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

Our top choices for Winchester condo rentals

A covered porch with a wooden door, white railings, and a view of a grassy yard and parked cars.

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 CA $104
CA $422 total
includes taxes & fees
Sep 7 - Sep 8
Cozy 2-bedroom condo with WiFi, AC in marvelous Lexington
A modern apartment with a living room, kitchen, and dining area.

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 CA $131
CA $237 total
includes taxes & fees
Sep 8 - Sep 9
This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
A modern living room with a black leather sofa, a white ottoman, and a large window with blue curtains.

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 CA $165
CA $304 total
includes taxes & fees
Sep 8 - Sep 9
Lex In The City - Downtown Condo
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

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 CA $151
CA $281 total
includes taxes & fees
Sep 6 - Sep 7
175 LEX - Walkable Downtown Lexington Condo
A compact, modern laundry room with a built-in washer and dryer, a blue mop, and a door handle.

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.
The price is CA $160
CA $294 total
includes taxes & fees
Sep 6 - Sep 7
175 LEX - Walkable Downtown Lexington - Top Floor
A modern living room with a sofa, armchairs, and a coffee table. There is a kitchen area with a bar and pendant lights.

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 CA $102
CA $274 total
includes taxes & fees
Sep 8 - Sep 9
Graffiti Art Haus - Walk to Central Bank Arena
A modern kitchen with stainless steel appliances, white countertops, and dark wooden cabinets.

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.
The price is CA $151
CA $281 total
includes taxes & fees
Sep 6 - Sep 7
Downtown Lex Full Friends Condo
A modern kitchen with a central island, a dining area with a round table, a sofa, and artwork on the walls.

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 CA $190
CA $370 total
includes taxes & fees
Sep 6 - Sep 7
Bourbon Condo Downtown Lexington
A hallway with a wooden floor, a mirror, a small table with a vase, and a bed in the background.

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 CA $181
CA $354 total
includes taxes & fees
Sep 6 - Sep 7
175 LEX - Spacious Two Bedroom! Walkable Downtown!
A modern living room with a dining area, large windows, and a ceiling fan.

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 CA $151
CA $281 total
includes taxes & fees
Sep 6 - Sep 7
Quiet Downtown Lexington Bougie Apartment

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 CA $234
CA $308 total
includes taxes & fees
Sep 7 - Sep 8
1 Bedroom | Indoor Pool. Free Daily Breakfast
A modern living room with a leather sofa, a round coffee table, and a large window with curtains.

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 CA $158
CA $294 total
includes taxes & fees
Sep 20 - Sep 21
Downtown LEX - Keeneland Condo
A bedroom with a bed, a nightstand, a ceiling fan, a wall-mounted light, and a ceiling vent.

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 CA $150
CA $284 total
includes taxes & fees
Sep 8 - Sep 9
175 LEX - Walkable Loft to Rupp Arena & Downtown!
A modern apartment with a grey sofa, a small wooden table, a kitchen with grey cabinets, a microwave, and a stove.

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.
The price is CA $151
CA $285 total
includes taxes & fees
Sep 7 - Sep 8
175 LEX - Loft in Downtown Lexington, Rupp Arena
A modern kitchen with a central island, bar stools, a coffee bar, and a trash can.

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 CA $181
CA $356 total
includes taxes & fees
Sep 8 - Sep 9
175 LEX - Spacious Two Bedroom - Near Rupp Arena!
A modern living room with a ceiling fan, a flat-screen TV mounted on the wall, a round coffee table, and a sofa.

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 CA $150
CA $284 total
includes taxes & fees
Sep 8 - Sep 9
175 LEX - Walk to Rupp Arena Downtown Top Floor
A wooden deck leading to a red door, brick walls, and a white door in the background.

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.
The price is CA $179
CA $357 total
includes taxes & fees
Sep 8 - Sep 9
War Admiral @ The HoM- KY Horse Park 11min, Ark 30min, Walk Downtown/GT College
A hallway with two grey louvered doors, a bench, and a poster on the wall.

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.
The price is CA $151
CA $285 total
includes taxes & fees
Sep 7 - Sep 8
175 LEX - Walkable Downtown Lexington Condo
A modern kitchen with a central island, dark cabinetry, and pendant lighting.

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.
The price is CA $160
CA $294 total
includes taxes & fees
Sep 6 - Sep 7
175 LEX - Walkable Downtown - Rupp Arena - Keeneland
A modern living room with a large window, a gray sofa, white chairs, and a ceiling fan.

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
The price is CA $166
CA $305 total
includes taxes & fees
Sep 7 - Sep 8
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 1 hour ago
Holiday Inn Express Lexington - Horse Park Area by IHG

Find out more about Winchester

Winchester Condo Rentals information

Number of reviews
198
Accommodation
51 Condo Rentals
Lowest Price
CA $244
Highest Price
CA $447

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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