Winchester Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Nawa Aseen

Top hotels in Winchester

Value Stay

Value Stay

2 out of 5
5100 Revilo Rd, Winchester, KY
Fully refundableReserve now, pay when you stay
The price is 1.549.458 ₫ per night from 16 Aug to 17 Aug
1.549.458 ₫
1.708.080 ₫ total
16 Aug - 17 Aug
includes taxes & fees
7.8/10 Good! (89 reviews)
"Room not fancy. But what you need for a good night stay. Clean, comfortable and for the price it was definitely worth it. Would definitely recommend and go back to."

Reviewed on 9 Aug 2025

Value Stay
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 1.892.304 ₫ per night from 7 Sept to 8 Sept
1.892.304 ₫
2.086.076 ₫ total
7 Sept - 8 Sept
includes taxes & fees
7/10 Good! (738 reviews)
"Nice"

Reviewed on 8 Aug 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 1.653.138 ₫ per night from 31 Aug to 1 Sept
1.653.138 ₫
1.918.797 ₫ total
31 Aug - 1 Sept
includes taxes & fees
8.2/10 Very Good! (1,651 reviews)
"Need to have better customer service. Some what rude. As far as the room, it was very nice, but beds a little hard."

Reviewed on 12 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.

Popular places to visit

Fayette Mall

Fayette Mall

3/5(2 reviews)

You can do some window-shopping at Fayette Mall during your trip to Lexington. Discover the area's acclaimed theatre scene or seek out its horse riding.

Fayette Mall
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
Eastern Kentucky University

Eastern Kentucky University

4/5(1 review)

Enjoy the student vibe when you visit Eastern Kentucky University during your travels in Richmond. While in this family-friendly area, you can savour the top-notch restaurants.

Eastern Kentucky University

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.