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Condo Rentals in Winchester

175 LEX - Walkable Downtown - Rupp Arena - Keeneland

7.2 out of 10, Good, (5)
"Positive place"
175 LEX - Walkable Downtown - Rupp Arena - Keeneland

175 LEX - Stunning Downtown Views on Main Street!

9.8 out of 10, Exceptional, (41)
"Very clean and convenient to Rupp arena "
The price is AED 422
AED 774 total
includes taxes & fees
26 Oct - 27 Oct
175 LEX - Stunning Downtown Views on Main Street!

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! "
3-bedroom family friendly condo conveniently located near downtown Lexington

175 LEX - Walkable Downtown Condo - Stunning View

9.6 out of 10, Exceptional, (8)
"Great stay"
The price is AED 422
AED 774 total
includes taxes & fees
29 Sep - 30 Sep
175 LEX - Walkable Downtown Condo - Stunning View

175 LEX - Spacious Two Bedroom! Walkable Downtown!

9.0 out of 10, Wonderful, (10)
"Great place to stay for a weekend, had everything we needed and convenient location."
The price is AED 459
AED 892 total
includes taxes & fees
29 Sep - 30 Sep
175 LEX - Spacious Two Bedroom! Walkable Downtown!

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

175 LEX - Two Bedroom Condo, Walkable Downtown!

9.8 out of 10, Exceptional, (11)
"Great stay!"
The price is AED 437
AED 865 total
includes taxes & fees
29 Sep - 30 Sep
175 LEX - Two Bedroom Condo, Walkable Downtown!

Graffiti Art Haus - Walk to Central Bank Arena

10.0 out of 10, Exceptional, (34)
"Perfect place to stay for visiting downtown Lexington. "
The price is AED 309
AED 772 total
includes taxes & fees
8 Oct - 9 Oct
Graffiti Art Haus - Walk to Central Bank Arena

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 !"
The price is AED 459
AED 760 total
includes taxes & fees
30 Sep - 1 Oct
This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.

175 LEX - Spacious Two Bedroom - Near Rupp Arena!

9.6 out of 10, Exceptional, (15)
"Great location, easy access to all things downtown"
The price is AED 459
AED 892 total
includes taxes & fees
29 Sep - 30 Sep
175 LEX - Spacious Two Bedroom - Near Rupp Arena!

The Gatsby Getaway, Downtown LEX

10.0 out of 10, Exceptional, (15)
"Comfortable room and great downtown location."
The price is AED 422
AED 774 total
includes taxes & fees
28 Oct - 29 Oct
The Gatsby Getaway, Downtown LEX

Lex In The City - Downtown Condo

9.8 out of 10, Exceptional, (7)
"The place was great. Good location downtown. The bed was one of the most comfortable I have had at a rental space. "
The price is AED 422
AED 774 total
includes taxes & fees
29 Sep - 30 Sep
Lex In The City - Downtown Condo

175 LEX - Quiet Loft Near Rupp Arena & Restaurants

10.0 out of 10, Exceptional, (1)
"Very convenient apartment in downtown Lexington. Loved being able to walk to the great restaurants nearby and to visit our student at the University of Kentucky."
175 LEX - Quiet Loft Near Rupp Arena & Restaurants

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"
Downtown Lex Full Friends Condo

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

Bourbon Condo Downtown Lexington

10.0 out of 10, Exceptional, (11)
"Perfect location, clean and great place to stay. Will stay here again next time we attend an event."
Bourbon Condo Downtown Lexington

Quiet Downtown Lexington Bougie Apartment

9.4 out of 10, Exceptional, (3)
"Beautifully appointed condo, amazingly quiet, given downtown location. Excellent communication with owner. No parking on-site, so you have to find parking in nearby garages, very limited street parking. Convenient location, would definitely stay again."
The price is AED 364
AED 703 total
includes taxes & fees
29 Sep - 30 Sep
Quiet Downtown Lexington Bougie Apartment

175 LEX - Spacious Two Bedroom Downtown Lexington

9.6 out of 10, Exceptional, (30)
"Claire was wonderful to work with"
The price is AED 459
AED 892 total
includes taxes & fees
29 Oct - 30 Oct
175 LEX - Spacious Two Bedroom Downtown Lexington

Downtown LEX - Keeneland Condo

8.0 out of 10, Very Good, (3)
"Great accommodations !!Stayed for one night dropping my daughter off for her fall semester at UK.Convenient to downtown restaurants !"
Downtown LEX - Keeneland Condo

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
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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