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Compare 97 Apartments in Winchester with updated reviews, rates, and availability.

Treetops Solar Sanctuary
Your stairway to magnolia treetops!
Treetops Solar Sanctuary
10.0 out of 10, Exceptional, (69)
"This space was very cozy and clean. Lots of thoughtful touches such as soft music playing on the big projection screen when we entered the room and a Keurig with several coffee options. The owner was a very good communicator. We had no trouble checking in. Very nice neighborhood. We would stay here again!"
The price is AED 253
AED 610 total
includes taxes & fees
13 Nov - 14 Nov
Treetops Solar Sanctuary
Quaint Apartment in Historic Georgetown!
Georgetown Vacation Rental | 2BR | 1BA | 865 Sq Ft | 2nd-Floor Unit
Quaint Apartment in Historic Georgetown!
9.8 out of 10, Exceptional, (37)
"We booked this location based on the reviews and pictures and they were not wrong. The location was amazing to hit up all the major distilleries on the Bourbon Trail and the downtown Georgetown area was beautiful. The apartment was clean and just as described. Would recommend and stay again! "
Quaint Apartment in Historic Georgetown!
The Scholars Apartment is a freshly renovated 2bedroom 1bath downtown Richmond apartment
Living area
The Scholars Apartment is a freshly renovated 2bedroom 1bath downtown Richmond apartment
9.4 out of 10, Exceptional, (15)
"Enjoyed our stay. Well equipped, up-to-date and comfortable. Only 2 minor issues. Some of the dishes from the previous guest had been put away dirty and had to be re-washed. It would be nice have a clear path (or sidewalk) to get to the stairs leading up to the entrance instead of having to walk through wet, dewy grass."
The price is AED 327
AED 661 total
includes taxes & fees
8 Dec - 9 Dec
The Scholars Apartment is a freshly renovated 2bedroom 1bath downtown Richmond apartment
Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!
Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!
9.8 out of 10, Exceptional, (10)
"They aren’t kidding when they say no cell service! We really enjoyed this place, it was simple but had everything you need. If you need some time to unplug and relax on a great swinging bench, this is the place for you. The hot tub is awesome as well. If for some reason you do need service, hike up the military wall trail that’s right down the road and you’ll be in contact with the world again:) Thank you for a relaxing get away!"
Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!
This apartment is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
Living area
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.
Private One Bedroom Apartment in Downtown Lexington near Rupp Arena
Living area
Private One Bedroom Apartment in Downtown Lexington near Rupp Arena
10.0 out of 10, Exceptional, (118)
"Great location and great place. Owners were great at communicating. Thanks so much and would definitely stay again."
The price is AED 364
AED 614 total
includes taxes & fees
19 Nov - 20 Nov
Private One Bedroom Apartment in Downtown Lexington near Rupp Arena
Lexington Apt. with parking & private entrance Preview listing
Exterior
Lexington Apt. with parking & private entrance Preview listing
10.0 out of 10, Exceptional, (118)
"This was a planned vacation for my wife and I that turned into 4. Joyce was more than accommodating to that change. Every time that I messaged her, she responded quickly. We absolutely loved the apartment. It was immaculate. It was 100% accurate on description. Very quiet neighborhood but also within 10 minutes of downtown Lexington. When we come back next year, I'm definitely gonna book this place again. 5 star place and host"
The price is AED 268
AED 524 total
includes taxes & fees
24 Nov - 25 Nov
Lexington Apt. with parking & private entrance Preview listing
Newly Renovated 2BR Apartment w/ Free Parking in Downtown
Living area
Newly Renovated 2BR Apartment w/ Free Parking in Downtown
10.0 out of 10, Exceptional, (24)
"We had a great stay at this fabulous apartment! We will definitely book this place again! "
Newly Renovated 2BR Apartment w/ Free Parking in Downtown
Cozy upstairs 2 bed/1 bath Richmond apt near EKU
Living area
Cozy upstairs 2 bed/1 bath Richmond apt near EKU
10.0 out of 10, Exceptional, (15)
"Perfect for four adults and the location is close to EKU campus and anything else you could want. Cozy two bedroom with everything you need. Owner supplies more than enough things for the stay. TV continuously resets the “guest mode” but we were not in town for watching television. Wi-Fi spotty at best until one of the other guests left after the first night. Overall a nice place and we would stay again. "
The price is AED 312
AED 526 total
includes taxes & fees
10 Nov - 11 Nov
Cozy upstairs 2 bed/1 bath Richmond apt near EKU
Charming & Inviting Apartment in Historic Downtown Paris, Ky.
Room
Charming & Inviting Apartment in Historic Downtown Paris, Ky.
9.8 out of 10, Exceptional, (106)
"Exactly as advertised. Host is very helpful. "
Charming & Inviting Apartment in Historic Downtown Paris, Ky.
Beautifully Designed Studio in Downtown Lexington
bedroom space
Beautifully Designed Studio in Downtown Lexington
10.0 out of 10, Exceptional, (1)
"Super convenient apartment. It’s a college apartment, but a nice size. Safe, right by campus, and I didn’t have any problems parking."
The price is AED 356
AED 630 total
includes taxes & fees
11 Nov - 12 Nov
Beautifully Designed Studio in Downtown Lexington
Stylish Studio Apartment in Downtown Lexington
Bedroom
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
Hidden Gem Charming 2-bedroom apartment in delightful Lexington
Interior
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!
Georgetown Vacation Rental | Studio | 1BA | 700 Sq Ft | Stairs Required
Chic Main Street Retreat < 7 Mi to KY Horse Park!
10.0 out of 10, Exceptional, (49)
"We enjoyed our stay in Georgetown and couldn’t be happier with our stay in this lovely, quirky, comfortable flat. Got our steps and cardio in going up and down the stairs! 😉"
Chic Main Street Retreat < 7 Mi to KY Horse Park!
Location location location-#15015318-1
Exterior
Location location location-#15015318-1
10.0 out of 10, Exceptional, (25)
"Will definitely be staying there again!"
Location location location-#15015318-1
This serviced apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Living area
This serviced apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
6.8 out of 10, (3)
"The pictures posted of the home gave the perception of an older home with charm. Before we arrived we arrived I had to contact the host for check-in instructions. I sent a message through the app and did not get a response. We tried not to panic but we were less than an 2 hours away and very tired from driving. After 30 minutes I called and left a voicemail. The host called back shortly after voicemail and text the check-in instructions. After arriving we were able to get my 2 grandkids in the...
This serviced apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
The Tiny Feather Summ
Tiny Feather cabin tucked in the heart of the Daniel Boon National forest.
The Tiny Feather Summ
9.2 out of 10, Wonderful, (9)
"The Tiny Feather is so cute! We enjoyed the comfy beds and outdoor living space. Our daughter didn’t want to leave at the end of the weekend!"
The Tiny Feather Summ
Luxury on Main / West
Living area
Luxury on Main / West
9.6 out of 10, Exceptional, (44)
"Comfortable and easy-to-use, close to my dad "
The price is AED 349
AED 668 total
includes taxes & fees
12 Nov - 13 Nov
Luxury on Main / West
Comfy Upstairs 2 bed/1 bath near EKU in Richmond
Living area
Comfy Upstairs 2 bed/1 bath near EKU in Richmond
10.0 out of 10, Exceptional, (25)
"Went down for EKU parent weekend and the location was perfect. We were only a minute from my daughter’s dorm. The place was very clean. "
The price is AED 312
AED 526 total
includes taxes & fees
16 Nov - 17 Nov
Comfy Upstairs 2 bed/1 bath near EKU in Richmond
Springside Bourbon Getaway
Bedroom
Springside Bourbon Getaway
10.0 out of 10, Exceptional, (12)
"We love staying here and we choose this place every time we travel to Kentucky. It’s perfectly situated near plenty of attractions. Georgetown could not be a cuter town or have more wonderful people. We are so grateful for such a BEAUTIFUL and well manicured place to hang our hats for a few days!"
The price is AED 367
AED 692 total
includes taxes & fees
10 Nov - 11 Nov
Springside Bourbon Getaway
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
Hiking
Natural Bridge State Resort Park
3.5 star property
8.6 out of 10, Excellent, (1451)
"Beautiful lodge, great food in restaurant. Great KY state park."
The price is AED 352
AED 389 total
includes taxes & fees
17 Nov - 18 Nov
Natural Bridge State Resort Park
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
9.8 out of 10, Exceptional, (263)
"The Cozy Cabin was a great set up for our annual hiking trip. The cabin was very clean, had everything we needed and was very comfortable. All instructions were accurate and the listing was exactly as described. The hot tub was key after long days out on the trails. The host was very helpful and able to send over replacement propane tanks for the fire pit, which was much appreciated. We had a wonderful trip and would absolutely stay here again. "
The price is AED 340
AED 756 total
includes taxes & fees
2 Dec - 3 Dec
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
The Container Den-Shipping Container Cabin with HotTub-WIFI-Great View! BOOK IT!
Terrace/patio
The Container Den-Shipping Container Cabin with HotTub-WIFI-Great View! BOOK IT!
10.0 out of 10, Exceptional, (84)
"such a great weekend getaway! it’s the perfect spot for a romantic, secluded weekend away with your partner!"
The price is AED 547
AED 919 total
includes taxes & fees
1 Dec - 2 Dec
The Container Den-Shipping Container Cabin with HotTub-WIFI-Great View! BOOK IT!
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 960 lodging choices including 171 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.
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.