Photo by Hyelsinta

Search Condo Rentals in Winchester

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

Compare 55 Condo Rentals in Winchester with updated reviews, rates, and availability.

The Gatsby Getaway, Downtown LEX
Fridge, microwave, oven, stovetop

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 SAR 432
SAR 794 total
includes taxes & fees
20 Apr - 21 Apr
The Gatsby Getaway, Downtown LEX
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 - 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, (39)
"The condo was well maintained, clean and tastefully decorated. The wide windows were nice. It is downtown which means it can be a bit noisier than some places but it is very convenient and you can walk to most places downtown. My ife and I agreed we'd consider renting it again "
The price is SAR 432
SAR 808 total
includes taxes & fees
27 Apr - 28 Apr
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.

8.4 out of 10, Very Good, (5)
"Stayed here for a chemo visit at a local hospital for my hubby. Very close to hospital. The property is quaint, quiet, and funky. Enjoyed our stay, parking is excellent. It is tucked away in a cool neighborhood that is remarkably quiet. We loved the mural, the open concept, and the industrial feel. The unit has a TV in the living room and the bedroom- that's a definite plus. The kitchen is well stocked. Loved our stay; just the atmosphere we needed. Thank you!"
The price is SAR 375
SAR 669 total
includes taxes & fees
5 May - 6 May
This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
175 LEX - Spacious Two Bedroom! Walkable Downtown!
2 bedrooms, iron/ironing board, travel crib, free WiFi

175 LEX - Spacious Two Bedroom! Walkable Downtown!

10.0 out of 10, Exceptional, (6)
"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 SAR 484
SAR 955 total
includes taxes & fees
20 Apr - 21 Apr
175 LEX - Spacious Two Bedroom! 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, (72)
"Beautiful property in a great location! Thanks again! "
Paradiso - Divine Condo, Perfect Location Walkable to Everything Downtown
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, (25)
"Bright, nicely furnished and very comfortable. Bed mattresses are very important to us and these were very comfortable! Location is near to concert venues and great walkable areas and restaurants. Very happy with our stay! We will be back!"
The price is SAR 469
SAR 915 total
includes taxes & fees
28 Apr - 29 Apr
175 LEX - Spacious Two Bedroom Downtown Lexington
175 LEX - Two Bedroom Condo, Walkable Downtown!
2 bedrooms, desk, iron/ironing board, travel crib

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 SAR 469
SAR 915 total
includes taxes & fees
28 Apr - 29 Apr
175 LEX - Two Bedroom Condo, Walkable Downtown!
175 LEX - Walkable Loft to Rupp Arena & Downtown!
Fridge, microwave, oven, stovetop

175 LEX - Walkable Loft to Rupp Arena & Downtown!

9.0 out of 10, Wonderful, (8)
"Great property, clean & easy access to downtown restaurants."
The price is SAR 432
SAR 794 total
includes taxes & fees
21 Apr - 22 Apr
175 LEX - Walkable Loft to Rupp Arena & Downtown!
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, (11)
"The unit is beautiful and in a perfect location. The host was great to work with and very responsive! Would definitely stay again!"
The price is SAR 1,107
SAR 1,941 total
includes taxes & fees
21 Apr - 22 Apr
Penthouse @ 175 LEX -Walk to Rupp Arena on Main St
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 SAR 507
SAR 987 total
includes taxes & fees
20 Apr - 21 Apr
Bourbon Condo Downtown Lexington
175 LEX - Walk to Rupp Arena Downtown Top Floor
1 bedroom, iron/ironing board, travel crib, free WiFi

175 LEX - Walk to Rupp Arena Downtown Top Floor

9.8 out of 10, Exceptional, (16)
"LEX 175 was an excellent property for our March Madness weekend. Great location for restaurants, bars and its proximity to Rupp Arena. Very Clean and quiet. Outstanding communication with the owner before, during and after our stay. Very accommodating with arrival time as we experienced lengthy weather delays. Would definitely stay again!"
The price is SAR 409
SAR 767 total
includes taxes & fees
29 Apr - 30 Apr
175 LEX - Walk to Rupp Arena Downtown 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 SAR 409
SAR 776 total
includes taxes & fees
27 Apr - 28 Apr
175 LEX - Loft in Downtown Lexington, Rupp Arena
Downtown Lex Full Friends Condo
Fridge, microwave, oven, stovetop

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 SAR 469
SAR 858 total
includes taxes & fees
5 May - 6 May
Downtown Lex Full Friends Condo
175 LEX - Spacious Two Bedroom - Near Rupp Arena!
Interior

175 LEX - Spacious Two Bedroom - Near Rupp Arena!

9.4 out of 10, Exceptional, (11)
"The location of this property was perfect. Right in the middle of downtown within walking distance of restaurants and Rupp arena. Condo was clean and just as described. Went for a girls trip and the condo was spacious and comfortable. We did have trouble getting in when we got there. Our code worked for the main door and elevator, but not the room. Reached out to owner and issue was resolved within 10 minutes. The other suggestion would be some TV instructions and potentially the cleaning person...
The price is SAR 469
SAR 946 total
includes taxes & fees
27 Apr - 28 Apr
175 LEX - Spacious Two Bedroom - Near Rupp Arena!
Castle Glow_Lex_Close to UK and Hospitals
Fridge, microwave, stovetop, dishwasher

Castle Glow_Lex_Close to UK and Hospitals

Castle Glow_Lex_Close to UK and Hospitals
175 LEX - Walkable Downtown Lexington - Top Floor
Smart TV

175 LEX - Walkable Downtown Lexington - Top Floor

9.0 out of 10, Wonderful, (8)
"Nice place, good location"
The price is SAR 469
SAR 858 total
includes taxes & fees
5 May - 6 May
175 LEX - Walkable Downtown Lexington - Top Floor
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 SAR 432
SAR 794 total
includes taxes & fees
20 Apr - 21 Apr
175 LEX - Walkable Downtown Condo - Stunning View
Lex In The City - Downtown Condo
Smart TV, fireplace, offices

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 SAR 432
SAR 808 total
includes taxes & fees
27 Apr - 28 Apr
Lex In The City - Downtown Condo
Man O'War @ The HoM/KY Horse Park 11min/Ark 30min/Walk to Georgetown College
Exterior

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 SAR 563
SAR 1,051 total
includes taxes & fees
20 Apr - 21 Apr
Man O'War @ The HoM/KY Horse Park 11min/Ark 30min/Walk to Georgetown College
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winchester

Natural Bridge State Resort Park
Seasonal outdoor pool

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1526)
"We stayed in a cottage. The cottage needs a lot of repairs. We had to climb 36 stairs in rainy conditions to reach our cabin. The complimentary breakfast was nice. The staff were all friendly and helpful. The walk to the restaurant from the cottages was outstanding and fun. Despite the state of disrepair to our cabin, we would still recommend this location as a must-do family adventure and destination."
The price is SAR 454
SAR 500 total
includes taxes & fees
16 Apr - 17 Apr
Natural Bridge State Resort Park
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
Outdoor spa tub

Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!

9.6 out of 10, Exceptional, (141)
"Cozy, clean and comfortable cabin!"
The price is SAR 425
SAR 877 total
includes taxes & fees
16 Apr - 17 Apr
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
Tranquil Getaway in the Woods ~ Sunset Ridge
Terrace/patio

Tranquil Getaway in the Woods ~ Sunset Ridge

9.8 out of 10, Exceptional, (53)
"My girlfriends and I loved the quaint cabin. The firepit was great! Beds are comfortable and comes with plenty of kitchen amenities! I would recommend adding a curtain option for the bed by the window.. Though it's off the beaten path, we were removed enough from others and no issue of safety."
The price is SAR 394
SAR 559 total
includes taxes & fees
16 Apr - 17 Apr
Tranquil Getaway in the Woods ~ Sunset Ridge
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

Why book your condo in Winchester with Expedia?
Getting away shouldn’t be difficult, so if you’re on the lookout for condos at an affordable rate, Expedia has got your back. Keep costs down and select something small and affordable, or splurge on a luxury condo and spoil your favorite people. Our search filters make it a breeze to find a property in Winchester that matches your needs.
How can I find cheap condos in Winchester?
A great way to score cheap condos in Winchester is with Expedia’s useful filter tool. Narrow down your search results by budget, amenities and star rating to snag unbeatable prices in just a few clicks.