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

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 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
9.6 out of 10, Exceptional, (5 reviews)
"A great one night stay! Plenty of room. Nice kitchen area and outside deck."
United States
Kevin P.
$124 nightly
The price is $144
Oct 25 - Oct 26
Total with taxes and fees
‘Edith’ Carriage House Getaway - Hamburg/I-75!
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.

2. 2 Full Beds | Non-Smoking, Micfridge

2 Full Beds | Non-Smoking, Micfridge
Lexington
9.8 out of 10, Exceptional, (353 reviews)
"It felt like home during our stay! Friendly staff made us feel welcome."
United States
Anonymous traveler
$59 nightly
The price is $64
Nov 1 - Nov 2
Total with taxes and fees
2 Full Beds | Non-Smoking, Micfridge
A modern kitchen with teal cabinets, a black stove, and a black microwave. There is a black and white rug on the floor.

3. Modern Studio - Stylish Apartment in Downtown Lexington

Modern Studio - Stylish Apartment in Downtown Lexington
Lexington
9.6 out of 10, Exceptional, (13 reviews)
"Nice, clean and pet friendly place to stay! Close to downtown!"
United States
Ruthie C.
$172 nightly
The price is $199
Oct 21 - Oct 22
Total with taxes and fees
Modern Studio - Stylish Apartment in Downtown Lexington
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, (92 reviews)
"Great place to stay!"
United States
Anna C.
$153 nightly
The price is $178
Oct 19 - Oct 20
Total with taxes and fees
Treetops Solar Sanctuary
A modern living room with a glass coffee table, leather armchair, dining area with chairs, and a chandelier.

5. Luxury on Main / South

Luxury on Main / South
Richmond
10.0 out of 10, Exceptional, (58 reviews)
"Clean, well stocked and comfortable. I always enjoy my stay here. "
United States
Robert T.
$165 nightly
The price is $182
Oct 19 - Oct 20
Total with taxes and fees
Luxury on Main / South
A bedroom with a bed, bedside tables, a ceiling fan, a mirror, and a door.

6. Westfield Blue

Westfield Blue
Richmond
9.4 out of 10, Exceptional, (12 reviews)
"Nice and easy lil spot"
United States
ZACHARY W.
$144 nightly
The price is $159
Oct 18 - Oct 19
Total with taxes and fees
Westfield Blue
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

7. 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.
$239 nightly
The price is $260
Oct 22 - Oct 23
Total with taxes and fees
Modern 2bd 2ba - Near I75, No Steps, Free Wifi
A modern kitchen with a central island, a dining area with a gray sofa, and a ceiling fan.

8. Charming studio apartment in Richmond, just minutes away from EKU

Charming studio apartment in Richmond, just minutes away from EKU
Richmond
9.0 out of 10, Wonderful, (2 reviews)
"The property was nice and clean. Easy access to shops close by and food. "
United States
Tyler C.
$173 nightly
The price is $191
Oct 19 - Oct 20
Total with taxes and fees
Charming studio apartment in Richmond, just minutes away from EKU
A living room with a wooden coffee table, a sofa, a lamp, and a potted plant.

9. 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.
$165 nightly
The price is $182
Oct 18 - Oct 19
Total with taxes and fees
Luxury on Main / West
A room with a wooden floor, a dining table with chairs, a sofa, and a television.

10. Seabiscuit Loft - Studio Stay in Downtown Lexington

Seabiscuit Loft - Studio Stay in Downtown Lexington
Lexington
9.0 out of 10, Wonderful, (4 reviews)
"We got this apartment for much needed rest while my husband was taking treatments. We were able to rest and enjoyed our stay."
United States
April S.
$189 nightly
The price is $219
Oct 18 - Oct 19
Total with taxes and fees
Seabiscuit Loft - Studio Stay in Downtown Lexington
A kitchen with a stove, microwave, black cabinets, a marble countertop, and a coffee maker.

11. 'Ralph' Comfortable Downtown/UK Apartment

'Ralph' Comfortable Downtown/UK Apartment
Downtown Lexington
8.2 out of 10, Very good, (27 reviews)
"Great location for what I needed. Loved the old house."
United States
Bill
$125 nightly
The price is $145
Oct 18 - Oct 19
Total with taxes and fees
'Ralph' Comfortable Downtown/UK Apartment
A hallway with a white wall, a door with a black handle, and a white shelf with black hooks.

12. Charming Modern Studio Stay - Walk to Chevy Chase

Charming Modern Studio Stay - Walk to Chevy Chase
Lexington
10.0 out of 10, Exceptional, (3 reviews)
"This unit is exactly as described! Great communication, great location!! Will definitely be back!!!"
United States
Wendy s.
$250 nightly
The price is $290
Oct 20 - Oct 21
Total with taxes and fees
Charming Modern Studio Stay - Walk to Chevy Chase
A bedroom with a fireplace, a bed with a patterned bedspread, a large painting on the wall, and a chandelier.

13. 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, (2 reviews)
"Wonderful stay and great location! The grocery store below was wonderful. The property was spacious and close to everything! As well as lots of great dining and coffee shops. It was a beautiful neighborhood for evening walks as well."
United States
Miranda M.
$295 nightly
The price is $342
Oct 18 - Oct 19
Total with taxes and fees
The Kenwick Pied-à-terre - Lexington Apartment with Historic Charm
A modern kitchen with white cabinets, a black stove, and a central island with stools.

14. Morning Glory - Cozy Apartment in Downtown Lexington

Morning Glory - Cozy Apartment in Downtown Lexington
Lexington
Morning Glory - Cozy Apartment in Downtown Lexington
A bedroom with a bed, a nightstand, a desk, a chair, a door, and a rug.

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

Stay Central in Style - UK/DT/Keeneland/Rupp
Lexington
10.0 out of 10, Exceptional, (2 reviews)
"Worked well for a short term stay."
United States
Tom L.
$200 nightly
The price is $232
Oct 21 - Oct 22
Total with taxes and fees
Stay Central in Style - UK/DT/Keeneland/Rupp
A living room with a flat-screen TV mounted on a wooden beam, a white console table with a plant, and a blue patterned rug.

16. Charming 2-bedroom apartment with AC, WiFi in brilliant Lexington

Charming 2-bedroom apartment with AC, WiFi in brilliant Lexington
Downtown Lexington
10.0 out of 10, Exceptional, (3 reviews)
"Very convenient to downtown Lexington"
United States
Chad C.
$204 nightly
The price is $237
Oct 19 - Oct 20
Total with taxes and fees
Charming 2-bedroom apartment with AC, WiFi in brilliant Lexington
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.

17. 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.
$182 nightly
The price is $211
Oct 21 - Oct 22
Total with taxes and fees
Bourbon Trail - Loft in Downtown Lexington
A kitchen with wooden cabinets, a white refrigerator, a stove, and a wooden countertop.

18. 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, (3 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.
$157 nightly
The price is $162
Oct 21 - Oct 22
Total with taxes and fees
The Loft at Kettlestone with Hot Tub in the RRG
A wooden deck with a table and chairs, surrounded by a house and greenery.

19. 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, (46 reviews)
"Great little place"
United States
Maria J.
$135 nightly
The price is $156
Oct 25 - Oct 26
Total with taxes and fees
Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington
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.

20. 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
$228 nightly
The price is $264
Oct 21 - Oct 22
Total with taxes and fees
Modern Loft - Parking Included, Walk to Downtown
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"It was great! Updated hotel, friendly staff and guests and good breakfast."
Ryan 1-night trip
Posted 7 hours ago
Embassy Suites by Hilton Lexington/UK Coldstream

Find out more about Winchester

Winchester Apartments information

Number of reviews
717
Accommodation
105 Apartments
Lowest Price
$64
Highest Price
$342

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.

Explore a world of travel with Expedia