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Cheap Winchester Hotels

Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave Winchester KY
$85 nightly
The price is $94 total per night
$94 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
1.5 mi from city center
With a stay at Best Western Winchester Hotel in Winchester, you'll be within a 5-minute drive of Clark Regional Medical Center and Bluegrass Heritage Museum.
Pool
Breakfast included
Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

2.5 out of 5
2381 Buena Vista Rd Lexington KY
$61 nightly
The price is $70 total per night
$70 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
13.68 mi from city center
A stay at Spark by Hilton Lexington Hamburg places you in the heart of Lexington, within a 10-minute drive of Lexington Public Library and Explorium.
Pool
Breakfast included
Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 out of 5
369 West Vine Street Lexington KY
$122 nightly
The price is $142 total per night
$142 total
Jan 3 - Jan 4, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
17.9 mi from city center
Hilton Lexington/Downtown is centrally located in Lexington, a 3-minute walk from Lexington Opera House and 5 minutes by foot from Rupp Arena.
Pool
Free airport shuttle
The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
$168 nightly
The price is $195 total per night
$195 total
Dec 28 - Dec 29
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
18.5 mi from city center
With a stay at The Manchester in Lexington (Distillery District), you'll be within a 5-minute drive of Lexington Convention Center and Rupp Arena.
Pet friendly
Free WiFi
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road Lexington KY
$67 nightly
The price is $78 total per night
$78 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
13.75 mi from city center
When you stay at GuestHouse Lexington in Lexington, you'll be in a shopping district, within a 10-minute drive of Rupp Arena and University of Kentucky.
Pool
Breakfast included
DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
2601 Richmond Rd Lexington KY
$87 nightly
The price is $101 total per night
$101 total
Dec 25 - Dec 26
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
15.08 mi from city center
When you stay at DoubleTree Suites by Hilton Hotel Lexington in Lexington, you'll be in the business district, within a 10-minute drive of University of Kentucky and Rupp Arena.
Pool
Free airport shuttle
Motel 6 Lexington, KY - Airport

Motel 6 Lexington, KY - Airport

2 out of 5
750 Newtown Court Lexington KY
$51 nightly
The price is $60 total per night
$60 total
Dec 29 - Dec 30
Total with taxes and fees
Free Cancellation
18.1 mi from city center
When you stay at Motel 6 Lexington, KY - Airport in Lexington, you'll be near the airport, within a 5-minute drive of Mary Todd Lincoln House and Legends Field.
Pet friendly
Parking included
Candlewood Suites Lexington Medical District by IHG

Candlewood Suites Lexington Medical District by IHG

2.5 out of 5
501 Waller Avenue Lexington KY
$78 nightly
The price is $91 total per night
$91 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Free Cancellation
18.85 mi from city center
With a stay at Candlewood Suites Lexington Medical District by IHG, you'll be centrally located in Lexington, within a 5-minute drive of University of Kentucky and Rupp Arena.
Pet friendly
Parking included
Hyatt Regency Lexington

Hyatt Regency Lexington

3.5 out of 5
401 W High St Lexington KY
$107 nightly
The price is $124 total per night
$124 total
Dec 26 - Dec 27
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
17.97 mi from city center
With a stay at Hyatt Regency Lexington, you'll be centrally located in Lexington, just a 4-minute walk from Rupp Arena and 10 minutes by foot from University of Kentucky.
Pool
Free airport shuttle
GLō Best Western Lexington

GLō Best Western Lexington

3 out of 5
1935 Stanton Way Lexington KY
$99 nightly
The price is $115 total per night
$115 total
Dec 22 - Dec 23
Total with taxes and fees
18.19 mi from city center
Located in Lexington, GLō Best Western Lexington is in the business district, within a 10-minute drive of Lexington Convention Center and Lexington Brewing & Distilling Co..
Pool
Breakfast included
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

3 out of 5
100 Canebrake Drive Lexington KY
$87 nightly
The price is $101 total per night
$101 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
11.31 mi from city center
With a stay at La Quinta Inn & Suites by Wyndham Lexington South / Hamburg in Lexington, you'll be within a 15-minute drive of Rupp Arena and University of Kentucky.
Pool
Breakfast included
Staybridge Suites Lexington S Medical Ctr Area by IHG

Staybridge Suites Lexington S Medical Ctr Area by IHG

3 out of 5
209 RUCCIO WAY Lexington KY
$97 nightly
The price is $113 total per night
$113 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Free Cancellation
19 mi from city center
When you stay at Staybridge Suites Lexington S Medical Ctr Area by IHG in Lexington, you'll be near the airport, within a 10-minute drive of University of Kentucky and Rupp Arena.
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.

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Winchester hotels essential information

Accommodation
1,182 hotels
Lowest Price
$60
Highest Price
$195
Popular hotels
Best Western Winchester Hotel, Spark by Hilton Lexington Hamburg, Hilton Lexington/Downtown, The Manchester , GuestHouse Lexington, DoubleTree Suites by Hilton Hotel Lexington, Motel 6 Lexington, KY - Airport, Candlewood Suites Lexington Medical District by IHG, Hyatt Regency Lexington, GLō Best Western Lexington, La Quinta Inn & Suites by Wyndham Lexington South / Hamburg, Staybridge Suites Lexington S Medical Ctr Area by IHG

Most Recent Winchester Hotel Reviews

Motel 6 Lexington, KY - Airport

Motel 6 Lexington, KY - Airport

5 out of 5
Posted 22 hours ago
CheapTickets Verified Review
"Everything was great."
A verified traveler stayed at Motel 6 Lexington, KY - Airport
Motel 6 Lexington, KY - Airport