Winchester Holidays

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Top hotels in Winchester

Hilton Lexington/Downtown
Hilton Lexington/Downtown
3.5 out of 5
369 West Vine Street, Lexington, KY
The price is €154 per night from 5 Mar to 6 Mar
€154
includes taxes & fees
5 Mar - 6 Mar
8.2/10 Very Good! (1,001 reviews)
"the bathroom door would not close and the bathroom filled with steam because there was no fan going to vent it. heater was too loud at night. wish you had a complimentary breakfast room was nice"

Reviewed on 18 Feb 2025

Hilton Lexington/Downtown
The Manchester
The Manchester
4 out of 5
941 Manchester St, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is €226 per night from 24 Feb to 25 Feb
€226
includes taxes & fees
24 Feb - 25 Feb
9.4/10 Exceptional! (710 reviews)
I want to go back!
"We went for a weekend getaway and it was amazing! Beautiful, wonderful staff, and very clean"

Reviewed on 16 Feb 2025

The Manchester
Hyatt Regency Lexington
Hyatt Regency Lexington
3.5 out of 5
401 W High St, Lexington, KY
The price is €144 per night from 5 Mar to 6 Mar
€144
includes taxes & fees
5 Mar - 6 Mar
8.4/10 Very Good! (1,001 reviews)
"It was clean and loved the view! Staff was very friendly!!!"

Reviewed on 17 Feb 2025

Hyatt Regency Lexington
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

What to do in Winchester

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.