Winchester Holidays

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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 S$108 per night from 12 Jul to 13 Jul
S$108
12 Jul - 13 Jul
includes taxes & fees
7.2/10 Good! (821 reviews)
"quiet, clean room!!"

Reviewed on 10 Jul, 2026

Baymont by Wyndham Winchester
Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

4.5 out of 5
1800 Newtown Pike Lexington KY
Fully refundableReserve now, pay when you stay
The price is S$193 per night from 19 Jul to 20 Jul
S$193
19 Jul - 20 Jul
includes taxes & fees
8.4/10 Very good! (744 reviews)
"Everything was great."

Reviewed on 11 Jul, 2026

Marriott Lexington Griffin Gate Golf Resort & Spa
The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is S$301 per night from 10 Aug to 11 Aug
S$301
10 Aug - 11 Aug
includes taxes & fees
9.6/10 Exceptional! (1,347 reviews)
"Loved everything about this hotel"

Reviewed on 6 Jul, 2026

The Manchester
See all 1,215 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.

Stay near popular Winchester attractions

Winchester Traveling Trail

This serene mile-long pathway winds through meadows of Kentucky bluegrass, offering a peaceful escape. Benches and shaded areas make it perfect for a leisurely morning stroll with your leashed dog.
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What to do in Winchester

Picture 1 for Activity Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass

Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass

S$58
per adult
98% of travellers recommend
Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass
Buffalo Trace, Bulleit Distilling and Rabbit Hole Bourbon Tour

Buffalo Trace, Bulleit, Pappy & Co. and Rabbit Hole Bourbon Tour

S$355
per adult
Buffalo Trace, Bulleit, Pappy & Co. and Rabbit Hole Bourbon Tour
Makers Mark, Four Roses or Woodford Reserve or Bulleit or Others

Bourbon group: Makers Mark OR Buffalo Trace OR Woodford or Others

S$284
per adult
Bourbon group: Makers Mark OR Buffalo Trace OR Woodford or Others
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.

Explore a world of travel with Expedia

* 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.