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Compare 100 Apartments in Winchester with updated reviews, rates, and availability.

Private One Bedroom Apartment in Downtown Lexington near Rupp Arena

10.0 out of 10, Exceptional, (124)
"Cute little place. Walking distance from a wide variety of activities and food places. Apartment was clean and had everything we needed. Bathroom is a bit small but manageable. Loved our stay!"
The price is AED 404
AED 661 total
includes taxes & fees
26 Jan - 27 Jan
Private One Bedroom Apartment in Downtown Lexington near Rupp Arena

Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!

10.0 out of 10, Exceptional, (12)
"Gorgeous Fall foliage @ a quaint cabin close to everything "
Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!

Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena

9.8 out of 10, Exceptional, (87)
"This location is perfect for anyone who goes to Rupp Arena for an event. Within walking distance!!"
The price is AED 441
AED 810 total
includes taxes & fees
26 Jan - 27 Jan
Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena

Springside Bourbon Getaway

10.0 out of 10, Exceptional, (14)
"This was perfectly located for us to visit our favorite spots around Georgetown & Lexington. It was wonderfully quiet & cozy."
The price is AED 367
AED 688 total
includes taxes & fees
11 Feb - 12 Feb
Springside Bourbon Getaway

Stylish Studio Apartment in Downtown Lexington

2.0 out of 10, (1)
"The first night we stayed here, we got locked out of the house because the batteries for the automatic lock had died. We called the maintenance guy, but he was not able to get in as there was not a spare key where the owner said it was. The owner stopped answering his phone and essentially left us stranded. We ended up having to crawl through a window to get in. Additionally, the water pressure in the shower is no more than a trickle."
Stylish Studio Apartment in Downtown Lexington

Solar Sanctuary

10.0 out of 10, Exceptional, (4)
"The property was way better than advertised. A perfect place to stay one night or a week. The owner was great; kind, courteous and very cool. "
Solar Sanctuary

Hidden Gem Charming 2-bedroom apartment in delightful Lexington

2.0 star property
Hidden Gem Charming 2-bedroom apartment in delightful Lexington

Chic Main Street Retreat < 7 Mi to KY Horse Park!

10.0 out of 10, Exceptional, (52)
"This place is too cute! And it's convenient to all the stores and it's really nice being in a loft overlooking main Street! Had a great experience!"
Chic Main Street Retreat < 7 Mi to KY Horse Park!

Lexington Apt. with parking & private entrance Preview listing

10.0 out of 10, Exceptional, (121)
"A wonderful Christmas visit with our grandchildren from this outstanding home base. Well equipped kitchen and homey apartment. Tastefully decorated for the holidays and very welcoming."
The price is AED 268
AED 524 total
includes taxes & fees
25 Jan - 26 Jan
Lexington Apt. with parking & private entrance Preview listing

The Scholars Apartment is a freshly renovated 2bedroom 1bath downtown Richmond apartment

9.6 out of 10, Exceptional, (17)
"The apartment had everything needed for a great stay. The bed was very comfortable and there were extras making the stay very nice and comfortable. The lockbox for the door had an issue but host was respondent and helpful. It truly was a great stay and if ever in the area, we would stay again! "
The price is AED 327
AED 657 total
includes taxes & fees
24 Jan - 25 Jan
The Scholars Apartment is a freshly renovated 2bedroom 1bath downtown Richmond apartment

Newly Renovated 2BR Apartment w/ Free Parking in Downtown

10.0 out of 10, Exceptional, (28)
"This apartment was very comfortable. We enjoyed our stay."
Newly Renovated 2BR Apartment w/ Free Parking in Downtown

PROMO 5% WEEKLY AND 10% MONTHLY DISCOUNT! New building Urban Studio

9.4 out of 10, Exceptional, (64)
"Host was very helpful and accom9dating. Great coffee shop and breackfast/brunch right across the street. I highly reccomend."
PROMO 5% WEEKLY AND 10% MONTHLY DISCOUNT! New building Urban Studio

Springside Equine Getaway

10.0 out of 10, Exceptional, (8)
"We enjoyed staying spring side for the holiday. Baked four pies in the fully stocked kitchen to share at our family thanksgiving down the road. Will definitely be back when we’re next in town. "
Springside Equine Getaway

Cozy Lexington Townhome ~ 3 Mi to UK Campus!

3.0 star property
Cozy Lexington Townhome ~ 3 Mi to UK Campus!

Quaint Apartment in Historic Georgetown!

9.8 out of 10, Exceptional, (39)
"A well-appointed apartment in the middle of downtown. In the midst of cute shops and restaurants."
Quaint Apartment in Historic Georgetown!

This apartment is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.

7.0 out of 10, Good, (2)
"Good location, was able to walk to the UK football game. Coffee shop/restaurants/drug store all within walking distance. The inside of the apartment and the apartment building is a bit run down. Paint chipping off walls, beat up floors. The price and location make it worth it, but inside of apartment needs some fixing up. "
The price is AED 331
AED 794 total
includes taxes & fees
27 Jan - 28 Jan
This apartment is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.

Beautiful Downtown Hideaway

9.4 out of 10, Exceptional, (3)
"Lived in Lexington 50 years ago. I could walk any where. Felt safe and price is right"
Beautiful Downtown Hideaway

This apartment is a 3 bedroom(s), 1 bathrooms, located in Lexington, KY.

2.0 star property
9.0 out of 10, Wonderful, (2)
"I went to lexington with my friend to see Matt Rife at Ruff Stadium. The house is within walking distance, which was really nice. The house itself was cute. It had 3 bedrooms but one of the bedrooms was really odd. It did not have a door, just curtains. However, it didn't really matter because there ended only being 2 of us that went. The king size bed was super comfortable and the living room was nice sized. They weren't lying about the driveway being super narrow. I drive a Chevy Equinox and...
The price is AED 551
AED 962 total
includes taxes & fees
26 Jan - 27 Jan
This apartment is a 3 bedroom(s), 1 bathrooms, located in Lexington, KY.

This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.

2.0 star property
10.0 out of 10, Exceptional, (2)
"We took our teenaged son and his friend to a Kentucky basketball game and this was the PERFECT location for us to walk to campus and Rupp Arena. Plenty of space to stretch out with two bedrooms, a nice sized living room and kitchen. The guest bedroom has a queen bed and day bed which was great. The best part of this rental is the location. It can’t be beat! I highly recommend. "
The price is AED 422
AED 790 total
includes taxes & fees
26 Jan - 27 Jan
This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.

Treetops Solar Sanctuary

10.0 out of 10, Exceptional, (70)
"It makes no sense to stay in a hotel when this unit is available. Perfect for a single or couple. Close to Chevy Chase and downtown. Very clean and has all you need for a comfortable stay. Dru is a first class host. Very attentive. "
The price is AED 217
AED 567 total
includes taxes & fees
10 Feb - 11 Feb
Treetops Solar Sanctuary
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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Other property types in Winchester

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1487)
"This was our second time staying here. The staff at the hotel are very friendly and helpful. The rooms are clean and well maintained. Our only complaint about the room is that during the winter season they are cold. There are no heavy blankets or comforters provided. Only a thin bedspread. Also the breakfast is very sparse. Only waffles, toast, bagels, cold cereal and instant oatmeal. The coffee is really bad as well, very muddy"
The price is AED 316
AED 348 total
includes taxes & fees
24 Jan - 25 Jan
Natural Bridge State Resort Park

Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!

9.8 out of 10, Exceptional, (274)
"My husband and I enjoyed a relaxing getaway! We loved the house, the balcony, and hot tub."
The price is AED 340
AED 749 total
includes taxes & fees
29 Jan - 30 Jan
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!

Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB

10.0 out of 10, Exceptional, (127)
"Clean and quaint. Good communication with the renter. "
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
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.

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 927 lodging choices including 170 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 more popular apartments in the area: 2nd Story Historic Downtown 2BR with Modern Amenities: Includes free WiFi and sofa beds. Private One Bedroom Apartment in Downtown Lexington near Rupp Arena: Located 18.3 mi/29.4 km away in Lexington. Free WiFi, private patios, and fireplaces are included. Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!: Located in Stanton, 30.3 mi/48.8 km away. Includes private patios. Access to a spa tub is available on site. Treetops Solar Sanctuary: 16.7 mi/26.9 km away in Lexington. Free WiFi, private balconies, and sofa beds are included.
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 Clark County Public Library and Community Park.
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.