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.

Apartments in Winchester for Rent

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Winchester apartments

Private kitchen

‘Edith’ Carriage House Getaway - Hamburg/I-75!

‘Edith’ Carriage House Getaway - Hamburg/I-75!
Lexington
9.6 out of 10, Exceptional, (5 reviews)
"Had difficulties checking in other than that felt right at home!"
United States
Kaydance
$114 nightly
The price is $133
Aug 10 - Aug 11
Total with taxes and fees
‘Edith’ Carriage House Getaway - Hamburg/I-75!
Private kitchen

The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling

The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling
Mount Sterling
10.0 out of 10, Exceptional, (1 review)
"Everything was perfect!"
United States
Miguel
$134 nightly
The price is $148
Aug 4 - Aug 5
Total with taxes and fees
The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling
Dining

1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Lexington
9.8 out of 10, Exceptional, (48 reviews)
"The property is misrepresented in the listing. It is not a non-smoking apartment but is a sketchy motel room that has definitely been smoked in. The smoke detector was wrapped in plastic wrap. It was dirty and we couldn’t stay there. We had to book another room for the night which was amazing."
United States
Tracy
$65 nightly
The price is $72
Jul 30 - Jul 31
Total with taxes and fees
1 King Bed | Non-Smoking, Micfridge
Dining

Luxury on Main / South

Luxury on Main / South
Richmond
10.0 out of 10, Exceptional, (53 reviews)
"Clean, well stocked and comfortable. I always enjoy my stay here. "
United States
Robert T.
$141 nightly
The price is $155
Jul 30 - Jul 31
Total with taxes and fees
Luxury on Main / South
Exterior

Mint Julep - Studio Apartment in Downtown Lexington

Mint Julep - Studio Apartment in Downtown Lexington
Lexington
10.0 out of 10, Exceptional, (1 review)
$170 nightly
The price is $197
Aug 2 - Aug 3
Total with taxes and fees
Mint Julep - Studio Apartment in Downtown Lexington
Coffee/tea maker, fridge, microwave, oven

Modern 2bd 2ba - Near I75, No Steps, Free Wifi

Modern 2bd 2ba - Near I75, No Steps, Free Wifi
Richmond
9.8 out of 10, Exceptional, (90 reviews)
"Everything was fantastic!!"
United States
Leah Anne G.
$207 nightly
The price is $225
Aug 2 - Aug 3
Total with taxes and fees
Modern 2bd 2ba - Near I75, No Steps, Free Wifi
Exterior detail

Treetops Solar Sanctuary

Treetops Solar Sanctuary
Chevy Chase
10.0 out of 10, Exceptional, (92 reviews)
"Such a wonderful little hidden gem! The host was fantastic and was perfect for a trip up to Lexington! Would use again and would highly recommend!"
United States
Matthew Y.
$153 nightly
The price is $178
Jul 30 - Jul 31
Total with taxes and fees
Treetops Solar Sanctuary
2 bedrooms, iron/ironing board, travel crib, WiFi (free)

The Kenwick Pied-à-terre - Lexington Apartment with Historic Charm

The Kenwick Pied-à-terre - Lexington Apartment with Historic Charm
Kenwick
10.0 out of 10, Exceptional, (1 review)
"Great communication!"
United States
Myles P.
$287 nightly
The price is $333
Aug 2 - Aug 3
Total with taxes and fees
The Kenwick Pied-à-terre - Lexington Apartment with Historic Charm
Smart TV, fireplace

Luxury on Main / West

Luxury on Main / West
Richmond
9.6 out of 10, Exceptional, (58 reviews)
"Wonderful place to stay. Would gladly return."
United States
Joshua N.
$156 nightly
The price is $171
Aug 24 - Aug 25
Total with taxes and fees
Luxury on Main / West
1 bedroom, iron/ironing board, WiFi, bed sheets

Westfield Blue

Westfield Blue
Richmond
9.0 out of 10, Wonderful, (8 reviews)
"This is a fantastic property. Incredible comfort, walkable to all of the historic downtown, and delightfully and tastefully decorated. I even took ideas for a home I am designing."
United States
Keith G.
$158 nightly
The price is $174
Aug 3 - Aug 4
Total with taxes and fees
Westfield Blue
Microwave, oven, stovetop, dishwasher

Earl Grey - Studio Space in Downtown Lexington

Earl Grey - Studio Space in Downtown Lexington
Lexington
$266 nightly
The price is $309
Aug 2 - Aug 3
Total with taxes and fees
Earl Grey - Studio Space in Downtown Lexington
Outdoor dining

Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington

Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington
Downtown Lexington
10.0 out of 10, Exceptional, (33 reviews)
"Great spot, great location, great host."
United States
Jill
$124 nightly
The price is $144
Aug 5 - Aug 6
Total with taxes and fees
Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington
Interior

Morning Glory - Cozy Apartment in Downtown Lexington

Morning Glory - Cozy Apartment in Downtown Lexington
Lexington
$182 nightly
The price is $211
Aug 3 - Aug 4
Total with taxes and fees
Morning Glory - Cozy Apartment in Downtown Lexington
Exterior

1200 sf Apt -3 BR-Amazing Beds-Walk to EKU & Downtown Venues - 5 minutes to I-75

1200 sf Apt -3 BR-Amazing Beds-Walk to EKU & Downtown Venues - 5 minutes to I-75
Richmond
9.8 out of 10, Exceptional, (15 reviews)
"Everything was great. Looking forward to coming back in the future."
United States
Jacob D.
$270 nightly
The price is $298
Aug 2 - Aug 3
Total with taxes and fees
1200 sf Apt -3 BR-Amazing Beds-Walk to EKU & Downtown Venues - 5 minutes to I-75
Interior

Westfield Green

Westfield Green
Richmond
10.0 out of 10, Exceptional, (20 reviews)
"Wonderful place to stay. Te bathroom door squeaked a little. "
United States
Jean W.
$144 nightly
The price is $159
Jul 30 - Jul 31
Total with taxes and fees
Westfield Green
Living area

Modern Loft - Parking Included, Walk to Downtown

Modern Loft - Parking Included, Walk to Downtown
Downtown Lexington
10.0 out of 10, Exceptional, (7 reviews)
"Our stay was perfect. Very clean, the bed was amazing. "
United States
Haylee W.
$234 nightly
The price is $272
Aug 5 - Aug 6
Total with taxes and fees
Modern Loft - Parking Included, Walk to Downtown
Outdoor spa tub

The Loft at Kettlestone with Hot Tub in the RRG

The Loft at Kettlestone with Hot Tub in the RRG
Powell County
10.0 out of 10, Exceptional, (2 reviews)
"The Loft was a great place to relax. It was well equipped and had everything we needed for our stay. Location was perfect for us. The hot tub was a nice touch. We loved being greeted by the dog. He was super friendly."
United States
Mary C.
$146 nightly
The price is $151
Jul 30 - Jul 31
Total with taxes and fees
The Loft at Kettlestone with Hot Tub in the RRG
Interior

Beautifully Designed Studio in Downtown Lexington

Beautifully Designed Studio in Downtown Lexington
Downtown Lexington
10.0 out of 10, Exceptional, (1 review)
"Super convenient apartment. It’s a college apartment, but a nice size. Safe, right by campus, and I didn’t have any problems parking."
United States
Jenny
$177 nightly
The price is $199
Aug 4 - Aug 5
Total with taxes and fees
Beautifully Designed Studio in Downtown Lexington
Smart TV

Central Location! Walk 2 UK campus/Chandler Hospital, Mins to Downtown

Central Location! Walk 2 UK campus/Chandler Hospital, Mins to Downtown
Lexington
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was very clean and nice. We were staying for the music festival Railbird at the Red Mile, so it was a very easy walk making the weekend nice not having to worry with parking or taxis service. Traffic was a mess and we just walked right on by. Thanks for a great weekend"
United States
Mark B.
$199 nightly
The price is $231
Aug 16 - Aug 17
Total with taxes and fees
Central Location! Walk 2 UK campus/Chandler Hospital, Mins to Downtown
Smart TV

Convenient & Comfortable - Walkable to UK Campus, near Downtown, Keeneland, Rupp

Convenient & Comfortable - Walkable to UK Campus, near Downtown, Keeneland, Rupp
Lexington
10.0 out of 10, Exceptional, (2 reviews)
"Great spot close to UK campus, Kroger Field, Hospitals, and downtown Lexington. HIGHLY recommend for a football weekend for its convenience. We were in-town for the UGA UK football game and would stay in this same place in two years if we make the return trip. Across the street is KSR bar which is a great sports bar for drinks pre/post game. Also, there were shuttle busses that you could hop on for $1/person that would take you closer to Kroger Field and back after the game. This saved us $$$ on...
United States
Andrew
$214 nightly
The price is $249
Aug 12 - Aug 13
Total with taxes and fees
Convenient & Comfortable - Walkable to UK Campus, near Downtown, Keeneland, Rupp
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

The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

10/10 Excellent
"Very friendly staff, room was clean, bathroom was rather small, some parts of the hotel were dated."
Christa 1-night trip
Posted 2 hours ago
The Campbell House Lexington, Curio Collection by Hilton

Find out more about Winchester

Winchester Apartments information

Number of reviews
438
Accommodation
114 Apartments
Lowest Price
$72
Highest Price
$333

Frequently asked questions

What's it like to stay at an apartment in Winchester?
There are plenty of places to stay with in the larger Lexington area, with 1009 lodging choices including 146 apartments. Any visit to a new destination can be a culinary trip so why not visit the local restaurants?
How do you know if an apartment is the best choice for you?
An apartment features a kitchen for convenient meals, and often has more space than a traditional hotel room. Apartments are a good option for solo travelers who want to live like locals, but also for families who want the conveniences of home.
What's a favorite apartment for a stay in Winchester?
Here are some of the favorite apartments in the area to choose from: 2 Full Beds | Non-Smoking, Micfridge: Situated in Lexington, 18.1 mi/29.1 km from the heart of Winchester. Includes free WiFi and Smart TVs. 1 King Bed | Non-Smoking, Micfridge: Located 18.1 mi/29.1 km away in Lexington. Free WiFi and Smart TVs are included. Modern Studio - Stylish Apartment in Downtown Lexington: It's situated in Lexington, 17 mi/27.3 km away. Includes Smart TVs. Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington: Located 18 mi/29 km away in Lexington. Amenities include Smart TVs. Access to onsite laundry facilities is available on site. Treetops Solar Sanctuary: It's located in Lexington, 16.7 mi/26.9 km from Winchester. Includes free WiFi, private balconies, and sofa beds.
What can I expect from the weather in Winchester?
Weather is only one factor, but it can really affect your travel plans, especially if you are planning a longer stay in Winchester. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Winchester is 56 inches.
What should I see and do in Winchester?
Winchester is known for its restaurants. Wiseman Park and Winchester Traveling Trail are a couple of scenic spots to enjoy the outdoors, whereas Bluegrass Heritage Museum is one of the cultural attractions. Other places in town to visit include Winchester Opera House and Clark County Courthouse.
What's the best way to get to and around Winchester?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Blue Grass Airport (LEX), which is located 23 mi (37.1 km) from the heart of the city. If you'd like to venture out around the area, you may want a rental car for your journey.

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