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Check prices for these dates

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8 Aug - 10 Aug
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15 Aug - 17 Aug
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29 Aug - 31 Aug
In two months
26 Sep - 28 Sep

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, (137)
"This place is super cute as is the surrounding neighborhood! Walking distance to downtown but set in a quiet and charming residential neighborhood - best of both worlds! We will definitely book here again the next time we are in Lexington. "
The price is AED 404
AED 661 total
includes taxes & fees
Jul 30 - Jul 31
Private One Bedroom Apartment in Downtown Lexington near Rupp Arena
Graffiti Art Haus - Walk to Central Bank Arena
Exterior

Graffiti Art Haus - Walk to Central Bank Arena

10.0 out of 10, Exceptional, (34)
"Perfect place to stay for visiting downtown Lexington. "
The price is AED 309
AED 772 total
includes taxes & fees
Jul 30 - Jul 31
Graffiti Art Haus - Walk to Central Bank Arena
Charming & Inviting Apartment in Historic Downtown Paris, Ky.
Exterior detail

Charming & Inviting Apartment in Historic Downtown Paris, Ky.

9.8 out of 10, Exceptional, (111)
"Property is spacious and period architecture. Road noise can be a bit much unless you are an early riser. Very close to Secretariat park (walking) and Claiborne farms. Easy drive to Kentucky Horse Park. Upstairs above business on the Main Street of Paris. Enjoyed the space and location. "
Charming & Inviting Apartment in Historic Downtown Paris, Ky.
The Colonels Apartment is a freshly renovated 3bedroom 1bath downtown Richmond apartment
Private kitchen

The Colonels Apartment is a freshly renovated 3bedroom 1bath downtown Richmond apartment

8.4 out of 10, Very Good, (8)
"You are awesome"
The price is AED 386
AED 781 total
includes taxes & fees
Aug 19 - Aug 20
The Colonels Apartment is a freshly renovated 3bedroom 1bath downtown Richmond apartment
Simply sweet - Entire 1 bed upstairs apt near EKU
Smart TV

Simply sweet - Entire 1 bed upstairs apt near EKU

10.0 out of 10, Exceptional, (8)
"We had a great time. The place was very clean, in a good area, and the perfect size for 2. "
The price is AED 305
AED 518 total
includes taxes & fees
Aug 28 - Aug 29
Simply sweet - Entire 1 bed upstairs apt near EKU
Springside Bourbon Getaway
Interior

Springside Bourbon Getaway

10.0 out of 10, Exceptional, (23)
"Wonderful stay at this property, just the right size. Highly recommend and would stay here again. Owner has prompt response time, very accommodating and very clear with check in and check out instructions. Close to excellent restaurants and quaint shops."
The price is AED 422
AED 863 total
includes taxes & fees
Aug 25 - Aug 26
Springside Bourbon Getaway
Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!
Terrace/patio

Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!

9.2 out of 10, Wonderful, (19)
"It was pretty good stay.Clean and cozy but the water pressure is a little bit low. We love staying at the cabin it was awesome."
Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!
Treetops Solar Sanctuary
Property grounds

Treetops Solar Sanctuary

9.8 out of 10, Exceptional, (77)
"Very easy to find and check in. I was by myself so I usually stay in hotels but felt very safe here. All details were taken care of and it was a fabulous place to stay!"
The price is AED 309
AED 674 total
includes taxes & fees
Aug 18 - Aug 19
Treetops Solar Sanctuary
Lexington Apt. with parking & private entrance Preview listing
Exterior

Lexington Apt. with parking & private entrance Preview listing

10.0 out of 10, Exceptional, (133)
"This is a very clean and comfortable place to stay when visiting Lexington . "
Lexington Apt. with parking & private entrance Preview listing
Chic Main Street Retreat < 7 Mi to KY Horse Park!
Coffee/tea maker

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

10.0 out of 10, Exceptional, (65)
"Beautiful, spacious, well equipped loft on a charming small town downtown."
Chic Main Street Retreat < 7 Mi to KY Horse Park!
Hot Tub & Fire Pit: Romantic Getaway in Frenchburg
Fridge, microwave, stovetop, dishwasher

Hot Tub & Fire Pit: Romantic Getaway in Frenchburg

9.4 out of 10, Exceptional, (3)
"Better than expected. My only issue was the blanket, but I could just be a picky sleeper. Can't wait to visit again!"
The price is AED 400
AED 1,017 total
includes taxes & fees
Jul 30 - Jul 31
Hot Tub & Fire Pit: Romantic Getaway in Frenchburg
Lafferty House-Walk to UofK, Woodland Pk, Dn Town, near Bourbon Trl, Horse Farms
Exterior

Lafferty House-Walk to UofK, Woodland Pk, Dn Town, near Bourbon Trl, Horse Farms

10.0 out of 10, Exceptional, (49)
"The check in process was easy, the house was clean and communication with the owner was great! I would definitely stay here again."
Lafferty House-Walk to UofK, Woodland Pk, Dn Town, near Bourbon Trl, Horse Farms
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
9.6 out of 10, Exceptional, (5)
"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 661
AED 1,113 total
includes taxes & fees
Aug 27 - Aug 28
This apartment is a 3 bedroom(s), 1 bathrooms, located in Lexington, KY.
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, (37)
"Very nice property! Blocks from downtown and UK, quiet, clean, and well appointed. Would stay again!"
Newly Renovated 2BR Apartment w/ Free Parking in Downtown
'Ralph' Comfortable Downtown/UK Apartment
Private kitchen

'Ralph' Comfortable Downtown/UK Apartment

8.4 out of 10, Very Good, (17)
"We stayed one night after a concert at Rupp Arena. The apartment was very homey with a really comfortable bed. The vintage tile floor in the bathroom was amazing!"
The price is AED 228
AED 550 total
includes taxes & fees
Jul 30 - Jul 31
'Ralph' Comfortable Downtown/UK Apartment
Location location location-#15015318-1
Exterior

Location location location-#15015318-1

10.0 out of 10, Exceptional, (29)
"Will definitely be staying there again!"
Location location location-#15015318-1
Bluegrass Getaway
Fridge, microwave, oven, stovetop

Bluegrass Getaway

10.0 out of 10, Exceptional, (11)
"The place was spotless, bed was comfortable 1 mile from Georgetown. Would stay again. "
The price is AED 459
AED 1,037 total
includes taxes & fees
Aug 17 - Aug 18
Bluegrass Getaway
Beautiful Downtown Hideaway
Fridge, microwave, oven, stovetop

Beautiful Downtown Hideaway

9.4 out of 10, Exceptional, (3)
"The property is in a perfect location to downtown and surrounding Lexington areas. It’s safe and walkable to restaurants. Easy parking and quiet. You are surrounded by parks, bars, restaurants, historical sites, and walking trails. "
Beautiful Downtown Hideaway
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, (95)
"Loved this apartment-so many nooks and crannies! Very clean and had everything we needed for an overnight stay. The bed sheets smelled amazing! The hosts were very helpful answering questions. The neighborhood is very conveniently located."
The price is AED 408
AED 772 total
includes taxes & fees
Jul 30 - Jul 31
Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena
Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington
1 bedroom, iron/ironing board, WiFi, bed sheets

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

10.0 out of 10, Exceptional, (9)
"Amazing stay! Highly recommend and would stay again!! Great location! Comfy beds, clean clean clean!! Can’t say enough good things about this place and the hosts!!"
The price is AED 352
AED 536 total
includes taxes & fees
Aug 25 - Aug 26
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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Top Winchester Hotel Reviews

Candlewood Suites Lexington Medical District by IHG

Candlewood Suites Lexington Medical District by IHG

10/10 Excellent
"Amazing hotel. Amazing rooms and great location. Highly recommend. "
Glen 2-night trip
Posted 7 hours ago
Candlewood Suites Lexington Medical District by IHG

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 976 lodging choices including 173 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. Graffiti Art Haus - Walk to Central Bank Arena: Located 18.2 mi/29.2 km away in Lexington. Free WiFi, private patios, and sofa beds are included. Access to onsite laundry facilities is available on site. 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.