Travel to Winchester

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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 RM319 per night from 9 Jul to 10 Jul
RM319
RM352 total
9 Jul - 10 Jul
includes taxes & fees
7/10 Good! (715 reviews)
"Quick stay after delayed flight. It had what we needed. Free breakfast that we were not expecting"

Reviewed on 4 Jul 2025

Baymont by Wyndham Winchester
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 RM280 per night from 20 Jul to 21 Jul
RM280
RM326 total
20 Jul - 21 Jul
includes taxes & fees
8.2/10 Very Good! (1,630 reviews)
Impressed!
"I was impressed and surprised with how nice this hotel was! The room was beautiful, spotless, and comfortable. The bathroom was clean and had all the amenities. The gym was a lot better than most hotels. It had free weights and a machine. The breakfast was amazing... eggs, sausage, waffles, cereal, ..."

Reviewed on 4 Jul 2025

Quality Inn Lexington -Horse Park
Spark by Hilton Lexington Hamburg
Spark by Hilton Lexington Hamburg
2.5 out of 5
2381 Buena Vista Rd, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is RM284 per night from 3 Aug to 4 Aug
RM284
RM329 total
3 Aug - 4 Aug
includes taxes & fees
8.8/10 Excellent! (45 reviews)
"Excellent hotel."

Reviewed on 4 Jul 2025

Spark by Hilton Lexington Hamburg
See all 1,133 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.

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
Kentucky State University

Kentucky State University

Walk around the campus at Kentucky State University as part of your travels around Frankfort. You can seek out the hiking trails while in the area.

Kentucky State University

Keene Trace Golf Club

Play a round of golf in Nicholasville at Keene Trace Golf Club, and enjoy other activities such as horse riding. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Keene Trace Golf Club

What to do in Winchester

Buffalo Trace,Four Roses,Woodford,Bulleit Frontier/Stitzel, Castle&Key or Jeptha

Buffalo Trace,Four Roses,Woodford,Bulleit Frontier/Stitzel, Castle&Key or Jeptha

RM1,016
per adult
Buffalo Trace,Four Roses,Woodford,Bulleit Frontier/Stitzel, Castle&Key or Jeptha
Picture 1 for Activity Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass

Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass

RM178
per adult
98% of travellers recommend
Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

RM127
per traveller
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries
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.