Search Castles in Winchester from CA $75

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3
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, (614 reviews)
"This is one of the nicest and cleanest Holiday Inns I’ve ever been to. Very friendly staff too."
United States
Stephen
The price is CA $138
CA $153 total
includes taxes & fees
Dec 6 - Dec 7
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, (1,000 reviews)
"They have a really good Breakfast..."
United States
David
The price is CA $119
CA $132 total
includes taxes & fees
Dec 1 - Dec 2
Best Western Winchester Hotel
A Hampton Inn hotel with a large parking lot, a prominent sign, and a clear sky.

3. 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
The price is CA $163
CA $179 total
includes taxes & fees
Nov 26 - Nov 27
Hampton Inn Winchester
A Baymont Inn & Suites building with a 'Newly Renovated' sign, featuring a modern design with large windows and a prominent corner tower.

4. Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.4 out of 10, Good, (867 reviews)
"Room was clean beds were comfortable"
United States
Ronald
The price is CA $112
CA $123 total
includes taxes & fees
Nov 12 - Nov 13
Baymont by Wyndham 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, (196 reviews)
"Well worth the money"
United States
Ronald
The price is CA $75
CA $83 total
includes taxes & fees
Nov 14 - Nov 15
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, (397 reviews)
"Pool was closed other than that overall good hotel"
United States
james
The price is CA $107
CA $118 total
includes taxes & fees
Dec 1 - Dec 2
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
The price is CA $102
CA $563 total
includes taxes & fees
Nov 9 - Nov 10
Charming Victorian Apartment | Downtown Winchester
A black leather sofa with a center console, a glass table, and two boxes on the table.

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
The price is CA $189
CA $394 total
includes taxes & fees
Nov 9 - Nov 10
The Winchester
A two-story house with a garage, a basketball hoop, and a well-maintained lawn.

9. 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.
The price is CA $189
CA $394 total
includes taxes & fees
Nov 9 - Nov 10
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
A two-story wooden cabin with a balcony, surrounded by trees.

10. River Relaxation - Calm Riverfront Home in Winchester Kentucky

River Relaxation - Calm Riverfront Home in Winchester Kentucky
Winchester
8.0 out of 10, Very good, (7 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.
The price is CA $171
CA $499 total
includes taxes & fees
Nov 8 - Nov 9
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.

11. 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.
The price is CA $339
CA $440 total
includes taxes & fees
Nov 9 - Nov 10
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
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, (1,173 reviews)
"Comfy beds, clean, quiet, good breakfast."
United States
Sheila
The price is CA $122
CA $141 total
includes taxes & fees
Nov 30 - Dec 1
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
A modern hotel with a prominent red and grey facade, multiple windows, and a well-lit entrance.

13. 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, (1,006 reviews)
"Nice hotel."
United States
Beth
The price is CA $117
CA $136 total
includes taxes & fees
Nov 9 - Nov 10
avid hotel Lexington - Hamburg Area by IHG
A guesthouse with a covered entrance, a large building with a tower, and a sign indicating an indoor pool.

14. GuestHouse Lexington

GuestHouse Lexington
2.5 star property
Lexington
8.4 out of 10, Very good, (1,724 reviews)
"Great location, clean rooms, nice pool."
United States
Dillom
The price is CA $100
CA $116 total
includes taxes & fees
Nov 9 - Nov 10
GuestHouse Lexington
A modern hotel building with a blue and grey facade, multiple windows, and a prominent 'tru by Hilton' sign.

15. Tru By Hilton Lexington Hamburg

Tru By Hilton Lexington Hamburg
2.5 star property
Liberty Area
9.4 out of 10, Exceptional, (304 reviews)
"Very clean room, and super friendly staff."
United States
Nicholas
The price is CA $113
CA $131 total
includes taxes & fees
Dec 1 - Dec 2
Tru By Hilton Lexington Hamburg
A hotel with a covered entrance, multiple floors, and a flagpole with flags.

16. Hilton Garden Inn Lexington Hamburg

Hilton Garden Inn Lexington Hamburg
3.0 star property
Liberty Area
8.6 out of 10, Excellent, (945 reviews)
"Great overall stay!"
United States
Eric Deithloff
The price is CA $119
CA $138 total
includes taxes & fees
Dec 6 - Dec 7
Hilton Garden Inn Lexington Hamburg
A Holiday Inn Express & Suites building with a modern design, featuring a covered entrance and stone pillars.

17. 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
The price is CA $165
CA $182 total
includes taxes & fees
Nov 24 - Nov 25
Holiday Inn Express & Suites Mt Sterling North by IHG
A Holiday Inn hotel with a modern facade, multiple floors, and a well-lit entrance.

18. Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1,001 reviews)
"Nice stay and good convenient location."
United States
John
The price is CA $108
CA $125 total
includes taxes & fees
Dec 4 - Dec 5
Holiday Inn Lexington - Hamburg by IHG
A hotel sign with "HOME 2 SUITES BY HILTON" and a building in the background.

19. Home2 Suites by Hilton Lexington Hamburg

Home2 Suites by Hilton Lexington Hamburg
3.0 star property
Lexington
9.2 out of 10, Wonderful, (1,003 reviews)
"Close to the interstate and plenty of restaurants nearby."
United States
Kevin
The price is CA $141
CA $164 total
includes taxes & fees
Dec 4 - Dec 5
Home2 Suites by Hilton Lexington Hamburg
A modern hotel building with a prominent "HOME" sign, multiple windows, and a green accent on the facade.

20. Home2 Suites By Hilton Richmond, Ky

Home2 Suites By Hilton Richmond, Ky
3.0 star property
Richmond
9.6 out of 10, Exceptional, (325 reviews)
"The staff was super friendly, the room was very clean and the property felt safe."
United States
Melinda
The price is CA $141
CA $156 total
includes taxes & fees
Nov 27 - Nov 28
Home2 Suites By Hilton Richmond, Ky
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

Learn more about Winchester

Stroll through charming downtown streets lined with local shops and eateries. Tee off at Cassell Creek or Southwind Golf Course, then explore local history at the Bluegrass Heritage Museum.

See all hotels in Winchester
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.

Top reviews in Winchester

A Holiday Inn Express building with a modern design, featuring a large entrance and a well-lit facade.
Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
Winchester

8/10 Good

Good place to stay
Canada
martin
Reviewed April 30, 2025
Holiday Inn Express Lexington East - Winchester by IHG

Explore a world of travel with Expedia