Deals on vacations and trips to Winchester

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Price found within the past 48 hours. Click for updated prices.
Springhill Suites by Marriott Lexington Fritz Farm

Springhill Suites by Marriott Lexington Fritz Farm

3 out of 5
Price was $568, price is now $520 per person
$520
per person
Nov 13 - Nov 15
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Lexington (LEX)
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 buffet breakfast and free self parking.
Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

3.5 out of 5
Save 100% on your flight
Price was $2,424, price is now $1,994 per person
$1,994
per person
Oct 23 - Oct 30
found 14 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Lexington (LEX)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 2 conference rooms, along with free WiFi in public areas. Free self parking and a coffee shop are also offered on site.
The Delegate

The Delegate

3.5 out of 5
Price was $739, price is now $646 per person
$646
per person
Oct 15 - Oct 17
found 17 hours ago
Roundtrip flight included
New York (LGA) 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.
Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
Price was $733, price is now $656 per person
$656
per person
Nov 13 - Nov 15
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Lexington (LEX)
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.
Candlewood Suites Lexington Medical District by IHG

Candlewood Suites Lexington Medical District by IHG

2.5 out of 5
South Broadway Park
Price was $616, price is now $570 per person
$570
per person
Nov 13 - Nov 15
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Lexington (LEX)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and a communal living room are also provided.

Top Winchester hotels deals

Hyatt Regency Lexington

Hyatt Regency Lexington

3.5 out of 5
401 W High St Lexington KY
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $157 total per night
$157 total
Sep 27 - Sep 28
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. There's a 24-hour gym on site, and a 24-hour front desk and a coffee shop are also provided.
Pool
Free airport shuttle
Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

4.5 out of 5
1800 Newtown Pike Lexington KY
$128 nightly
The price is $149 total per night
$149 total
Sep 20 - Sep 21
Total with taxes and fees
This luxury resort features a golf course, a full-service spa, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Enjoy the indoor pool and perks like free self parking.
Pool
Hot Tub
The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Free Cancellation
Reserve now, pay when you stay
$246 nightly
The price is $285 total per night
$285 total
Sep 29 - Sep 30
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
21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
167 West Main Street Lexington KY
Free Cancellation
Reserve now, pay when you stay
$148 nightly
The price is $172 total per night
$172 total
Sep 8 - Sep 9
Total with taxes and fees
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.
Pet friendly
Free WiFi
Natural Bridge State Resort Park

Natural Bridge State Resort Park

3.5 out of 5
2135 Natural Bridge Road Slade KY
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $117 total per night
$117 total
Sep 13 - Sep 14
Total with taxes and fees
A restaurant and a bar/lounge are featured at this cabin. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A picnic area is provided and the front desk is staffed around-the-clock.
Breakfast included
Pet friendly
Holiday Inn Express Lexington - Horse Park Area by IHG

Holiday Inn Express Lexington - Horse Park Area by IHG

3 out of 5
1935 Stanton Way, 1935 4 yes Lexington KY
Free Cancellation
$99 nightly
The price is $115 total per night
$115 total
Sep 8 - Sep 9
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-in are also on offer.
Pool
Breakfast 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.

Stay near popular Winchester attractions

Winchester Traveling Trail

Explore the great outdoors at Winchester Traveling Trail, a lovely green space in Winchester. You can enjoy the restaurants while in the area.
See properties

Frequently asked questions

How much are vacation packages to Winchester?
Adventure calls in Winchester, with Travelocity vacation packages starting from as low as $520. 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.

Photos of local treasures

Browse Winchester vacation photos for more inspiration

An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.
A historic downtown area with a prominent clock tower and a green-roofed building.
A town with a prominent red brick church, a clock tower, and a large parking lot.
A brick building with a central entrance, columns, and the name 'Winchester Hall' above the door.
A clear river with visible rocks and a rocky cliff in the background.