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Villas in Winchester

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Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

Exterior
Best Western Winchester Hotel

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
8.4 out of 10, Very Good, (1000)
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
$72 nightly
The price is $80
Dec 16 - Dec 17
Total with taxes and fees
Best Western Winchester Hotel
Front of property - evening/night
Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
9.4 out of 10, Exceptional, (523)
"Nice room, great staff and just and overall great stay."
United States
Kirk A.
$97 nightly
The price is $107
Dec 21 - Dec 22
Total with taxes and fees
Holiday Inn Express Lexington East - Winchester by IHG
Exterior
Hampton Inn Winchester

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
9.2 out of 10, Wonderful, (451)
"Would stay there again"
United States
Patricia
$109 nightly
The price is $120
Dec 28 - Dec 29
Total with taxes and fees
Hampton Inn Winchester
Exterior
Value Stay

Motel in Winchester

Value Stay
2.0 star property
7.8 out of 10, Good, (124)
"Awesome rooms and service"
United States
Brandon
$63 nightly
The price is $69
Dec 12 - Dec 13
Total with taxes and fees
Value Stay
Exterior
Comfort Inn Winchester

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
7.0 out of 10, Good, (352)
"The pool had no water. There was no pool available. There wasn't any hot water in our room. Unless you run it for 15/20 min"
United States
teresa
$68 nightly
The price is $75
Jan 11 - Jan 12, 2026
Total with taxes and fees
Comfort Inn Winchester
Exterior
Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
7.2 out of 10, Good, (771)
"The room was all that we expected very good. Staff was very friendly."
United States
LEROY
$80 nightly
The price is $88
Dec 18 - Dec 19
Total with taxes and fees
Baymont by Wyndham Winchester
Exterior
Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East
2.0 star property
6.4 out of 10, (586)
"Great stay"
United States
Walter
$62 nightly
The price is $69
Dec 15 - Dec 16
Total with taxes and fees
Red Roof Inn Winchester - Lexington East
Exterior
River Relaxation - Calm Riverfront Home in Winchester Kentucky

Vacation Home in Winchester

River Relaxation - Calm Riverfront Home in Winchester Kentucky
7.0 out of 10, Good, (4)
"We loved the house, the hosts were great and super communicative! The house is also close to Lexington and Winchester so we had plenty to do and places to eat out! "
United States
Maeve R.
$281 nightly
The price is $309
Dec 12 - Dec 13
Total with taxes and fees
River Relaxation - Calm Riverfront Home in Winchester Kentucky
Exterior
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.

Farmstay in Winchester

Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
10.0 out of 10, Exceptional, (42)
"Beautiful location and great service. The owner was very responsive and provided great value for the stay."
United States
Spencer H.
$297 nightly
The price is $327
Dec 15 - Dec 16
Total with taxes and fees
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
Exterior
Quality Inn Richmond

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
9.0 out of 10, Wonderful, (1003)
"The room was clean, staff so kind"
United States
Flor
$94 nightly
The price is $104
Dec 12 - Dec 13
Total with taxes and fees
Quality Inn Richmond
Exterior
Everhome Suites Lexington - Horse Park

Everhome Suites Lexington - Horse Park

Everhome Suites Lexington - Horse Park
2.5 star property
9.2 out of 10, Wonderful, (404)
"Great place to stay!"
United States
Kristin
$80 nightly
The price is $93
Dec 12 - Dec 13
Total with taxes and fees
Everhome Suites Lexington - Horse Park
Exterior
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
3.0 star property
8.8 out of 10, Excellent, (1231)
"Friendly and Clean!"
United States
Roy
$72 nightly
The price is $84
Dec 25 - Dec 26
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Cabin, 2 Bedrooms, Kitchen | Terrace/patio
Natural Bridge State Resort Park

Cabin in Slade

Natural Bridge State Resort Park
3.5 star property
8.6 out of 10, Excellent, (1783)
"Front desk staff was super nice, room was perfect as we were hiking and needed a place to relax and get some sleep! "
United States
Kathy
$86 nightly
The price is $95
Dec 12 - Dec 13
Total with taxes and fees
Natural Bridge State Resort Park
Exterior
Holiday Inn Express & Suites Mt Sterling North by IHG

Holiday Inn Express & Suites Mt Sterling North by IHG

Holiday Inn Express & Suites Mt Sterling North by IHG
2.5 star property
8.8 out of 10, Excellent, (572)
"Room was super clean and the woman at the front desk was really nice and very helpful"
United States
mark
$89 nightly
The price is $98
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn Express & Suites Mt Sterling North by IHG
Exterior
Black Bear Lodge Motel

Motel in Slade

Black Bear Lodge Motel
2.5 star property
8.0 out of 10, Very Good, (633)
"Really great place to stay. "
United States
Barbara
$88 nightly
The price is $97
Dec 12 - Dec 13
Total with taxes and fees
Black Bear Lodge Motel
Exterior
Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling
2.5 star property
7.6 out of 10, Good, (701)
"We stay here anytime we are in town "
United States
Donn
$75 nightly
The price is $83
Jan 11 - Jan 12, 2026
Total with taxes and fees
Comfort Inn & Suites Mount Sterling
Exterior
Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY
3.0 star property
9.0 out of 10, Wonderful, (1000)
"Room was very clean and staff very courteous. Great stay."
United States
Doug
$81 nightly
The price is $89
Jan 7 - Jan 8, 2026
Total with taxes and fees
Country Inn & Suites by Radisson, Georgetown, KY
Front of property - evening/night
Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg
2.5 star property
8.6 out of 10, Excellent, (274)
"Staff was super friendly, beds were nice and rooms were clean. "
United States
Justine
$59 nightly
The price is $69
Jan 4 - Jan 5, 2026
Total with taxes and fees
Spark by Hilton Lexington Hamburg
Exterior
Hampton Inn Richmond

Hampton Inn Richmond

Hampton Inn Richmond
2.5 star property
9.2 out of 10, Wonderful, (1005)
"Clean room, newly remodeled, very comfy bed, great breakfast, nice indoor pool and great location!"
United States
Carla Sue
$95 nightly
The price is $105
Dec 21 - Dec 22
Total with taxes and fees
Hampton Inn Richmond
Exterior
Super 8 by Wyndham Richmond

Motel in Richmond

Super 8 by Wyndham Richmond
2.0 star property
7.6 out of 10, Good, (992)
"The whole property was well kept up and nice to stay at."
United States
Ellen B.
$55 nightly
The price is $60
Dec 14 - Dec 15
Total with taxes and fees
Super 8 by Wyndham Richmond
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

Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"The staff was wonderful. The building was undergoing renovations but still clean. Room clean and very nice set up. The one thing not so good was the weak coffee."
Laura 1-night trip
Posted 17 hours ago
Embassy Suites by Hilton Lexington/UK Coldstream

Find out more about Winchester

Winchester Villas information

Number of reviews
13,440
Accommodation
0 Villas
Lowest Price
$60
Highest Price
$327

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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