Winchester Hotels from S$74

Top reasons to visit Winchester

• Outdoor Adventures: Winchester offers a variety of hiking trails, campgrounds, and parks for nature enthusiasts to explore.
• Cultural Attractions: Visit the Winchester City Museum, the stunning Winchester Cathedral, and the Theatre Royal for a taste of local culture.
• Vibrant Events: Enjoy lively events like the Winchester Christmas Market, showcasing the city's festive spirit.
• Charming Downtown: Stroll through the city centre, filled with quaint shops and delightful dining options.
• Diverse Accommodation: Find a range of lodging options, from hotels to agritourism, catering to all travellers.

Find great hotels near Winchester

Winchester, Kentucky, offers a diverse selection of accommodation options to cater to every traveller's needs. From business-focused hotels to charming agritourism properties, you can find the perfect place to unwind. Many establishments are pet-friendly and LGBTQIA welcoming, ensuring a comfortable stay for all. Whether you're seeking the best Winchester hotels or a convenient Travelodge, this quaint town has something for everyone.

• WoodSpring Suites Lexington: This hotel offers a practical and welcoming atmosphere, ideal for business-oriented travellers seeking a pet-friendly stay. Located 24.1km from Winchester, WoodSpring Suites Lexington provides essential amenities tailored for professionals, including a designated Business District. Guests appreciate the flexibility of having pets onsite, with specific policies permitting dogs, ensuring a comfortable experience for furry companions. Its focus on functionality, combined with friendly service, makes it a suitable choice for those on work assignments or extended visits.
• GuestHouse Lexington: Perfectly situated 22.5km from Winchester, GuestHouse Lexington caters to families and business travellers alike. The hotel features a family-friendly environment with thoughtful amenities, such as window guards for children and a first aid kit, ensuring a safe stay for guests with young ones. Its business facilities include a dedicated Business Centre, making it a convenient option for those attending meetings or conferences. The inviting atmosphere and comprehensive services create a home-away-from-home experience, appealing to both leisure and work-related visitors.
• Hyatt Place Lexington: A distinctive 3-star hotel located 20.9km from Winchester, Hyatt Place Lexington combines the best of family, business, and pet-friendly accommodations. With multiple meeting rooms and a 24-hour accessible Business Centre, it is well-equipped for business professionals. Families will appreciate the complimentary cribs and the hotel’s pet policy, which allows dogs, ensuring a worry-free stay for guests travelling with pets. The spacious rooms and modern amenities create a comfortable and enjoyable environment for both work and leisure, making it an excellent choice for diverse travellers.

Where to stay in Winchester

Winchester, Kentucky, offers a delightful blend of outdoor adventures and scenic beauty for travellers. Explore the friendly city centre, where charming shops invite leisurely strolls. Nearby, the surrounding regions provide ample opportunities for excursions and family-friendly activities, ensuring a memorable stay. Whether you're seeking an adventurous outing or a peaceful retreat, Winchester's inviting atmosphere and vibrant community will make your vacation truly special.

• Lexington: As a vibrant metropolis, Lexington is the heart of the Bluegrass region, situated conveniently near Winchester. This dynamic city offers a year-round appeal, with peak visitor numbers during the summer months of June to July and the beautiful autumn in October. Lexington is famed for its outdoor adventures and family-friendly experiences. Visitors can explore recreational areas, campgrounds, and scenic hiking trails. Notable landmarks include the expansive parks, the stunning national state park, and local stadiums, making it an ideal destination for both relaxation and adventure.
• Clintonville: Located a mere 12.9km from Winchester, Clintonville is a quaint village that encapsulates the charm of rural Kentucky. Like its neighbours, it attracts visitors year-round, particularly in the warmer months and autumn. Outdoor enthusiasts flock to Clintonville for its picturesque scenery and various activities, including golf, hiking trails, and campgrounds. The village is surrounded by natural beauty, with local landmarks such as serene parks, a national state park, and the impressive canyon gorge, making it a perfect spot for nature lovers and those seeking tranquillity.
• North Middletown: Just 17.7km away from Winchester, North Middletown is a delightful village known for its strong sense of community and cultural experiences. It welcomes visitors throughout the year, with peak travel during the summer and autumn months. North Middletown is ideal for sports enthusiasts and families alike, offering activities such as golf and educational experiences at local facilities. Highlights in the area include a sports facility stadium, a well-stocked library, and a modern college university, ensuring that visitors can enjoy both leisure and learning in a charming setting.

Things to do in and around Winchester

Winchester, Kentucky, is an ideal destination for outdoor enthusiasts, offering a range of activities such as hiking trails, campgrounds, and recreational areas. Visitors can explore the Winchester City Museum, savour local cuisine at various restaurants, and stroll through downtown Winchester. Additionally, the city hosts vibrant events, including the charming Winchester Christmas Market, making it a delightful spot for both adventure and cultural experiences.

Shopping

In Winchester, you can enjoy shopping at local boutiques and shops. If you're up for a drive, Hamburg Place, located 22.5km away, offers a vibrant shopping experience with entertainment and dining. Richmond Peddler's Mall, 30.6km away, features a variety of unique finds in a family-friendly atmosphere.

Recreation

Southwind Golf Course offers a tranquil setting for golf enthusiasts, surrounded by lush greenery and scenic views. For a blend of fun and fitness, visit Lexington Ice Center, where you can enjoy ice skating and exhilarating activities, perfect for all skill levels. Old Silo Golf Course provides a picturesque backdrop for a leisurely round of golf.

Adventure

The Legacy Trail, located 29.0km from Winchester, offers an invigorating hiking experience amidst stunning scenery, perfect for nature enthusiasts. Alternatively, visit the Shillito Park Tennis Center, situated 30.6km away, where you can engage in thrilling tennis matches while enjoying the vibrant outdoor atmosphere.

Nightlife

Experience the enchanting nightlife in Winchester, starting with the Hummel Planetarium for a cosmic show. For a romantic film night, visit the Regal Hamburg Pavilion. Lastly, immerse yourself in the cultural vibes at the Lyric Theatre and Cultural Arts Center, perfect for family outings and entertainment.

Booking tips and Expedia advantages for Winchester

To save money during your visit to Winchester, consider travelling between December and February for lower accommodation rates. Mondays are generally the most affordable days to stay, while Saturdays tend to be pricier. Use Expedia’s search tool to filter options by budget and location, and arrange results from lowest to highest price. Additionally, combining your hotel, flights, and activities into an Expedia package can yield substantial savings. Utilise public transport for cost-effective travel, and explore free local attractions to make the most of your trip without overspending.

• 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: Utilise Expedia’s search tool to refine your preferences, such as budget, preferred location, and the type of accommodation you desire. To discover the most affordable prices and offers, arrange the price filter from lowest to highest.
• Consider bundling your trip: You can enjoy significant savings by combining your hotel accommodation in Winchester with your flights and activities through an Expedia package.

Find the best attractions in and around Winchester

Winchester, Kentucky, is perfect for outdoor enthusiasts seeking adventure and beautiful scenery. The area boasts a variety of attractions, including national and urban parks, ideal for culture-seekers and families alike. Notable sites to explore include the stunning Winchester Cathedral, the historic Winchester Guildhall, and the Theatre Royal Winchester, offering a blend of culture and entertainment to enrich your visit.

• Fort Boonesborough State Park: Experience the thrill of adventure in this historic park, which offers scenic views and outdoor activities. Explore the reconstructed fort and immerse yourself in the rich history of early American settlers while enjoying hiking trails and picnicking areas amidst nature.
• Lykins Park: A perfect urban retreat, Lykins Park is ideal for families seeking outdoor fun. With playgrounds, walking paths, and open spaces, it provides a welcoming atmosphere for relaxation and leisure right in the heart of Winchester.
• Kentucky River Museum: Discover the cultural heritage of the region at this engaging museum. Exhibits recount the significance of the Kentucky River, showcasing local history, art, and the river's impact on the community.

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 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

To reach Winchester, Kentucky, the nearest major airport is Lexington, KY (LEX-Blue Grass), situated 37.0km away. This airport serves various airlines, making it a convenient entry point for visitors. Nearby accommodation options include the 4-star Marriott Lexington Griffin Gate Golf Resort & Spa, along with the 4-star Montgomery Inn BnB, both located 11.3km from the airport. The 3.5-star Embassy Suites by Hilton Lexington/UK Coldstream is also a great choice, offering comfort and accessibility. Transportation services from these hotels to the airport are readily available, ensuring a smooth journey for travellers.