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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Winchester condo rentals

TV

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
9.2 out of 10, Wonderful, (11 reviews)
"Very clean and a very nice, quiet area."
United States
Mollie M.
$169 nightly
The price is $172
Feb 16 - Feb 17
Total with taxes and fees
This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
Smart TV

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 reviews)
"Like new condo well equipped in a good location - highly recommended!"
United States
Jim F.
$193 nightly
The price is $221
Feb 15 - Feb 16
Total with taxes and fees
175 LEX - Walk to Rupp Arena Downtown Top Floor
Smart TV, offices

175 LEX - Walkable Downtown Lexington Condo

175 LEX - Walkable Downtown Lexington Condo
Downtown Lexington
10.0 out of 10, Exceptional, (1 review)
"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.
$178 nightly
The price is $204
Feb 19 - Feb 20
Total with taxes and fees
175 LEX - Walkable Downtown Lexington Condo
Fridge, microwave, oven, dishwasher

175 LEX - Spacious Two Bedroom - Near Rupp Arena!

175 LEX - Spacious Two Bedroom - Near Rupp Arena!
Downtown Lexington
9.6 out of 10, Exceptional, (18 reviews)
"Great location, easy access to all things downtown"
United States
Alex
$231 nightly
The price is $263
Mar 1 - Mar 2
Total with taxes and fees
175 LEX - Spacious Two Bedroom - Near Rupp Arena!
Lobby

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 reviews)
"Perfect place to stay for visiting downtown Lexington. "
United States
Amy B.
$193 nightly
The price is $206
Feb 15 - Feb 16
Total with taxes and fees
Graffiti Art Haus - Walk to Central Bank Arena
Smart TV, fireplace, offices

Lex In The City - Downtown Condo

Lex In The City - Downtown Condo
Downtown Lexington
9.8 out of 10, Exceptional, (8 reviews)
"We had a quick visit for my daughter’s graduation. Easy access and good location. "
United States
Sarah S.
$200 nightly
The price is $229
Feb 15 - Feb 16
Total with taxes and fees
Lex In The City - Downtown Condo
Interior

Quiet Downtown Lexington Bougie Apartment

Quiet Downtown Lexington Bougie Apartment
Downtown Lexington
9.6 out of 10, Exceptional, (4 reviews)
"Great location in downtown Lexington! The place was clean and well appointed. We would definitely rent again! "
United States
Bernadette R.
$193 nightly
The price is $221
Feb 15 - Feb 16
Total with taxes and fees
Quiet Downtown Lexington Bougie Apartment
Fridge, microwave, oven, stovetop

Downtown Lex Full Friends Condo

Downtown Lex Full Friends Condo
Downtown Lexington
9.0 out of 10, Wonderful, (2 reviews)
"Very clean, nice place, well furnished. Wnjoyed our stay. Convenient downtown location."
United States
Paul B.
$193 nightly
The price is $221
Feb 15 - Feb 16
Total with taxes and fees
Downtown Lex Full Friends Condo
Exterior detail

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 reviews)
"Very nice place. It fit our needs for a quick stop in Georgetown. Communication with the host was excellent."
United States
Rebecca M.
$282 nightly
The price is $311
Feb 16 - Feb 17
Total with taxes and fees
Man O'War @ The HoM/KY Horse Park 11min/Ark 30min/Walk to Georgetown College
2 bedrooms, iron/ironing board, travel crib, free WiFi

175 LEX - Spacious Two Bedroom! Walkable Downtown!

175 LEX - Spacious Two Bedroom! Walkable Downtown!
Downtown Lexington
9.4 out of 10, Exceptional, (14 reviews)
"Great downtown location with nice view. Comfortable and clean space. Convenient parking. "
United States
Holly L.
$231 nightly
The price is $263
Mar 1 - Mar 2
Total with taxes and fees
175 LEX - Spacious Two Bedroom! Walkable Downtown!
Exterior

1 Bedroom | Indoor Pool. Free Daily Breakfast

1 Bedroom | Indoor Pool. Free Daily Breakfast
Lexington
$161 nightly
The price is $187
Feb 14 - Feb 15
Total with taxes and fees
1 Bedroom | Indoor Pool. Free Daily Breakfast
Smart TV

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 review)
"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.
$189 nightly
The price is $217
Feb 19 - Feb 20
Total with taxes and fees
175 LEX - Loft in Downtown Lexington, Rupp Arena
Smart TV

175 LEX - Spacious Two Bedroom Downtown Lexington

175 LEX - Spacious Two Bedroom Downtown Lexington
Downtown Lexington
9.6 out of 10, Exceptional, (34 reviews)
"Location, location, location! Great views of Main Street from the bedrooms and living rooms."
United States
Fisher S.
$231 nightly
The price is $263
Feb 16 - Feb 17
Total with taxes and fees
175 LEX - Spacious Two Bedroom Downtown Lexington
Interior

175 LEX - Two Bedroom Condo, Walkable Downtown!

175 LEX - Two Bedroom Condo, Walkable Downtown!
Downtown Lexington
9.8 out of 10, Exceptional, (13 reviews)
"Great location, walking distance to downtown. Clean condo with plenty of space. "
United States
Charlu F.
$228 nightly
The price is $259
Feb 18 - Feb 19
Total with taxes and fees
175 LEX - Two Bedroom Condo, Walkable Downtown!
Fridge, microwave, oven, stovetop

175 LEX - Walkable Downtown Lexington - Top Floor

175 LEX - Walkable Downtown Lexington - Top Floor
Downtown Lexington
9.2 out of 10, Wonderful, (9 reviews)
"The property is accessible to everything downtown. It was clean and comfortable, just as advertised and the host was responsive and helpful."
United States
Jeremy N.
$180 nightly
The price is $206
Feb 15 - Feb 16
Total with taxes and fees
175 LEX - Walkable Downtown Lexington - Top Floor
Interior

Bourbon Condo Downtown Lexington

Bourbon Condo Downtown Lexington
Downtown Lexington
10.0 out of 10, Exceptional, (12 reviews)
"Great stay and very clean!"
United States
Nathan L.
$248 nightly
The price is $283
Feb 16 - Feb 17
Total with taxes and fees
Bourbon Condo Downtown Lexington
1 bedroom, desk, iron/ironing board, travel crib

175 LEX - Walkable Downtown Lexington Condo

175 LEX - Walkable Downtown Lexington Condo
Downtown Lexington
8.8 out of 10, Excellent, (5 reviews)
"Just what we needed for our stay."
United States
C R.
$196 nightly
The price is $225
Mar 1 - Mar 2
Total with taxes and fees
175 LEX - Walkable Downtown Lexington Condo
Interior

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 reviews)
"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.
$193 nightly
The price is $221
Feb 15 - Feb 16
Total with taxes and fees
175 LEX - Quiet Loft Near Rupp Arena & Restaurants
Interior

The Gatsby Getaway, Downtown LEX

The Gatsby Getaway, Downtown LEX
Downtown Lexington
9.8 out of 10, Exceptional, (16 reviews)
"Great location. Easy check in process. "
United States
Kim Y.
$193 nightly
The price is $221
Feb 15 - Feb 16
Total with taxes and fees
The Gatsby Getaway, Downtown LEX
Smart TV, fireplace

175 LEX - Walkable Downtown Condo - Stunning View

175 LEX - Walkable Downtown Condo - Stunning View
Downtown Lexington
8.8 out of 10, Excellent, (11 reviews)
"Great stay"
United States
Anonymous traveler
$207 nightly
The price is $238
Feb 22 - Feb 23
Total with taxes and fees
175 LEX - Walkable Downtown Condo - Stunning View
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

The Manchester

The Manchester

10/10 Excellent
"Friendly and attentive staff. Great location, bar and onsite restaurant. "
Donna 1-night trip
Posted 2 days ago
The Manchester

Find out more about Winchester

Winchester Condo Rentals information

Number of reviews
212
Accommodation
54 Condo Rentals
Lowest Price
$172
Highest Price
$311

Frequently asked questions

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What is there to do in Winchester near my condo?
Once you've settled into your hotel, venture out and discover the fantastic things Winchester has on offer. Southwind Golf Course is a top attraction to add to your travel itinerary.

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