to be the priciest. Use Expedia to compare hotel options and book packages that include flights and activities for better deals. Joining Expedia's One Key membership can unlock exclusive discounts and earn you rewards for future stays. Don't forget to explore free local attractions and utilize public transportation for affordable travel around the area.

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winchester are December to February, where the prices are slightly lower. This is in comparison to April to May and October, 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 customize your options by setting your budget, choosing your desired location, and selecting your preferred type of hotel. To find the best prices and deals, simply arrange the price filter from lowest to highest.
• Consider bundling your trip: You can save money by booking an Expedia package that combines your hotel stay in Winchester with your flights and activities.
• 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, Kentucky, is perfect for outdoor enthusiasts and adventure seekers, offering stunning scenery and a variety of parks to explore. Visitors can enjoy national and urban parks that provide opportunities for cultural experiences and family-friendly activities. With its diverse attractions, Winchester promises a memorable vacation filled with both relaxation and excitement.

• Fort Boonesborough State Park: Located 8 miles from Winchester, this historic park offers a chance to explore Kentucky's frontier history. Enjoy outdoor activities like hiking and picnicking amidst beautiful scenery, and take in the adventurous spirit of early settlers at the reconstructed fort.
• Lykins Park: Situated within Winchester, Lykins Park is a perfect family-friendly destination featuring walking trails, playgrounds, and picnic areas. It’s an excellent spot for outdoor fun and relaxation while enjoying the vibrant city atmosphere.
• Kentucky River Museum: Also 8 miles from Winchester, this museum showcases the rich cultural heritage of the Kentucky River. Discover fascinating exhibits and engage with local history, making it a must-visit for culture enthusiasts.

Best time to go to Winchester

The best time to visit Winchester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Winchester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Winchester falls in January, visitor numbers are average and weather is mostly cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	32.9°F (0.5°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
February	36.9°F (2.7°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
March	45.3°F (7.4°C)	Light Rain	Mostly Cloudy	Average	Average
April	54.7°F (12.6°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
May	64.4°F (18.0°C)	Light Rain	Mostly Sunny	Average	Slightly High
June	72.1°F (22.3°C)	Light Rain	Mostly Sunny	Average	Average
July	75.4°F (24.1°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	74.1°F (23.4°C)	Light Rain	Mostly Sunny	Average	Average
September	68.2°F (20.1°C)	Light Rain	Mostly Sunny	Slightly High	Average
October	57.0°F (13.9°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly High
November	45.1°F (7.3°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	38.8°F (3.8°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low

The nearest major airports for your trip to Winchester

If you're planning a trip to Winchester, Kentucky, the nearest major airport is Lexington, KY (LEX-Blue Grass), located 23 miles away. Excellent hotel options near the airport include the DoubleTree Suites by Hilton, situated 8 miles from LEX, offering free airport transportation and limited hours for its shuttle service. The Campbell House Lexington, a mere 4 miles from LEX, provides easy access to the airport. Another great option is the Marriott Lexington Griffin Gate Golf Resort & Spa, located 7 miles from LEX. These accommodations ensure a comfortable stay with convenient access to airport transportation for your journey to Winchester.