Winchester Holidays

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Your Winchester Holiday

Take away the hard part of organising your next epic adventure with a Winchester holiday package. Whether you're visiting for its landmarks, food or other highlights, this city offers endless possibilities for fun. Every trip to Winchester needs a well-thought-out itinerary. Fill yours with attractions like Bluegrass Heritage Museum, Lykins Park and Southwind Golf Course. Your ultimate Winchester holiday is just a few clicks away. Browse hotels, airfares and more on Expedia for an adventure that's tailored to suit your travel style.

Winchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Blue Grass Airport (LEX)
Population
18,400
Max Temp Winter
4ºC
Max Temp Summer
29ºC
Top Sights
Bluegrass Heritage Museum, Community Park and Lykins Park

Our pick of the best Winchester Hotel Deals

Baymont by Wyndham Winchester
Baymont by Wyndham Winchester
2.5 out of 5
960 Interstate Dr, Winchester, KY
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the clean rooms in their reviews. Popular ...
7/10 Good! (706 reviews)
"Very nice hotel. Staff was wonderful."

Reviewed on 25 Jun 2025

Baymont by Wyndham Winchester
DoubleTree Suites by Hilton Hotel Lexington
DoubleTree Suites by Hilton Hotel Lexington
4 out of 5
2601 Richmond Rd, Lexington, KY
Stay at this 4-star hotel in Lexington. Enjoy free Wi-Fi, an outdoor pool and breakfast (surcharge). Our guests praise the helpful staff in their reviews. Popular ...
8.6/10 Excellent! (1,012 reviews)
"The outdoor pool was too close to the dumpster. The room is nice but the AC unit is way loud. Parking was plenty and easy. Most guests were supper friendly and courteous. Some guests on the same floor we stayed on Friday were inconsiderate and constantly entering and leaving and knocking and slamming ..."

Reviewed on 24 Jun 2025

DoubleTree Suites by Hilton Hotel Lexington
Embassy Suites by Hilton Lexington/UK Coldstream
Embassy Suites by Hilton Lexington/UK Coldstream
3.5 out of 5
1801 Newtown Pike, Lexington, KY
Stay at this 3.5-star business-friendly hotel in Lexington. Enjoy free breakfast, room service and a fitness centre. Our guests praise the breakfast and the ...
8.6/10 Excellent! (1,010 reviews)
Good place for a night or two
"Good place, it is just getting old without having any updates. It had peeling paint, old carpet, things like that. Good place to stay for a night or two. Rooms were clean and comfortable."

Reviewed on 24 Jun 2025

Embassy Suites by Hilton Lexington/UK Coldstream
See all 1,139 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Winchester holiday with Expedia?
Expedia has you covered for every aspect of your next Winchester holiday. You'll always land the best prices around, but when you bundle your accommodation, airfares and/or car hire into a holiday package, you'll get even more savings. Want to truly make the most of your adventure? Add some tours and activities to your package. Expedia offers flexible cancellation policies on almost all bookings, so you won't need to stress if you have to change your plans. Head over to our Customer Service Portal link to discover more.
When is the best time of year to holiday in Winchester?
Winchester is busy in May, August and October, so if you want to escape the crowds, visit in December, January and February. With daytime average temperatures of 0ºC, January is the coolest period in Winchester. The warmest month is July, when you can expect average temperatures of 24ºC during the day. Whatever the weather, you'll find loads to keep you occupied here.
What is the top hotel for my holiday in Winchester?
Offering plenty of amenities and a cosy place to relax between adventures, Baymont by Wyndham Winchester will make the ideal base for your Winchester holiday.
How do I get a cheap holiday to Winchester?
Book everything in one place with our Winchester holidays. You'll find bargains on hotels, flights, tours and more that'll keep your credit card happy and your adventurous spirit alive. And, with more than 400 air carriers and 321,000 properties around the world to choose from, you'll have endless opportunities to mix and match as you like. Learn more about how you can save money on your next holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Winchester holiday?
Make sure your next holiday in Winchester is an unforgettable one by checking out its major attractions. Clark Regional Medical Centre, Bluegrass Heritage Museum, Lykins Park and Southwind Golf Course are a few of the things you should see while you're in this city.
What is the best area to stay in when on holiday in Winchester?
A getaway in Winchester wouldn't be complete without paying a visit to Bluegrass Heritage Museum. Why not stay near this popular tourist attraction?
Do I need a visa for my Winchester holiday?
Official government websites are the best source of information on visa requirements, application procedures and necessary documentation. Your nationality and reason for your visit, whether it be for tourism or business, will determine if you'll need a visa for Winchester. Also check that your passport is up to date and has a minimum of six months validity remaining beyond your return date. Do all your travel planning well in advance to avoid any nasty last-minute surprises.
What should I wear on my Winchester holiday?
Do some research into the types of clothing people in Winchester wear, and maybe even look up fashion pages on social media for inspiration. You'll want to create a versatile wardrobe filled with pieces that work for your destination and showcase your unique sense of style. Daytime temperatures during January, Winchester's coolest month, average 0ºC. July marks this destination's warmest month when the average reaches 24ºC. Our advice? Take the guesswork out of packing and check the local weather conditions.
What does an Expedia Winchester holiday include?
Select from any combination of flights, hire cars and hotels. Once you've made your booking, add the fun stuff like activities and tours. Want to pick your fare class? That's easily done too. The choice is all yours when it comes to organising your perfect Winchester trip. Explore an excellent range of property types and choose one that suits the size of your group. The most popular holiday rentals here are private holiday homes and hotels. With Expedia, it's easy to tailor your Winchester escape any way you like.
Does Expedia offer Book Now, Pay Later Winchester holidays?
Expedia has joined forces with online lender Klarna to make your next trip a bit easier on the wallet. Paying in instalments means you can spread the costs of your dream holiday, leaving you with more money to play with while you're away. Klarna has several payment plans to pick from, so you're sure to find one that falls within your budget. Check out these flexible payment options:

  • Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's manageable instalment plans. If making small repayments each month sounds right for you, choose this option at checkout.
  • No-deposit holidays: When you want to grab an incredible deal but your budget doesn't quite cover it yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock it in.

Can I choose my airline with a Winchester Expedia holiday?
With a holiday package, you're in control. Whether you want to fly to Winchester in coach or business class, simply choose from the available airline options. Expedia has access to more than 400 partner airlines throughout the world.

Discover the most popular places to visit in Winchester

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
University of Kentucky

University of Kentucky

5/5(1 review)

Take a campus tour or just explore the area of University of Kentucky during your travels in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.

University of Kentucky
Lexington Opera House

Lexington Opera House

4/5(1 review)

You can get tickets for a performance at Lexington Opera House during your stay in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Lexington Opera House

Unmissable things to do in Winchester

Experience Rebecca Ruth Chocolate Tour & Museum!

Experience Rebecca Ruth Chocolate Tour & Museum!

£7
per adult
Experience Rebecca Ruth Chocolate Tour & Museum!
Lexington: Downtown Walking Food & History Tour

Lexington: Downtown Walking Food & History Tour

£73
per adult
Lexington: Downtown Walking Food & History Tour
Lexington: Ashland Henry Clay Estate Ticket with Guided Tour

Lexington: Ashland Henry Clay Estate Ticket with Guided Tour

£18
per adult
80% of travellers recommend
Lexington: Ashland Henry Clay Estate Ticket with Guided Tour
See all activities in Winchester

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.