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 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Winchester apartments

A bedroom with a bed, a chair, a wooden cabinet, and a door leading to another room.

1. 2nd Story Historic Downtown 2BR with Modern Amenities

2nd Story Historic Downtown 2BR with Modern Amenities
Winchester
9.0 out of 10, Wonderful, (13 reviews)
"We had a great stay, the unit has lots of charm and is very cozy. We enjoyed the walkability to great local shops and restaurants. It's within a short driving distance to other great areas to check out!"
United States
Brian M.
$162 nightly
The price is $178
Oct 29 - Oct 30
Total with taxes and fees
2nd Story Historic Downtown 2BR with Modern Amenities
A kitchen with white cabinets, a black countertop, and a patterned rug.

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

‘Edith’ Carriage House Getaway - Hamburg/I-75!
Lexington
8.8 out of 10, Excellent, (6 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
Nov 1 - Nov 2
Total with taxes and fees
‘Edith’ Carriage House Getaway - Hamburg/I-75!
A bedroom with a bed, bedside tables, a ceiling fan, a mirror, and a door.

3. Westfield Blue & Gazebo Luxury & Privacy Getaway

Westfield Blue & Gazebo Luxury & Privacy Getaway
Richmond
9.4 out of 10, Exceptional, (13 reviews)
"Nice and easy lil spot"
United States
ZACHARY W.
$134 nightly
The price is $148
Oct 26 - Oct 27
Total with taxes and fees
Westfield Blue & Gazebo Luxury & Privacy Getaway
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.

4. 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 living room with a glass coffee table, leather armchair, dining area with chairs, and a chandelier.

5. Luxury on Main / South & Downtown Hideaway

Luxury on Main / South & Downtown Hideaway
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 26 - Oct 27
Total with taxes and fees
Luxury on Main / South & Downtown Hideaway
A modern kitchen with a central island, a dining area with a gray sofa, and a ceiling fan.

6. 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.
$172 nightly
The price is $190
Oct 27 - Oct 28
Total with taxes and fees
Charming studio apartment in Richmond, just minutes away from EKU
A wooden deck with two chairs and a small round table, surrounded by lush greenery.

7. Treetops Solar Sanctuary

Treetops Solar Sanctuary
Chevy Chase
10.0 out of 10, Exceptional, (93 reviews)
"Great place to stay!"
United States
Anna C.
$153 nightly
The price is $178
Oct 27 - Oct 28
Total with taxes and fees
Treetops Solar Sanctuary
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

8. 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.
$243 nightly
The price is $265
Oct 26 - Oct 27
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.

9. 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.
$165 nightly
The price is $182
Oct 28 - Oct 29
Total with taxes and fees
Luxury on Main / West & Live Plants & Juliet Balcony
A modern kitchen with teal cabinets, a black stove, and a black microwave. There is a black and white rug on the floor.

10. 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.
$165 nightly
The price is $192
Oct 26 - Oct 27
Total with taxes and fees
Modern Studio - Stylish Apartment in Downtown Lexington
A red house with a balcony and a covered porch.

11. 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, (4 reviews)
"Hot tub is great and clean!"
United States
Abby J.
$159 nightly
The price is $164
Oct 29 - Oct 30
Total with taxes and fees
The Loft at Kettlestone with Hot Tub in the RRG
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.

12. 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.
$172 nightly
The price is $200
Oct 26 - Oct 27
Total with taxes and fees
Bourbon Trail - Loft in Downtown Lexington
A wooden deck with a table and chairs, surrounded by a house and greenery.

13. 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, (48 reviews)
"Great little place"
United States
Maria J.
$135 nightly
The price is $156
Nov 1 - Nov 2
Total with taxes and fees
Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington
A bedroom with a fireplace, a bed with a patterned bedspread, a large painting on the wall, and a chandelier.

14. 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.
$280 nightly
The price is $325
Oct 26 - Oct 27
Total with taxes and fees
The Kenwick Pied-à-terre - Lexington Apartment with Historic Charm
A kitchen with a stove, microwave, black cabinets, a marble countertop, and a coffee maker.

15. '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
Nov 1 - Nov 2
Total with taxes and fees
'Ralph' Comfortable Downtown/UK Apartment
A room with a wooden floor, a dining table with chairs, a sofa, and a television.

16. 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.
$172 nightly
The price is $200
Oct 26 - Oct 27
Total with taxes and fees
Seabiscuit Loft - Studio Stay in Downtown Lexington
A dining area with a round table, chairs, a chandelier, and a view through an archway to another room.

17. Eclectic Luxury Loft

Eclectic Luxury Loft
Richmond
$156 nightly
The price is $172
Oct 26 - Oct 27
Total with taxes and fees
Eclectic Luxury Loft
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.
$174 nightly
The price is $202
Oct 26 - Oct 27
Total with taxes and fees
Central Location! Walk 2 UK campus/Chandler Hospital, Mins to Downtown
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.

19. 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
$189 nightly
The price is $219
Oct 26 - Oct 27
Total with taxes and fees
Modern Loft - Parking Included, Walk to Downtown
A dining area with a black table, a patterned placemat, and a bowl of green apples.

20. Westfield Green & Wood Accents & Live Greenery

Westfield Green & Wood Accents & Live Greenery
Richmond
10.0 out of 10, Exceptional, (24 reviews)
"Beautifully decorated and appointed with nice touches throughout the property."
United States
Christian P.
$188 nightly
The price is $207
Oct 28 - Oct 29
Total with taxes and fees
Westfield Green & Wood Accents & Live Greenery
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
"N/A"
SM Redwan 1-night trip
Posted 11 hours ago
GuestHouse Lexington

Find out more about Winchester

Winchester Apartments information

Number of reviews
802
Accommodation
105 Apartments
Lowest Price
$64
Highest Price
$325

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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