Winchester Holidays

Photo by Nawa Aseen

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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 €71 per night from 30 Jun to 1 Jul
€71
30 Jun - 1 Jul
includes taxes & fees
7/10 Good! (706 reviews)
"Very nice hotel. Staff was wonderful."

Reviewed on 25 Jun 2025

Baymont by Wyndham Winchester
DoubleTree Suites by Hilton Hotel Lexington
DoubleTree Suites by Hilton Hotel Lexington
4 out of 5
2601 Richmond Rd, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is €121 per night from 20 Jul to 21 Jul
€121
20 Jul - 21 Jul
includes taxes & fees
8.6/10 Excellent! (1,011 reviews)
"The outdoor pool was too close to the dumpster. The room is nice but the AC unit is way loud. Parking was plenty and easy. Most guests were supper friendly and courteous. Some guests on the same floor we stayed on Friday were inconsiderate and constantly entering and leaving and knocking and slamming ..."

Reviewed on 24 Jun 2025

DoubleTree Suites by Hilton Hotel Lexington
Embassy Suites by Hilton Lexington/UK Coldstream
Embassy Suites by Hilton Lexington/UK Coldstream
3.5 out of 5
1801 Newtown Pike, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is €101 per night from 6 Jul to 7 Jul
€101
6 Jul - 7 Jul
includes taxes & fees
8.6/10 Excellent! (1,018 reviews)
"We had a nice quiet overnight stay to break up our long travel weekend. We booked a King suite for our family of 4. It was a great size! We were able to stretch out and not feel like we were in each other’s way. I usually hate hotels because of how noisy they can be, but I can say even with a convention ..."

Reviewed on 23 Jun 2025

Embassy Suites by Hilton Lexington/UK Coldstream
See all 1,135 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?
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.

Popular places to visit

Kentucky Horse Park

Kentucky Horse Park

4.5/5(5 reviews)

Explore Kentucky Horse Park, a favourite green space in Lexington, and also enjoy the area's horse riding. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Kentucky Horse Park
The Kentucky Castle

The Kentucky Castle

Enjoy a trip to The Kentucky Castle and popular activities such as horse riding in Versailles. Attend a sporting event or simply enjoy the lively bars while you're in the area.

The Kentucky Castle

What to do in Winchester

Experience Rebecca Ruth Chocolate Tour & Museum!

Experience Rebecca Ruth Chocolate Tour & Museum!

€9
per adult
Experience Rebecca Ruth Chocolate Tour & Museum!
Lexington: Downtown Walking Food & History Tour

Lexington: Downtown Walking Food & History Tour

€86
per adult
Lexington: Downtown Walking Food & History Tour
Lexington: Ashland Henry Clay Estate Ticket with Guided Tour

Lexington: Ashland Henry Clay Estate Ticket with Guided Tour

€22
per adult
80% of travellers recommend
Lexington: Ashland Henry Clay Estate Ticket with Guided Tour
See all activities in Winchester
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.