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
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

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 HK$649
HK$2,246 total
includes taxes & fees
9 Nov - 10 Nov
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 HK$632
HK$1,498 total
includes taxes & fees
16 Nov - 17 Nov
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 HK$745
HK$1,269 total
includes taxes & fees
16 Nov - 17 Nov
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 HK$1,019
HK$1,927 total
includes taxes & fees
10 Nov - 11 Nov
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 HK$1,943
HK$4,095 total
includes taxes & fees
8 Nov - 9 Nov
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 HK$1,176
HK$2,351 total
includes taxes & fees
10 Nov - 11 Nov
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 HK$1,176
HK$2,351 total
includes taxes & fees
10 Nov - 11 Nov
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 HK$1,019
HK$1,927 total
includes taxes & fees
10 Nov - 11 Nov
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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Top Winchester Hotel Reviews

GuestHouse Lexington

GuestHouse Lexington

8/10 Good
"Everything was good except the bed,every time you moved it would make loud noises and it was very uncomfortable."
Michael t 1-night trip
Posted less than an hour ago
GuestHouse Lexington

Find out more about Winchester

Winchester Condo Rentals information

Number of reviews
53
Accommodation
46 Condo Rentals
Lowest Price
HK$1,269
Highest Price
HK$4,095

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What is there to do in Winchester near my condo?
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