Winchester Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Winchester

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! (107 reviews)
"Awesome hosts"

Reviewed on 19 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 S$125 per night from 3 Sept to 4 Sept
S$125
3 Sept - 4 Sept
includes taxes & fees
7/10 Good! (524 reviews)
Perfect stopover
"This is a very convenient, easily accessible, reasonably priced, property run by a hands on staff working hard to catch up on some deferred maintenance. Lots of food options nearby. Overall, I would stay there again if in the area."

Reviewed on 11 Aug, 2025

Countryside Inn & Suites
Days Inn by Wyndham Maysville Kentucky

Days Inn by Wyndham Maysville Kentucky

2.5 out of 5
484 Moody Dr, Maysville, KY
Fully refundableReserve now, pay when you stay
The price is S$103 per night from 24 Aug to 25 Aug
S$103
24 Aug - 25 Aug
includes taxes & fees
7/10 Good! (358 reviews)
"It was good for maysville"

Reviewed on 11 Aug, 2025

Days Inn by Wyndham Maysville Kentucky
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.

Frequently asked questions

How much does a Winchester holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday to Winchester costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Winchester?
The off-season is the best time to travel to Winchester if you're trying to save. Another tip for finding cheap Winchester holiday packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for Winchester?
Usually, a handful of days is enough to go to the top attractions during your Winchester holiday. But if you want to have more time to rest or take day trips, think about extending your trip.
How to find the best Winchester package deals?
Landing a cheap Winchester package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most affordable Winchester package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Winchester holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging stays and flights individually. Better still, you can tailor your Winchester getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a holiday package to Winchester?
Score amazing discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Winchester break.
How to plan a trip to Winchester?

  1. Choose when to get away: Check your diary and get packing. Your favourite season and the activities on offer will also help you decide when to holiday in Winchester.
  2. Figure out your budget: Ensure you have enough money to pay for everything from meals and transportation to flights and activities. Your hotel will probably be the biggest expense during your trip to Winchester.
  3. Decide your trip length: Consider how much time you want to spend discovering Winchester. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Winchester holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.