Winchester Trips (flight + hotel)

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Top hotels in Winchester

Randolph Inn and Suites

Randolph Inn and Suites

2.5 out of 5
890 E Washington, Winchester, IN
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (229 reviews)
"It was very clean and the staff was very accommodating. It was close to the Walmart for anything that you would need and restaurants."

Reviewed on Jul 20, 2025

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Randolph Inn and Suites
Baymont by Wyndham Richmond I-70

Baymont by Wyndham Richmond I-70

2.5 out of 5
912 Mendleson Dr, Richmond, IN
Fully refundableReserve now, pay when you stay
The price is P4,188 per night from Aug 17 to Aug 18
P4,188
P4,691 total
Aug 17 - Aug 18
includes taxes & fees
8/10 Very Good! (1,010 reviews)
"The hotel was easily accessed, clean, the staff were friendly, the bed was comfortable, and the breakfast was adequate. Adequate. The made to order eggs were an unexpected treat."

Reviewed on Aug 11, 2025

Baymont by Wyndham Richmond I-70
Baymont by Wyndham Muncie Near Ball State University

Baymont by Wyndham Muncie Near Ball State University

2.5 out of 5
3400 North Chadam Lane, Muncie, IN
Fully refundableReserve now, pay when you stay
The price is P3,830 per night from Sep 1 to Sep 2
P3,830
P4,290 total
Sep 1 - Sep 2
includes taxes & fees
5.6/10 (1,007 reviews)
10 plus rating
"Everything you would want in a home away from home. Great staff, friendly, welcoming."

Reviewed on Aug 7, 2025

Baymont by Wyndham Muncie Near Ball State University
See all 110 properties in Winchester
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.

Popular places to visit

Randolph County Courthouse

After visiting Randolph County Courthouse, make a plan to see the other sights and activities in Winchester.

Randolph County Courthouse

Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices on Expedia for your Winchester getaway. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Winchester costs.
What are the cheapest months to go to Winchester?
If you're hoping to snag a cheap Winchester vacation package, consider visiting in January, February and May. You'll usually find better prices on flights and hotels during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Winchester?
The ideal length of your Winchester vacation depends on what you'd like to do and see. Generally, a handful of days to a week will give you plenty of time to check out all the main attractions and explore some hidden treasures along the way.
Is it worth booking a vacation package to Winchester?
Winchester is a good vacation destination with attractions like Winchester Speedway among the many things to keep you busy. Whether you're traveling with the family or planning a trip with friends, a Winchester vacation promises fun for everyone.
How to find the best Winchester package deals?
Start your search for a Winchester package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Winchester package deal right away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winchester adventure underway.
Is it cheaper to book a Winchester vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and accommodations individually. Better still, you can personalize your Winchester trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Winchester?
If you have your Winchester travel dates locked in, book early to snap up some incredible deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Winchester?

  1. Choose your dates: The things you plan to do in Winchester and your favorite season can help you decide when to get away.
  2. Set your budget: Consider costs such as flights, transportation and food when working out how much to save for your trip to Winchester. Then, choose a hotel that suits your budget, whether that's a low-cost stay or a lavish retreat.
  3. Work out your trip length: Think about how long you'd like to spend discovering Winchester. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customized Winchester vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.