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Compare 97 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, (125)
"My wife and I stayed at this quaint one bedroom apartment as we were in town for a concert. The place is adorable, clean, and wound up being the perfect place to stay. In fact, we have plans to come back to Lexington for another concert next month and I’m in the process of trying to rebook."
The price is AED 404
AED 661 total
includes taxes & fees
24 Feb - 25 Feb
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
24 Feb - 25 Feb
Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena

Springside Bourbon Getaway

10.0 out of 10, Exceptional, (15)
"We loved staying at this property and would stay again in the future! It was so convenient to Local Feed for dinner and brunch and their food was yummy. It had everything we needed! "
The price is AED 459
AED 790 total
includes taxes & fees
24 Feb - 25 Feb
Springside Bourbon Getaway

Hidden Gem Charming 2-bedroom apartment in delightful Lexington

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

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

Lexington Apt. with parking & private entrance Preview listing

10.0 out of 10, Exceptional, (122)
"This location was perfect for us. Right between my kids college and their Church ."
The price is AED 268
AED 524 total
includes taxes & fees
24 Feb - 25 Feb
Lexington Apt. with parking & private entrance Preview listing

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

10.0 out of 10, Exceptional, (52)
"We absolutely loved our stay! The apartment was just perfect for our long anniversary weekend. Shops and restaurants within walking distance, easy parking and was very private as we were the only ones on the top floor. If you need to visit Georgetown this is the rental you want! We will definitely visit again!"
Chic Main Street Retreat < 7 Mi to KY Horse Park!

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

2.0 star property
10.0 out of 10, Exceptional, (2)
"Stayed overnight for the late game. Easy walk to Rupp and dinner places. Parking is an issue but we found a paid lot maybe 2 min walk away and parked for 18hours for 11. Super easy solution. House is probably 100 years old but was super clean. Beds were great. We were barely there but location to Rupp and dinner/breakfast for walking was great. "
The price is AED 422
AED 801 total
includes taxes & fees
24 Feb - 25 Feb
This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.

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

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 665 total
includes taxes & fees
24 Feb - 25 Feb
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, (29)
"This was our second time staying here. We love it and you can’t beat the location! We walked everywhere. Highly recommend. "
Newly Renovated 2BR Apartment w/ Free Parking in Downtown

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!

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

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 981 total
includes taxes & fees
24 Feb - 25 Feb
This apartment is a 3 bedroom(s), 1 bathrooms, located in Lexington, KY.

Cozy Lexington Townhome ~ 3 Mi to UK Campus!

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

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

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 235
AED 588 total
includes taxes & fees
3 Mar - 4 Mar
Treetops Solar Sanctuary

Westfield Blue

9.6 out of 10, Exceptional, (4)
"Second floor apartment was a cozy space. The small shared back yard area was nice, it was fenced in and had a dog clean up post for cleaning up after your dog. "
The price is AED 275
AED 587 total
includes taxes & fees
21 Mar - 22 Mar
Westfield Blue
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, (1496)
"Hiking trail was nice"
The price is AED 316
AED 348 total
includes taxes & fees
24 Feb - 25 Feb
Natural Bridge State Resort Park

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

9.8 out of 10, Exceptional, (279)
"Loved the location but 4 wheel drive is highly recommend. Very steep driveway."
The price is AED 340
AED 729 total
includes taxes & fees
24 Feb - 25 Feb
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!

Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!

9.4 out of 10, Exceptional, (62)
"We needed a short convenient layover in the middle of a trip and this worked perfectly. "
The price is AED 378
AED 800 total
includes taxes & fees
24 Feb - 25 Feb
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!
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 942 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?
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. Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!: Located 30.3 mi/48.8 km away in Stanton. Amenities include private patios. Access to a hot tub is available on site. Private One Bedroom Apartment in Downtown Lexington near Rupp Arena: It’s situated in Lexington, 18.3 mi/29.4 km away. Includes free WiFi, private patios, and fireplaces. Treetops Solar Sanctuary: It’s located in Lexington, 16.7 mi/26.9 km from Winchester. Includes free WiFi, private balconies, and sofa beds.
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. Lykins Park and College 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 Clark County Public Library.
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.