Winchester Holidays

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Your Winchester Holiday

History, cuisine, art and more … There's so much to experience with a Winchester holiday package. And with the ability to customise your city getaway, you know it'll be one that's tough to forget. Want to explore? Winchester Speedway, Winchester Golf Club and Historic Shopping & Dining District of Winchester, Indiana are among the leading places to visit during your trip to Winchester. Expedia has what you need to escape your routine. Tailor your holiday to Winchester to suit your style of travel, whatever that may look like.

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

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 20 Jul 2025

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Randolph Inn and Suites
Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!

Winchester, IN
9.6/10 Exceptional! (175 reviews)
"Had a great time. Location is excellent and really enjoyed everything the house had to offer."

Reviewed on 2 Aug 2025

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Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
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 £61 per night from 10 Aug to 11 Aug
£61
10 Aug - 11 Aug
includes taxes & fees
8/10 Very Good! (1,004 reviews)
richmond
"It was amazing and in good location"

Reviewed on 5 Aug 2025

Baymont by Wyndham Richmond I-70
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Winchester Speedway

Catch an event at Winchester Speedway during your trip to Winchester.

Winchester Speedway

Frequently asked questions

How much does a Winchester travel package cost?
Maybe less than you might think — from a low , actually! By combining hotels, flights and car rentals into your own tailor-made travel package, your trip to Winchester is only clicks away.
If I'm not able to travel, can I cancel my Winchester travel package?
If your holiday plans in Winchester have been upended, it's a relief to know that it's possible to cancel or amend your booking. If you made your booking less than 24 hours ago, you may be eligible for a refund. If your booking is older than that, your hotel, airline or car rental company may charge a fee. To find out more, visit our Customer Service Portal.
How do I get a cheap travel package to Winchester?
Our Winchester travel packages promise plenty of savings for the savvy explorer. For the best deal, simply bundle your flights, hotels and extras (including tours) into a handy package. But low prices are only the start of your next epic adventure. When you book with Expedia, you'll have more than 550 airlines and 1,000,000 hotel options globally to choose from. No matter your budget, there's a travel package to suit you.
Does Expedia offer Book Now, Pay Later Winchester holidays?
Your bank balance shouldn't stop you from escaping on holiday, so Expedia has devised a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a fabulous getaway without hurting your hip pocket. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your trip. Consider one of these flexible payment options:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's manageable monthly instalment plans. If paying a little each month sounds right for you, pick this option at checkout.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay off your trip across multiple transactions.
  • Low deposit holidays: Hitting the "book now" button is easier with this option. Simply put down a small deposit on your escape and then get on your way.

Where should I stay in Winchester?
Stay where the action is. Many people like to book hotels within easy reach of popular sights, like Winchester Golf Club, Winchester Speedway and Historic Shopping & Dining District of Winchester, Indiana.
What are the top hotels in Winchester?
Get your holiday off to a great start by staying at Sheraton Indianapolis Hotel at Keystone Crossing. It's one of most sought-after hotels in Winchester. Another cosy option is Hilton Fort Wayne at the Grand Wayne Convention Centre.
How far in advance should I book my Winchester holiday?
Earlier is always better. Airlines usually advertise flights nearly 12 months prior to departure, and this is when you can score some of the cheapest prices. Boss just told you to use up your holiday time in a few weeks? No need to worry. Expedia are never short of fantastic bargains to whisk you away on the getaway of your dreams, at an affordable price.
What does an Expedia Winchester travel package include?
You can select from a combination of hotels, flights and rental cars. Once you've made your booking, you can add the fun stuff like experiences and activities. Want to pick your fare class? That's possible too. The choice is all yours when it comes to planning your ideal Winchester getaway.
What should I know before booking a Winchester travel package?
You can save big by bundling your hotels, flights and rental cars. Once you've created your package, you can add on tours and activities. Your next unforgettable adventure is only a couple of clicks away.
Can I choose my airline with a Winchester Expedia travel package?
Yes — that's one of the best things about an Expedia travel package. You get to choose. We have access to more than 550 airline partners globally, so you have loads of choice when creating your Winchester getaway.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.