Winchester Holidays

Book a Hotel + Flight or Car together to unlock savings

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! (230 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 20 Jul 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 2.016.387 ₫ per night from 24 Aug to 25 Aug
2.016.387 ₫
2.258.353 ₫ total
24 Aug - 25 Aug
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
"Great place and staff"

Reviewed on 19 Aug 2025

Baymont by Wyndham Richmond I-70
Comfort Suites

Comfort Suites

2.5 out of 5
421 Commerce Road, Richmond, IN
Fully refundableReserve now, pay when you stay
The price is 2.464.473 ₫ per night from 31 Aug to 1 Sept
2.464.473 ₫
2.812.925 ₫ total
31 Aug - 1 Sept
includes taxes & fees
9.2/10 Wonderful! (566 reviews)
"Property was in great shape. Everything was clean and working. Very impressive."

Reviewed on 21 Aug 2025

Comfort Suites
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

Historic Shopping & Dining District of Winchester, Indiana

You can find out about the history of Winchester when you stop by Historic Shopping & Dining District of Winchester, Indiana.

Historic Shopping & Dining District of Winchester, Indiana

Frequently asked questions

How much does a Winchester holiday 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 holiday to Winchester costs.
What are the cheapest months to go to Winchester?
If you're hoping to snag a cheap Winchester holiday 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 travellers.
How many days is enough for Winchester?
The ideal length of your Winchester holiday 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 holiday package to Winchester?
Winchester is a good holiday destination with attractions like Winchester Speedway among the many things to keep you busy. Whether you're travelling with the family or planning a trip with friends, a Winchester holiday 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 holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to booking flights and accommodation individually. Better still, you can personalise 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 holiday 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 favourite 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 customised Winchester holiday package.