Photo by Hyelsinta

Search Villas in Winchester

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec
In one month
19 Dec - 21 Dec
In two months
16 Jan - 18 Jan

Villas in Winchester

No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

Exterior
Hampton Inn Winchester

Hampton Inn Winchester

2.5 star property
Winchester
9.2 out of 10, Wonderful, (447)
"Would stay there again"
United States
Patricia
The price is AED 299
AED 329 total
includes taxes & fees
26 Nov - 27 Nov
Hampton Inn Winchester
Front of property - evening/night
Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG

2.5 star property
Winchester
9.2 out of 10, Wonderful, (514)
"Nice room, great staff and just and overall great stay."
United States
Kirk A.
The price is AED 342
AED 377 total
includes taxes & fees
18 Dec - 19 Dec
Holiday Inn Express Lexington East - Winchester by IHG
Free self parking
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 star property
Winchester
8.4 out of 10, Very Good, (998)
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
The price is AED 297
AED 327 total
includes taxes & fees
23 Nov - 24 Nov
Best Western Winchester Hotel
Exterior
Comfort Inn Winchester

Comfort Inn Winchester

2.5 star property
Winchester
7.0 out of 10, Good, (349)
" Nice, new facilities"
United States
Francis
The price is AED 247
AED 272 total
includes taxes & fees
9 Dec - 10 Dec
Comfort Inn Winchester
Exterior
Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 star property
Winchester
7.2 out of 10, Good, (767)
"The room was all that we expected very good. Staff was very friendly."
United States
LEROY
The price is AED 293
AED 323 total
includes taxes & fees
23 Nov - 24 Nov
Baymont by Wyndham Winchester
Exterior
Value Stay

Value Stay

2.0 star property
Winchester
7.8 out of 10, Good, (124)
"Awesome rooms and service"
United States
Brandon
The price is AED 217
AED 239 total
includes taxes & fees
1 Dec - 2 Dec
Value Stay
Private kitchen
The Perch - NEW / Downtown!

The Perch - NEW / Downtown!

Winchester
10.0 out of 10, Exceptional, (2)
"The place was amazing! Very clean and comfortable. Great Italian restaurant down the street. Delicious dounuts around the corner.We went down to go into Lexington for Bourbon and wine tours. Would have liked to have a folder/ binder with information on what is in the area ( we did explore downtown) and also for information about checking out.We had 4 adults and could have used more towels (had 1 towel for each person) But we did make due.All in all would give this place 5 stars! We will be...
United States
Angela G.
The price is AED 444
AED 953 total
includes taxes & fees
18 Nov - 19 Nov
The Perch - NEW / Downtown!
Exterior
Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East

2.0 star property
Winchester
6.6 out of 10, (583)
"Nice overnight hotel"
United States
Jeffrey Frank
The price is AED 229
AED 252 total
includes taxes & fees
20 Nov - 21 Nov
Red Roof Inn Winchester - Lexington East
Exterior
River Relaxation - Calm Riverfront Home in Winchester Kentucky

River Relaxation - Calm Riverfront Home in Winchester Kentucky

Winchester
7.0 out of 10, Good, (4)
"Stayed Thursday-Monday. I had a number of interactions with the owner’s representative who was responsive and timely. "
United States
Sue W.
The price is AED 380
AED 1,136 total
includes taxes & fees
18 Nov - 19 Nov
River Relaxation - Calm Riverfront Home in Winchester Kentucky
Exterior
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, (42)
"What a lovely property! We only got to stay one night, but would have enjoyed a longer stay. The house is super roomy, with lots of comfy places to sleep. We enjoyed the game room immensely as we were winding down from a long day on the road. Easy access to food and shopping. "
United States
Angela P.
The price is AED 918
AED 1,243 total
includes taxes & fees
1 Dec - 2 Dec
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
Exterior
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

3.0 star property
Lexington
8.6 out of 10, Excellent, (1211)
"Our stay was really good . Look forward to staying again!"
United States
Connie
The price is AED 309
AED 358 total
includes taxes & fees
27 Nov - 28 Nov
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Terrace/patio
Hampton Inn Nicholasville Brannon Crossing

Hampton Inn Nicholasville Brannon Crossing

2.5 star property
Nicholasville
9.4 out of 10, Exceptional, (225)
"Clean room, staff very helpful."
United States
Janice
The price is AED 335
AED 369 total
includes taxes & fees
29 Nov - 30 Nov
Hampton Inn Nicholasville Brannon Crossing
Exterior
Everhome Suites Lexington - Horse Park

Everhome Suites Lexington - Horse Park

2.5 star property
Lexington
9.2 out of 10, Wonderful, (368)
"Great place to stay!"
United States
Kristin
The price is AED 311
AED 361 total
includes taxes & fees
18 Nov - 19 Nov
Everhome Suites Lexington - Horse Park
View from room
Natural Bridge State Resort Park

Natural Bridge State Resort Park

3.5 star property
Slade
8.6 out of 10, Excellent, (1772)
"Beautiful autumn stay."
United States
Cheryl
Natural Bridge State Resort Park
Exterior
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, (562)
"Clerk was very nice at check in."
United States
Jerry
The price is AED 411
AED 454 total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express & Suites Mt Sterling North by IHG
Exterior
Hampton Inn I-75 Lexington/Hamburg Area

Hampton Inn I-75 Lexington/Hamburg Area

2.5 star property
Lexington
8.6 out of 10, Excellent, (937)
"It was nice and clean. The food choices was okay."
United States
Mary Ann
The price is AED 262
AED 304 total
includes taxes & fees
1 Dec - 2 Dec
Hampton Inn I-75 Lexington/Hamburg Area
Front of property - evening/night
Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

2.5 star property
Lexington
8.6 out of 10, Excellent, (247)
"Not much in terms of breakfast options but overall clean and nice place."
United States
Karen
The price is AED 217
AED 252 total
includes taxes & fees
30 Nov - 1 Dec
Spark by Hilton Lexington Hamburg
Exterior
Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG

3.0 star property
Lexington
9.0 out of 10, Wonderful, (1003)
"Great stay! "
United States
Tonya
The price is AED 309
AED 358 total
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn Lexington - Hamburg by IHG
Exterior
Quality Inn Richmond

Quality Inn Richmond

2.5 star property
Richmond
9.0 out of 10, Wonderful, (1006)
"We have stayed a few times here and have always been pleased with cleanliness, nice staff and cost. "
United States
Johnna
The price is AED 353
AED 389 total
includes taxes & fees
23 Nov - 24 Nov
Quality Inn Richmond
Exterior
Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY

3.0 star property
Georgetown
9.0 out of 10, Wonderful, (1003)
"The staff are awesome room is clean check in was easy "
Canada
Darran
The price is AED 320
AED 353 total
includes taxes & fees
9 Dec - 10 Dec
Country Inn & Suites by Radisson, Georgetown, 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
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

Candlewood Suites Lexington Medical District by IHG

Candlewood Suites Lexington Medical District by IHG

10/10 Excellent
"Quick check in, courteous staff, spotless room, easy free parking, free Wi-Fi."
Clay 1-night trip
Posted 21 hours ago
Candlewood Suites Lexington Medical District by IHG

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.