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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sep - 7 Sep
In one month
19 Sep - 21 Sep
In two months
17 Oct - 19 Oct

Condo Rentals in Winchester

Our top choices for Winchester condo rentals

175 LEX - Stunning Downtown Views on Main Street!
1 bedroom, iron/ironing board, travel crib, free WiFi

175 LEX - Stunning Downtown Views on Main Street!

9.8 out of 10, Exceptional, (40)
"Very clean and convenient to Rupp arena "
The price is SAR 409
SAR 764 total
includes taxes & fees
24 Aug - 25 Aug
175 LEX - Stunning Downtown Views on Main Street!
War Admiral @ The HoM- KY Horse Park 11min, Ark 30min, Walk Downtown/GT College
Exterior

War Admiral @ The HoM- KY Horse Park 11min, Ark 30min, Walk Downtown/GT College

9.6 out of 10, Exceptional, (4)
"Relaxing and well appointed. Location was convenient. Parking was plentiful. On site manager was friendly and accommodating. "
War Admiral @ The HoM- KY Horse Park 11min, Ark 30min, Walk Downtown/GT College
Castle Glow_Lex_Close to UK and Hospitals
Fridge, microwave, stovetop, dishwasher

Castle Glow_Lex_Close to UK and Hospitals

10.0 out of 10, Exceptional, (3)
"This property is great! It’s in a very convenient location off Nicholasville Road, it was clean, comfortable, and well equipped. I stayed for over a week and had everything I needed for cooking, cleaning, etc. I would definitely stay here again. "
Castle Glow_Lex_Close to UK and Hospitals
175 LEX - Walkable Downtown Condo - Stunning View
Smart TV, fireplace

175 LEX - Walkable Downtown Condo - Stunning View

9.4 out of 10, Exceptional, (6)
"Great stay"
The price is SAR 732
SAR 1,214 total
includes taxes & fees
20 Sep - 21 Sep
175 LEX - Walkable Downtown Condo - Stunning View
2 Beds/2 Full Baths, Fenced Yard, 1 Car Garage, One Level, Pets Welcomed!
Fridge, microwave, oven, dishwasher

2 Beds/2 Full Baths, Fenced Yard, 1 Car Garage, One Level, Pets Welcomed!

9.4 out of 10, Exceptional, (3)
"Nice place. Would stay again. Thanks. "
2 Beds/2 Full Baths, Fenced Yard, 1 Car Garage, One Level, Pets Welcomed!
This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
Fridge, coffee/tea maker, cookware/dishes/utensils

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

8.8 out of 10, Excellent, (8)
"We enjoyed our girls weekend and this place was perfect !"
This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
The Gatsby Getaway, Downtown LEX
Fridge, microwave, oven, stovetop

The Gatsby Getaway, Downtown LEX

10.0 out of 10, Exceptional, (15)
"Comfortable room and great downtown location."
The price is SAR 409
SAR 764 total
includes taxes & fees
24 Aug - 25 Aug
The Gatsby Getaway, Downtown LEX
The Retreat- a perfect-sized condo for your Bourbon Trail adventure
Dining

The Retreat- a perfect-sized condo for your Bourbon Trail adventure

10.0 out of 10, Exceptional, (1)
The Retreat- a perfect-sized condo for your Bourbon Trail adventure
HUGE Penthouse Suite- 3 BR & 2 Bath w/Elevator. Walk to UK-Downtown-Rupp
Interior

HUGE Penthouse Suite- 3 BR & 2 Bath w/Elevator. Walk to UK-Downtown-Rupp

HUGE Penthouse Suite- 3 BR & 2 Bath w/Elevator. Walk to UK-Downtown-Rupp
Walk everywhere from this 2 bedroom, 2 bath condo in downtown Lexington
Interior

Walk everywhere from this 2 bedroom, 2 bath condo in downtown Lexington

8.0 out of 10, Very Good, (1)
"This downtown home was a great place to stay for my daughter's graduation at Rupp Arena which was only one block away! Home was spacious w all necessities including, sheets, towels, soap, shampoo & kerig coffee."
Walk everywhere from this 2 bedroom, 2 bath condo in downtown Lexington
Penthouse @ 175 LEX -Walk to Rupp Arena on Main St
Smart TV, fireplace

Penthouse @ 175 LEX -Walk to Rupp Arena on Main St

10.0 out of 10, Exceptional, (14)
"Beautiful place in excellent location!"
The price is SAR 3,561
SAR 5,312 total
includes taxes & fees
20 Sep - 21 Sep
Penthouse @ 175 LEX -Walk to Rupp Arena on Main St
175 LEX - Two Bedroom Condo, Walkable Downtown!
2 bedrooms, desk, iron/ironing board, travel crib

175 LEX - Two Bedroom Condo, Walkable Downtown!

9.8 out of 10, Exceptional, (11)
"Wonderful place to stay, great location with walking distance to restaurants and local shops. The apartment was clean and well appointed with all the necessary items for a great stay. Claire was very communicative with check in and out process. "
The price is SAR 1,107
SAR 1,811 total
includes taxes & fees
20 Sep - 21 Sep
175 LEX - Two Bedroom Condo, Walkable Downtown!
3-bedroom family friendly condo conveniently located near downtown Lexington
Private kitchen

3-bedroom family friendly condo conveniently located near downtown Lexington

8.0 out of 10, Very Good, (1)
"The condo worked perfect for us as we went to baseball games at UK. Location was great. Acess to restaurants and coffee shops was great! "
The price is SAR 694
SAR 1,533 total
includes taxes & fees
22 Aug - 23 Aug
3-bedroom family friendly condo conveniently located near downtown Lexington
Paradiso - Divine Condo, Perfect Location Walkable to Everything Downtown
Dining

Paradiso - Divine Condo, Perfect Location Walkable to Everything Downtown

10.0 out of 10, Exceptional, (78)
"Wonderful condo in fun location, great parking, comfy beds, helpful Hosts!"
Paradiso - Divine Condo, Perfect Location Walkable to Everything Downtown
175 LEX - Loft in Downtown Lexington, Rupp Arena
Fridge, microwave, oven, stovetop

175 LEX - Loft in Downtown Lexington, Rupp Arena

10.0 out of 10, Exceptional, (1)
"We had a great stay! The location was perfect for downtown and within easy walking distance from attraction and Target market. Very clean and easy access!"
175 LEX - Loft in Downtown Lexington, Rupp Arena
Bourbon Condo Downtown Lexington
2 bedrooms, desk, iron/ironing board, travel crib

Bourbon Condo Downtown Lexington

9.8 out of 10, Exceptional, (9)
"Perfect location, clean and great place to stay. Will stay here again next time we attend an event."
Bourbon Condo Downtown Lexington
175 LEX - Spacious Two Bedroom Downtown Lexington
2 bedrooms, desk, iron/ironing board, travel crib

175 LEX - Spacious Two Bedroom Downtown Lexington

9.6 out of 10, Exceptional, (29)
"Claire was wonderful to work with"
The price is SAR 469
SAR 920 total
includes taxes & fees
25 Aug - 26 Aug
175 LEX - Spacious Two Bedroom Downtown Lexington
Downtown Lex Full Friends Condo
Fridge, microwave, oven, stovetop

Downtown Lex Full Friends Condo

9.0 out of 10, Wonderful, (2)
"Overall, the condo was clean, spacious, and well-maintained. Security was exceptional with key codes needed for doors and elevator. Felt safe in the downtown urban setting. Enjoyed our two-night stay but noise from the central heating unit interrupted our sleep. The TV and Wi-Fi worked great and problem-free, and the electronic fireplace was a nice touch. Parking can be tricky and is not on-site but we managed to find free street parking thanks to the holiday hours"
The price is SAR 394
SAR 746 total
includes taxes & fees
24 Aug - 25 Aug
Downtown Lex Full Friends Condo
Downtown LEX - Keeneland Condo
Interior

Downtown LEX - Keeneland Condo

8.0 out of 10, Very Good, (3)
"Check in was easy and property manager was easy to reach and communicate with. We used their portable infant crib (Pack n play) which was a nice amenity. The space was clean and well cared for. Building felt safe with access codes for building and elevator after hours and a customized access code to our door. You can hear sirens outside very often which is to be expected for the location, but difficult for a small child to sleep through. There is also a vent from the bedroom to the main living...
The price is SAR 409
SAR 764 total
includes taxes & fees
24 Aug - 25 Aug
Downtown LEX - Keeneland Condo
175 LEX - Spacious Two Bedroom! Walkable Downtown!
2 bedrooms, iron/ironing board, travel crib, free WiFi

175 LEX - Spacious Two Bedroom! Walkable Downtown!

9.8 out of 10, Exceptional, (8)
"Great place to stay for a weekend, had everything we needed and convenient location."
175 LEX - Spacious Two Bedroom! Walkable Downtown!
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

GuestHouse Lexington

GuestHouse Lexington

10/10 Excellent
"Nice Place especially for the Rate. Good Breakfast except coffee weak and none in the rooms!"
VINCENT M. 1-night trip
Posted 12 hours ago
GuestHouse Lexington

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