Find hotels in Winchester, IN from NT$1,485

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

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Winchester hotels

Randolph Inn and Suites

Randolph Inn and Suites
2.5 star property
Winchester
9.0 out of 10, Wonderful, (243)
"Nice hotel"
United States
William
Randolph Inn and Suites

Holiday Inn Express & Suites Portland by IHG

Holiday Inn Express & Suites Portland by IHG
2.5 star property
Portland
9.2 out of 10, Wonderful, (354)
"Excellent stay every time we are there friendly staff all around awesome stay"
United States
Rebecca
The price is NT$3,026
NT$3,389 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Express & Suites Portland by IHG

Richmond Inn & Suites

Richmond Inn & Suites
2.0 star property
Richmond
7.0 out of 10, Good, (360)
"Good staff good stay"
United States
Terrance
The price is NT$1,123
NT$1,726 total
includes taxes & fees
Dec 16 - Dec 17
Richmond Inn & Suites

The Golden Inn

The Golden Inn
2.5 star property
New Paris
9.2 out of 10, Wonderful, (432)
"Wonderful place to stay, clean rooms and quiet, very comfortable, would stay here again so nice."
United States
Renee
The price is NT$2,464
NT$2,791 total
includes taxes & fees
Dec 16 - Dec 17
The Golden Inn

Travelodge by Wyndham Richmond IN

Travelodge by Wyndham Richmond IN
2.0 star property
Richmond
7.0 out of 10, Good, (440)
"Nice place and staff. "
United States
Russell
The price is NT$1,571
NT$1,759 total
includes taxes & fees
Dec 21 - Dec 22
Travelodge by Wyndham Richmond IN

Cozy Garden Inn By OYO Hwy 40 Richmond

Cozy Garden Inn By OYO Hwy 40 Richmond
2.5 star property
Richmond
6.8 out of 10, (66)
"The location was great and next to Culver's."
United States
Verne
The price is NT$1,583
NT$1,867 total
includes taxes & fees
Dec 28 - Dec 29
Cozy Garden Inn By OYO Hwy 40 Richmond

Hoosier Inn

Hoosier Inn
2.5 star property
Portland
8.8 out of 10, Excellent, (134)
"Had a pleasant stay. Room was very clean and staff was very friendly. "
United States
ned
The price is NT$2,527
NT$2,830 total
includes taxes & fees
Dec 18 - Dec 19
Hoosier Inn

Motel 6 Portland, IN

Motel 6 Portland, IN
2.0 star property
Portland
6.8 out of 10, (78)
"clean"
United States
Shane
The price is NT$2,339
NT$2,620 total
includes taxes & fees
Dec 16 - Dec 17
Motel 6 Portland, IN

Red Roof Inn Richmond, IN

Red Roof Inn Richmond, IN
2.0 star property
Richmond
7.0 out of 10, Good, (912)
"Room was clean, staff friendly "
United States
Rolin
The price is NT$1,460
NT$1,635 total
includes taxes & fees
Dec 21 - Dec 22
Red Roof Inn Richmond, IN

Fairfield Inn by Marriott Richmond

Fairfield Inn by Marriott Richmond
2.5 star property
New Paris
9.0 out of 10, Wonderful, (517)
"The room was clean, the staff was polite and friendly. "
United States
Leslie
The price is NT$3,151
NT$3,568 total
includes taxes & fees
Dec 19 - Dec 20
Fairfield Inn by Marriott Richmond

Super 8 by Wyndham Centerville-Richmond

Super 8 by Wyndham Centerville-Richmond
2.0 star property
Centerville
6.0 out of 10, (332)
"Nice managed motel. Will definitely be staying here again. "
United States
Kenny
The price is NT$1,493
NT$1,672 total
includes taxes & fees
Dec 21 - Dec 22
Super 8 by Wyndham Centerville-Richmond

Home2 Suites by Hilton Richmond

Home2 Suites by Hilton Richmond
3.0 star property
Richmond
9.2 out of 10, Wonderful, (402)
"Very spacious room, great amenities, and delicious breakfast every morning!"
United States
Kiana
The price is NT$3,119
NT$3,494 total
includes taxes & fees
Jan 4 - 2026/1/5
Home2 Suites by Hilton Richmond

Quality Inn and Conference Center

Quality Inn and Conference Center
2.5 star property
Richmond
6.6 out of 10, (1000)
"nice place to stay"
United States
Onda
The price is NT$1,326
NT$1,485 total
includes taxes & fees
Dec 21 - Dec 22
Quality Inn and Conference Center

Holiday Inn Express Richmond by IHG

Holiday Inn Express Richmond by IHG
3.0 star property
Richmond
8.4 out of 10, Very Good, (774)
"It was great."
United States
Chris
The price is NT$3,026
NT$3,389 total
includes taxes & fees
Jan 4 - 2026/1/5
Holiday Inn Express Richmond by IHG

Home2 Suites By Hilton Muncie

Home2 Suites By Hilton Muncie
3.0 star property
Muncie
9.6 out of 10, Exceptional, (15)
"Staff was amazing. Everything was new and clean. "
United States
Nicole
The price is NT$3,344
NT$3,745 total
includes taxes & fees
Jan 4 - 2026/1/5
Home2 Suites By Hilton Muncie

Hampton Inn & Suites Richmond, IN

Hampton Inn & Suites Richmond, IN
2.5 star property
Richmond
9.2 out of 10, Wonderful, (941)
"The breakfast service was excellent tasty and well presented "
United States
Terence
The price is NT$2,970
NT$3,326 total
includes taxes & fees
Jan 4 - 2026/1/5
Hampton Inn & Suites Richmond, IN

Days Inn by Wyndham Muncie -Ball State University

Days Inn by Wyndham Muncie -Ball State University
2.0 star property
Muncie
6.8 out of 10, (888)
"Room was clean and staff was courteous!"
United States
Thomas
The price is NT$2,028
NT$2,271 total
includes taxes & fees
Dec 17 - Dec 18
Days Inn by Wyndham Muncie -Ball State University

Motel 6 Richmond, IN

Motel 6 Richmond, IN
2.0 star property
Richmond
7.8 out of 10, Good, (1000)
"Yes the room was clean the staff was helpful and courteous and informative about the festivities that were going on in town"
United States
James
The price is NT$1,503
NT$1,684 total
includes taxes & fees
Dec 28 - Dec 29
Motel 6 Richmond, IN

Baymont by Wyndham Muncie Near Ball State University

Baymont by Wyndham Muncie Near Ball State University
2.5 star property
Muncie
5.6 out of 10, (1006)
"It was a nice stay the staff were really nice and welcoming"
United States
Amie
The price is NT$2,215
NT$2,481 total
includes taxes & fees
Dec 16 - Dec 17
Baymont by Wyndham Muncie Near Ball State University

Fairfield Inn by Marriott Muncie

Fairfield Inn by Marriott Muncie
2.5 star property
Muncie
8.2 out of 10, Very Good, (751)
"Staff was really nice. Breakfast was great. Even supplied complementary ice scraper and gloves during a winter storm. That was nice because we forgot ours at home. Heater was a little noisy in the room. Good price "
United States
Steven
The price is NT$3,201
NT$3,585 total
includes taxes & fees
Dec 19 - Dec 20
Fairfield Inn by Marriott Muncie
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

Stay near popular Winchester attractions

Top Winchester Hotel Reviews

More cheap stays in Winchester

Hotels in Winchester with star-rating

Find out more about Winchester

Top reasons to visit Winchester

  • Outdoor Adventures: Winchester offers thrilling activities like motor racing and hiking through nature preserves, perfect for adventure seekers.
  • Charming Downtown: Explore the friendly downtown area with unique shops and local eateries, all within walking distance.
  • Live Music Scene: Enjoy vibrant live music at local venues, adding a lively atmosphere to your visit.
  • Wine Country Excursions: Venture into the nearby wine country to savor local wines and flavors.
  • Family-Friendly Attractions: Visit fairgrounds and parks, making it an ideal destination for families.

Find great hotels near Winchester

Winchester, Indiana offers a variety of lodging options, including hotels and motels, catering to diverse traveler needs. Whether you're seeking a pet-friendly stay, a welcoming environment for LGBTQIA guests, or accommodations suited for business travel, you'll find quality choices here. Explore the best hotels, read reviews, and compare room rates to ensure a comfortable and enjoyable vacation experience in this charming town.

  • Surestay By Best Western Greenville: Surestay By Best Western Greenville is a welcoming and inclusive hotel, located 32.2km from Winchester, perfect for families and business travelers alike. This hotel proudly supports LGBTQIA travelers and is affiliated with LGBTQI travel guides. The property features family-friendly amenities, including cribs available for a fee, ensuring a comfortable stay for guests of all ages. With its modern facilities and commitment to diversity, this hotel offers a warm atmosphere where everyone feels at home.
  • Holiday Inn Express & Suites Portland by IHG: Situated 29.0km from Winchester, the Holiday Inn Express & Suites Portland by IHG is an ideal choice for business travelers and those seeking a welcoming environment. This hotel is also affiliated with LGBTQI travel guides, showcasing its commitment to inclusivity. Guests can enjoy comfortable accommodations paired with modern amenities, including a business center and complimentary breakfast. Its convenient location and focus on guest satisfaction make it an excellent base for exploring the area.
  • Holiday Inn Express Hotel & Suites Greenville by IHG: Located 32.2km from Winchester, the Holiday Inn Express Hotel & Suites Greenville by IHG offers a blend of comfort and convenience for both business and leisure travelers. This hotel is committed to LGBTQIA inclusivity, ensuring all guests feel welcome. With a range of modern amenities including a fitness center and complimentary breakfast, it provides a great environment for relaxation and productivity. The friendly staff is dedicated to making your stay enjoyable and memorable.

Where to stay near Winchester

Winchester, Indiana, offers an exciting blend of adventure and history, perfect for outdoor enthusiasts and culture seekers alike. Explore the charming downtown area, where friendly locals and unique shops await within walking distance. Venture into the surrounding wine country, dotted with numerous wineries that invite you to savor local flavors. Whether you're seeking thrilling sports or a leisurely stroll through historic streets, Winchester promises an unforgettable vacation experience.

  • Saratoga: Nestled just 9.7km from Winchester, Saratoga is a charming city that draws visitors year-round, with a peak in travel during the summer months. Known for its family-friendly atmosphere and outdoor adventures, Saratoga offers a delightful experience for all ages. Thrill-seekers can enjoy a nearby amusement park, while those seeking relaxation can explore the local theme park's attractions. The city's proximity to nature provides ample opportunities for hiking and picnicking, making it a perfect spot for a family getaway.
  • Farmland: Located 12.9km from Winchester, Farmland is a vibrant city with seasonal appeal. Visitors flock here in January, June, August, and October, eager to engage in outdoor activities, family bonding, and exciting adventures. The city boasts a variety of recreational areas, golf courses, and educational venues that cater to diverse interests. Nature lovers will appreciate the nearby lake, urban park, and national state park, which offer stunning landscapes and recreational opportunities, ensuring a memorable visit for all.
  • Ridgeville: Also situated 12.9km from Winchester, Ridgeville is a lively city that welcomes travelers throughout the year, particularly during the summer months. Known for its outdoor activities and family-friendly environment, Ridgeville is an excellent destination for those seeking adventure and leisure. Visitors can explore recreational areas, indulge in shopping at local malls, or unwind at picturesque parks and lakes. With close proximity to national state parks, Ridgeville offers a perfect blend of nature and urban convenience for an enjoyable vacation experience.

Things to do in and around Winchester

Winchester, Indiana, is perfect for sports and outdoor adventures, offering exciting activities like motor racing and various recreational areas. Visitors can enjoy live music at local venues, play a round of golf, and relax in outdoor seating while taking in the beautiful scenery. Don't miss the stunning waterfalls that enhance the area's natural charm, making Winchester an ideal destination for an adventurous getaway.

Shopping

In Winchester, you can visit the Southway Centre Shopping Center for a variety of city and family-friendly shops. If you're up for a drive, check out Warm Glow Candle Company and Richmond Mall for unique gifts and a wider selection of stores.

Recreation

Winchester Golf Club offers a tranquil golfing experience amidst lush greens, perfect for sports enthusiasts. For relaxation, visit Prairie Creek Reservoir and Campground, where you can unwind by the water. Cardinal Hills Golf Course, surrounded by nature, provides an inviting atmosphere for outdoor activities and friendly competition.

Adventure

Experience the thrill of motor racing at Winchester Speedway, where adrenaline runs high in an exciting sports atmosphere. For more high-speed action, visit Eldora Speedway, located 33.8km away, or enjoy a friendly match at Cardinal Creek Tennis Center, situated 37.0km from Winchester.

Nightlife

Experience the charm of Muncie Civic Theatre, just 33.8km away, offering a delightful mix of romance and culture. Alternatively, head to Richmond Civic Theatre, 38.6km from Winchester, for captivating performances that enhance your evening with entertainment and artistic flair.

*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 during your trip to Winchester, plan your visit from November to January when hotel prices are lower, especially on Mondays, which are the cheapest days to stay. Avoid Saturdays for better rates. Use Expedia’s search tool to find budget-friendly accommodations and sort by price or hotel type, such as Eco-certified options. Consider bundling your hotel, flights, and activities for additional savings. Lastly, take advantage of free local activities to enhance your experience 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 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: Expedia’s search tool makes it easy to customize your travel experience by letting you choose your budget, preferred location, and additional preferences. You can sort the results to display hotels from the least expensive to the most expensive, ensuring you find the best deals first. Additionally, you can narrow your choices by hotel type; for instance, selecting the Eco-certified filter will highlight sustainable and environmentally-friendly hotels that you can book.
  • Consider bundling your trip: You can save money by bundling your hotel reservations in Winchester with your flights and activities by choosing an Expedia package.

Find the best attractions in and around Winchester

Winchester, Indiana, offers a perfect blend of sports and outdoor adventure for vacationers. Visitors can explore local attractions such as fairgrounds, nature preserves, and urban parks, making it ideal for families seeking cultural and outdoor experiences. Whether you're enjoying a day at the fairground or hiking through the picturesque reserve, Winchester promises a memorable getaway filled with fun and exploration.

  • Levi Coffin House: Located 24.1km from Winchester, this historic house offers a glimpse into the life of Levi Coffin, known as the President of the Underground Railroad. Experience the rich cultural history and learn about the significant role this house played in the fight for freedom.
  • Randolph County Courthouse: Situated in the heart of Winchester, this stunning building is a prime example of 19th-century architecture. Explore its beautiful interiors and appreciate the cultural significance it holds within the community.
  • Historic Shopping & Dining District of Winchester, Indiana: Immerse yourself in the vibrant city vibes of this charming district, featuring unique shops and delightful dining options that reflect the local culture and hospitality.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.8°F (-2.9°C)Light RainMostly CloudySlightly LowSlightly Low
February29.7°F (-1.3°C)Light RainMostly CloudyAverageAverage
March40.5°F (4.7°C)Light RainMostly CloudyAverageAverage
April50.7°F (10.4°C)Light RainMostly SunnyAverageAverage
May61.9°F (16.6°C)Light RainMostly SunnyAverageSlightly High
June69.8°F (21.0°C)Light RainMostly SunnyAverageAverage
July72.9°F (22.7°C)Light RainMostly SunnySlightly HighSlightly High
August71.1°F (21.7°C)Light RainMostly SunnySlightly HighAverage
September65.5°F (18.6°C)Light RainMostly SunnySlightly HighSlightly High
October54.1°F (12.3°C)Light RainMostly SunnyAverageAverage
November41.7°F (5.4°C)Light RainMostly SunnySlightly LowSlightly Low
December33.4°F (0.8°C)Light RainMostly CloudySlightly LowSlightly Low

The nearest major airports for your trip to Winchester

When visiting Winchester, Indiana, you have several airport options for your arrival. Dayton International Airport (DAY) is located 70.8km away and offers nearby hotels like the Wingate by Wyndham Dayton North and DoubleTree by Hilton Dayton Fairborn, both about 4 to 19.3km from the airport. Fort Wayne International Airport (FWA) is 91.7km away, with hotel choices such as The Bradley Hotel and Hilton Fort Wayne at the Grand Wayne Convention Center, both 11.3km from the airport. Muncie Delaware County Airport (MIE) is the closest at 35.4km, with options like Courtyard Muncie at Horizon Convention Center just 4.8km away.

Frequently asked questions

What's the best place for a stay in Winchester?
Based on our traveler data, Randolph Inn and Suites is one of the top choices for your stay. This hotel offers free breakfast and an indoor pool. Two other choices for your visit to the area are Baymont by Wyndham Richmond I-70 and Comfort Suites Richmond East. 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! You'll find that most hotel room reservations are fully refundable provided that you cancel before the hotel's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
Where can I learn more about changing or cancelling my trip to Winchester?
For more information about rescheduling or cancelling your trip to Winchester, go to https://www.expedia.com/service/.
What's the best hotel to stay near Winchester Speedway?
Randolph Inn and Suites is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and an indoor pool. It's located 3.2 mi (5.2 km) from Winchester Speedway. Other good options around the area include Courtyard Muncie at Horizon Convention Center and Holiday Inn Express & Suites Portland, an IHG Hotel.
What about the best place to stay near Winchester Golf Club?
One of the top choices for your stay is Randolph Inn and Suites, located 1.3 mi (2.1 km) from Winchester Golf Club, and this hotel offers free breakfast and an indoor pool. Courtyard Muncie at Horizon Convention Center and Holiday Inn Express & Suites Portland, an IHG Hotel are a couple of other good options within the area.
What's the best hotel for staying near Indianapolis International Airport (IND)?
Crowne Plaza Indianapolis Airport is a popular 3.5-star hotel featuring a restaurant and an indoor pool. It's located a short 1.8 mi (3 km) from Indianapolis Intl. Airport. Other options near the airport are Clarion Hotel Airport and Catalina Airport Motel.
What's it like staying in Winchester?
Visitors can enjoy all that Winchester has to offer including its golf courses. In Winchester, there are 2 hotels and other accommodations to choose from. Find out more about Winchester.
What are the top places to visit in Winchester?
A couple of favorite places to visit are Winchester Golf Club and Winchester Speedway. You'll also find Prairie Creek Reservoir and Campground and Darke County Fairgrounds 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 70°F, while the coldest months are January and February with an average of 33°F. Average annual precipitation for Winchester is 47 inches.

Explore a world of travel with Expedia