Winchester Holidays from £883

Book a Hotel + Flight or Car together to unlock savings

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.

Top Winchester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Indy, Indianapolis, a Tribute Portfolio Hotel

Hotel Indy, Indianapolis, a Tribute Portfolio Hotel

4 out of 5
Downtown Indianapolis
Price was £1,013, price is now £883 per person
£883
per person
20 Aug - 24 Aug
found 4 hours ago
Return flight included
Dublin (DUB) to Indianapolis (IND)
9.2/10 Wonderful! (393 reviews)
While we found the staff to be friendly and helpful, the problem with the hotel is the location. It is right next to the bus station, and on a busy street (S. Delaware) that has LOUD cars and motorcycles racing by at all hours of the night. In addition, there is a lot of homeless people around the building. There is an abandoned building across the street on E. Washington and a number of homeless hang out there. We also saw a guy on drugs bent over and just standing there in a daze. I realize that the hotel can't do much about it, but I wouldn't stay there again. Rooms were also very cramped.

Reviewed on 24 Jun 2026

The Alexander, Autograph Collection

The Alexander, Autograph Collection

4 out of 5
Downtown Indianapolis
Price was £1,208, price is now £989 per person
£989
per person
20 Aug - 24 Aug
found 4 hours ago
Return flight included
Dublin (DUB) to Indianapolis (IND)
8.8/10 Excellent! (1,000 reviews)
The rooms were so clean and comfortable while being styled beautifully modern.

Reviewed on 5 Jul 2026

Hampton Inn Indianapolis Downtown Across from Circle Centre

Hampton Inn Indianapolis Downtown Across from Circle Centre

2.5 out of 5
Downtown Indianapolis
Price was £1,037, price is now £886 per person
£886
per person
20 Aug - 24 Aug
found 4 hours ago
Return flight included
Dublin (DUB) to Indianapolis (IND)
8.8/10 Excellent! (1,006 reviews)
The parking situation was the only negative thing to say about this hotel. Too expensive and they should offer parking at a discounted rate!

Reviewed on 9 Jul 2026

Motel 6 Indianapolis, IN - Southport

Motel 6 Indianapolis, IN - Southport

2 out of 5
Price was £1,090, price is now £958 per person
£958
per person
20 Aug - 24 Aug
found 4 hours ago
Return flight included
Dublin (DUB) to Indianapolis (IND)
6.6/10 (1,001 reviews)
OK for the price. Out of date. Lobby area smelled bad. Room was clean and smelled fine. Had more TV channels than other similar priced rooms. Only had coffee in lobby for breakfast. Long term residents in lawn chairs in entrance areas.

Reviewed on 3 Jul 2026

Le Méridien Indianapolis

Le Méridien Indianapolis

4 out of 5
Downtown Indianapolis
Price was £1,006, price is now £902 per person
£902
per person
20 Aug - 24 Aug
found 4 hours ago
Return flight included
Dublin (DUB) to Indianapolis (IND)
9.2/10 Wonderful! (1,002 reviews)
Perfect stay! Great location. Clean.

Reviewed on 18 Jun 2026

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
The price is £81 per night from 7 Aug to 8 Aug
£81
7 Aug - 8 Aug
includes taxes & fees
9/10 Wonderful! (262 reviews)
"Very nice. Loved the location"

Reviewed on 6 Jul 2026

Randolph Inn and Suites
Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA

Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA

Winchester IN
9.8/10 Exceptional! (206 reviews)
"Great property with plenty of room for family gatherings."

Reviewed on 6 Jul 2026

Get rates
Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA
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 £56 per night from 12 Jul to 13 Jul
£56
12 Jul - 13 Jul
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
"Clean nice room. Good breakfast. Richard made me 2 eggs how I wanted them with bacon."

Reviewed on 9 Jul 2026

Baymont by Wyndham Richmond I-70
See all 139 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

Stay near popular Winchester attractions

Winchester Speedway

7.8/10 (26 reviews)
Experience heart-pounding action at the world's fastest half-mile paved track with its legendary steep, high-banked turns. Arrive early to secure prime seating for the electrifying races.
See properties

Frequently asked questions

How much does a Winchester travel package cost?
Maybe less than you might think — from a low £883, 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.

Explore a world of travel with Expedia

* 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.