Winchester Vacations from CNY2,497

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Your Winchester Vacation

The fascinating city of Winchester is calling. Discover its highlights and hidden gems with a Winchester vacation package that's tailored to you. You'll want to take in the sights during your trip to Winchester. Find time for top attractions such as Bluegrass Heritage Museum, Southwind Golf Course and Lykins Park. Don't put off your visit to this destination any longer. Your ultimate Winchester vacation is a few clicks away with Expedia.

The Latest Winchester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Corbin Inn

Corbin Inn

2 out of 5
per person
Jul 15 - Jul 18
found 5 hours ago
Roundtrip flight included
New York (JFK) to Lexington (LEX)
6.8/10 (401 reviews)
For the price you can’t beat it. The king bed was extremely comfortable and when I’m in town again I will stay here for sure.

Reviewed on 2 Jun 2024

Derby Inn & Suites

Derby Inn & Suites

2.5 out of 5
per person
Jul 15 - Jul 18
found 5 hours ago
Roundtrip flight included
New York (JFK) to Lexington (LEX)
6.4/10 (145 reviews)
People in the rooms next to us and above us were so noisy that we couldn’t sleep

Reviewed on 8 Apr 2024

Historic Boone Tavern Hotel and Restaurant

Historic Boone Tavern Hotel and Restaurant

3 out of 5
per person
Jul 15 - Jul 18
found 15 hours ago
Roundtrip flight included
New York (JFK) to Lexington (LEX)
9.4/10 Exceptional! (1,000 reviews)
We enjoy the historic inn vibe and the Berea College Campus. Unfortunately, some of the small businesses, eg a local coffee shop, have gone out of business since the pandemic. We hope there is a resurgence for the area.

Reviewed on 4 Jun 2024

MainStay Suites

MainStay Suites

2.5 out of 5
per person
Aug 6 - Aug 9
found 9 hours ago
Roundtrip non-stop flight included
New York (JFK) to Lexington (LEX)
7.6/10 Good! (128 reviews)
New and comfortable

Reviewed on 8 Jun 2024

Super 8 by Wyndham Prestonsburg

Super 8 by Wyndham Prestonsburg

2 out of 5
per person
Jul 15 - Jul 18
found 5 hours ago
Roundtrip flight included
New York (JFK) to Lexington (LEX)
6.4/10 (410 reviews)
So basically, my thinking is that the base rating for a hotel should be a 3/5. I liked the shower pressure so that brought it up a point, and I also thought the beds were comfortable so that also brings it up another point. However, the building is like in disrepair and falling apart to the point where I have to take a point away as funny as it was. No bugs or inconveniences or anything like that, but I don’t feel like it deserves to be on the same level as like Embassy Suites and Home2. So to sum it up, it provided comfort that was above average but looked pretty bad, so I’ll give it a solid 4/5. Good value. 👍

Reviewed on 31 May 2024

Winchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Blue Grass Airport (LEX)
Population
18,400
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Bluegrass Heritage Museum, Southwind Golf Course and Lykins Park

Winchester Hotel Deals

GLō Best Western Lexington
GLō Best Western Lexington
3 out of 5
1935 Stanton Way, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is CNY737 per night from Jun 16 to Jun 17
CNY737
CNY855 total
includes taxes & fees
16 Jun - 17 Jun
9.2/10 Wonderful! (2,292 reviews)
"Modern, clean, spacious"

Reviewed on 8 Jun 2024

GLō Best Western Lexington
GuestHouse Lexington
GuestHouse Lexington
2.5 out of 5
2261 Elkhorn Road, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is CNY487 per night from Jun 13 to Jun 14
CNY487
CNY565 total
includes taxes & fees
13 Jun - 14 Jun
8/10 Very Good! (1,019 reviews)
"Tudo bem"

Reviewed on 7 Jun 2024

GuestHouse Lexington
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 CNY626 per night from Jun 30 to Jul 1
CNY626
CNY872 total
includes taxes & fees
30 Jun - 1 Jul
8.4/10 Very Good! (199 reviews)
"My husband and I had a great stay! The amenities were perfect! Pool and grounds were fabulous! We golfed at Griffon Gate, the course and service is excellent! Will definitely be back!"

Reviewed on 6 Jun 2024

Marriott Lexington Griffin Gate Golf Resort & Spa
See all 1,188 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Winchester vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Winchester from just CNY2,497. And the more you bundle, the more cash you save. Your dream vacation has never been so affordable.
How do I get a cheap travel package to Winchester?
Browse and lock in everything in one place with our Winchester vacation packages. You’ll discover bargains on hotels, flights, tours and more that’ll keep your hip pocket happy and your adventurous side busy. And, with more than 550 air carriers and 1,000,000 properties globally to pick from, you’ll have endless opportunities to mix and match however you please.
Where should I stay in Winchester?
With popular attractions such as Bluegrass Heritage Museum and Clark Regional Medical Center in this neighborhood, try to find a hotel near either of them. Community Park is another sight in Winchester that draws in the crowds.
What are the top hotels in Winchester?
If this will be your first visit to Winchester, secure a room at Holiday Inn Express Lexington East - Winchester, an IHG Hotel or 2nd Story Historic Downtown 2bedroom With Modern Amenities. Both hotels offer friendly service and are popular options with lots of travelers.
How far in advance should I book my Winchester vacation?
While prices change frequently, we generally recommend booking your seats as early as possible. Most international fares become available on Expedia up to a year in advance. If you’re booking last minute, you might still be lucky. Cheap journeys to Winchester sometimes emerge only weeks before departure.
What does an Expedia Winchester travel package include?
Hotels, rental cars and flights, or any combination of the three — it’s up to you! Whether you’re visiting Winchester with the whole family or traveling with your friends, there’s a package to fit your budget and style. Once you’ve made your booking, why not add on one or two activities?
What should I know before booking a Winchester travel package?
A travel package can be tailored to your budget and is a simple way to stretch your hard-earned dollars. How much you include is up to you. Hotels, rental cars and flights — come up with a combination that suits your style.
Can I choose my airline with a Winchester Expedia vacation package?
You certainly can. We offer more than 550 partner airlines throughout the world, so opt for the carrier that best suits your budget needs.
If I'm not able to travel, can I cancel my Winchester vacation package?
You sure can, and we’ll help you every step of the way. You may be able to change or cancel your Winchester vacation package at no cost within 24 hours of booking. But you may be charged a fee by your airline, hotel or car rental company for older bookings. If life throws you a curveball, browse our Customer Service Portal for further information.

Discover the most popular places to visit in Winchester

Image for University of Kentucky

University of Kentucky

4.5/5(384 reviews)

Explore the campus 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
Image for Kentucky Horse Park

Kentucky Horse Park

4.5/5(328 reviews)

Experience the exciting worlds of horses and horseracing at this equine theme park with multiple museums in the middle of Kentucky’s horse country.

Kentucky Horse Park
Image for The Kentucky Castle

The Kentucky Castle

4.5/5(24 reviews)

Enjoy a trip to The Kentucky Castle and popular activities like horseback riding in Versailles. Attend a sporting event or simply enjoy the lively bars while you're in the area.

The Kentucky Castle

What to do in Winchester

Image for Lexington: Ashland Henry Clay Estate Ticket with Guided Tour

Lexington: Ashland Henry Clay Estate Ticket with Guided Tour

CNY25
Per adult
80% of travellers recommend
Lexington: Ashland Henry Clay Estate Ticket with Guided Tour
Image for Experience Rebecca Ruth Chocolate Tour & Museum!

Experience Rebecca Ruth Chocolate Tour & Museum!

CNY10
Per adult
Experience Rebecca Ruth Chocolate Tour & Museum!
Image for Bourbon Boat Tour in Frankfort with Tasting

Bourbon Boat Tour in Frankfort with Tasting

CNY90
Per adult
Bourbon Boat Tour in Frankfort with Tasting
See all activities in Winchester

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