Winchester Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Winchester

Comfort Inn Winchester

Comfort Inn Winchester

2.5 out of 5
5250 Revilo Rd Winchester KY
Fully refundable
The price is S$95 per night from 16 Nov to 17 Nov
S$95
16 Nov - 17 Nov
includes taxes & fees
Comfort Inn Winchester
Value Stay

Value Stay

2 out of 5
5100 Revilo Rd Winchester KY
Fully refundableReserve now, pay when you stay
The price is S$79 per night from 10 Nov to 11 Nov
S$79
10 Nov - 11 Nov
includes taxes & fees
Value Stay
Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

2.5 out of 5
1938 Stanton Way Lexington KY
Fully refundableReserve now, pay when you stay
The price is S$77 per night from 23 Nov to 24 Nov
S$77
23 Nov - 24 Nov
includes taxes & fees
Quality Inn Lexington -Horse Park
See all 1,229 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.
See properties

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$57
per adult
98% of travellers recommend
Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass
Bourbon group: Makers Mark OR Buffalo Trace OR Woodford or Others

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

S$281
per adult
Bourbon group: Makers Mark OR Buffalo Trace OR Woodford or Others
Woodford Reserve, Castle & Key, and Stitzel Weller Bourbon Tour

Woodford Reserve, Castle & Key, and Stitzel Weller Bourbon Tour

S$369
per adult
Woodford Reserve, Castle & Key, and Stitzel Weller Bourbon 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. 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.