Winchester Vacation Packages 2026 from $631

Winchester flight + hotel vacation packages

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

Montgomery Inn BnB

$631

per person

May 26 - May 28

found 23 hours ago

Roundtrip non-stop flight included

New York (NYC) to Lexington (LEX)

This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free full breakfast each morning. A terrace, a garden, and a lobby fireplace are also on offer.

21c Museum Hotel Lexington

Downtown Lexington

$690

per person

May 23 - May 25

found 6 hours ago

Roundtrip flight included

New York (NYC) to Lexington (LEX)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a 24-hour business center, and a snack bar/deli are also offered.

Capital Plaza Hotel

$651

per person

Jun 28 - Jun 30

found 21 hours ago

Roundtrip flight included

New York (NYC) to Lexington (LEX)

This hotel features a restaurant, an indoor pool, and a bar/lounge. There's a gym on site, and laundry facilities and concierge services are also offered.

DoubleTree Suites by Hilton Hotel Lexington

$652

per person

Jun 28 - Jun 30

found 21 hours ago

Roundtrip flight included

New York (NYC) to Lexington (LEX)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi and a free airport shuttle. Self parking, a business center, and a coffee shop are also offered.

The Delegate

$704

per person

Jun 28 - Jun 30

found 21 hours ago

Roundtrip flight included

New York (NYC) to Lexington (LEX)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Self parking and express check-out are also offered on site.

Top Winchester hotels deals

Baymont by Wyndham Winchester

960 Interstate Dr Winchester KY

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$88 total

Apr 30 - May 1

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference space. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Spark by Hilton Lexington Hamburg

2381 Buena Vista Rd Lexington KY

Free Cancellation

Reserve now, pay when you stay

$71 nightly

$83 total

May 19 - May 20

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Holiday Inn Express Lexington Horse Park Area by IHG

1935 Stanton Way, 1935 4 yes Lexington KY

Free Cancellation

$98 nightly

$114 total

May 3 - May 4

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A 24-hour business center, a snack bar/deli, and express check-out are also on offer.

Pool

Breakfast included

DoubleTree Suites by Hilton Hotel Lexington

2601 Richmond Rd Lexington KY

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$140 total

May 17 - May 18

Total with taxes and fees

Pool

Free airport shuttle

The Manchester

941 Manchester St Lexington KY

Free Cancellation

Reserve now, pay when you stay

$183 nightly

$212 total

May 17 - May 18

Total with taxes and fees

This smoke-free hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, express check-in, and express check-out are also offered.

Pet friendly

Free WiFi

Elwood Hotel & Suites

444 Parkway Drive Lexington KY

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$123 total

Apr 28 - Apr 29

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A lobby fireplace, express check-out, and dry cleaning are also on offer.

Pet friendly

Parking included

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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

Kentucky Horse Park

4.5/5(333 reviews)

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

Keeneland Racing Course

4.5/5(267 reviews)

Enjoy a trip to Keeneland Racing Course and popular activities like horseback riding in Lexington. You can attend a sporting event while in the area.

Panorama of an autumn, colorful lawn surrounded by buildings in downtown Lexington, Kentucky

University of Kentucky

4.5/5(389 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.

Frequently asked questions

How much are vacation packages to Winchester?

Adventure calls in Winchester, with Travelocity vacation packages starting from as low as $631. Providing both flights and hotels, these great deals make it simple to explore all corners of the world.

How long should my Winchester vacation be?

There's no hard and fast rule for how long you should spend in Winchester, but many people opt to stay around 2 nights. Got some leeway with your departure date? Consider extending your trip by a couple of extra nights. That way, you'll have ample time to check out the nearby areas too.

Where can I get the best vacation package deals for Winchester?

You'll discover a tempting selection of Winchester package deals on Travelocity. With as many as 400 partner airlines and 1,000,000 properties around the globe, organizing your ideal getaway will be easy.

Why should I book my Winchester vacation package via Travelocity?

Nothing tops the peace of mind knowing you've scored the best price in town — that's our Price Match Guarantee. Add to that our impressive range of destinations and 24/7 team of customer service professionals and you've got the blueprint for a hassle-free vacation.

Can I save money on my Winchester car rental if I bundle it with hotels and flights?

Absolutely — bundle your car, hotel and flight into a Winchester vacation package and you'll save a handsome sum. With so much to see in Winchester, having your own set of wheels will make it easy to explore. Once you're in the driver's seat, turn up the stereo and head toward Churchill Downs, a top attraction around 90 mi from Winchester.

Which airport is best for Winchester?

Blue Grass Airport (LEX), the main terminal in Winchester, is where you'll come in to land. It's situated 25 mi west of the downtown area.

What is there to do in Winchester?

Winchester has more than its fair share of sights to discover, such as Bluegrass Heritage Museum and Lykins Park. These two impressive attractions top most tourists' to-do lists.

Where should I stay when visiting Winchester?

If you're after somewhere to base yourself, take a look at the Best Western Winchester Hotel. It's the top choice for many visitors.