Search Apartment Rentals in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Winchester apartments

Private kitchen

1. 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.
The price is CA $179
CA $216 total
includes taxes & fees
Nov 30 - Dec 1
The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling
A modern kitchen with teal cabinets, a black stove, and a black microwave. There is a black and white rug on the floor.

2. 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.
The price is CA $98
CA $255 total
includes taxes & fees
Nov 10 - Nov 11
Modern Studio - Stylish Apartment in Downtown Lexington
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
The price is CA $82
CA $90 total
includes taxes & fees
Nov 10 - Nov 11
2 Full Beds | Non-Smoking, Micfridge
A wooden deck with two chairs and a small round table, surrounded by lush greenery.

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.
The price is CA $112
CA $238 total
includes taxes & fees
Nov 10 - Nov 11
Treetops Solar Sanctuary
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.

5. 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.
The price is CA $109
CA $268 total
includes taxes & fees
Nov 10 - Nov 11
Bourbon Trail - Loft in Downtown Lexington
A modern kitchen with white cabinets, a black stove, and a central island with stools.

6. Morning Glory - Cozy Apartment in Downtown Lexington

Morning Glory - Cozy Apartment in Downtown Lexington
Lexington
The price is CA $109
CA $268 total
includes taxes & fees
Nov 10 - Nov 11
Morning Glory - Cozy Apartment in Downtown Lexington
A kitchen with a stove, microwave, black cabinets, a marble countertop, and a coffee maker.

7. '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
The price is CA $73
CA $203 total
includes taxes & fees
Nov 10 - Nov 11
'Ralph' Comfortable Downtown/UK Apartment
A modern living room with a glass coffee table, leather armchair, dining area with chairs, and a chandelier.

8. 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.
The price is CA $134
CA $246 total
includes taxes & fees
Nov 12 - Nov 13
Luxury on Main / South & Downtown Hideaway
Living area

9. Westfield Gold & Nearby Park & Private Paradise

Westfield Gold & Nearby Park & Private Paradise
Richmond
9.4 out of 10, Exceptional, (16 reviews)
"Perfect rental for us to stay while visiting our daughter at EKU. We will definitely be back!"
United States
Kelley B.
The price is CA $116
CA $224 total
includes taxes & fees
Nov 10 - Nov 11
Westfield Gold & Nearby Park & Private Paradise
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

10. 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.
The price is CA $160
CA $314 total
includes taxes & fees
Dec 1 - Dec 2
Modern 2bd 2ba - Near I75, No Steps, Free Wifi
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.

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

Charming 2-bedroom apartment with AC, WiFi in brilliant Lexington
Downtown Lexington
9.0 out of 10, Wonderful, (4 reviews)
"Great price and location. Host was quick to communicate."
United States
Blake B.
The price is CA $106
CA $336 total
includes taxes & fees
Nov 15 - Nov 16
Charming 2-bedroom apartment with AC, WiFi in brilliant Lexington
A wooden deck with a table and chairs, surrounded by a house and greenery.

12. 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.
The price is CA $148
CA $207 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington
A living room with a wooden coffee table, a sofa, a lamp, and a potted plant.

13. 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.
The price is CA $130
CA $241 total
includes taxes & fees
Nov 16 - Nov 17
Luxury on Main / West & Live Plants & Juliet Balcony
A bedroom with a bed, a nightstand, a desk, a chair, a door, and a rug.

14. 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.
The price is CA $98
CA $305 total
includes taxes & fees
Nov 22 - Nov 23
Stay Central in Style - UK/DT/Keeneland/Rupp
A modern two-story building with a flat roof, large windows, and a stone facade.

15. 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.
The price is CA $139
CA $324 total
includes taxes & fees
Nov 11 - Nov 12
Charming Modern Studio Stay - Walk to Chevy Chase
A hot tub on a wooden deck with a railing, surrounded by autumn foliage.

16. 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.
The price is CA $114
CA $193 total
includes taxes & fees
Nov 10 - Nov 11
The Loft at Kettlestone with Hot Tub in the RRG
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
The price is CA $128
CA $302 total
includes taxes & fees
Nov 15 - Nov 16
Modern Loft - Parking Included, Walk to Downtown
A dining area with a black table, a patterned placemat, and a bowl of green apples.

18. Westfield Green & Wood Accents & Live Greenery

Westfield Green & Wood Accents & Live Greenery
Richmond
9.8 out of 10, Exceptional, (25 reviews)
"Beautifully decorated and appointed with nice touches throughout the property."
United States
Christian P.
The price is CA $131
CA $243 total
includes taxes & fees
Nov 11 - Nov 12
Westfield Green & Wood Accents & Live Greenery
A two-story brick house with a front porch, a garage, and a driveway.

19. 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, (19 reviews)
"We enjoyed our stay. Location was amazing for our trip!"
United States
Deanna E.
The price is CA $157
CA $425 total
includes taxes & fees
Nov 10 - Nov 11
1200 sf Apt -3 BR-Amazing Beds-Walk to EKU & Downtown Venues - 5 minutes to I-75
A living room with a glass coffee table, wooden side tables, a dark wooden cabinet, a flat-screen TV, and a decorative vase.

20. 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.
The price is CA $78
CA $264 total
includes taxes & fees
Nov 10 - Nov 11
Central Stay! Near UK/Downtown/Campus.
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

Learn more about Winchester

Stroll through charming downtown streets lined with local shops and eateries. Tee off at Cassell Creek or Southwind Golf Course, then explore local history at the Bluegrass Heritage Museum.

See all hotels in Winchester
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.

Top reviews in Winchester

A Holiday Inn Express building with a covered entrance, stone pillars, and potted plants.
Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
Winchester

8/10 Good

Good place to stay
Canada
martin
Reviewed April 30, 2025
Holiday Inn Express Lexington East - Winchester by IHG

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