Winchester Holidays from £1,380

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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.

Top Winchester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hyatt House Indianapolis Downtown

Hyatt House Indianapolis Downtown

3 out of 5
Downtown Indianapolis
Price was £1,533, price is now £1,380 per person
£1,380
per person
3 Jan - 10 Jan
found 1 day ago
Return flight included
Birmingham (BHX) to Indianapolis (IND)
9.2/10 Wonderful! (1,270 reviews)

Omni Severin Hotel

Omni Severin Hotel

4 out of 5
Downtown Indianapolis
Price was £1,640, price is now £1,445 per person
£1,445
per person
3 Jan - 10 Jan
found 1 day ago
Return flight included
Birmingham (BHX) to Indianapolis (IND)
9.4/10 Exceptional! (1,496 reviews)
Great staf

Reviewed on 11 Nov 2026

Hyatt Place Indianapolis Downtown

Hyatt Place Indianapolis Downtown

3 out of 5
Downtown Indianapolis
Price was £1,537, price is now £1,383 per person
£1,383
per person
3 Jan - 10 Jan
found 1 day ago
Return flight included
Birmingham (BHX) to Indianapolis (IND)
9/10 Wonderful! (1,586 reviews)
The lack of eye contact, clear articulate information and overall welcoming experience at the front desk set the tone for the visit. It was very, very poor. Staf did not actively engage or welcome us, we had to ask for everything vice having it presented to us. No was the answer for almost every request. Not having an ID to pick up a held bag was painful. Staff member immediately took a tone of being accusatory and only relented once a precise description of items in the bag was identified prior to examining the contents. Toasters are broken too. Why is there no operating fan in the bathrooms? Why do none of the staff seem happy or greet guests? Just a place to sleep when downtown for business or a game. I would never, ever consider your venue for anything else. Unfortunate, Hyatt is premium brand, but your franchise is not.

Reviewed on 10 Nov 2026

Embassy Suites by Hilton Indianapolis Downtown

Embassy Suites by Hilton Indianapolis Downtown

3.5 out of 5
Downtown Indianapolis
Price was £1,600, price is now £1,451 per person
£1,451
per person
3 Jan - 10 Jan
found 1 day ago
Return flight included
Birmingham (BHX) to Indianapolis (IND)
8.6/10 Excellent! (1,007 reviews)
Good stay. Good location. Friendly staff. Thx

Reviewed on 10 Nov 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 12 Dec to 13 Dec
£81
12 Dec - 13 Dec
includes taxes & fees
8.8/10 Excellent! (289 reviews)
"Everything was clean. The bathroom could use a exhaust fan but the room was comfortable. We did not use the pool but it looked clean and nice. The workout room was nice. Hallways and breakfast area very clean. Love, love the 24 hr coffee bar, the best coffee I have ever had in a hotel. We stayed ..."

Reviewed on 2 Nov 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
Get rates
Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA
Days Inn by Wyndham Muncie -Ball State University

Days Inn by Wyndham Muncie -Ball State University

2 out of 5
3509 N Everbrook Ln Muncie IN
Fully refundableReserve now, pay when you stay
The price is £49 per night from 22 Nov to 23 Nov
£49
22 Nov - 23 Nov
includes taxes & fees
7/10 Good! (988 reviews)
"The hotel room had a microwave which is definitely a plus in my books!"

Reviewed on 10 Nov 2026

Days Inn by Wyndham Muncie -Ball State University
See all 143 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 £1,380, 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.