Winchester Holidays

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Top hotels in Winchester

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
The price is S$145 per night from 3 May to 4 May
S$145
3 May - 4 May
includes taxes & fees
9.4/10 Exceptional! (2,180 reviews)
We absolutely loved our stay here! Very clean the staff was amazing, and they were very accommodating with our small dog!

Reviewed on 11 Apr, 2026

Holiday Inn Express Lexington Horse Park Area by IHG
The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is S$320 per night from 26 Apr to 27 Apr
S$320
26 Apr - 27 Apr
includes taxes & fees
9.6/10 Exceptional! (1,230 reviews)
Breakfast and cocktails in the bar were excellent. The rooms are well appointed. My issue is that there is no room for your toiletries in the bathroom. We moved a table from the living room into the bathroom. The clean towels they store in the shower on the bench. We had to put them on the floor. ...

Reviewed on 11 Apr, 2026

The Manchester
Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
444 Parkway Drive Lexington KY
Fully refundableReserve now, pay when you stay
The price is S$157 per night from 26 Apr to 27 Apr
S$157
26 Apr - 27 Apr
includes taxes & fees
9.4/10 Exceptional! (1,074 reviews)
The rooms are spacious and well appointed. The food at the restaurant is amazing. We will stay here again!

Reviewed on 11 Apr, 2026

Elwood Hotel & Suites
See all 1,192 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.

Popular places to visit

Horse barn in Kentucky

Keeneland Racing Course

4.5/5(3 reviews)

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

Keeneland Racing Course
Aerial photograph of the Lexington, Kentucky skyline at night with the city alite.

Rupp Arena

4/5(1 review)

Catch an event at Rupp Arena and enjoy other activities in Lexington such as horse riding.Attend a sporting event or simply enjoy the lively bars while you're in the area.

Rupp Arena

What to do in Winchester

Picture 1 for Activity Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass

Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass

S$58
per adult
98% of travellers recommend
Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass
Experience Rebecca Ruth Chocolate Tour & Museum!

Experience Rebecca Ruth Chocolate Tour & Museum!

S$13
per adult
80% of travellers recommend
Experience Rebecca Ruth Chocolate Tour & Museum!
Unique Horse Farm Tours with Insider Access to Private Farms

Unique Horse Farm Tours with Insider Access to Private Farms

S$76
per adult
90% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
See all activities in Winchester

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