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
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Winchester condo rentals

Interior

1. 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.
The price is HK$586
HK$2,364 total
includes taxes & fees
7 Sept - 8 Sept
Cozy 2-bedroom condo with WiFi, AC in marvelous Lexington
TV

2. 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, (16 reviews)
"Great location and very clean. "
United States
Andrew K.
The price is HK$1,701
HK$2,399 total
includes taxes & fees
6 Oct - 7 Oct
This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
Smart TV, fireplace, offices

3. Lex In The City - Downtown Condo

Lex In The City - Downtown Condo
Downtown Lexington
9.8 out of 10, Exceptional, (9 reviews)
"Clean and close to everything. Excellent place to stay and I hope to stay there again "
United States
Alison W.
The price is HK$1,078
HK$1,865 total
includes taxes & fees
6 Oct - 7 Oct
Lex In The City - Downtown Condo
Smart TV, offices

4. 175 LEX - Walkable Downtown Lexington Condo

175 LEX - Walkable Downtown Lexington Condo
Downtown Lexington
10.0 out of 10, Exceptional, (3 reviews)
"Were out of shampoo and conditioner when i arrived which showed potential lack of attention to detail. But the place was amazing location downtown, great keurig coffee, clean otherwise. Very comfortable stay. Would recommend others!"
United States
Andrew K.
The price is HK$992
HK$1,761 total
includes taxes & fees
6 Oct - 7 Oct
175 LEX - Walkable Downtown Lexington Condo
Interior

5. 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.
175 LEX - Walkable Downtown Lexington - Top Floor
Lobby

6. Graffiti Art Haus - Walk to Central Bank Arena

Graffiti Art Haus - Walk to Central Bank Arena
Downtown Lexington
10.0 out of 10, Exceptional, (56 reviews)
"Awesome property in great location, host was very helpful, highly recommend!"
United States
Kyle B.
The price is HK$576
HK$1,545 total
includes taxes & fees
8 Sept - 9 Sept
Graffiti Art Haus - Walk to Central Bank Arena
Coffee/tea maker, fridge, microwave, oven

7. 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.
Downtown Lex Full Friends Condo
Interior

8. Bourbon Condo Downtown Lexington

Bourbon Condo Downtown Lexington
Downtown Lexington
10.0 out of 10, Exceptional, (17 reviews)
"We only stayed for a quick night but the apartment was really cute, clean, and right off main street. The beds were comfortable too."
United States
Michele G.
The price is HK$1,078
HK$2,077 total
includes taxes & fees
6 Sept - 7 Sept
Bourbon Condo Downtown Lexington
2 bedrooms, iron/ironing board, travel cot, free WiFi

9. 175 LEX - Spacious Two Bedroom! Walkable Downtown!

175 LEX - Spacious Two Bedroom! Walkable Downtown!
Downtown Lexington
9.4 out of 10, Exceptional, (18 reviews)
"Cleanliness was superb!"
United States
Carla R.
The price is HK$1,164
HK$2,162 total
includes taxes & fees
6 Oct - 7 Oct
175 LEX - Spacious Two Bedroom! Walkable Downtown!
Interior

10. 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$854
HK$1,595 total
includes taxes & fees
6 Sept - 7 Sept
Quiet Downtown Lexington Bougie Apartment
Exterior

11. 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$1,325
HK$1,756 total
includes taxes & fees
7 Sept - 8 Sept
1 Bedroom | Indoor Pool. Free Daily Breakfast
Smart TV, fireplace

12. 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$992
HK$1,761 total
includes taxes & fees
6 Oct - 7 Oct
Downtown LEX - Keeneland Condo
1 bedroom, desk, iron/ironing board, travel cot

13. 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)
"I enjoyed this property. Well cared for and in a good location close to everything downtown. Would stay again."
United States
Brian
The price is HK$992
HK$1,761 total
includes taxes & fees
6 Oct - 7 Oct
175 LEX - Walkable Loft to Rupp Arena & Downtown!
Smart TV

14. 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.
175 LEX - Loft in Downtown Lexington, Rupp Arena
Coffee/tea maker, fridge, microwave, oven

15. 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)
"Overall, this location was great for our trip. We were in town for our daughter's graduation from UofK. We were able to walk everywhere, including Rupp arena for the graduation ceremony. Parking was easy and the condo had everything we needed. The host quickly responded to any messages and check-in was a breeze. I gave the price a 4-star because I thought it was a bit expensive, but every location increased their prices due to the number of people traveling to Lexington for graduation."
United States
Denise C.
The price is HK$1,164
HK$2,162 total
includes taxes & fees
6 Oct - 7 Oct
175 LEX - Spacious Two Bedroom - Near Rupp Arena!
Smart TV

16. 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$854
HK$1,595 total
includes taxes & fees
7 Sept - 8 Sept
175 LEX - Walk to Rupp Arena Downtown Top Floor
Exterior detail

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

War Admiral @ The HoM- KY Horse Park 11min, Ark 30min, Walk Downtown/GT College
Georgetown
9.6 out of 10, Exceptional, (5 reviews)
"Very cute historical property, parking in back, fun location walking distance to shops and restaurants. "
United States
Kiri B.
War Admiral @ The HoM- KY Horse Park 11min, Ark 30min, Walk Downtown/GT College
Interior

18. 175 LEX - Walkable Downtown Lexington Condo

175 LEX - Walkable Downtown Lexington Condo
Downtown Lexington
9.0 out of 10, Wonderful, (6 reviews)
"Just what we needed for our stay."
United States
C R.
175 LEX - Walkable Downtown Lexington Condo
Interior

19. 175 LEX - Walkable Downtown - Rupp Arena - Keeneland

175 LEX - Walkable Downtown - Rupp Arena - Keeneland
Downtown Lexington
7.6 out of 10, Good, (7 reviews)
"Good place to stay. Local to lots of food and fun."
United States
Laura B.
175 LEX - Walkable Downtown - Rupp Arena - Keeneland
Smart TV, fireplace

20. 175 LEX - Walkable Downtown Condo - Stunning View

175 LEX - Walkable Downtown Condo - Stunning View
Downtown Lexington
9.0 out of 10, Wonderful, (12 reviews)
"Great stay"
United States
Anonymous traveller
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

Holiday Inn Express Lexington - Horse Park Area by IHG

Holiday Inn Express Lexington - Horse Park Area by IHG

8/10 Good
"Perfect weekend, wonderful staff!"
Jamie 2-night trip
Posted 4 hours ago
Holiday Inn Express Lexington - Horse Park Area by IHG

Find out more about Winchester

Winchester Condo Rentals information

Number of reviews
198
Accommodation
52 Condo Rentals
Lowest Price
HK$1,545
Highest Price
HK$2,399

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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