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Check prices for these dates

Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan
In one month
23 Jan - 25 Jan
In two months
20 Feb - 22 Feb

Our top choices for Winchester condo rentals

1 bedroom, iron/ironing board, travel crib, free WiFi
175 LEX - Walk to Rupp Arena Downtown Top Floor

175 LEX - Walk to Rupp Arena Downtown Top Floor

175 LEX - Walk to Rupp Arena Downtown Top Floor
Downtown Lexington
9.8 out of 10, Exceptional, (20)
"The place was perfect for the weekend. Great location easy to walk to bars, restaurants and the local farmers market. "
United States
Karen R.
The price is AED 364
AED 703 total
includes taxes & fees
30 Dec - 31 Dec
175 LEX - Walk to Rupp Arena Downtown Top Floor
Interior
175 LEX - Spacious Two Bedroom - Near Rupp Arena!

175 LEX - Spacious Two Bedroom - Near Rupp Arena!

175 LEX - Spacious Two Bedroom - Near Rupp Arena!
Downtown Lexington
9.6 out of 10, Exceptional, (16)
"Great location, easy access to all things downtown"
United States
Alex
The price is AED 422
AED 848 total
includes taxes & fees
29 Dec - 30 Dec
175 LEX - Spacious Two Bedroom - Near Rupp Arena!
Fridge, coffee/tea maker, cookware/dishes/utensils
This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.

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

This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
Lexington
9.0 out of 10, Wonderful, (10)
"We enjoyed our girls weekend and this place was perfect !"
United States
Allison G.
The price is AED 349
AED 629 total
includes taxes & fees
29 Dec - 30 Dec
This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
1 bedroom, iron/ironing board, travel crib, free WiFi
175 LEX - Stunning Downtown Views on Main Street!

175 LEX - Stunning Downtown Views on Main Street!

175 LEX - Stunning Downtown Views on Main Street!
Downtown Lexington
9.8 out of 10, Exceptional, (44)
"Very clean and convenient to Rupp arena "
United States
Randy R.
The price is AED 386
AED 730 total
includes taxes & fees
5 Jan - 6 January 2026
175 LEX - Stunning Downtown Views on Main Street!
Exterior
Graffiti Art Haus - Walk to Central Bank Arena

Graffiti Art Haus - Walk to Central Bank Arena

Graffiti Art Haus - Walk to Central Bank Arena
Downtown Lexington
10.0 out of 10, Exceptional, (36)
"Perfect place to stay for visiting downtown Lexington. "
United States
Amy B.
The price is AED 409
AED 896 total
includes taxes & fees
28 Jan - 29 January 2026
Graffiti Art Haus - Walk to Central Bank Arena
Fridge, microwave, oven, stovetop
Cozy 2-bedroom condo with WiFi, AC in marvelous Lexington

Cozy 2-bedroom condo with WiFi, AC in marvelous Lexington

Cozy 2-bedroom condo with WiFi, AC in marvelous Lexington
2.0 star property
Lexington
The price is AED 347
AED 1,033 total
includes taxes & fees
30 Dec - 31 Dec
Cozy 2-bedroom condo with WiFi, AC in marvelous Lexington
Smart TV, fireplace, offices
Lex In The City - Downtown Condo

Lex In The City - Downtown Condo

Lex In The City - Downtown Condo
Downtown Lexington
9.8 out of 10, Exceptional, (8)
"We had a quick visit for my daughter’s graduation. Easy access and good location. "
United States
Sarah S.
The price is AED 386
AED 730 total
includes taxes & fees
29 Dec - 30 Dec
Lex In The City - Downtown Condo
Smart TV
Quiet Downtown Lexington Bougie Apartment

Quiet Downtown Lexington Bougie Apartment

Quiet Downtown Lexington Bougie Apartment
Downtown Lexington
9.6 out of 10, Exceptional, (4)
"Great location in downtown Lexington! The place was clean and well appointed. We would definitely rent again! "
United States
Bernadette R.
The price is AED 364
AED 703 total
includes taxes & fees
4 Jan - 5 January 2026
Quiet Downtown Lexington Bougie Apartment
2 bedrooms, iron/ironing board, travel crib, free WiFi
175 LEX - Spacious Two Bedroom! Walkable Downtown!

175 LEX - Spacious Two Bedroom! Walkable Downtown!

175 LEX - Spacious Two Bedroom! Walkable Downtown!
Downtown Lexington
9.4 out of 10, Exceptional, (14)
"Nice little apartment for business travel. Great location - loved the library and Kentucky Theater just across the street. "
United States
Melissa J.
The price is AED 422
AED 848 total
includes taxes & fees
29 Dec - 30 Dec
175 LEX - Spacious Two Bedroom! Walkable Downtown!
Exterior
1 Bedroom | Near the University of Kentucky.

1 Bedroom | Near the University of Kentucky.

1 Bedroom | Near the University of Kentucky.
Lexington
The price is AED 413
AED 565 total
includes taxes & fees
28 Jan - 29 January 2026
1 Bedroom | Near the University of Kentucky.
Fridge, microwave, oven, stovetop
Downtown Lex Full Friends Condo

Downtown Lex Full Friends Condo

Downtown Lex Full Friends Condo
Downtown Lexington
9.0 out of 10, Wonderful, (2)
"Very clean, nice place, well furnished. Wnjoyed our stay. Convenient downtown location."
United States
Paul B.
The price is AED 364
AED 703 total
includes taxes & fees
4 Jan - 5 January 2026
Downtown Lex Full Friends Condo
Outdoor dining
Man O'War @ The HoM/KY Horse Park 11min/Ark 30min/Walk to Georgetown College

Man O'War @ The HoM/KY Horse Park 11min/Ark 30min/Walk to Georgetown College

Man O'War @ The HoM/KY Horse Park 11min/Ark 30min/Walk to Georgetown College
Georgetown
10.0 out of 10, Exceptional, (5)
"Very nice place. It fit our needs for a quick stop in Georgetown. Communication with the host was excellent."
United States
Rebecca M.
The price is AED 588
AED 1,190 total
includes taxes & fees
29 Dec - 30 Dec
Man O'War @ The HoM/KY Horse Park 11min/Ark 30min/Walk to Georgetown College
Fridge, microwave, oven, stovetop
175 LEX - Loft in Downtown Lexington, Rupp Arena

175 LEX - Loft in Downtown Lexington, Rupp Arena

175 LEX - Loft in Downtown Lexington, Rupp Arena
Downtown Lexington
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!"
United States
M M.
The price is AED 386
AED 730 total
includes taxes & fees
4 Jan - 5 January 2026
175 LEX - Loft in Downtown Lexington, Rupp Arena
2 bedrooms, desk, iron/ironing board, travel crib
Bourbon Condo Downtown Lexington

Bourbon Condo Downtown Lexington

Bourbon Condo Downtown Lexington
Downtown Lexington
10.0 out of 10, Exceptional, (11)
"Great stay and very clean!"
United States
Nathan L.
The price is AED 422
AED 848 total
includes taxes & fees
4 Jan - 5 January 2026
Bourbon Condo Downtown Lexington
2 bedrooms, desk, iron/ironing board, travel crib
175 LEX - Spacious Two Bedroom Downtown Lexington

175 LEX - Spacious Two Bedroom Downtown Lexington

175 LEX - Spacious Two Bedroom Downtown Lexington
Downtown Lexington
9.6 out of 10, Exceptional, (33)
"Location, location, location! Great views of Main Street from the bedrooms and living rooms."
United States
Fisher S.
The price is AED 422
AED 848 total
includes taxes & fees
29 Dec - 30 Dec
175 LEX - Spacious Two Bedroom Downtown Lexington
Smart TV, fireplace
175 LEX - Walkable Downtown Condo - Stunning View

175 LEX - Walkable Downtown Condo - Stunning View

175 LEX - Walkable Downtown Condo - Stunning View
Downtown Lexington
8.8 out of 10, Excellent, (11)
"Convenient, clean, and easy!"
United States
Tracey H.
The price is AED 386
AED 730 total
includes taxes & fees
4 Jan - 5 January 2026
175 LEX - Walkable Downtown Condo - Stunning View
Smart TV, offices
175 LEX - Walkable Downtown Lexington Condo

175 LEX - Walkable Downtown Lexington Condo

175 LEX - Walkable Downtown Lexington Condo
Downtown Lexington
10.0 out of 10, Exceptional, (1)
"I don't have a single complaint. I enjoyed my stay very much! It was exactly as advertised. If I find myself in Lexington again, I would love to stay here again. 10/10"
United States
Alex A.
The price is AED 386
AED 730 total
includes taxes & fees
4 Jan - 5 January 2026
175 LEX - Walkable Downtown Lexington Condo
Smart TV
175 LEX - Quiet Loft Near Rupp Arena & Restaurants

175 LEX - Quiet Loft Near Rupp Arena & Restaurants

175 LEX - Quiet Loft Near Rupp Arena & Restaurants
Downtown Lexington
9.0 out of 10, Wonderful, (2)
"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."
United States
Kathleen S.
The price is AED 364
AED 703 total
includes taxes & fees
29 Dec - 30 Dec
175 LEX - Quiet Loft Near Rupp Arena & Restaurants
2 bedrooms, desk, iron/ironing board, travel crib
175 LEX - Two Bedroom Condo, Walkable Downtown!

175 LEX - Two Bedroom Condo, Walkable Downtown!

175 LEX - Two Bedroom Condo, Walkable Downtown!
Downtown Lexington
9.8 out of 10, Exceptional, (12)
"Great stay!"
United States
Brian M.
The price is AED 437
AED 882 total
includes taxes & fees
8 Jan - 9 January 2026
175 LEX - Two Bedroom Condo, Walkable Downtown!
Fridge, microwave, oven, stovetop
The Gatsby Getaway, Downtown LEX

The Gatsby Getaway, Downtown LEX

The Gatsby Getaway, Downtown LEX
Downtown Lexington
9.8 out of 10, Exceptional, (16)
"Great location. Easy check in process. "
United States
Kim Y.
The price is AED 364
AED 703 total
includes taxes & fees
4 Jan - 5 January 2026
The Gatsby Getaway, Downtown LEX
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

Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

10/10 Excellent
"Great staff and facility. "
Nathan 1-night trip
Posted 3 days ago
Origin Lexington a Wyndham Hotel

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