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.

Villas in Winchester

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

A hotel with a modern design, featuring a large building with multiple balconies and a well-maintained lawn.

1. Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.6 out of 10, Excellent, (1,000 reviews)
"Clean, staff was friendly and accommodating."
United States
Miguel
$100 nightly
The price is $110
Sep 22 - Sep 23
Total with taxes and fees
Best Western Winchester Hotel
A Hampton Inn hotel with a large parking lot, a prominent sign, and a clear sky.

2. Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (482 reviews)
"Nice clean hotel. No complaints."
United States
Jeff
$114 nightly
The price is $126
Oct 4 - Oct 5
Total with taxes and fees
Hampton Inn Winchester
A Holiday Inn Express building with a modern design, featuring a large entrance and a well-lit facade.

3. 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, (600 reviews)
"The property is coveniently located near food, shopping, and the movies. The staff is very helpful. Breakfast is nice (but the pancake machine was broken and eggs were overcooked). Overall, great location and rooms."
United States
Brian
$124 nightly
The price is $137
Sep 20 - Sep 21
Total with taxes and fees
Holiday Inn Express Lexington East - Winchester by IHG
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
7.2 out of 10, Good, (844 reviews)
"Very accommodating unlike some other hotels I am disabled asked for first floor and they did accommodate me. Pool was clean room was clean. I travel from Arkansas to Pennsylvania for 1 week every month this is my 2nd month staying there I will definitely continue to use this hotel."
United States
Jason
$84 nightly
The price is $92
Oct 1 - Oct 2
Total with taxes and fees
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
7.4 out of 10, Good, (175 reviews)
"It was an inexpensive stay and provided a basic but clean and comfortable room."
United States
Robert
$57 nightly
The price is $62
Sep 18 - Sep 19
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
7.0 out of 10, Good, (385 reviews)
"I like hire helpful they are here"
United States
Slick
$72 nightly
The price is $79
Oct 15 - Oct 16
Total with taxes and fees
Comfort Inn Winchester
A two-story house with a garage, a basketball hoop, and a well-maintained lawn.

7. 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
9.8 out of 10, Exceptional, (12 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
$255 nightly
The price is $281
Sep 19 - Sep 20
Total with taxes and fees
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
A two-story house with a front porch, a garage, and a well-maintained lawn.

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
$265 nightly
The price is $292
Sep 21 - Sep 22
Total with taxes and fees
The Winchester
A two-story house with a front porch, surrounded by a well-maintained lawn and large trees.

9. 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, (49 reviews)
"We stayed there for a weekend of going to keeneland race track, it was a little far from the track 40 minutes to an hour depending on traffic, but such a nice place at a fair price that we will definitely stay there again."
United States
tracy d.
$299 nightly
The price is $329
Sep 20 - Sep 21
Total with taxes and fees
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
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
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.
$403 nightly
The price is $444
Oct 12 - Oct 13
Total with taxes and fees
River Relaxation - Calm Riverfront Home in Winchester Kentucky
A multi-story hotel with a prominent 'LaQuinta' sign, a covered entrance, and a parking lot.

11. 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, (1,200 reviews)
"The staff was super welcoming and sweet the food was good and the pool was a nice way to unwind with the kids after a long day"
United States
Brittany
$90 nightly
The price is $105
Oct 11 - Oct 12
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
A spacious lobby with a modern design, featuring a blue sofa, yellow armchairs, and a dining area with blue chairs.

12. Hyatt Place Lexington

Hyatt Place Lexington
3.0 star property
Lexington
8.6 out of 10, Excellent, (1,001 reviews)
"Breakfast was ok. Parking and staff were good."
United States
Janice
$101 nightly
The price is $117
Sep 20 - Sep 21
Total with taxes and fees
Hyatt Place Lexington
A guesthouse with a covered entrance, a large building with a tower, and a sign indicating an indoor pool.

13. GuestHouse Lexington

GuestHouse Lexington
2.5 star property
Lexington
8.4 out of 10, Very good, (1,667 reviews)
"Close to everything the staff was excellent clean and quiet rooms"
United States
Michael
$71 nightly
The price is $83
Sep 20 - Sep 21
Total with taxes and fees
GuestHouse Lexington
A Holiday Inn Express & Suites building with a modern design, featuring a covered entrance and stone pillars.

14. 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, (643 reviews)
"Very friendly staff,great breakfast"
United States
JANICE
$144 nightly
The price is $159
Oct 4 - Oct 5
Total with taxes and fees
Holiday Inn Express & Suites Mt Sterling North by IHG
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, (790 reviews)
"We stayed 3 nights and will definitely stay again. Our rooms were clean and cool, bed was comfortable, and the pool was great. The breakfast was really good and the staff was very friendly."
United States
Patsy
$108 nightly
The price is $120
Oct 4 - Oct 5
Total with taxes and fees
Comfort Inn & Suites Mount Sterling
A Comfort Inn hotel with a covered entrance, a parking lot, and a clear sky.

16. Comfort Inn Lexington I-75

Comfort Inn Lexington I-75
2.5 star property
Lexington
7.4 out of 10, Good, (818 reviews)
"Nice place to stay friendly staff!"
United States
Steve
$71 nightly
The price is $83
Oct 18 - Oct 19
Total with taxes and fees
Comfort Inn Lexington I-75
A modern hotel building with a blue and grey facade, multiple windows, and a prominent 'tru by Hilton' sign.

17. Tru By Hilton Lexington Hamburg

Tru By Hilton Lexington Hamburg
2.5 star property
Liberty Area
9.4 out of 10, Exceptional, (281 reviews)
"clean rooms, friendly staff perfect for our travels"
United States
Kristin
$89 nightly
The price is $104
Sep 29 - Sep 30
Total with taxes and fees
Tru By Hilton Lexington Hamburg
A hotel with a covered entrance, multiple floors, and a flagpole with flags.

18. Hilton Garden Inn Lexington Hamburg

Hilton Garden Inn Lexington Hamburg
3.0 star property
Liberty Area
8.6 out of 10, Excellent, (933 reviews)
"Excellent location, nice property!!!"
United States
Michael
$93 nightly
The price is $109
Sep 29 - Sep 30
Total with taxes and fees
Hilton Garden Inn Lexington Hamburg
A Holiday Inn hotel with a modern facade, multiple floors, and a well-lit entrance.

19. Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1,000 reviews)
"Great location Easy access Great dining"
United States
MARIA
$99 nightly
The price is $115
Oct 18 - Oct 19
Total with taxes and fees
Holiday Inn Lexington - Hamburg by IHG
A modern hotel with a prominent red and grey facade, multiple windows, and a well-lit entrance.

20. 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, (1,007 reviews)
"For just the basics, it is just right"
United States
Kathleen
$93 nightly
The price is $108
Sep 21 - Sep 22
Total with taxes and fees
avid hotel Lexington - Hamburg Area 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.
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Top Winchester Hotel Reviews

Motel 6 Lexington I-75 Hamburg

Motel 6 Lexington I-75 Hamburg

10/10 Excellent
"Everything was perfect"
Brittany 2-night trip
Posted 2 hours ago
Motel 6 Lexington I-75 Hamburg

Find out more about Winchester

Winchester Villas information

Number of reviews
8,465
Accommodation
0 Villas
Lowest Price
$62
Highest Price
$468

Frequently asked questions

Why book your villa in Winchester with Expedia?
Use Expedia to find your dream villa in Winchester. Getting away with the kids? Take advantage of our filters to search for stays with amenities like WiFi and a pool. If you have a budget in mind, choose how much you want to spend and your preferred star rating. We'll help you find the perfect stay in tune with your taste and style.
How can I find cheap villas in Winchester?
With Expedia's user-friendly filter tool, booking cheap villas in Winchester has never been easier. To discover accommodations that won't break the bank, refine your search results by star rating, amenities and budget.
What is there to do near my villa in Winchester?
If you want to see the sights of Winchester, don't miss Southwind Golf Course. It's a favorite among locals and visitors alike.

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