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.

Winchester Castle Hotels

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

A Holiday Inn Express building with a modern design, featuring a large entrance and a well-lit facade.

1. Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
Winchester
9.4 out of 10, Exceptional, (617 reviews)
"This is one of the nicest and cleanest Holiday Inns I’ve ever been to. Very friendly staff too."
United States
Stephen
$102 nightly
The price is $112
Dec 13 - Dec 14
Total with taxes and fees
Holiday Inn Express Lexington East - Winchester by IHG
A hotel with a modern design, featuring a large building with multiple balconies and a well-maintained lawn.

2. Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1,003 reviews)
"They have a really good Breakfast..."
United States
David
$85 nightly
The price is $94
Nov 19 - Nov 20
Total with taxes and fees
Best Western Winchester Hotel
A Baymont Inn & Suites building with a 'Newly Renovated' sign, featuring a modern design with large windows and a prominent corner tower.

3. Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.4 out of 10, Good, (868 reviews)
"Room was clean beds were comfortable"
United States
Ronald
$80 nightly
The price is $88
Nov 22 - Nov 23
Total with taxes and fees
Baymont by Wyndham Winchester
A Hampton Inn hotel with a large parking lot, a prominent sign, and a clear sky.

4. Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (487 reviews)
"Close to Red River Gorge hiking."
United States
kelly
$113 nightly
The price is $125
Nov 26 - Nov 27
Total with taxes and fees
Hampton Inn Winchester
A ValueStay hotel entrance with a clear sign, a covered walkway, and a parking lot.

5. Value Stay

Value Stay
2.0 star property
Winchester
7.6 out of 10, Good, (202 reviews)
"Room was clean"
United States
Kristie
$55 nightly
The price is $61
Dec 15 - Dec 16
Total with taxes and fees
Value Stay
A hotel with a central entrance, covered parking, and a building with a beige facade and arched windows.

6. Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (398 reviews)
"Pool was closed other than that overall good hotel"
United States
james
$50 nightly
The price is $55
Dec 14 - Dec 15
Total with taxes and fees
Comfort Inn Winchester
A two-story house with a porch and a front yard.

7. Charming Victorian Apartment | Downtown Winchester

Charming Victorian Apartment | Downtown Winchester
Winchester
$334 nightly
The price is $368
Nov 16 - Nov 17
Total with taxes and fees
Charming Victorian Apartment | Downtown Winchester
A two-story house with a covered porch, a brick exterior, and a small garden area with shrubs.

8. The Winchester

The Winchester
Winchester
8.6 out of 10, Excellent, (11 reviews)
"The house was clean and had all amenities needed. Love the location and was adorable. Wish I could have stayed longer. Love that there is a park across the street and the neighbors were very friendly"
United States
Gina
$253 nightly
The price is $279
Nov 16 - Nov 17
Total with taxes and fees
The Winchester
A two-story wooden cabin with a balcony, surrounded by trees.

9. River Relaxation - Calm Riverfront Home in Winchester Kentucky

River Relaxation - Calm Riverfront Home in Winchester Kentucky
Winchester
8.0 out of 10, Very good, (8 reviews)
"Good communication, great location and peaceful! Back deck to River does need a little work but it was overall a good stay! "
United States
Polly H.
$330 nightly
The price is $363
Nov 19 - Nov 20
Total with taxes and fees
River Relaxation - Calm Riverfront Home in Winchester Kentucky
A two-story house with a front porch, surrounded by a well-maintained lawn and large trees.

10. Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.

Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
Winchester
10.0 out of 10, Exceptional, (50 reviews)
"The layout of the Farmhouse with suites was perfect for for families traveling together. It allowed for each family to have plenty of private time."
United States
Linda G.
$286 nightly
The price is $315
Nov 23 - Nov 24
Total with taxes and fees
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
A two-story house with a garage, a basketball hoop, and a well-maintained lawn.

11. 4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Winchester
9.6 out of 10, Exceptional, (14 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
$244 nightly
The price is $269
Nov 16 - Nov 17
Total with taxes and fees
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
A multi-story hotel with a prominent 'LaQuinta' sign, a covered entrance, and a parking lot.

12. La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1,184 reviews)
"10/10 would stay again."
United States
Beania
$87 nightly
The price is $101
Nov 16 - Nov 17
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
A Holiday Inn hotel with a modern facade, multiple floors, and a well-lit entrance.

13. Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1,006 reviews)
"Nice stay and good convenient location."
United States
John
$91 nightly
The price is $106
Dec 13 - Dec 14
Total with taxes and fees
Holiday Inn Lexington - Hamburg by IHG
A modern hotel building with a blue and grey facade, multiple windows, and a prominent 'tru by Hilton' sign.

14. Tru By Hilton Lexington Hamburg

Tru By Hilton Lexington Hamburg
2.5 star property
Liberty Area
9.4 out of 10, Exceptional, (309 reviews)
"Very clean room, and super friendly staff."
United States
Nicholas
$81 nightly
The price is $94
Nov 29 - Nov 30
Total with taxes and fees
Tru By Hilton Lexington Hamburg
A Comfort Inn & Suites building with a yellow facade, brick accents, and a clear blue sky.

15. Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling
2.5 star property
Mount Sterling
7.8 out of 10, Good, (812 reviews)
"Nice clean friendly staff stayed 5 nights"
United States
Ricardo
$93 nightly
The price is $103
Nov 23 - Nov 24
Total with taxes and fees
Comfort Inn & Suites Mount Sterling
A guesthouse with a covered entrance, a large building with a tower, and a sign indicating an indoor pool.

16. GuestHouse Lexington

GuestHouse Lexington
2.5 star property
Lexington
8.4 out of 10, Very good, (1,733 reviews)
"Great location, clean rooms, nice pool."
United States
Dillom
$71 nightly
The price is $83
Nov 16 - Nov 17
Total with taxes and fees
GuestHouse Lexington
A modern hotel with a prominent red and grey facade, multiple windows, and a well-lit entrance.

17. avid hotel Lexington - Hamburg Area by IHG

avid hotel Lexington - Hamburg Area by IHG
3.0 star property
Lexington
9.2 out of 10, Wonderful, (1,003 reviews)
"We had a great time"
United States
Donnie
$87 nightly
The price is $101
Dec 13 - Dec 14
Total with taxes and fees
avid hotel Lexington - Hamburg Area by IHG
A hotel entrance with a covered walkway, a sign for 'Home 2 Suites by Hilton', and a parking area with cars.

18. Home2 Suites Lexington Keeneland Airport, KY

Home2 Suites Lexington Keeneland Airport, KY
3.0 star property
Beaumont Residential
9.8 out of 10, Exceptional, (456 reviews)
"Clean room, helpful staff."
United States
Marc
$77 nightly
The price is $89
Dec 12 - Dec 13
Total with taxes and fees
Home2 Suites Lexington Keeneland Airport, KY
A Comfort Inn hotel with a covered entrance, a parking lot, and a clear sky.

19. Comfort Inn Lexington I-75

Comfort Inn Lexington I-75
2.5 star property
Lexington
7.4 out of 10, Good, (845 reviews)
"Nice place to stay friendly staff!"
United States
Steve
$70 nightly
The price is $82
Dec 6 - Dec 7
Total with taxes and fees
Comfort Inn Lexington I-75
A Holiday Inn Express & Suites hotel with a modern design, featuring a covered entrance and multiple floors.

20. Holiday Inn Express & Suites Mt Sterling North by IHG

Holiday Inn Express & Suites Mt Sterling North by IHG
2.5 star property
Mount Sterling
8.8 out of 10, Excellent, (654 reviews)
"Great stay!!! Will definitely stay again"
United States
Charity
$111 nightly
The price is $122
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn Express & Suites Mt Sterling North by IHG
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Studio 6 Suites Lexington, Kentucky

Studio 6 Suites Lexington, Kentucky

8/10 Good
"The room was clean and the AC worked well. The only downside was that the bed frames creaked at every movement."
Carley 1-night trip
Posted 4 hours ago
Studio 6 Suites Lexington, Kentucky

Find out more about Winchester

Winchester Castles information

Number of reviews
6,152
Accommodation
0 Castles
Lowest Price
$55
Highest Price
$363

Explore a world of travel with Expedia