Winchester Holidays

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

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    Better together

    Save up to Rp173.195 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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Top hotels in Winchester

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 out of 5
960 Interstate Dr, Winchester, KY
Fully refundableReserve now, pay when you stay
The price is Rp1.149.616 per night from 7 Sept to 8 Sept
Rp1.149.616
Rp1.267.326 total
7 Sept - 8 Sept
includes taxes & fees
7/10 Good! (739 reviews)
"Nice"

Reviewed on 8 Aug 2025

Baymont by Wyndham Winchester
Value Stay

Value Stay

2 out of 5
5100 Revilo Rd, Winchester, KY
Fully refundableReserve now, pay when you stay
The price is Rp953.971 per night from 19 Aug to 20 Aug
Rp953.971
Rp1.051.632 total
19 Aug - 20 Aug
includes taxes & fees
7.8/10 Good! (90 reviews)
"It was right next to the expressway, clean and cheap."

Reviewed on 14 Aug 2025

Value Stay
Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

2.5 out of 5
1938 Stanton Way, Bldg A, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is Rp1.017.030 per night from 31 Aug to 1 Sept
Rp1.017.030
Rp1.180.466 total
31 Aug - 1 Sept
includes taxes & fees
8.2/10 Very Good! (1,652 reviews)
"Na"

Reviewed on 15 Aug 2025

Quality Inn Lexington -Horse Park
See all 1,119 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.

What to do in Winchester

Experience Rebecca Ruth Chocolate Tour & Museum!

Experience Rebecca Ruth Chocolate Tour & Museum!

Rp165.130
per adult
Experience Rebecca Ruth Chocolate Tour & Museum!
Unique Horse Farm Tours with Insider Access to Private Farms

Unique Horse Farm Tours with Insider Access to Private Farms

Rp809.137
per adult
88% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
Lexington: Downtown Walking Food & History Tour

Lexington: Downtown Walking Food & History Tour

Rp1.634.787
per adult
Lexington: Downtown Walking Food & History Tour
See all activities in Winchester

Frequently asked questions

How much does a Winchester holiday package cost?
You'll find cheap prices on Expedia for your Winchester escape. However, factors like the season, choice of hotel and length of stay will determine how much your holiday to Winchester costs.
What are the cheapest months to go to Winchester?
December, January and February are the best times to search for cheap Winchester holiday packages. Travelling in quieter months means you can generally find better prices on accommodation and flights.
How many days is enough for Winchester?
With a well-organised travel plan, you can easily visit the most popular Winchester sights in a few days. But if you prefer to discover lesser-known spots or take day trips, consider booking your Winchester holiday for longer.
Is it worth booking a holiday package to Winchester?
Known for its dining, nature and plenty of other highlights, you can be certain Winchester is a good holiday destination. Some of the most popular attractions to add to your itinerary? Don't miss Bluegrass Heritage Museum and Lykins Park during your Winchester holiday.
How to find the best Winchester package deals?
Use Expedia's handy filters to help you find some of the best Winchester package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Winchester package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your holiday package well in advance.
Is it cheaper to book a Winchester holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalised Winchester holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Winchester?
Secure fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Winchester adventure.
How to plan a trip to Winchester?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Winchester.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and food to experiences and flights. Your hotel will probably be the largest expense during your trip to Winchester.
  3. Decide how long to go away for: Now that you know more about Winchester, you can work out the right length of your holiday. Pull together a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Combine your accommodation and airfare: After you've nailed down your travel dates and duration, lock in the ideal Winchester holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.