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Holiday Homes in Winchester

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Holiday Homes in Winchester

Location, Location, Location
Fridge, microwave, oven, stovetop

Location, Location, Location

9.2 out of 10, Wonderful, (58)
"My week stay was great! Hosts were flexible and accommodated a reservation change to add two additional days. Would highly recommend for anyone staying in Lexington!"
The price is NZ$370
includes taxes & fees
25 Aug - 26 Aug
Location, Location, Location
Spacious 5-bedroom House, Garage/Hot Tub/Bar, Close to RRG, Fiber WiFi
Fridge, microwave, oven, stovetop

Spacious 5-bedroom House, Garage/Hot Tub/Bar, Close to RRG, Fiber WiFi

3.0 star property
10.0 out of 10, Exceptional, (12)
"House was as described and worked out great for our group. "
Spacious 5-bedroom House, Garage/Hot Tub/Bar, Close to RRG, Fiber WiFi
This house is a 3 bedroom(s), 2 bathrooms, located in Lexington, KY.
TV, offices

This house is a 3 bedroom(s), 2 bathrooms, located in Lexington, KY.

9.2 out of 10, Wonderful, (67)
"Everything was exquisite!!! Clean, Inviting and cozy!!!"
The price is NZ$457
includes taxes & fees
24 Aug - 25 Aug
This house is a 3 bedroom(s), 2 bathrooms, located in Lexington, KY.
Luxurious 1-bedroom with Free Parking
Exterior

Luxurious 1-bedroom with Free Parking

9.8 out of 10, Exceptional, (43)
"Nicely upgraded unit, relaxing and comfortable. Close to everything!"
The price is NZ$421
includes taxes & fees
28 Aug - 29 Aug
Luxurious 1-bedroom with Free Parking
This house is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Interior

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

9.4 out of 10, Exceptional, (58)
"Super location, amenities, very clean, fenced yard for our dog was a definite bonus. Would rent again for sure!"
The price is NZ$385
includes taxes & fees
24 Aug - 25 Aug
This house is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Morning View Ranch- Red River Gorge- Indoor Pool open March-Nov. Pet friendly.
Interior

Morning View Ranch- Red River Gorge- Indoor Pool open March-Nov. Pet friendly.

9.8 out of 10, Exceptional, (42)
"We had a really relaxing stay with our dogs! They really enjoyed the yard & we enjoyed the pool! We will be back again! Thank you again!"
Morning View Ranch- Red River Gorge- Indoor Pool open March-Nov. Pet friendly.
This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Exterior

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

9.0 out of 10, Wonderful, (31)
"Just a few days in Lexington "
The price is NZ$324
includes taxes & fees
24 Aug - 25 Aug
This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location
Property grounds

Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location

10.0 out of 10, Exceptional, (138)
"A lovely combination of historical charm with all the modern conveniences you need. And you can’t beat the location! Loved our stay."
The price is NZ$816
includes taxes & fees
24 Aug - 25 Aug
Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location
Stay in a newly renovated home in the heart of Dtown Lexington
Terrace/patio

Stay in a newly renovated home in the heart of Dtown Lexington

2.0 star property
10.0 out of 10, Exceptional, (14)
"Had fabulous stay. Neat, clean, plenty of room, and well taken care of. Would absolutely stay here again! "
Stay in a newly renovated home in the heart of Dtown Lexington
This house is a 3 bedroom(s), 2.5 bathrooms, located in Lexington, KY.
Fridge, microwave, oven, stovetop

This house is a 3 bedroom(s), 2.5 bathrooms, located in Lexington, KY.

2.0 star property
10.0 out of 10, Exceptional, (8)
"We absolutely loved our stay! The property was super nice and very spacious, it was in a perfect location to reach anywhere in downtown Lex. Will definitely book again!"
The price is NZ$587
includes taxes & fees
24 Aug - 25 Aug
This house is a 3 bedroom(s), 2.5 bathrooms, located in Lexington, KY.
The Luxe/Hot Tub/10 Min Keenland/12 Min Downtown/Fenced In Yard/ Pet Friendly
Terrace/patio

The Luxe/Hot Tub/10 Min Keenland/12 Min Downtown/Fenced In Yard/ Pet Friendly

10.0 out of 10, Exceptional, (11)
"We truly enjoyed our stay here. The large kitchen is impressive. The hot tub worked well and the outdoor space was delightful."
The price is NZ$708
includes taxes & fees
24 Aug - 25 Aug
The Luxe/Hot Tub/10 Min Keenland/12 Min Downtown/Fenced In Yard/ Pet Friendly
Cinderella’s Guest House
Exterior

Cinderella’s Guest House

10.0 out of 10, Exceptional, (77)
"We were in Lexington for my daughter’s graduation from UK and this home was clean and comfortable. There were lots of little things provided (lots of comfy blankets, snacks, etc). The location was great for us because we wanted to be close to downtown but not too close. It was very relaxing and peaceful!"
Cinderella’s Guest House
Modern 2bd 2ba- Near I-75, Free WiFi, No Steps
Fridge, microwave, oven, stovetop

Modern 2bd 2ba- Near I-75, Free WiFi, No Steps

9.8 out of 10, Exceptional, (80)
"Had a great time "
The price is NZ$383
includes taxes & fees
8 Sept - 9 Sept
Modern 2bd 2ba- Near I-75, Free WiFi, No Steps
3 Bedroom Downtown Townhouse, Close to All!
Fridge, microwave, oven, stovetop

3 Bedroom Downtown Townhouse, Close to All!

9.2 out of 10, Wonderful, (55)
"Walking distance to Rupp!! It was great!"
3 Bedroom Downtown Townhouse, Close to All!
Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's
3 bedrooms, iron/ironing board, WiFi, bed sheets

Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's

10.0 out of 10, Exceptional, (4)
"My overall stay was very relaxing and stress free .The house was very clean & beautiful inside & out. I would recommend staying at the property to anyone who is ever in town. Great communication with the host😁"
Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Fridge, microwave, oven, stovetop

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

10.0 out of 10, Exceptional, (5)
"We came into town for a work event in Lexington and Wayne was an outstanding host. Beautiful home with plenty of bedrooms to sleep a big group. Wayne was very accommodating and checked in with us throughout the stay. They made sure to provide extra towels/linens/garbage bags knowing we had a large group! I would absolutely recommend this home if you are looking in this area!"
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Beautiful 4-bedroom home, close to Downtown/UK
Fridge, microwave, oven, stovetop

Beautiful 4-bedroom home, close to Downtown/UK

10.0 out of 10, Exceptional, (1)
"We had a great stay at this property. The house was clean and 100% ready to go. Great location. "
The price is NZ$536
includes taxes & fees
24 Aug - 25 Aug
Beautiful 4-bedroom home, close to Downtown/UK
💙Modern Downtown with Parking - Keeneland - Horse Park
Outdoor dining

💙Modern Downtown with Parking - Keeneland - Horse Park

9.6 out of 10, Exceptional, (19)
"Enjoyed our stay. Location was great. "
The price is NZ$462
includes taxes & fees
24 Aug - 25 Aug
💙Modern Downtown with Parking - Keeneland - Horse Park
Your Home Away From Home
Interior

Your Home Away From Home

9.8 out of 10, Exceptional, (212)
"My family and I had a wonderful time here. I would definitely recommend it to others."
The price is NZ$963
includes taxes & fees
25 Aug - 26 Aug
Your Home Away From Home
Westwood Luxury Ranch Home includes washer/dryer
Fridge, microwave, oven, stovetop

Westwood Luxury Ranch Home includes washer/dryer

9.8 out of 10, Exceptional, (36)
"Place was just as advertised. Great location, nice clean and plenty of room for our group."
The price is NZ$570
includes taxes & fees
25 Aug - 26 Aug
Westwood Luxury Ranch Home includes washer/dryer
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

Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

10/10 Excellent
"Rooms look a little older with dings and paint missing on tiles and door frames, but overall really nice room for the price. Big free breakfast with nice lobby. "
Jonathan 1-night trip
Posted 12 hours ago
Quality Inn Lexington -Horse Park