Winchester Hotels

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Our top choices for Winchester hotels

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
2.5 star property
Jacksonville
9.4 out of 10, Exceptional, (624)
This hotel offers free breakfast, WiFi, and parking near Prairie Land Heritage Museam. Take a refreshing swim in the indoor pool or work out at the fitness center. Business travelers appreciate the convenient amenities and friendly service.

"Courteous staff and clean rooms. Hard to beat. "
United States
Daniel
The price is P4,734
P5,254 total
includes taxes & fees
Jan 18 - Jan 19
Sleep Inn & Suites South Jacksonville

Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (501)
Experience tranquility at this quiet Jacksonville hotel with an indoor pool and fitness center. Enjoy free breakfast, WiFi, and parking near Prairie Land Heritage Museum. The helpful staff ensures a comfortable business or leisure stay.

"Great property, great staff, comfy beds"
United States
Mary Ann
The price is P4,798
P5,469 total
includes taxes & fees
Jan 15 - Jan 16
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, (439)
Located near I-72, this hotel features a refreshing indoor pool and fitness center for active travelers. Enjoy free breakfast, WiFi, and parking while exploring nearby Prairie Land Heritage Museum and Jacksonville Community Park.

"Room was clean, staff was very friendly. "
United States
Mike
The price is P3,317
P3,681 total
includes taxes & fees
Feb 7 - Feb 8
Quality Inn Jacksonville near I-72

William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (348)
William Watson Hotel welcomes guests with a fitness center and convenient snack bar. Enjoy nearby John Greene Shastid House and Pike County Historic Museum, plus 24-hour front desk service. Quincy Regional Airport is just an hour's drive away.

"Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance "
United States
Druann
The price is P5,024
P5,526 total
includes taxes & fees
Jan 11 - Jan 12
William Watson Hotel

Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (127)
Conveniently situated in Pittsfield near King Park and John Greene Shastid House, this hotel offers free WiFi, parking, and daily on-the-go breakfast. Guests enjoy comfortable rooms with easy access to local attractions.

"Our stay was pleasant and quiet, the only problem was that the heat was not sufficient to keep the room warm during extreme cold wave. Other than that it was fairly clean, and the staff was very friendly and helpful."
United States
Tod
The price is P3,671
P4,037 total
includes taxes & fees
Jan 11 - Jan 12
Rodeway Inn Pittsfield

Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very Good, (753)
"It was a great location and front desk staff was very friendly"
United States
Charise
The price is P4,432
P5,052 total
includes taxes & fees
Jan 8 - Jan 9
Best Western Jacksonville Inn

Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (57)
Cozy accommodations in Pittsfield with convenient access to John Greene Shastid House and Pike County Historic Museum. This hotel offers complimentary WiFi, free parking, and daily housekeeping for a comfortable, hassle-free stay.

"We had a great stay and would recommend others to stay here!"
United States
Brady
The price is P5,778
P6,355 total
includes taxes & fees
Jan 11 - Jan 12
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, (443)
This serene hotel offers an escape with its indoor pool and 24-hour fitness center. Enjoy complimentary breakfast, WiFi, and parking while being close to Prairie Land Heritage Museum. The peaceful atmosphere ensures a restful experience for business and leisure travelers.

"Staff was welcoming upon arrival, my bed was super comfortable, and not a lot of noise considering the hotel was full. Breakfast was a highlight although the waffle machine was broken and generic cereal was used with name brand labels. Love the Dove products. Overall good experience and I would return. "
United States
A
The price is P4,906
P5,445 total
includes taxes & fees
Jan 11 - Jan 12
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, (141)
Green Acres Hotel offers a relaxing stay near King Park and John Greene Shastid House. Enjoy the complimentary continental breakfast served daily, plus free WiFi and parking. This comfortable hotel provides the perfect base for exploring Pittsfield attractions.

"Great stay"
United States
Jeramy
The price is P6,330
P6,962 total
includes taxes & fees
Jan 11 - Jan 12
Green Acres Hotel

Villa DeWolf

Villa DeWolf
4.0 star property
Jacksonville
10.0 out of 10, Exceptional, (11)
Located near the train station, this welcoming B&B offers free cooked-to-order breakfast, WiFi, and parking. Close to Governor Duncan Mansion and Small Eli Ferris Wheel, it's a perfect base for exploring local attractions.

"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, (619)
Set in a peaceful environment, this motel offers complimentary breakfast, WiFi, and parking. Guests praise the helpful staff and quiet atmosphere. Prairie Land Heritage Museum and Jacksonville Community Park are located nearby for convenient exploration.

"It was a fantastic stay!"
United States
Albert
The price is P3,266
P3,722 total
includes taxes & fees
Jan 25 - Jan 26
Super 8 by Wyndham Jacksonville

Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (165)
Start your day with complimentary continental breakfast served from 5:30 AM at this convenient Jacksonville motel. Free parking makes exploring easy, with Small Eli Ferris Wheel and Jacksonville Community Park nearby.

"The room was very clean and comfortable we only stayed one night. I would stay here again."
United States
Shannon
The price is P3,842
P4,379 total
includes taxes & fees
Jan 8 - Jan 9
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews

More cheap stays in Winchester

Find out more about Winchester

Top reasons to visit Winchester

  • Outdoor Adventures: Winchester is perfect for families and outdoor enthusiasts, offering scenic parks and recreational activities.
  • Cultural Experiences: Enjoy local theatre productions and explore historic colleges and universities in the area.
  • Family-Friendly Activities: The town features attractions suitable for all ages, ensuring a fun-filled visit.
  • Charming Accommodations: Winchester provides a range of lodging options, including pet-friendly and LGBTQIA-friendly places.
  • Scenic Getaway: This quaint town serves as a gateway to picturesque landscapes, ideal for weekend retreats.

Find great hotels near Winchester

Discover the charming lodging options in Winchester, Illinois, where a variety of hotels cater to diverse traveller needs. Whether you're seeking pet-friendly accommodations, a welcoming atmosphere for LGBTQIA guests, or facilities designed for business travel, Winchester offers a delightful array of choices. With competitive room rates and comfortable holiday rentals, you’ll find the perfect base for exploring this quaint town and its surroundings.

  • Best Western Jacksonville Inn: The Best Western Jacksonville Inn is a welcoming retreat for pet lovers and those seeking a comfortable stay. Located a mere 19.3km from Winchester, this hotel offers a home-like atmosphere with amenities tailored for both leisure and business travellers. The property is particularly noted for its pet-friendly policy, permitting dogs and service animals with waived fees, making it an ideal choice for those who wish to travel with their furry companions. Guests appreciate the blend of cosy accommodations and convenient facilities, ensuring a pleasant and hassle-free experience.
  • Holiday Inn Express Hotel & Suites Jacksonville by IHG: The Holiday Inn Express Hotel & Suites Jacksonville by IHG is a modern haven that caters to both business and leisure travellers, situated 20.9km from Winchester. This hotel stands out for its commitment to inclusivity, welcoming LGBTQIA travellers and offering a range of amenities for a comfortable stay. With a pet-friendly policy that allows pets on-site and service animals with waived fees, it ensures every guest feels at home. The hotel’s contemporary design, business-friendly facilities, and inviting atmosphere make it a perfect choice for those looking to blend work and leisure.
  • Sleep Inn & Suites: Sleep Inn & Suites is a stylish and practical option for travellers seeking a comfortable stay 20.9km from Winchester. Known for its modern décor and functional amenities, this hotel is particularly favoured by business travellers and pet owners alike. With a pet-friendly policy that allows pets with certain restrictions and waived fees for service animals, it caters to a diverse range of guests. The hotel’s focus on providing a restful environment, combined with its convenient location, makes it an excellent choice for those visiting the area.

Where to stay near Winchester

Winchester, Illinois, offers a delightful blend of outdoor adventure and family-friendly activities. Nestled conveniently for weekend getaways, this charming small town is a gateway to scenic landscapes and cultural experiences. Explore the picturesque parks, engage in outdoor pursuits, or simply soak in the local charm. Nearby, you'll find inviting Louisville vacation rentals, making it a perfect base for your explorations. Embrace the tranquillity and adventure that Winchester and its surroundings have to offer.

  • Exeter: Nestled 11.3km from Winchester, Exeter is a charming village that offers a peaceful retreat for those seeking wellness and relaxation. The area enjoys a steady flow of visitors year-round, with peak arrivals during the summer months of June to August. Exeter boasts a recreational area, perfect for outdoor activities and unwinding amidst nature. Whether you fancy a leisurely stroll or a more vigorous workout, Exeter’s tranquil environment provides the ideal backdrop for a rejuvenating experience.
  • Lynnville: Also located 11.3km from Winchester, Lynnville is a delightful village that caters to families and outdoor enthusiasts alike. With visitor numbers peaking from June to August, this area is perfect for those looking for a vibrant mix of outdoor activities and urban experiences. Lynnville is home to an array of attractions, including educational venues, a shopping mall centre, and a theatre. Families can enjoy the local urban park, historic sites, and a serene lake, making it an ideal spot for a fun-filled day out.
  • Florence: Situated 12.9km from Winchester, Florence is a city rich in culture and history. Visitors flock here for a city-themed experience, particularly during the bustling summer months. Florence offers a range of local landmarks, including historic places and charming neighbourhoods that showcase the city’s heritage. Take a leisurely walk through its streets, discover hidden gems, and immerse yourself in the vibrant culture that Florence has to offer.

Things to do near Winchester

Winchester, Illinois, is ideal for outdoor family adventures and cultural experiences. Visitors can enjoy arena entertainment, local theatre productions, and recreational areas that cater to all ages. With its charming city attractions and picturesque outdoor settings, Winchester promises a delightful getaway filled with engaging activities and memorable moments.

Shopping

In Winchester, you can enjoy local shops and boutiques for unique gifts and souvenirs. If you're up for a drive, visit the Quincy Mall about 48.3km away, offering a wide selection of shops, restaurants, and entertainment options for a more extensive shopping experience.

Recreation

At Future Champions Sport Complex, immerse yourself in invigorating sports activities, perfect for the active traveller. For a more tranquil experience, Jacksonville Community Park offers serene walking paths and relaxation spots amidst nature. Don’t miss a round of golf at Old Orchard Country Club for a refreshing outdoor escape.

Adventure

In Winchester, explore the scenic beauty of the nearby Jim Edgar Panther Creek State Fish and Wildlife Area, perfect for hiking and wildlife watching. Experience the thrill of canoeing on the local rivers, where you can enjoy the serene surroundings while paddling through nature's wonders.

Nightlife

A vibrant evening in Winchester can start with a thrilling ride on the Small Eli Ferris Wheel, located a mere 22.5km away. After the excitement, explore local pubs and eateries for a relaxed atmosphere, enjoying the friendly charm and warm hospitality of the town.

*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 visit to Winchester, plan your trip during the off-peak months of January to February or November, when accommodation prices are lower. Opt for a Tuesday stay, as it tends to be the least expensive day. Use Expedia’s search tool to find budget-friendly hotels, filtering for eco-certified options for sustainable stays. Consider booking a package that combines your hotel, flights, and activities for additional savings. Lastly, explore the town on foot to minimise transport costs and enjoy free local attractions.

  • 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, chosen location, and additional preferences. You can arrange your search results to display prices from lowest to highest, ensuring you see the most affordable hotels first. Furthermore, you can refine your options by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels available for booking.
  • Consider bundling your trip: You can save money by combining your Winchester hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Winchester

Winchester is an ideal destination for outdoor enthusiasts, families, and culture lovers alike. Visitors can explore historic colleges and universities, enjoy activities at local fairgrounds, and relax by the picturesque lake. The attractions in and around Winchester provide a delightful blend of outdoor experiences, cultural insights, and family-friendly fun, making it a perfect getaway for travellers seeking a memorable adventure.

  • Illinois College: A historic institution steeped in culture, Illinois College offers a glimpse into the academic heritage of the area. Wander through its picturesque campus, admire the architecture, and perhaps catch a lively campus event that reflects its vibrant community spirit.
  • Morgan County Fairgrounds: This lively fairground is perfect for families seeking outdoor fun. Enjoy various events, from agricultural fairs to concerts, all while soaking in the friendly atmosphere and community engagement that characterises this local hub.
  • Lake Jacksonville: A serene lake setting ideal for romance and relaxation. Revel in the stunning scenery, take leisurely walks along the beach, or enjoy a picnic as you immerse yourself in the natural beauty surrounding you.

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

Accessing Winchester, Illinois, is convenient via several major airports. St. Louis Lambert International Airport (STL) is situated 99.8km away, with notable nearby hotels including The Ritz-Carlton and Ameristar Casino Resort and Spa, both within 11.3km. Springfield Abraham Lincoln Capital Airport (SPI) is 70.8km distant, offering options like Wyndham Springfield City Centre, just 4.8km away. Quincy Regional Airport (UIN) is also 70.8km from Winchester, with the Holiday Inn Quincy East located 12.9km from the airport. Transportation services are available from these hotels to their respective airports, ensuring a smooth journey for visitors.

Frequently asked questions

What's 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 traveler data. Other good options for your trip to the area are Sleep Inn & Suites South Jacksonville and Hampton Inn 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 reservations are fully refundable as long as you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might be able to still cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
What's it like to stay in Winchester?
Those traveling to Winchester are sure to enjoy the sights to see and things to do. There are 35 hotels and other accommodations 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 Jacksonville Community Park and Governor Duncan Mansion in the area. Check out what more to see and do in Expedia's Winchester guide.
What's the seasonal weather like in Winchester?
The hottest months are usually July and August with an average temp of 73°F, while the coldest months are January and February with an average of 35°F. Average annual precipitation for Winchester is 49 inches.

Explore a world of travel with Expedia