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Check prices for these dates

Next weekend
20 Jun - 22 Jun
In two weeks
27 Jun - 29 Jun
In one month
11 Jul - 13 Jul
In two months
8 Aug - 10 Aug

Apartments in Winchester

Private One Bedroom Apartment in Downtown Lexington near Rupp Arena
Property grounds

Private One Bedroom Apartment in Downtown Lexington near Rupp Arena

10.0 out of 10, Exceptional, (135)
"Very accommodating. Great location.Walking distance to downtown area. "
Private One Bedroom Apartment in Downtown Lexington near Rupp Arena
Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!
Terrace/patio

Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!

9.4 out of 10, Exceptional, (16)
"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
Property grounds

Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena

9.8 out of 10, Exceptional, (93)
"Good place. Beds a little hard for older people"
The price is AED 441
AED 810 total
includes taxes & fees
8 Jul - 9 Jul
Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena
Hot Tub & Fire Pit: Romantic Getaway in Frenchburg
Fridge, microwave, stovetop, dishwasher

Hot Tub & Fire Pit: Romantic Getaway in Frenchburg

9.0 out of 10, Wonderful, (2)
"Very clean cabin, in perfect condition. Had a hard time finding it in the dark, I would suggest ariving in the daylight it is in the woods with many cabins on the same road so it can be a little confusing to find at night. Everything worked properly and we had a great time!"
The price is AED 400
AED 1,013 total
includes taxes & fees
12 Jun - 13 Jun
Hot Tub & Fire Pit: Romantic Getaway in Frenchburg
Amazing Beds, Fast WiFi - Walk to EKU & Downtown Venues - 5 minutes to I-75
Fridge, microwave, oven, stovetop

Amazing Beds, Fast WiFi - Walk to EKU & Downtown Venues - 5 minutes to I-75

2.0 star property
9.8 out of 10, Exceptional, (7)
"I’m so glad I found this rental for our trip. Will definitely book again! "
The price is AED 452
AED 1,000 total
includes taxes & fees
18 Jun - 19 Jun
Amazing Beds, Fast WiFi - Walk to EKU & Downtown Venues - 5 minutes to I-75
The Scholars Apartment is a freshly renovated 2bedroom 1bath downtown Richmond apartment
Fridge, coffee/tea maker, cookware/dishes/utensils

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

9.2 out of 10, Wonderful, (21)
"Effective for an over nite stay"
The price is AED 327
AED 665 total
includes taxes & fees
12 Jun - 13 Jun
The Scholars Apartment is a freshly renovated 2bedroom 1bath downtown Richmond apartment
This apartment is a 3 bedroom(s), 1 bathrooms, located in Lexington, KY.
Fridge, microwave, oven, stovetop

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

2.0 star property
9.4 out of 10, Exceptional, (3)
"Stayed her for Keenland trip and it was great and close to everything. we had a great time."
The price is AED 694
AED 1,154 total
includes taxes & fees
24 Jun - 25 Jun
This apartment is a 3 bedroom(s), 1 bathrooms, located in Lexington, KY.
Graffiti Art Haus - Walk to Central Bank Arena
Exterior

Graffiti Art Haus - Walk to Central Bank Arena

10.0 out of 10, Exceptional, (29)
"Loved staying at this property. Location was great, property was very clean and well stocked. Owner was responsive and available. Would definitely stay here again."
The price is AED 309
AED 772 total
includes taxes & fees
15 Jun - 16 Jun
Graffiti Art Haus - Walk to Central Bank Arena
Newly Renovated 2BR Apartment w/ Free Parking in Downtown
Property grounds

Newly Renovated 2BR Apartment w/ Free Parking in Downtown

10.0 out of 10, Exceptional, (35)
"We have stayed at this property twice and it's really great. Looks just like the photos, clean and well appointed. We were located close enough to walk to downtown and restaurants. Great value. Eee would stay here over and over"
Newly Renovated 2BR Apartment w/ Free Parking in Downtown
PROMO 5% WEEKLY AND 10% MONTHLY DISCOUNT! New building Urban Studio
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (66)
"Was a convenient place for us to stay, close to several locations. Would stay here again."
PROMO 5% WEEKLY AND 10% MONTHLY DISCOUNT! New building Urban Studio
Lexington Apt. with parking & private entrance Preview listing
Exterior

Lexington Apt. with parking & private entrance Preview listing

10.0 out of 10, Exceptional, (129)
"Great stay and amazing communication. We had a last minute booking and the host was very accommodating "
The price is AED 264
AED 563 total
includes taxes & fees
15 Jun - 16 Jun
Lexington Apt. with parking & private entrance Preview listing
Cozy upstairs 2 bed/1 bath Richmond apt near EKU
Aerial view

Cozy upstairs 2 bed/1 bath Richmond apt near EKU

10.0 out of 10, Exceptional, (23)
"Very clean. Easy access. Nice little apartment. "
The price is AED 281
AED 492 total
includes taxes & fees
13 Jun - 14 Jun
Cozy upstairs 2 bed/1 bath Richmond apt near EKU
Lafferty House-Walk to UK, Woodland Pk, Dn Town, near Bourbon Trail, Horse Farms
Exterior

Lafferty House-Walk to UK, Woodland Pk, Dn Town, near Bourbon Trail, Horse Farms

10.0 out of 10, Exceptional, (48)
"Responsive and professional host, great area and clean apartment with lots of character."
The price is AED 823
AED 1,488 total
includes taxes & fees
12 Jun - 13 Jun
Lafferty House-Walk to UK, Woodland Pk, Dn Town, near Bourbon Trail, Horse Farms
Safe & Secure 2br near UKPD in Lex - Rest easy, walk 2 UK
Private kitchen

Safe & Secure 2br near UKPD in Lex - Rest easy, walk 2 UK

2.0 star property
10.0 out of 10, Exceptional, (2)
"Cute, clean place. Excellent and responsive host."
Safe & Secure 2br near UKPD in Lex - Rest easy, walk 2 UK
Springside Equine Getaway
Smart TV, books

Springside Equine Getaway

10.0 out of 10, Exceptional, (10)
"I have stayed here a few times and love it! The place is very clean and comfortable! I also love the location!"
The price is AED 459
AED 927 total
includes taxes & fees
23 Jun - 24 Jun
Springside Equine Getaway
Comfy Upstairs 2 bed/1 bath near EKU in Richmond
Fridge, microwave, oven, stovetop

Comfy Upstairs 2 bed/1 bath near EKU in Richmond

10.0 out of 10, Exceptional, (30)
"I came to visit my brother and it was perfect for a quick stay to spend time with him while getting to see EKU. Very clean and accurate listing, highly reccomend!"
The price is AED 281
AED 492 total
includes taxes & fees
13 Jun - 14 Jun
Comfy Upstairs 2 bed/1 bath near EKU in Richmond
The merchant above Indigo steps from Rupp Arena
Interior

The merchant above Indigo steps from Rupp Arena

7.0 out of 10, Good, (2)
"We really loved the historic features and feel of this property. It was spacious, comfortable and updated just enough without taking away from the historic appeal. We could walk everywhere we wanted, especially downtown. Most importantly, for this stay, it is a very short distance to Rupp. We were in town for graduation and easily walked the two short blocks to the arena while watching the heavy traffic all day long. We used the kitchen island and living room as a place for our graduate and a...
The merchant above Indigo steps from Rupp Arena
Quaint Apartment in Historic Georgetown!
Fridge, microwave, stovetop, coffee/tea maker

Quaint Apartment in Historic Georgetown!

9.8 out of 10, Exceptional, (44)
"This apartment was perfect. I look forward to staying there again."
Quaint Apartment in Historic Georgetown!
Bluegrass Getaway
Fridge, microwave, oven, stovetop

Bluegrass Getaway

10.0 out of 10, Exceptional, (10)
"The place was spotless, bed was comfortable 1 mile from Georgetown. Would stay again. "
The price is AED 459
AED 1,041 total
includes taxes & fees
23 Jun - 24 Jun
Bluegrass Getaway
Westfield Gold
Interior

Westfield Gold

8.6 out of 10, Excellent, (7)
"Beautiful and comfortable apartment"
The price is AED 290
AED 603 total
includes taxes & fees
17 Jun - 18 Jun
Westfield Gold
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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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 952 lodging choices including 151 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. Access to onsite laundry facilities is available on site. Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!: Located in Stanton, 30.3 mi/48.8 km away. Includes private patios. Access to a hot tub is available on site. Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena: 18.3 mi/29.4 km away in Lexington. 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 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.