Winchester Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Winchester Holiday

The vibrant city of Winchester is calling your name. Discover its hot spots and hidden treasures with a Winchester holiday package that's customised to you. If your trip to Winchester includes some sightseeing, don't miss popular attractions like Winchester Speedway, Winchester Golf Club and Historic Shopping & Dining District of Winchester, Indiana. Expedia will help you escape the everyday. Tailor your holiday to Winchester to suit your style of travel, whatever that may look like.

Winchester Holiday

Winchester Essential Information

Language
English
Currency
U.S dollars
Population
4,800
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Winchester Speedway, Winchester Golf Club and Historic Shopping & Dining District of Winchester, Indiana

Our pick of the best Winchester Hotel Deals

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
The price is AU$190 per night from 20 Feb to 21 Feb
AU$190
includes taxes & fees
20 Feb - 21 Feb
8.8/10 Excellent! (211 reviews)
"Very nice"

Reviewed on 26 Dec. 2024

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 AU$113 per night from 23 Feb to 24 Feb
AU$113
includes taxes & fees
23 Feb - 24 Feb
8/10 Very Good! (1,000 reviews)
"Staff was kind and caring! Love the rain shower head in the shower! Very clean!"

Reviewed on 7 Feb. 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 AU$175 per night from 2 Mar to 3 Mar
AU$175
includes taxes & fees
2 Mar - 3 Mar
9.2/10 Wonderful! (427 reviews)
"This place was fairly new. It was extremely clean and smelled clean which we truly appreciated. Our room was very nice and the bed was so comfortable. The staff was very friendly, and polite. The only downfall that we found was the water pressure.. it was awful. The shower wasn't cleaned thorly, ..."

Reviewed on 17 Feb. 2025

Comfort Suites
See all 111 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

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.

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