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.

Search Inns in Winchester

  • 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 6 - Nov 8
In two weeks
Nov 13 - Nov 15
In one month
Nov 27 - Nov 29
In two months
Dec 25 - Dec 27
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

A hotel room with a large bed, a desk with a chair, a window with a view of the outside, and a wall-mounted TV.

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, (613 reviews)
"This is one of the nicest and cleanest Holiday Inns I’ve ever been to. Very friendly staff too."
United States
Stephen
$114 nightly
The price is $126
Nov 28 - Nov 29
Total with taxes and fees
Holiday Inn Express Lexington East - Winchester by IHG
A hotel room with a large bed, a television, a desk with a chair, a wardrobe, and a window with curtains.

2. 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
$101 nightly
The price is $112
Nov 26 - Nov 27
Total with taxes and fees
Hampton Inn Winchester
A restaurant with a counter, tables, chairs, and a kitchen area with appliances and food items.

3. Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1,001 reviews)
"They have a really good Breakfast..."
United States
David
$90 nightly
The price is $99
Nov 4 - Nov 5
Total with taxes and fees
Best Western Winchester Hotel
A hotel room with a bed, a desk, a chair, a desk lamp, a window with curtains, an air conditioner, and a view of the outside.

4. Value Stay

Value Stay
2.0 star property
Winchester
7.6 out of 10, Good, (193 reviews)
"Well worth the money"
United States
Ronald
$53 nightly
The price is $59
Nov 11 - Nov 12
Total with taxes and fees
Value Stay
A swimming pool with wooden walls and large windows offering views of greenery.

5. Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.4 out of 10, Good, (864 reviews)
"Room was clean beds were comfortable"
United States
Ronald
$80 nightly
The price is $88
Nov 8 - Nov 9
Total with taxes and fees
Baymont by Wyndham Winchester
An indoor swimming pool with tiled flooring, orange walls, and potted plants.

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
$76 nightly
The price is $84
Nov 28 - Nov 29
Total with taxes and fees
Comfort Inn Winchester
A black leather sofa with a center console, a glass table, and two boxes on the table.

7. 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
$262 nightly
The price is $289
Nov 1 - Nov 2
Total with taxes and fees
The Winchester
A bedroom with a bed, a chair, a wooden cabinet, and a door leading to another room.

8. 2nd Story Historic Downtown 2BR with Modern Amenities

2nd Story Historic Downtown 2BR with Modern Amenities
Winchester
9.0 out of 10, Wonderful, (13 reviews)
"We had a great stay, the unit has lots of charm and is very cozy. We enjoyed the walkability to great local shops and restaurants. It's within a short driving distance to other great areas to check out!"
United States
Brian M.
$181 nightly
The price is $199
Nov 1 - Nov 2
Total with taxes and fees
2nd Story Historic Downtown 2BR with Modern Amenities
A two-story house with a porch and a front yard.

9. Charming Victorian Apartment | Downtown Winchester

Charming Victorian Apartment | Downtown Winchester
Winchester
$368 nightly
The price is $423
Nov 4 - Nov 5
Total with taxes and fees
Charming Victorian Apartment | Downtown Winchester
A compact kitchen with a refrigerator, microwave, stove, and a dining area with a table and chairs.

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.
$301 nightly
The price is $331
Nov 2 - Nov 3
Total with taxes and fees
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
A kitchen with white cabinets, a stainless steel oven, and a dishwasher.

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.
$262 nightly
The price is $289
Nov 1 - Nov 2
Total with taxes and fees
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.

12. River Relaxation - Calm Riverfront Home in Winchester Kentucky

River Relaxation - Calm Riverfront Home in Winchester Kentucky
Winchester
7.8 out of 10, Good, (6 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.
$343 nightly
The price is $379
Oct 31 - Nov 1
Total with taxes and fees
River Relaxation - Calm Riverfront Home in Winchester Kentucky
An indoor swimming pool with a wooden ceiling, tiled walls, and a seating area with chairs and a table.

13. 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, (1,177 reviews)
"Comfy beds, clean, quiet, good breakfast."
United States
Sheila
$87 nightly
The price is $101
Nov 8 - Nov 9
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
An outdoor patio area with tables and chairs, a wooden pergola, and a brick wall.

14. Home2 Suites By Hilton Richmond, Ky

Home2 Suites By Hilton Richmond, Ky
3.0 star property
Richmond
9.6 out of 10, Exceptional, (322 reviews)
"Enjoyed our overnight stay"
United States
James
$101 nightly
The price is $112
Nov 22 - Nov 23
Total with taxes and fees
Home2 Suites By Hilton Richmond, Ky
A modern hotel with a prominent red and grey facade, multiple windows, and a well-lit entrance.

15. 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, (1,000 reviews)
"Nice hotel."
United States
Beth
$87 nightly
The price is $101
Nov 30 - Dec 1
Total with taxes and fees
avid hotel Lexington - Hamburg Area by IHG
A large indoor swimming pool with a tiled floor, surrounded by large windows and a seating area with tables and chairs.

16. Holiday Inn Express Lexington - Horse Park Area by IHG

Holiday Inn Express Lexington - Horse Park Area by IHG
3.0 star property
Lexington
9.4 out of 10, Exceptional, (2,226 reviews)
"Excellent hotel and amazing staff."
United States
SEQUANA
$85 nightly
The price is $99
Nov 29 - Nov 30
Total with taxes and fees
Holiday Inn Express Lexington - Horse Park Area by IHG
A spacious kitchen with granite countertops, wooden bar stools, and a large island.

17. Hilton Garden Inn Lexington Hamburg

Hilton Garden Inn Lexington Hamburg
3.0 star property
Liberty Area
8.6 out of 10, Excellent, (941 reviews)
"Staff were extremely friendly and helpful."
United States
Paul
$89 nightly
The price is $104
Nov 19 - Nov 20
Total with taxes and fees
Hilton Garden Inn Lexington Hamburg
A hotel lobby with blue walls, a seating area with blue chairs, a bar, and artwork on the walls.

18. GuestHouse Lexington

GuestHouse Lexington
2.5 star property
Lexington
8.4 out of 10, Very good, (1,709 reviews)
"Place was very convenient to the highway & shoppng and restaurants- clean & very comfortable"
United States
Gail
$71 nightly
The price is $83
Nov 1 - Nov 2
Total with taxes and fees
GuestHouse Lexington
A modern food court with a variety of food stalls, a coffee station, and a seating area with a view of the outside.

19. Tru By Hilton Lexington Hamburg

Tru By Hilton Lexington Hamburg
2.5 star property
Liberty Area
9.4 out of 10, Exceptional, (301 reviews)
"Very clean room, and super friendly staff."
United States
Nicholas
$81 nightly
The price is $94
Nov 8 - Nov 9
Total with taxes and fees
Tru By Hilton Lexington Hamburg
A restaurant with booths and tables, overhead lighting, and a TV screen.

20. 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
$83 nightly
The price is $96
Nov 29 - Nov 30
Total with taxes and fees
Holiday Inn Lexington - Hamburg 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

Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"Property was very clean and staff were exceptional.. breakfast was awesome.excellent place to stop."
Gary 1-night trip
Posted less than an hour ago
Embassy Suites by Hilton Lexington/UK Coldstream

Find out more about Winchester

Winchester Inns information

Number of reviews
9,067
Accommodation
0 Inns
Lowest Price
$59
Highest Price
$379

Explore a world of travel with Expedia