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Compare 351 Vacation Homes in Winchester with updated reviews, rates, and availability.

Golf Simulator | Hot Tub | Game Room | Pool Table
Indulge in a fully stocked, high-end kitchen oasis. Impeccable design, top-of-the-line appliances, and all the culinary essentials create a haven for extraordinary culinary experiences.

Golf Simulator | Hot Tub | Game Room | Pool Table

10.0 out of 10, Exceptional, (38)
"The house was as advertised. Clean and spacious with a lot of activities."
Golf Simulator | Hot Tub | Game Room | Pool Table
This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.
Exterior

This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.

9.6 out of 10, Exceptional, (54)
"8 friends spending 3 days on the Bourbon Trail. Perfect location!"
The price is AED 551
AED 1,377 total
includes taxes & fees
12 Jan - 13 Jan
This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.
Fully Renovated | Finished Basement | Luxury Beds | Games
New Kitchen

Fully Renovated | Finished Basement | Luxury Beds | Games

10.0 out of 10, Exceptional, (50)
"Very clean and spacious! "
The price is AED 624
AED 1,846 total
includes taxes & fees
5 Feb - 6 Feb
Fully Renovated | Finished Basement | Luxury Beds | Games
Trailside Oasis•Entire house,12 guests, 7mi to KHP
Living area

Trailside Oasis•Entire house,12 guests, 7mi to KHP

9.8 out of 10, Exceptional, (20)
"Everything was above and beyond our expectations!! Jeremy answered all questions within minutes and was so gracious!!"
Trailside Oasis•Entire house,12 guests, 7mi to KHP
WiFi, Hot Tub, Pets, Prime Location in Red River Gorge!

WiFi, Hot Tub, Pets, Prime Location in Red River Gorge!

9.6 out of 10, Exceptional, (15)
"It was nice and quiet. I will definitely be back "
The price is AED 477
AED 920 total
includes taxes & fees
12 Jan - 13 Jan
WiFi, Hot Tub, Pets, Prime Location in Red River Gorge!
Totally renovated downtown home walk to all
Exterior

Totally renovated downtown home walk to all

9.4 out of 10, Exceptional, (59)
"This place is awesome and convenient. We will definitely stay here again. Regina is fantastic host. We loved it. Great stay!! "
The price is AED 826
AED 1,155 total
includes taxes & fees
12 Jan - 13 Jan
Totally renovated downtown home walk to all
Isla's Landing - Charming Historic 1940s Home
Living Room

Isla's Landing - Charming Historic 1940s Home

10.0 out of 10, Exceptional, (33)
"Isla was perfect for our Christmas celebration. Love that the kitchen has a gas stove. The beds are comfortable. I think the back yard would be great for summer. Highly recommend."
Isla's Landing - Charming Historic 1940s Home
Bourbon Run - HotTub/ Ark 30min/ Horse Park 12min/ Walk Downtown/ 4BR Sleeps 8
Living Room

Bourbon Run - HotTub/ Ark 30min/ Horse Park 12min/ Walk Downtown/ 4BR Sleeps 8

10.0 out of 10, Exceptional, (11)
"Everything was great! "
The price is AED 643
AED 1,255 total
includes taxes & fees
12 Jan - 13 Jan
Bourbon Run - HotTub/ Ark 30min/ Horse Park 12min/ Walk Downtown/ 4BR Sleeps 8
Lexington Home ~ 5 Mi to University of Kentucky!
Lexington Vacation Rental | 3BR | 2.5BA | 2,806 Sq Ft | Stairs Required

Lexington Home ~ 5 Mi to University of Kentucky!

10.0 out of 10, Exceptional, (4)
"This property was located in a very nice area near the outer belt so it was easy to get around Lexington. House was tastefully decorated and very clean. We travel a lot and this might have had the best amenities of any house we have stayed at. "
Lexington Home ~ 5 Mi to University of Kentucky!
My Old Kentucky Home
Private kitchen

My Old Kentucky Home

10.0 out of 10, Exceptional, (15)
"Beautiful property, perfect for a night stay or more!! Easy to find, close to the Rupp arena & other places. 10/10 recommend. We will stay/book again if we are in the area! "
The price is AED 290
AED 870 total
includes taxes & fees
15 Jan - 16 Jan
My Old Kentucky Home
Celebrate the best of Kentucky while staying at Kentucky's Best on Berry
Living area

Celebrate the best of Kentucky while staying at Kentucky's Best on Berry

10.0 out of 10, Exceptional, (4)
"We had a great stay. Owners were accommodating and the house was great. Walkable to surrounding restaurants and bars"
The price is AED 1,010
AED 1,811 total
includes taxes & fees
12 Jan - 13 Jan
Celebrate the best of Kentucky while staying at Kentucky's Best on Berry
Your Home Away From Home
Exterior

Your Home Away From Home

9.8 out of 10, Exceptional, (200)
"Love the house ... steps and steep driveway to concider for the impaired. "
Your Home Away From Home
Kim's Retreat: 3-BR Cabin w/ Hot Tub near Natural Bridge & Red River Gorge
front porch

Kim's Retreat: 3-BR Cabin w/ Hot Tub near Natural Bridge & Red River Gorge

9.4 out of 10, Exceptional, (11)
"Sweet, quaint, cute, intimate, and special. We both look forward to returning."
Kim's Retreat: 3-BR Cabin w/ Hot Tub near Natural Bridge & Red River Gorge
Robin's Nest luxury cabin, Red River Gorge
Interior

Robin's Nest luxury cabin, Red River Gorge

9.8 out of 10, Exceptional, (141)
"My family spent the weekend at this cabin to celebrate our Thanksgiving. The kids had a blast in the hot tub, singing karaoke in the living room, making ornaments at the huge kitchen table, roasting marshmallows around the fire pit, and eating Miguel’s pizza while watching football on Sunday! We will definitely return! "
Robin's Nest luxury cabin, Red River Gorge
Enriched with history & tradition is where you will find Lexington's Carriage House
Living area

Enriched with history & tradition is where you will find Lexington's Carriage House

9.8 out of 10, Exceptional, (15)
"Overall, we had a great stay at this location! Heath and his crew were very good at responding to messages and we enjoyed this beautiful carriage house. I hosted our family Thanksgiving here since my family is spread out between three states and all in all, it went very well! "
The price is AED 713
AED 1,183 total
includes taxes & fees
12 Jan - 13 Jan
Enriched with history & tradition is where you will find Lexington's Carriage House
Luxurious 1-bedroom with Free Parking
Private kitchen

Luxurious 1-bedroom with Free Parking

9.8 out of 10, Exceptional, (25)
"We had an awesome stay in Lexington! The house was very clean. Communication was clear and responses to any questions that we had were very timely. The house was very close to the UK campus and about a mile to downtown. We would absolutely stay here again!"
The price is AED 253
AED 806 total
includes taxes & fees
15 Jan - 16 Jan
Luxurious 1-bedroom with Free Parking
Cute Crib with Wide Screen Home Theater and Games
Living area

Cute Crib with Wide Screen Home Theater and Games

9.8 out of 10, Exceptional, (12)
"Will visit again."
Cute Crib with Wide Screen Home Theater and Games
This house is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Living area

This house is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.

9.2 out of 10, Wonderful, (35)
"Very clean property....and well equipped kitchen....great location!!! Will be back next month!!"
The price is AED 422
AED 790 total
includes taxes & fees
12 Jan - 13 Jan
This house is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Bourbon Chaser-Horse Park 12min, Ark 30min, Hot Tub, 4BR Sleeps 8, Walk Downtown
Exterior

Bourbon Chaser-Horse Park 12min, Ark 30min, Hot Tub, 4BR Sleeps 8, Walk Downtown

10.0 out of 10, Exceptional, (11)
"Everything was clean and easily accessible "
The price is AED 643
AED 1,255 total
includes taxes & fees
12 Jan - 13 Jan
Bourbon Chaser-Horse Park 12min, Ark 30min, Hot Tub, 4BR Sleeps 8, Walk Downtown
Cozy Home on Golf Course - 6 miles from I-75, Free WiFi
Exterior

Cozy Home on Golf Course - 6 miles from I-75, Free WiFi

8.8 out of 10, Excellent, (15)
"The bath tub showers do not work or very difficult to figure out how to work. We had to take baths instead of showers."
Cozy Home on Golf Course - 6 miles from I-75, Free WiFi
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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Other property types in Winchester

Natural Bridge State Resort Park
Hiking

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1481)
"We stayed in a cabin and the satellite tv did not work. We put in a work order on the same day but no one came to fix it until we were checking out. "
The price is AED 316
AED 348 total
includes taxes & fees
12 Jan - 13 Jan
Natural Bridge State Resort Park
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!

Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!

9.8 out of 10, Exceptional, (273)
"My husband and I enjoyed a relaxing getaway! We loved the house, the balcony, and hot tub."
The price is AED 340
AED 749 total
includes taxes & fees
12 Jan - 13 Jan
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
Property grounds

Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB

10.0 out of 10, Exceptional, (126)
"Clean and quaint. Good communication with the renter. "
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
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.