Winchester Hotels from ₹5,969

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Our top choices for Winchester hotels

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
3.0 star property
Jacksonville
9.4 out of 10, Exceptional, (629 reviews)
  • cleanliness
    Contemporary Jacksonville hotel with an indoor pool and welcoming staff.
"Great stay!"
United States
Alexis
The price is ₹7,134
₹7,917 total
includes taxes & fees
9 Feb - 10 Feb
Sleep Inn & Suites South Jacksonville

William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (348 reviews)
  • cleanliness
    Charming historic retreat near Pittsfield attractions with free parking.
"Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance "
United States
Druann
The price is ₹7,632
₹8,394 total
includes taxes & fees
24 Feb - 25 Feb
William Watson Hotel

Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (503 reviews)
  • cleanliness
    Peaceful Jacksonville stay with an indoor pool perfect for relaxation.
"Clean room. Great friendly staff. "
United States
Lawrence
The price is ₹7,465
₹8,509 total
includes taxes & fees
31 Jan - 1 Feb
Hampton Inn Jacksonville

Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (443 reviews)
  • cleanliness
    Wake up to countryside comfort at this Jacksonville hotel offering an indoor pool.
"Staff was very friendly and room was clean and comfortable."
United States
Jim
The price is ₹5,711
₹6,338 total
includes taxes & fees
31 Jan - 1 Feb
Quality Inn Jacksonville near I-72

Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very good, (753 reviews)
"It was a great location and front desk staff was very friendly"
United States
Charise
The price is ₹6,871
₹7,831 total
includes taxes & fees
3 Feb - 4 Feb
Best Western Jacksonville Inn

Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (58 reviews)
  • cleanliness
    Experience charming Monroe Street Suites in Pittsfield with free WiFi and parking.
"We had a great stay and would recommend others to stay here!"
United States
Brady
The price is ₹8,989
₹9,886 total
includes taxes & fees
25 Jan - 26 Jan
Monroe Street Suites

Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG
2.5 star property
Jacksonville
7.8 out of 10, Good, (447 reviews)
  • cleanliness
    Enjoy peaceful stays near Jacksonville attractions with quiet comfort and free amenities.
"Clean room and great breakfast."
United States
Maureen
The price is ₹7,265
₹8,062 total
includes taxes & fees
22 Feb - 23 Feb
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (142 reviews)
  • cleanliness
    Stay in Pittsfield with free breakfast, WiFi, and parking at this convenient hotel.
"Great stay"
United States
Jeramy
The price is ₹9,813
₹10,791 total
includes taxes & fees
24 Feb - 25 Feb
Green Acres Hotel

Villa DeWolf

Villa DeWolf
4.0 star property
Jacksonville
10.0 out of 10, Exceptional, (11 reviews)
  • cleanliness
    Enjoy cosy charm at this Jacksonville B&B with free gourmet morning meals.
"If you want the kindest hospitality, delicious breakfast and a memorable experience at a gorgeous historical home instead of a generic hotel, you must stay here!"
Canada
Catherine
Villa DeWolf

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very good, (620 reviews)
  • cleanliness
    Enjoy tranquil accommodation just minutes from Jacksonville Community Park.
"It was a fantastic stay!"
United States
Albert
The price is ₹5,237
₹5,969 total
includes taxes & fees
22 Feb - 23 Feb
Super 8 by Wyndham Jacksonville

Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (128 reviews)
  • cleanliness
    Stay at a budget-friendly hotel with free breakfast and WiFi in Pittsfield.
"No heat and had mice"
United States
George
The price is ₹5,442
₹5,986 total
includes taxes & fees
24 Feb - 25 Feb
Rodeway Inn Pittsfield

Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (165 reviews)
  • cleanliness
    Affordable Jacksonville motel offering early breakfast and convenient parking options.
"The room was very clean and comfortable we only stayed one night. I would stay here again."
United States
Shannon
The price is ₹5,956
₹6,788 total
includes taxes & fees
3 Feb - 4 Feb
Knights Inn Jacksonville East Morton Ave
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.
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Top Winchester Hotel Reviews

More cheap stays in Winchester

Find out more about Winchester

Top reasons to visit Winchester

  • Outdoor Adventures: Winchester offers a range of outdoor activities, including hiking scenic trails and enjoying the local lakes for a relaxing experience.
  • Family-Friendly Entertainment: The vibrant arena and local theatre provide various entertainment options suitable for all ages.
  • Historic Exploration: Discover historic colleges and quaint neighbourhoods like Bishop's Waltham, rich in charm and local attractions.
  • Beautiful Landscapes: The picturesque countryside surrounding Winchester is perfect for leisurely strolls and photography.
  • Diverse Accommodation: Enjoy a variety of lodgings, from pet-friendly options to business facilities, catering to all traveller needs.

Find great hotels near Winchester

Discover a charming retreat in historic Winchester, Illinois, where a variety of accommodation options cater to diverse preferences. Whether you seek pet-friendly lodging, business-themed facilities, or an LGBTQIA welcoming environment, you'll find the perfect fit. Enjoy modern amenities such as free Wi-Fi and picturesque garden views, ensuring a delightful stay for every traveller. Experience the warmth and hospitality that Winchester has to offer.

  • Best Western Jacksonville Inn: Ideally situated 19.3km from Winchester, Best Western Jacksonville Inn is a welcoming hotel that prides itself on being pet-friendly. This accommodation is perfect for travellers who wish to bring their furry companions along for the adventure. Guests appreciate the hotel's generous pet policy, which permits dogs and waives fees for service animals. A comfortable and convenient stay awaits, characterised by the hotel's warm hospitality and essential amenities, ensuring both pets and their owners enjoy a restful retreat.
  • Sleep Inn & Suites: Located 20.9km from Winchester, Sleep Inn & Suites offers a blend of comfort and functionality, making it an excellent choice for business travellers and pet owners alike. The hotel features a dedicated Business Centre, providing essential services for those on work-related trips. With a welcoming environment for pets, this hotel ensures that your furry friends are accommodated as well. Guests commend the stylishly appointed rooms and the overall commitment to guest satisfaction, making it a smart choice for both business and leisure stays.
  • Holiday Inn Express Hotel & Suites Jacksonville by IHG: This inviting hotel, also 20.9km from Winchester, stands out for its inclusive approach, welcoming LGBTQIA travellers and their pets. The Holiday Inn Express offers extensive business facilities including conference spaces and an accessible Business Centre, catering to the needs of corporate guests. With a commitment to comfort and service, this hotel provides a warm atmosphere for all visitors, making it an ideal choice for those seeking a blend of work and leisure during their stay.

Where to stay near Winchester

Winchester, Illinois, offers a delightful escape for families and outdoor enthusiasts alike. Explore the picturesque countryside, where beautiful scenery beckons at every turn. Nearby, the charming town of Bishop's Waltham boasts quaint streets and local attractions. For those seeking adventure, the region's outdoor activities are plentiful, from hiking scenic trails to enjoying family-friendly entertainment. Experience the perfect blend of relaxation and adventure in this central location that promises lasting memories.

  • Lynnville: A charming village located 11.3km from Winchester, Lynnville offers a delightful glimpse into local culture and history. With a steady flow of visitors, particularly from June to August, this quaint spot is perfect for those seeking a culture-themed experience. Explore its local museums, historic buildings, and significant sites that reflect the rich heritage of the area. Strolling through Lynnville, you can immerse yourself in the community's spirit while enjoying the serene surroundings.
  • Florence: Situated 12.9km away from Winchester, Florence is a picturesque city renowned for its stunning scenery and outdoor activities. Although visitor numbers remain consistent year-round, the peak season is during the summer months, making it an ideal time to explore its beautiful riverfront. Enjoy leisurely walks, picnics by the water, or simply bask in the natural beauty that Florence has to offer. This city promises a refreshing outdoor experience for all who visit.
  • Manchester: Located 14.5km from Winchester, Manchester is an exciting destination for outdoor enthusiasts and families alike. With a focus on adventure and recreation, visitors flock here in the summer months to enjoy campgrounds and various outdoor activities. The nearby national state park offers breathtaking landscapes, historic buildings, and charming historic sites, making it a well-rounded destination for those looking to connect with nature while also exploring local history. Manchester promises a memorable experience for all ages.

Things to do near Winchester

Winchester, Illinois, is an excellent destination for outdoor and family-oriented vacations, boasting a range of entertainment options. Visitors can explore the recreational area, enjoy the vibrant arena entertainment facility, and catch a performance at the local theatre. To truly immerse yourself in the charm of the town, make sure to discover Winchester and all it has to offer.

Shopping

In Winchester, you can explore charming local shops for unique gifts and souvenirs. If you're up for a drive, visit the nearby West Park Mall for a wider selection of stores, or head to the quaint shops at the Jacksonville Square for delightful finds.

Recreation

Future Champions Sport Complex offers an energetic atmosphere for sports enthusiasts, ideal for engaging in various athletic activities. Jacksonville Community Park provides a tranquil environment for relaxation and rejuvenation, while Old Orchard Country Club invites you to enjoy a round of golf amidst scenic outdoor beauty.

Adventure

In Winchester, explore the great outdoors at the nearby Great River Road, perfect for scenic drives and cycling. Experience thrilling canoeing on the Illinois River, or hike through local nature trails, immersing yourself in the region's natural beauty and wildlife.

Nightlife

In Winchester, the Small Eli Ferris Wheel offers a delightful amusement ride experience, located 22.5km away. It's a charming spot to enjoy the night under the stars, adding a touch of whimsy to your evening explorations.

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

Booking tips and Expedia advantages for Winchester

When planning your visit to Winchester, Illinois, consider travelling during the cheaper months of January to February and November, with Tuesdays being the most economical days to book accommodation. Utilise Expedia's search tool to find the best hotel deals by filtering for budget-friendly options and eco-certified hotels. Combining your hotel, flights, and activities into an Expedia package can also lead to significant savings. Additionally, explore free activities in the area to enjoy your trip without breaking the bank.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winchester are January to February and November, where the prices are slightly lower. This is in comparison to June to August, 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 Tuesday. The most expensive day to stay in Winchester is Friday.
  • Find cheap hotels on Expedia: Expedia's search tool enables you to specify your budget and preferred location, among other criteria. You can easily arrange the results to display prices from the lowest to the highest, ensuring you see the most affordable hotels first. Additionally, you can refine your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that are available for booking.
  • Consider bundling your trip: You can potentially save money by combining your Winchester hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Winchester

Winchester offers a delightful blend of outdoor and family-friendly activities, making it an ideal vacation spot. Visitors can enjoy the local fairground, explore historic colleges and universities, or relax by the scenic lakes. The area is perfect for those seeking a beach experience and beautiful landscapes, ensuring a memorable trip filled with enjoyment and adventure.

  • Morgan County Fairgrounds: Experience the charm of community spirit at Morgan County Fairgrounds, where outdoor events and family-friendly activities create a lively atmosphere. It's an ideal spot to immerse yourself in local culture and enjoy various fairs and festivals throughout the year.
  • Illinois College: Step back in time at Illinois College, a historic institution that boasts rich cultural heritage. Explore its beautiful campus and soak in the academic atmosphere, which reflects the deep-rooted traditions of education and community.
  • Lake Jacksonville: Discover the serene beauty of Lake Jacksonville, perfect for a romantic day out or a leisurely picnic. Its picturesque scenery and beach areas invite relaxation and outdoor activities, making it a lovely escape from the everyday hustle.

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 moderately 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.4°F (-2.0°C)Light RainMostly CloudyAverageSlightly Low
February31.3°F (-0.4°C)Light RainMostly CloudyModerately LowSlightly Low
March43.9°F (6.6°C)Light RainMostly SunnyAverageAverage
April53.8°F (12.1°C)Light RainMostly SunnyAverageAverage
May64.4°F (18.0°C)Light RainMostly SunnyAverageAverage
June73.6°F (23.1°C)Light RainMostly SunnyModerately HighSlightly High
July76.1°F (24.5°C)Light RainMostly SunnyModerately HighSlightly High
August74.7°F (23.7°C)Light RainMostly SunnyModerately LowSlightly High
September68.9°F (20.5°C)Light RainMostly SunnyModerately HighAverage
October56.5°F (13.6°C)Light RainMostly SunnyAverageAverage
November43.7°F (6.5°C)Light RainMostly SunnyModerately LowSlightly Low
December34.5°F (1.4°C)Light RainMostly SunnyAverageAverage

The nearest major airports for your trip to Winchester

To reach Winchester, Illinois, travellers can fly into several nearby airports. St. Louis Lambert International Airport (STL) is situated 99.8km away, with luxurious hotels such as The Ritz-Carlton and Ameristar Casino Resort, both around 11.3km from the airport. Springfield Abraham Lincoln Capital Airport (SPI) is 70.8km away, offering options like the DoubleTree by Hilton, just 4.8km from the airport. Quincy Regional Airport (UIN) is also 70.8km from Winchester, with nearby accommodations including the Holiday Inn Quincy East, located 12.9km away. Each hotel provides convenient transportation services to their respective airports, ensuring a smooth transition for visitors.

Frequently asked questions

Where is the best place for a stay in Winchester?
Located 12.3 mi (19.8 km) from the heart of Winchester, Best Western Jacksonville Inn is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Hampton Inn Jacksonville and Sleep Inn & Suites South Jacksonville. See all available top hotels, or vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes! The majority of hotel room reservations are fully refundable if cancelled before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you booked a non-refundable reservation, you might be able to still cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
How is it to stay in Winchester?
Those travelling to Winchester will definitely enjoy the sights to see and things to do. There are 35 hotels and other accommodation options in the surrounding area. Find out more about Winchester.
What is there to see in Winchester?
Places to visit in the wider area include Morgan County Fairgrounds, Lake Jacksonville and Future Champions Sport Complex. You'll also find Governor Duncan Mansion and Jacksonville Community Park in the area. Take a look at what more there is to see and do in Expedia's Winchester guide.
What's the weather like in Winchester?
The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 1°C. Average annual precipitation for Winchester is 1234 mm.