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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Compare 47 Condo Rentals in Winchester with updated reviews, rates, and availability.

The Gatsby Getaway, Downtown LEX
Exterior

The Gatsby Getaway, Downtown LEX

10.0 out of 10, Exceptional, (13)
"I stayed here for two weeks while I was interning at a local business, I enjoyed my stay here although I did have a few complaints. The air temperature wouldn’t go below 72 even though I had it set in the mid 60s for a few days which isn’t too warm but I would’ve preferred it being colder. I also didn’t care for the fact of there being no household cleaners available to wipe down surfaces when I was done cooking but that is an understandable thing to not have. Besides that it was a great place...
The price is AED 364
AED 703 total
includes taxes & fees
11 Mar - 12 Mar
The Gatsby Getaway, Downtown LEX
175 LEX - Spacious Two Bedroom Downtown Lexington
2 bedrooms, desk, iron/ironing board, travel crib

175 LEX - Spacious Two Bedroom Downtown Lexington

9.6 out of 10, Exceptional, (24)
"My husband and I and our oldest stayed at 175 lex and everything was perfect. Claire, our host, was very attentive and we even got to check in a bit early. Very clean and great location!!"
The price is AED 400
AED 825 total
includes taxes & fees
11 Mar - 12 Mar
175 LEX - Spacious Two Bedroom Downtown Lexington
2 Beds/2 Full Baths, Fenced Yard, 1 Car Garage, One Level, Pets Welcomed!
Fridge, microwave, oven, dishwasher

2 Beds/2 Full Baths, Fenced Yard, 1 Car Garage, One Level, Pets Welcomed!

2 Beds/2 Full Baths, Fenced Yard, 1 Car Garage, One Level, Pets Welcomed!
175 LEX - Walkable Loft to Rupp Arena & Downtown!
Miscellaneous

175 LEX - Walkable Loft to Rupp Arena & Downtown!

9.0 out of 10, Wonderful, (7)
"Great property, clean & easy access to downtown restaurants."
The price is AED 345
AED 681 total
includes taxes & fees
23 Mar - 24 Mar
175 LEX - Walkable Loft to Rupp Arena & Downtown!
175 LEX - Stunning Downtown Views on Main Street!
1 bedroom, iron/ironing board, travel crib, free WiFi

175 LEX - Stunning Downtown Views on Main Street!

9.8 out of 10, Exceptional, (36)
"View is awesome!!! Great communication with managers.. will definitely rebook here…"
The price is AED 364
AED 703 total
includes taxes & fees
23 Mar - 24 Mar
175 LEX - Stunning Downtown Views on Main Street!
This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
Fridge, coffee/tea maker, cookware/dishes/utensils

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

8.0 out of 10, Very Good, (4)
"An absolutely lovely place to stay. We chose it for etc. location to Lexington because we had family in Nicholasville Harrodsburg Brian station Tates Creek Richmond Road and this was easy to get back to no matter where we went. Nice property nice parking lot well lit everything you would need for a stay. "
The price is AED 349
AED 629 total
includes taxes & fees
11 Mar - 12 Mar
This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
175 LEX - Walkable Downtown Condo - Stunning View
Smart TV, fireplace

175 LEX - Walkable Downtown Condo - Stunning View

9.4 out of 10, Exceptional, (6)
"I loved that this space was so close to downtown and just a block or two away from busy traffic and street noise. The underground parking was a huge perk. We were able to walk to just about everything we wanted to do, and the space had all the necessary amenities."
The price is AED 386
AED 730 total
includes taxes & fees
11 Mar - 12 Mar
175 LEX - Walkable Downtown Condo - Stunning View
175 LEX - Two Bedroom Condo, Walkable Downtown!
Exterior

175 LEX - Two Bedroom Condo, Walkable Downtown!

9.6 out of 10, Exceptional, (9)
"We visited for a December graduation from UKY. The property was in excellent condition and the location was terrific."
The price is AED 422
AED 860 total
includes taxes & fees
16 Mar - 17 Mar
175 LEX - Two Bedroom Condo, Walkable Downtown!
Paradiso - Divine Condo, Perfect Location Walkable to Everything Downtown
2 bedrooms, iron/ironing board, WiFi, bed sheets

Paradiso - Divine Condo, Perfect Location Walkable to Everything Downtown

10.0 out of 10, Exceptional, (71)
"Could not have been happier. Even more beautiful than the pictures. The artwork and aesthetics are amazing. Beds are comfy and the apartment is spacious. Will def stay here again!"
Paradiso - Divine Condo, Perfect Location Walkable to Everything Downtown
175 LEX - Spacious Two Bedroom! Walkable Downtown!
Fridge, microwave, oven, stovetop

175 LEX - Spacious Two Bedroom! Walkable Downtown!

10.0 out of 10, Exceptional, (5)
"Perfect location for visiting downtown Lexington. Condo was very clean and had all the convinces of home. Pictures of the condo are accurate, however the distance to Rupp Area are a much longer walk than what I had thought. Parking is a challenge. The icing on the cake was the Halloween parade and Thriller reenactment were directly in from of our building. If I were coming at the same time of year would definitely rent this condo again. Our host was a jewel to work with. Would recommend friends...
The price is AED 386
AED 803 total
includes taxes & fees
13 Mar - 14 Mar
175 LEX - Spacious Two Bedroom! Walkable Downtown!
Bourbon Condo Downtown Lexington
2 bedrooms, desk, iron/ironing board, travel crib

Bourbon Condo Downtown Lexington

9.8 out of 10, Exceptional, (8)
"Very clean, comfortable and centrally located. Had a few hiccups but management were very helpful and responsive. "
The price is AED 437
AED 874 total
includes taxes & fees
11 Mar - 12 Mar
Bourbon Condo Downtown Lexington
Penthouse @ 175 LEX -Walk to Rupp Arena on Main St
Smart TV, fireplace

Penthouse @ 175 LEX -Walk to Rupp Arena on Main St

10.0 out of 10, Exceptional, (9)
"Lots of attractions and restaurants within walking distance. "
The price is AED 988
AED 1,763 total
includes taxes & fees
11 Mar - 12 Mar
Penthouse @ 175 LEX -Walk to Rupp Arena on Main St
175 LEX - Walk to Rupp Arena Downtown Top Floor
Miscellaneous

175 LEX - Walk to Rupp Arena Downtown Top Floor

9.8 out of 10, Exceptional, (15)
"Had a quick trip to Lexington for a barrel selection and this was exactly what we had in mind. Easy walk to dinner and easy access to everything."
The price is AED 345
AED 681 total
includes taxes & fees
23 Mar - 24 Mar
175 LEX - Walk to Rupp Arena Downtown Top Floor
Downtown Lex Full Friends Condo
Property grounds

Downtown Lex Full Friends Condo

9.0 out of 10, Wonderful, (2)
"Overall, the condo was clean, spacious, and well-maintained. Security was exceptional with key codes needed for doors and elevator. Felt safe in the downtown urban setting. Enjoyed our two-night stay but noise from the central heating unit interrupted our sleep. The TV and Wi-Fi worked great and problem-free, and the electronic fireplace was a nice touch. Parking can be tricky and is not on-site but we managed to find free street parking thanks to the holiday hours"
The price is AED 364
AED 703 total
includes taxes & fees
13 Mar - 14 Mar
Downtown Lex Full Friends Condo
Man O'War @ The HoM/KY Horse Park 11min/Ark 30min/Walk to Georgetown College
Outdoor dining

Man O'War @ The HoM/KY Horse Park 11min/Ark 30min/Walk to Georgetown College

10.0 out of 10, Exceptional, (4)
"Very nice place. It fit our needs for a quick stop in Georgetown. Communication with the host was excellent."
The price is AED 514
AED 980 total
includes taxes & fees
12 Mar - 13 Mar
Man O'War @ The HoM/KY Horse Park 11min/Ark 30min/Walk to Georgetown College
Lex In The City - Downtown Condo
Exterior

Lex In The City - Downtown Condo

9.6 out of 10, Exceptional, (5)
"Great stay, location and mgmt team is great. The only bathroom is ensuite so makes a little difficult if 4 people. Have stayed in a few of the 175 Lex locations and all have been pleasant."
The price is AED 364
AED 703 total
includes taxes & fees
16 Mar - 17 Mar
Lex In The City - Downtown Condo
175 LEX - Spacious Two Bedroom - Near Rupp Arena!
Interior

175 LEX - Spacious Two Bedroom - Near Rupp Arena!

9.4 out of 10, Exceptional, (10)
"This is a great location to walk downtown. Would like to see some TV or streaming services included. I'm not a fan of logging in at a VRBO. Place was very clean, check in was easy, check out was simple. Code set up for doors and elevator was the easiest, I appreciated that. Much better then trying to remember random codes we received from other stays."
The price is AED 400
AED 825 total
includes taxes & fees
11 Mar - 12 Mar
175 LEX - Spacious Two Bedroom - Near Rupp Arena!
175 LEX - Walkable Downtown Lexington - Top Floor
Property grounds

175 LEX - Walkable Downtown Lexington - Top Floor

9.0 out of 10, Wonderful, (8)
"Nice place, good location"
The price is AED 345
AED 681 total
includes taxes & fees
23 Mar - 24 Mar
175 LEX - Walkable Downtown Lexington - Top Floor
175 LEX - Loft in Downtown Lexington, Rupp Arena
Fridge, microwave, oven, stovetop

175 LEX - Loft in Downtown Lexington, Rupp Arena

10.0 out of 10, Exceptional, (1)
"We had a great stay! The location was perfect for downtown and within easy walking distance from attraction and Target market. Very clean and easy access!"
The price is AED 364
AED 703 total
includes taxes & fees
11 Mar - 12 Mar
175 LEX - Loft in Downtown Lexington, Rupp Arena
Quiet Downtown Lexington Bougie Apartment
Exterior

Quiet Downtown Lexington Bougie Apartment

9.0 out of 10, Wonderful, (2)
"Everything was perfect. Would stay there again!!"
The price is AED 364
AED 703 total
includes taxes & fees
16 Mar - 17 Mar
Quiet Downtown Lexington Bougie Apartment
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, (1501)
"We had a great stay. The breakfast was 110% better than expected. The workers there were so friendly and helpful. I would definitely stay there again when I’m in the area."
The price is AED 407
AED 449 total
includes taxes & fees
13 Mar - 14 Mar
Natural Bridge State Resort Park
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
TV, books

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

9.8 out of 10, Exceptional, (281)
"The cabin is lovely! Everything was clean and all the extras provided made this a comfortable stay. "
The price is AED 462
AED 876 total
includes taxes & fees
1 Apr - 2 Apr
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!
Exterior

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 783 total
includes taxes & fees
13 Mar - 14 Mar
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.

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