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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Winchester apartments

A kitchen with white cabinets, a black countertop, and a patterned rug.

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

‘Edith’ Carriage House Getaway - Hamburg/I-75!
Lexington
8.6 out of 10, Excellent, (9 reviews)
"A great one night stay! Plenty of room. Nice kitchen area and outside deck."
United States
Kevin P.
$130 nightly
The price is $151
Dec 9 - Dec 10
Total with taxes and fees
‘Edith’ Carriage House Getaway - Hamburg/I-75!
Private kitchen

2. 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, (3 reviews)
"Very easy check in and nice location"
United States
Robert G.
$139 nightly
The price is $153
Nov 30 - Dec 1
Total with taxes and fees
The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling
A hotel lobby with a flat-screen TV, a coat rack, a table with chairs, and a view of the outside through large glass doors.

3. 2 Full Beds | Non-Smoking, Micfridge

2 Full Beds | Non-Smoking, Micfridge
Lexington
9.8 out of 10, Exceptional, (357 reviews)
"Very poor looking motel, both inside and out!"
United States
Miguel
$58 nightly
The price is $64
Nov 15 - Nov 16
Total with taxes and fees
2 Full Beds | Non-Smoking, Micfridge
A wooden structure with a sign that reads 'TREETOPS ON GARDEN.'

4. Treetops Solar Sanctuary

Treetops Solar Sanctuary
Chevy Chase
10.0 out of 10, Exceptional, (93 reviews)
"Great place to stay!"
United States
Anna C.
$145 nightly
The price is $169
Nov 15 - Nov 16
Total with taxes and fees
Treetops Solar Sanctuary
A modern kitchen with teal cabinets, a black stove, and a black microwave. There is a black and white rug on the floor.

5. Modern Studio - Stylish Apartment in Downtown Lexington

Modern Studio - Stylish Apartment in Downtown Lexington
Lexington
9.6 out of 10, Exceptional, (15 reviews)
"Nice, clean and pet friendly place to stay! Close to downtown!"
United States
Ruthie C.
$161 nightly
The price is $187
Nov 15 - Nov 16
Total with taxes and fees
Modern Studio - Stylish Apartment in Downtown Lexington
A modern living room with a glass coffee table, leather armchair, dining area with chairs, and a chandelier.

6. Luxury on Main / South & Downtown Hideaway

Luxury on Main / South & Downtown Hideaway
Richmond
10.0 out of 10, Exceptional, (58 reviews)
"Adorable place. Very clean. Great location. Close to many restaurants and shops. Loved it."
United States
Jordan B.
$157 nightly
The price is $173
Nov 19 - Nov 20
Total with taxes and fees
Luxury on Main / South & Downtown Hideaway
A spacious loft with high ceilings, a large living area with a dark leather sofa, a coffee table, and a dining area with a brick wall and large windows.

7. Bourbon Trail - Loft in Downtown Lexington

Bourbon Trail - Loft in Downtown Lexington
Lexington
9.6 out of 10, Exceptional, (5 reviews)
"Great stay! Very convenient to all the must see places. Would stay here again "
United States
Taylor L.
$169 nightly
The price is $196
Nov 15 - Nov 16
Total with taxes and fees
Bourbon Trail - Loft in Downtown Lexington
A modern kitchen with white cabinets, a black stove, and a central island with stools.

8. Morning Glory - Cozy Apartment in Downtown Lexington

Morning Glory - Cozy Apartment in Downtown Lexington
Lexington
$169 nightly
The price is $196
Nov 15 - Nov 16
Total with taxes and fees
Morning Glory - Cozy Apartment in Downtown Lexington
A bedroom with a bed, bedside tables, a ceiling fan, a mirror, and a door.

9. Westfield Blue & Gazebo Luxury & Privacy Getaway

Westfield Blue & Gazebo Luxury & Privacy Getaway
Richmond
9.6 out of 10, Exceptional, (17 reviews)
"Nice and easy lil spot"
United States
ZACHARY W.
$136 nightly
The price is $150
Nov 17 - Nov 18
Total with taxes and fees
Westfield Blue & Gazebo Luxury & Privacy Getaway
A hot tub on a wooden deck with a railing, surrounded by autumn foliage.

10. 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, (6 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.
$141 nightly
The price is $144
Nov 15 - Nov 16
Total with taxes and fees
The Loft at Kettlestone with Hot Tub in the RRG
A kitchen with wooden cabinets, a black metal rack, a painting of a mountain landscape, and a sign that reads "MAGIC IS SOMETHING YOU MAKE".

11. Central Stay! Near UK/Downtown/Campus.

Central Stay! Near UK/Downtown/Campus.
Lexington
10.0 out of 10, Exceptional, (4 reviews)
"Everyone was great and we enjoyed our stay!"
United States
Abdul Rhman H.
$175 nightly
The price is $203
Nov 22 - Nov 23
Total with taxes and fees
Central Stay! Near UK/Downtown/Campus.
A kitchen with a stove, microwave, black cabinets, a marble countertop, and a coffee maker.

12. 'Ralph' Comfortable Downtown/UK Apartment

'Ralph' Comfortable Downtown/UK Apartment
Downtown Lexington
7.8 out of 10, Good, (29 reviews)
"Great location for what I needed. Loved the old house."
United States
Bill
$125 nightly
The price is $145
Nov 16 - Nov 17
Total with taxes and fees
'Ralph' Comfortable Downtown/UK Apartment
A modern two-story building with a flat roof, large windows, and a stone facade.

13. Charming Modern Studio Stay - Walk to Chevy Chase

Charming Modern Studio Stay - Walk to Chevy Chase
Lexington
10.0 out of 10, Exceptional, (6 reviews)
"Recommend"
United States
Jeff D.
$197 nightly
The price is $229
Nov 15 - Nov 16
Total with taxes and fees
Charming Modern Studio Stay - Walk to Chevy Chase
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

14. 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, (92 reviews)
"The place was just the right size and very convenient to where we had to go to!"
United States
Julie W.
$201 nightly
The price is $218
Nov 15 - Nov 16
Total with taxes and fees
Modern 2bd 2ba - Near I75, No Steps, Free Wifi
A living room with a wooden coffee table, a sofa, a lamp, and a potted plant.

15. Luxury on Main / West & Live Plants & Juliet Balcony

Luxury on Main / West & Live Plants & Juliet Balcony
Richmond
9.6 out of 10, Exceptional, (58 reviews)
"Wonderful place to stay. Would gladly return."
United States
Joshua N.
$157 nightly
The price is $173
Nov 16 - Nov 17
Total with taxes and fees
Luxury on Main / West & Live Plants & Juliet Balcony
A bedroom with a bed, a nightstand, a desk, a chair, a door, and a rug.

16. Stay Central in Style - UK/DT/Keeneland/Rupp

Stay Central in Style - UK/DT/Keeneland/Rupp
Lexington
10.0 out of 10, Exceptional, (3 reviews)
"Worked well for a short term stay."
United States
Tom L.
$186 nightly
The price is $216
Nov 22 - Nov 23
Total with taxes and fees
Stay Central in Style - UK/DT/Keeneland/Rupp
A spacious living area with a brown leather sofa, white fluffy chairs, and a coffee table. A kitchen is visible in the background with white cabinets and a flat-screen TV mounted on the wall.

17. Modern Loft - Parking Included, Walk to Downtown

Modern Loft - Parking Included, Walk to Downtown
Downtown Lexington
10.0 out of 10, Exceptional, (10 reviews)
"Clean, comfortable apartment. Walkable to downtown restaurants and bars. Great stay!"
United States
Stu
$185 nightly
The price is $215
Nov 15 - Nov 16
Total with taxes and fees
Modern Loft - Parking Included, Walk to Downtown
A living room with a sofa, a wooden coffee table, a TV on a stand, a striped rug, a potted plant, and a window with curtains.

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

Central Location! Walk 2 UK campus/Chandler Hospital, Mins to Downtown
Lexington
9.6 out of 10, Exceptional, (4 reviews)
"This place is walking distance to many local restaurants and cafes. Parking is available behind the building. And it's close to UK as well !"
United States
DZMITRY P.
$186 nightly
The price is $216
Nov 15 - Nov 16
Total with taxes and fees
Central Location! Walk 2 UK campus/Chandler Hospital, Mins to Downtown
A living room with a sofa, a coffee table with a hidden compartment, a lamp on a side table, and a window with curtains.

19. Yeti Escape I Cozy 2BR I 15m to RRG I Wi-Fi

Yeti Escape I Cozy 2BR I 15m to RRG I Wi-Fi
Stanton
9.4 out of 10, Exceptional, (3 reviews)
"This place was wonderful. After a day of being out in nature, it was great to arrive and find the place was ready for us to just unwind. We enjoyed the games left, especially Hangman. The local restaurants were good as well. Really enjoyed the atmosphere of Toads Barn and Grill. They had live music when we went and just an open environment. The house was clean and perfect for a family of 4 getaway."
United States
Kyle J.
$168 nightly
The price is $183
Nov 25 - Nov 26
Total with taxes and fees
Yeti Escape I Cozy 2BR I 15m to RRG I Wi-Fi
A wooden deck with a table and chairs, surrounded by a house and greenery.

20. 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, (49 reviews)
"Great little place"
United States
Maria J.
$127 nightly
The price is $147
Nov 19 - Nov 20
Total with taxes and fees
Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington
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

Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"Great onsite gym, nice bar, beds were great"
Nathan 1-night trip
Posted 3 hours ago
Elwood Hotel & Suites

Find out more about Winchester

Winchester Apartments information

Number of reviews
821
Accommodation
105 Apartments
Lowest Price
$64
Highest Price
$229

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 1025 lodging choices including 161 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. 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. Modern Studio - Stylish Apartment in Downtown Lexington: It's situated in Lexington, 17 mi/27.3 km away. Includes Smart TVs. 'Edith' Carriage House Getaway - Hamburg/I-75!: 10.9 mi/17.6 km away in Lexington. Bourbon Trail - Loft in Downtown Lexington: It's situated in Lexington, 17 mi/27.3 km from Winchester.
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. College Park and GRCHS Baseball Field 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 Cassell Creek Golf Course and Winchester Opera House.
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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