An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Winchester condo rentals

Interior

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

Cozy 2-bedroom condo with WiFi, AC in marvelous Lexington
Lexington
10.0 out of 10, Exceptional, (1 review)
"We were very much impressed with this condo. Felt safe. it was very quiet because a lot of people haven’t moved in yet and the outer construction is completed."
United States
V K.
Cozy 2-bedroom condo with WiFi, AC in marvelous Lexington
Interior

Bourbon Condo Downtown Lexington

Bourbon Condo Downtown Lexington
Downtown Lexington
10.0 out of 10, Exceptional, (16 reviews)
"This place worked out perfectly for us. It was as pictured, cute and trendy with everything we needed. Also, super close to UK campus. We really enjoyed our stay! "
United States
Amy G.
The price is HK$1,164
HK$2,199 total
includes taxes & fees
22 Jul - 23 Jul
Bourbon Condo Downtown Lexington
2 bedrooms, desk, iron/ironing board, travel cot

175 LEX - Two Bedroom Condo, Walkable Downtown!

175 LEX - Two Bedroom Condo, Walkable Downtown!
Downtown Lexington
9.8 out of 10, Exceptional, (14 reviews)
"Great location, walking distance to downtown. Clean condo with plenty of space. "
United States
Charlu F.
The price is HK$992
HK$1,982 total
includes taxes & fees
28 Jul - 29 Jul
175 LEX - Two Bedroom Condo, Walkable Downtown!
Interior

175 LEX - Stunning Downtown Views on Main Street!

175 LEX - Stunning Downtown Views on Main Street!
Downtown Lexington
9.6 out of 10, Exceptional, (49 reviews)
"Condo was exactly as advertised. Great views (floor to ceiling windows), very clean, excellent location. "
United States
Curtis
The price is HK$992
HK$1,789 total
includes taxes & fees
26 Jul - 27 Jul
175 LEX - Stunning Downtown Views on Main Street!
2 bedrooms, iron/ironing board, travel cot, free WiFi

175 LEX - Spacious Two Bedroom! Walkable Downtown!

175 LEX - Spacious Two Bedroom! Walkable Downtown!
Downtown Lexington
9.6 out of 10, Exceptional, (17 reviews)
"Cleanliness was superb!"
United States
Carla R.
The price is HK$1,078
HK$2,086 total
includes taxes & fees
22 Jul - 23 Jul
175 LEX - Spacious Two Bedroom! Walkable Downtown!
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
8.8 out of 10, Excellent, (15 reviews)
"The condo was beautiful and very clean and everything we needed from dishes and kitchen items to laundry, facilities, and soap and accessories. We enjoyed this place and will happily stay again."
United States
Sylvia B.
The price is HK$870
HK$1,477 total
includes taxes & fees
23 Jul - 24 Jul
This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
Smart TV

175 LEX - Walkable Loft to Rupp Arena & Downtown!

175 LEX - Walkable Loft to Rupp Arena & Downtown!
Downtown Lexington
9.6 out of 10, Exceptional, (17 reviews)
"Excellent communication with very timely responses. They worked through any concerns with great ease. Highly recommend this property in downtown Lexington in the heart of it all. It’s a very practical option that is well resourced and comfortable."
United States
Tafani
The price is HK$992
HK$1,761 total
includes taxes & fees
22 Jul - 23 Jul
175 LEX - Walkable Loft to Rupp Arena & Downtown!
Smart TV, fireplace, offices

Lex In The City - Downtown Condo

Lex In The City - Downtown Condo
Downtown Lexington
9.8 out of 10, Exceptional, (9 reviews)
"We had a quick visit for my daughter’s graduation. Easy access and good location. "
United States
Sarah S.
The price is HK$992
HK$1,761 total
includes taxes & fees
22 Jul - 23 Jul
Lex In The City - Downtown Condo
Exterior

1 Bedroom | Indoor Pool. Free Daily Breakfast

1 Bedroom | Indoor Pool. Free Daily Breakfast
Lexington
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,265
HK$1,651 total
includes taxes & fees
16 Aug - 17 Aug
1 Bedroom | Indoor Pool. Free Daily Breakfast
Coffee/tea maker, fridge, microwave, oven

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.
The price is HK$992
HK$1,789 total
includes taxes & fees
26 Jul - 27 Jul
Downtown Lex Full Friends Condo
Interior

Quiet Downtown Lexington Bougie Apartment

Quiet Downtown Lexington Bougie Apartment
Downtown Lexington
8.0 out of 10, Very good, (5 reviews)
"Great location in downtown Lexington! The place was clean and well appointed. We would definitely rent again! "
United States
Bernadette R.
The price is HK$992
HK$1,761 total
includes taxes & fees
22 Jul - 23 Jul
Quiet Downtown Lexington Bougie Apartment
Smart TV, fireplace

Downtown LEX - Keeneland Condo

Downtown LEX - Keeneland Condo
Downtown Lexington
8.0 out of 10, Very good, (3 reviews)
"Great accommodations !!Stayed for one night dropping my daughter off for her fall semester at UK.Convenient to downtown restaurants !"
United States
Karin P.
The price is HK$1,078
HK$1,865 total
includes taxes & fees
17 Aug - 18 Aug
Downtown LEX - Keeneland Condo
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, (49 reviews)
"Awesome property in great location, host was very helpful, highly recommend!"
United States
Kyle B.
The price is HK$576
HK$1,536 total
includes taxes & fees
22 Jul - 23 Jul
Graffiti Art Haus - Walk to Central Bank Arena
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.
The price is HK$1,176
HK$2,463 total
includes taxes & fees
20 Jul - 21 Jul
Man O'War @ The HoM/KY Horse Park 11min/Ark 30min/Walk to Georgetown College
3 bedrooms, desk, iron/ironing board, travel cot

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

Penthouse @ 175 LEX -Walk to Rupp Arena on Main St
Downtown Lexington
9.8 out of 10, Exceptional, (19 reviews)
"Great place in the heart of downtown walking distance to a great restaurant Nic and Norman and the Rupp arena. We enjoyed our stay! Spacious clean and lovely! "
United States
Carly K.
The price is HK$2,544
HK$4,333 total
includes taxes & fees
23 Jul - 24 Jul
Penthouse @ 175 LEX -Walk to Rupp Arena on Main St
Smart TV

175 LEX - Spacious Two Bedroom Downtown Lexington

175 LEX - Spacious Two Bedroom Downtown Lexington
Downtown Lexington
9.6 out of 10, Exceptional, (35 reviews)
"Great location. great stay. Thank you!"
United States
Diane D.
The price is HK$1,078
HK$2,104 total
includes taxes & fees
28 Jul - 29 Jul
175 LEX - Spacious Two Bedroom Downtown Lexington
Interior

The Gatsby Getaway, Downtown LEX

The Gatsby Getaway, Downtown LEX
Downtown Lexington
9.8 out of 10, Exceptional, (18 reviews)
"Great location. Easy check in process. "
United States
Kim Y.
The price is HK$992
HK$1,761 total
includes taxes & fees
22 Jul - 23 Jul
The Gatsby Getaway, Downtown LEX
Coffee/tea maker, fridge, microwave, oven

175 LEX - Spacious Two Bedroom - Near Rupp Arena!

175 LEX - Spacious Two Bedroom - Near Rupp Arena!
Downtown Lexington
9.4 out of 10, Exceptional, (22 reviews)
"Room needed to be swept and mopped. There was and trash in the floors. The couch needs a good cleaning, one of the bar stools is broken. We found bottle caps and q-tips left in the room that were used. The couch was very uncomfortable for one of our guests. We did find a roll out cot that was helpful. The elevator was out of service, which wa beyond control. The location was great and the condo was very pretty, there was just some additional cleaning/ maintenance that needed to be done."
United States
Lesa
The price is HK$1,078
HK$2,086 total
includes taxes & fees
4 Aug - 5 Aug
175 LEX - Spacious Two Bedroom - Near Rupp Arena!
Smart TV

175 LEX - Walk to Rupp Arena Downtown Top Floor

175 LEX - Walk to Rupp Arena Downtown Top Floor
Downtown Lexington
9.4 out of 10, Exceptional, (22 reviews)
"Like new condo well equipped in a good location - highly recommended!"
United States
Jim F.
The price is HK$992
HK$1,761 total
includes taxes & fees
22 Jul - 23 Jul
175 LEX - Walk to Rupp Arena Downtown Top Floor
Smart TV

175 LEX - Walkable Downtown Lexington - Top Floor

175 LEX - Walkable Downtown Lexington - Top Floor
Downtown Lexington
9.4 out of 10, Exceptional, (11 reviews)
"Everything was great. Wonderful place to stay. Great location. "
United States
Jennifer M.
The price is HK$992
HK$1,761 total
includes taxes & fees
22 Jul - 23 Jul
175 LEX - Walkable Downtown Lexington - Top Floor
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

8/10 Good
"Room clean and friendly staff. Good breakfast."
Samuel 4-night trip
Posted less than an hour ago
Quality Inn Lexington -Horse Park

Find out more about Winchester

Winchester Condo Rentals information

Number of reviews
263
Accommodation
52 Condo Rentals
Lowest Price
HK$1,477
Highest Price
HK$4,333

Frequently asked questions

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What is there to do in Winchester near my condo?
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