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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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.
$274 nightly
The price is $318
Oct 4 - Oct 5
Total with taxes and fees
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
9.0 out of 10, Wonderful, (18 reviews)
"Great location and very clean. "
United States
Andrew K.
$174 nightly
The price is $177
Oct 27 - Oct 28
Total with taxes and fees
This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
A modern living room with a sofa, armchairs, and a coffee table. There is a kitchen area with a bar and pendant lights.

3. Graffiti Art Haus - Walk to Central Bank Arena

Graffiti Art Haus - Walk to Central Bank Arena
Downtown Lexington
10.0 out of 10, Exceptional, (58 reviews)
"Awesome property in great location, host was very helpful, highly recommend!"
United States
Kyle B.
$185 nightly
The price is $197
Oct 26 - Oct 27
Total with taxes and fees
Graffiti Art Haus - Walk to Central Bank Arena
A modern hotel room with a flat-screen TV, a ceiling fan, a wardrobe, and a bedside table with a lamp.

4. 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.
$234 nightly
The price is $266
Oct 4 - Oct 5
Total with taxes and fees
175 LEX - Two Bedroom Condo, Walkable Downtown!
A modern kitchen with a central island, built-in microwave, and stainless steel appliances.

5. The Gatsby Getaway, Downtown LEX

The Gatsby Getaway, Downtown LEX
Downtown Lexington
9.8 out of 10, Exceptional, (18 reviews)
"Top notch communication- very responsive. Property was very nice. I'd definitely work with this host and stay in this property again."
United States
Bill T.
$199 nightly
The price is $228
Oct 4 - Oct 5
Total with taxes and fees
The Gatsby Getaway, Downtown LEX
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

6. 175 LEX - Walkable Downtown Lexington Condo

175 LEX - Walkable Downtown Lexington Condo
Downtown Lexington
10.0 out of 10, Exceptional, (4 reviews)
"Clean property located near lots of resturants/night-life places."
United States
Caitlyn B.
$199 nightly
The price is $228
Oct 4 - Oct 5
Total with taxes and fees
175 LEX - Walkable Downtown Lexington Condo
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.
$199 nightly
The price is $228
Oct 1 - Oct 2
Total with taxes and fees
Downtown Lex Full Friends Condo
A modern living room with a leather sofa, a round coffee table, and a large window with curtains.

8. 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.
$199 nightly
The price is $228
Oct 4 - Oct 5
Total with taxes and fees
Downtown LEX - Keeneland Condo
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
9.2 out of 10, Wonderful, (20 reviews)
"Cleanliness was superb!"
United States
Carla R.
$246 nightly
The price is $280
Oct 1 - Oct 2
Total with taxes and fees
175 LEX - Spacious Two Bedroom! Walkable Downtown!
A modern living room with a black leather sofa, a white ottoman, and a large window with blue curtains.

10. 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.
$199 nightly
The price is $228
Oct 4 - Oct 5
Total with taxes and fees
Lex In The City - Downtown Condo
A wooden deck leading to a red door, brick walls, and a white door in the background.

11. 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.
$232 nightly
The price is $256
Oct 1 - Oct 2
Total with taxes and fees
War Admiral @ The HoM- KY Horse Park 11min, Ark 30min, Walk Downtown/GT College
You will love this destination.

12. 1 Bedroom | Indoor Pool. Free Daily Breakfast

1 Bedroom | Indoor Pool. Free Daily Breakfast
Lexington
10.0 out of 10, Exceptional, (1 review)
$214 nightly
The price is $248
Oct 19 - Oct 20
Total with taxes and fees
1 Bedroom | Indoor Pool. Free Daily Breakfast
A modern living room with a dining area, large windows, and a ceiling fan.

13. 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.
$198 nightly
The price is $227
Oct 25 - Oct 26
Total with taxes and fees
Quiet Downtown Lexington Bougie Apartment
A compact, modern laundry room with a built-in washer and dryer, a blue mop, and a door handle.

14. 175 LEX - Walkable Downtown Lexington - Top Floor

175 LEX - Walkable Downtown Lexington - Top Floor
Downtown Lexington
9.4 out of 10, Exceptional, (12 reviews)
"Everything was great. Wonderful place to stay. Great location. "
United States
Jennifer M.
$211 nightly
The price is $243
Oct 1 - Oct 2
Total with taxes and fees
175 LEX - Walkable Downtown Lexington - Top Floor
A room with a desk, a lamp, a chair, and a poster on the wall.

15. 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.
$213 nightly
The price is $245
Oct 13 - Oct 14
Total with taxes and fees
175 LEX - Walkable Downtown Lexington Condo
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)
"Great place to stay downtown. Clean and fresh. Would recommend."
United States
Brad H.
$199 nightly
The price is $228
Oct 4 - Oct 5
Total with taxes and fees
175 LEX - Walk to Rupp Arena Downtown Top Floor
A modern apartment with a grey sofa, a small wooden table, a kitchen with grey cabinets, a microwave, and a stove.

17. 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.
$199 nightly
The price is $228
Oct 5 - Oct 6
Total with taxes and fees
175 LEX - Loft in Downtown Lexington, Rupp Arena
A modern living room with a sofa, chairs, a dining table, a TV, and a ceiling fan.

18. 175 LEX - Walkable Loft to Rupp Arena & Downtown!

175 LEX - Walkable Loft to Rupp Arena & Downtown!
Downtown Lexington
9.2 out of 10, Wonderful, (19 reviews)
"Room had black hair everywhere. It was gross. My husband is bald and I'm blonde so it wasn't ours. The kitchen sink doesn't drain. There was food all over the floor. Nasty. Not clean at all."
United States
John
$199 nightly
The price is $228
Oct 4 - Oct 5
Total with taxes and fees
175 LEX - Walkable Loft to Rupp Arena & Downtown!
A modern kitchen with a central island, a dining area with a round table, a sofa, and artwork on the walls.

19. Bourbon Condo Downtown Lexington

Bourbon Condo Downtown Lexington
Downtown Lexington
10.0 out of 10, Exceptional, (18 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.
$246 nightly
The price is $280
Oct 1 - Oct 2
Total with taxes and fees
Bourbon Condo Downtown Lexington
A modern kitchen with a central island, bar stools, a coffee bar, and a trash can.

20. 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.
$246 nightly
The price is $280
Oct 5 - Oct 6
Total with taxes and fees
175 LEX - Spacious Two Bedroom - Near Rupp Arena!
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

GuestHouse Lexington

GuestHouse Lexington

8/10 Good
"It was a pleasurable experience"
Richard 4-night trip
Posted 13 hours ago
GuestHouse Lexington

Find out more about Winchester

Winchester Condo Rentals information

Number of reviews
223
Accommodation
51 Condo Rentals
Lowest Price
$177
Highest Price
$318

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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