Search Condos Rentals in Winchester from CA $112

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Check prices for these dates

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Nov 13 - Nov 15
In two weeks
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In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

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 $123
CA $409 total
includes taxes & fees
Nov 9 - Nov 10
Cozy 2-bedroom condo with WiFi, AC in marvelous Lexington
A modern living room with a sofa, armchairs, and a coffee table. There is a kitchen area with a bar and pendant lights.

2. Graffiti Art Haus - Walk to Central Bank Arena

Graffiti Art Haus - Walk to Central Bank Arena
Downtown Lexington
10.0 out of 10, Exceptional, (59 reviews)
"Enjoyed the stay"
United States
Todd S.
The price is CA $112
CA $277 total
includes taxes & fees
Nov 18 - Nov 19
Graffiti Art Haus - Walk to Central Bank Arena
A modern apartment with a living room, kitchen, and dining area.

3. 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, (19 reviews)
"Great location and very clean. "
United States
Andrew K.
The price is CA $133
CA $226 total
includes taxes & fees
Nov 18 - Nov 19
This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
A wooden deck leading to a red door, brick walls, and a white door in the background.

4. 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
9.8 out of 10, Exceptional, (6 reviews)
"Very cute historical property, parking in back, fun location walking distance to shops and restaurants. "
United States
Kiri B.
The price is CA $182
CA $344 total
includes taxes & fees
Nov 29 - Nov 30
War Admiral @ The HoM- KY Horse Park 11min, Ark 30min, Walk Downtown/GT College
A modern kitchen with a central island, stainless steel appliances, and a dining area with wooden chairs and a table.

5. HUGE 3BR Penthouse King bed. Walk 2 RUPP elevator

HUGE 3BR Penthouse King bed. Walk 2 RUPP elevator
Downtown Lexington
10.0 out of 10, Exceptional, (7 reviews)
"Great place to stay! Convenient to downtown and very clean. We had a great stay."
United States
Heather C.
The price is CA $346
CA $702 total
includes taxes & fees
Nov 9 - Nov 10
HUGE 3BR Penthouse King bed. Walk 2 RUPP elevator
A wooden deck leading to a red door, brick walls, and a white door in the background.

6. 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, (8 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 CA $210
CA $399 total
includes taxes & fees
Nov 23 - Nov 24
Man O'War @ The HoM/KY Horse Park 11min/Ark 30min/Walk to Georgetown College
A wooden deck leading to a red door, brick walls, and a white door in the background.

7. Secretariat @ The HoM- Ky Horse Park 11min, Ark 30min, Walk Downtown/GT College

Secretariat @ The HoM- Ky Horse Park 11min, Ark 30min, Walk Downtown/GT College
Georgetown
9.6 out of 10, Exceptional, (8 reviews)
"The place was beautiful!! It was perfect to relax and unwind. "
United States
Danielle B.
The price is CA $210
CA $419 total
includes taxes & fees
Nov 16 - Nov 17
Secretariat @ The HoM- Ky Horse Park 11min, Ark 30min, Walk Downtown/GT College
A wooden deck leading to a red door, brick walls, and a white door in the background.

8. Sir Barton @ The HoM- KY Horse Park 11min, Ark 30min, Walk Downtown / GT College

Sir Barton @ The HoM- KY Horse Park 11min, Ark 30min, Walk Downtown / GT College
Georgetown
9.6 out of 10, Exceptional, (4 reviews)
"Great spot close to KHP!"
United States
Nicole B.
The price is CA $182
CA $345 total
includes taxes & fees
Nov 10 - Nov 11
Sir Barton @ The HoM- KY Horse Park 11min, Ark 30min, Walk Downtown / GT College
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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Learn more about Winchester

Stroll through charming downtown streets lined with local shops and eateries. Tee off at Cassell Creek or Southwind Golf Course, then explore local history at the Bluegrass Heritage Museum.

See all hotels in Winchester
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.

Top reviews in Winchester

A Holiday Inn Express building with a covered entrance, stone pillars, and potted plants.
Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
Winchester

8/10 Good

Good place to stay
Canada
martin
Reviewed April 30, 2025
Holiday Inn Express Lexington East - Winchester by IHG

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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