Winchester Holidays from £926

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    Save up to £335 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Packages with flights are ATOL protected

Top Winchester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
voco The Clair Cincinnati Downtown by IHG

voco The Clair Cincinnati Downtown by IHG

3 out of 5
Downtown Cincinnati
per person
21 Oct - 25 Oct
found 12 hours ago
Return direct flight included
London (LHR) to Cincinnati (CVG)
9.2/10 Wonderful! (1,027 reviews)
This is my second time staying at Voco the Clair, and I'll definitely be back. The location is great, front desk staff is wonderful, and it's both clean and quiet. The only downside is the parking garage is a little difficult to get into if using GPS, especially when it's busier with street traffic.

Reviewed on 12 Aug 2025

Hyatt Regency Cincinnati

Hyatt Regency Cincinnati

4 out of 5
Downtown Cincinnati
per person
21 Oct - 25 Oct
found 12 hours ago
Return direct flight included
London (LHR) to Cincinnati (CVG)
9/10 Wonderful! (1,484 reviews)
First class experience for 4 nights!

Reviewed on 12 Aug 2025

Hilton Cincinnati Netherland Plaza

Hilton Cincinnati Netherland Plaza

4 out of 5
Downtown Cincinnati
per person
21 Oct - 25 Oct
found 12 hours ago
Return direct flight included
London (LHR) to Cincinnati (CVG)
7.8/10 Good! (1,104 reviews)
The location was convenient. AC didn't work very well in the room, it was stuffy.

Reviewed on 12 Aug 2025

The Cincinnatian Hotel Curio Collection by Hilton

The Cincinnatian Hotel Curio Collection by Hilton

4 out of 5
Downtown Cincinnati
per person
21 Oct - 25 Oct
found 12 hours ago
Return direct flight included
London (LHR) to Cincinnati (CVG)
7.6/10 Good! (1,005 reviews)
Had air conditioning problems, did move us to a different room the 2nd night.

Reviewed on 5 Aug 2025

Homewood Suites by Hilton Cincinnati-Downtown

Homewood Suites by Hilton Cincinnati-Downtown

3 out of 5
Downtown Cincinnati
per person
21 Oct - 25 Oct
found 12 hours ago
Return direct flight included
London (LHR) to Cincinnati (CVG)
8/10 Very Good! (1,000 reviews)
There was nothing special. Couldnt close the bathroom door toilet was in way.

Reviewed on 10 Aug 2025

Winchester Essential Information

Language
English
Currency
U.S dollars
Population
1,050
Max Temp Winter
4ºC
Max Temp Summer
27ºC

Top hotels in Winchester

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

Winchester, OH
10/10 Exceptional! (269 reviews)
Great place
"Would definitely come back"

Reviewed on 11 Aug 2025

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Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
Beverly hills inn

Beverly hills inn

2.5 out of 5
1830 U.S. 52, Aberdeen, OH
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (97 reviews)
Gem!
"A hidden gem in the hills! Enjoyed my stay it was peaceful a perfect little hideaway was skeptical of the place because of the price but it was well worth the price! I will return when in the area"

Reviewed on 9 Aug 2025

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Beverly hills inn
Countryside Inn & Suites

Countryside Inn & Suites

2.5 out of 5
100 Leininger Street, Mount Orab, OH
Fully refundableReserve now, pay when you stay
The price is £73 per night from 27 Aug to 28 Aug
£73
27 Aug - 28 Aug
includes taxes & fees
7/10 Good! (523 reviews)
"Nice, clean room."

Reviewed on 29 Jul 2025

Countryside Inn & Suites
See all 140 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

Frequently asked questions

How much does a Winchester travel package cost?
Explore the best of Winchester from as low as £926. We offer a great selection of flights, hotels and rental cars to suit every budget and style. Land even better deals when you add some tours or experiences to your travel package.
If I'm not able to travel, can I cancel my Winchester travel package?
Because we understand life can throw you a few curveballs, the answer is yes. To find out more, head to our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or change it with no penalties. Your airline, hotel or car rental company may impose a fee if your booking is older than that.
How do I get a cheap travel package to Winchester?
Our Winchester travel packages promise plenty of savings for the savvy traveller. For the best deal, simply combine your flights, hotels and activities into a handy package. But great bargains are just the beginning of your next big adventure. When you book with Expedia, and you'll have over 550 air carriers and 1,000,000 hotels across the globe to select from. Whatever your budget, there's a travel package here just for you.
Does Expedia offer Book Now, Pay Later Winchester holidays?
Your bank balance shouldn't stop you from taking a holiday, so Expedia has devised a solution to help. Now that we've formed a partnership with online lender Klarna, it's easier than ever to book a fabulous getaway without eating away at your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your trip. Consider one of these flexible payment options:

  • Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's easy monthly instalment plans. If paying just a small amount each month works for you, choose this option during the checkout process.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay for your trip over multiple transactions.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to hit that "book now" button, choose a low deposit holiday payment plan with Klarna.

What are the top hotels in Winchester?
Book a room at Quality Inn. It's one of the neighbourhood's most in-demand properties. Another highly rated option in Winchester is Budget Host Inn.
How far in advance should I book my Winchester holiday?
The earlier, the better. Air carriers usually advertise flight tickets up to 12 months in advance, and this is an ideal opportunity to score some of the lowest prices. Just been told you should take your holiday time in a few weeks? That's fine too — Expedia are never short of fantastic deals to send you on the getaway of your dreams, at a price you can afford.
What does an Expedia Winchester travel package include?
With Expedia, you can choose any combination of hotels, car rentals and flights to create your perfect Winchester travel package. Once you've made your booking, you can add on the fun things like tours and activities. Don't forget — the more you bundle, the more dollars you'll save!
What should I know before booking a Winchester travel package?
You'll pick up excellent savings when you bundle your hotels, flights and rental cars into a travel package. Plus, booking everything in one spot just makes things easier. So why waste your time or money? Whether you're putting together a luxury city stay with your love or an affordable family break, have a look at our package deals today.
Can I choose my airline with a Winchester Expedia travel package?
Yes, the choice is yours. We have access to over 550 airlines throughout the world, so you can design your Winchester holiday according to your budget and travel needs.

* 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.