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Search Apartments in Winchester

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Compare 98 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, (121)
"The apartment had everything we needed. We loved the small details and decoration; the location was so peaceful and quiet as well! One thing, there was construction close to the apartment so it confused us for a bit but wasn’t a big deal :) we hope to come back in the future!"
The price is AED 327
AED 571 total
includes taxes & fees
25 Dec - 26 Dec
Private One Bedroom Apartment in Downtown Lexington near Rupp Arena

Comfy Upstairs 2 bed/1 bath near EKU in Richmond

10.0 out of 10, Exceptional, (26)
"We stayed for one night while visiting EKU for our son's baseball game. The place was clean and conveniently located, making it easy to get around. The host was very responsive. We were worried about noise but we never heard a peep from anyone! Overall, it was a comfortable stay that met our needs."
The price is AED 312
AED 526 total
includes taxes & fees
26 Dec - 27 Dec
Comfy Upstairs 2 bed/1 bath near EKU in Richmond

Newly Renovated 2BR Apartment w/ Free Parking in Downtown

10.0 out of 10, Exceptional, (27)
"The apartment is beautifully renovated and super spacious for a downtown apartment. It had parking included which is rare and awesome and was in walking distance to Rupp Arena and numerous shops and restaurants. Loved it!"
Newly Renovated 2BR Apartment w/ Free Parking in Downtown

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, (51)
"My parents and I stayed for 5 night and the place is perfect. Super adorable, the bed is comfy, couch is amazing for sleeping, super clean, great locations with cute restaurants around. Thank you Roy and team. "
Chic Main Street Retreat < 7 Mi to KY Horse Park!

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 814 total
includes taxes & fees
25 Dec - 26 Dec
Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena

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. "
The price is AED 459
AED 794 total
includes taxes & fees
25 Dec - 26 Dec
Springside Equine Getaway

'Ralph' Comfortable Downtown/UK Apartment

8.4 out of 10, Very Good, (14)
"Located near downtown. Which was convenient for work. Easy access to the rest of the city. "
The price is AED 228
AED 550 total
includes taxes & fees
14 Jan - 15 January 2025
'Ralph' Comfortable Downtown/UK Apartment

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, (38)
"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.

9.0 out of 10, Wonderful, (17)
"Wonderful small apartment with everything you need. Think hotel but better!! Bed is extremely comfortable and there is plenty of parking behind the house. Absolutely wonderful neighborhood and close to everything. One thing to note, the bathroom is small but plenty of room for a bathroom. Would definitely stay again."
The price is AED 311
AED 767 total
includes taxes & fees
25 Dec - 26 Dec
This apartment is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.

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. "
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 2 bedroom(s), 1 bathrooms, located in Lexington, KY.

The price is AED 487
AED 964 total
includes taxes & fees
5 Jan - 6 January 2025
This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.

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

2.0 star property
9.0 out of 10, Wonderful, (2)
"Location was great. Walking distance to campus and downtown. The apartment is charming. The third bedroom is a little odd with a non-latching door with a padlock on it separating this unit from another. You can hear everything in the adjacent unit. And no door between this bedroom and the kitchen. Enjoyed the rest of the space. It was perfect for our stay. The coffee bar was really nice."
The price is AED 551
AED 962 total
includes taxes & fees
30 Dec - 31 Dec
This apartment is a 3 bedroom(s), 1 bathrooms, located in Lexington, KY.

Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington

10.0 out of 10, Exceptional, (1)
"This apartment was super cute for our short little getaway. I loved having the whole place to ourselves and it definitely beat staying in a pricey hotel. It had everything we needed!"
The price is AED 404
AED 597 total
includes taxes & fees
30 Dec - 31 Dec
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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Other property types in Winchester

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1475)
"EVERYTHING GREAT. ROOM DID NOT HAVE A MICROWAVE OVEN. "
The price is AED 316
AED 348 total
includes taxes & fees
5 Jan - 6 January 2025
Natural Bridge State Resort Park

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

9.8 out of 10, Exceptional, (271)
"Quiet and peaceful retreat! Everything was as advertised and we had a great stay. "
The price is AED 340
AED 756 total
includes taxes & fees
8 Jan - 9 January 2025
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!

Nestled in the beautiful mountains of the Red River Gorge Area

9.0 out of 10, Wonderful, (6)
"Cabin was great but absolutely 0 service or wifi. Offered a great getaway from reality "
The price is AED 636
AED 1,009 total
includes taxes & fees
31 Dec - 1 January 2025
Nestled in the beautiful mountains of the Red River Gorge Area
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 932 lodging choices including 175 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?
Listed below are some of the top apartments in the area: 2nd Story Historic Downtown 2BR with Modern Amenities: Includes free WiFi and sofa beds. Treetops Solar Sanctuary: It’s situated in Lexington, 16.7 mi/26.9 km away. Includes free WiFi, private balconies, and sofa beds. Private One Bedroom Apartment in Downtown Lexington near Rupp Arena: 18.3 mi/29.4 km away in Lexington. Free WiFi, private patios, and fireplaces are included. Chic Main Street Retreat < 7 Mi to KY Horse Park!: It’s located in Georgetown, 25.6 mi/41.2 km from Winchester. Includes laundry facilities.
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. Community Park and Lykins Park 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 Southwind Golf Course and Cassell Creek Golf Course.
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.