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Check prices for these dates

Next weekend
21 Rab. I - 23 Rab. I
In two weeks
28 Rab. I - 30 Rab. I
In one month
11 Rab. II - 13 Rab. II
In two months
9 Jum. I - 11 Jum. I

Compare 104 Apartments in Winchester with updated reviews, rates, and availability.

Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!
Terrace/patio

Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!

9.6 out of 10, Exceptional, (13)
"Gorgeous Fall foliage @ a quaint cabin close to everything "
Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!
This apartment is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
Exterior

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

9.0 out of 10, Wonderful, (18)
"Check in was easy. Small but perfect for me and my S/O. The bed broke while sleeping Night 2. Messaged the P.M. Took a little while but she finally messaged back. They sent someone out and it was fixed when we got back from dinner. Overall, 4.5/5 would stay again. Area is quiet residential and had wonderful neighbors. 5 blocks from everything you need. "
The price is SAR 318
SAR 813 total
includes taxes & fees
17 Mar - 18 Mar
This apartment is a 1 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, (30)
"We were visiting UK and this was a perfect location! Adorable unit with a lot of space and very nicely decorated/furnished. It’s right on Limestone but the bedrooms are in the back of the unit so it was not loud at night, which I worried about. I just rebooked it for our next visit!"
Newly Renovated 2BR Apartment w/ Free Parking in Downtown
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, (54)
"Great location in the middle of Main Street. The loft was cute and cozy, perfect size for our needs. The bakery on the first floor was great for morning coffee and breakfast. Will book again when in the area."
Chic Main Street Retreat < 7 Mi to KY Horse Park!
This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Fridge, microwave, oven, stovetop

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 SAR 431
SAR 853 total
includes taxes & fees
17 Mar - 18 Mar
This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Luxury On Main / East
Private kitchen

Luxury On Main / East

10.0 out of 10, Exceptional, (1)
"I truly enjoyed my stay in this beautiful apartment. "
The price is SAR 356
SAR 682 total
includes taxes & fees
17 Mar - 18 Mar
Luxury On Main / East
Lexington Apt. with parking & private entrance Preview listing
Exterior

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 SAR 274
SAR 556 total
includes taxes & fees
24 Mar - 25 Mar
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, (18)
"This property was an absolute delight to stay at. Recently moved my daughter back into Eku after winter break and needed a close and convenient place to stay. The space was immaculate and the beds were a dream. Our host Freida was readily available to answer any questions. And she went above and beyond with our odd request for a vacuum for space saving our luggage. It was outside the door asap. Also she was extremely accommodating to our request for an extra night due to flight changes. A...
The price is SAR 319
SAR 538 total
includes taxes & fees
18 Mar - 19 Mar
Cozy upstairs 2 bed/1 bath Richmond apt near EKU
Hidden Gem Charming 2-bedroom apartment in delightful Lexington
Interior

Hidden Gem Charming 2-bedroom apartment in delightful Lexington

2.0 star property
Hidden Gem Charming 2-bedroom apartment in delightful Lexington
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, (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
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, (43)
"Responsive and professional host, great area and clean apartment with lots of character."
The price is SAR 934
SAR 1,691 total
includes taxes & fees
23 Mar - 24 Mar
Lafferty House-Walk to UK, Woodland Pk, Dn Town, near Bourbon Trail, Horse Farms
Quaint Apartment in Historic Georgetown!
Fridge, microwave, stovetop, coffee/tea maker

Quaint Apartment in Historic Georgetown!

9.8 out of 10, Exceptional, (41)
"Property was such a great place to use as a home base for our stay "
Quaint Apartment in Historic Georgetown!
Stylish Studio Apartment in Downtown Lexington
Iron/ironing board, WiFi

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
Treetops Solar Sanctuary
Property grounds

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 SAR 240
SAR 624 total
includes taxes & fees
17 Mar - 18 Mar
Treetops Solar Sanctuary
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

9.4 out of 10, Exceptional, (18)
"Effective for an over nite stay"
The price is SAR 334
SAR 679 total
includes taxes & fees
17 Mar - 18 Mar
The Scholars Apartment is a freshly renovated 2bedroom 1bath downtown Richmond apartment
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

7.8 out of 10, Good, (6)
"Nice little place to stay"
The price is SAR 375
SAR 762 total
includes taxes & fees
17 Mar - 18 Mar
The Colonels Apartment is a freshly renovated 3bedroom 1bath downtown Richmond apartment
Charming & Inviting Apartment in Historic Downtown Paris, Ky.
1 bedroom, iron/ironing board, travel crib, WiFi

Charming & Inviting Apartment in Historic Downtown Paris, Ky.

9.8 out of 10, Exceptional, (106)
"Exactly as advertised. Host is very helpful. "
Charming & Inviting Apartment in Historic Downtown Paris, Ky.
Springside Equine Getaway
Smart TV, books

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. "
The price is SAR 525
SAR 868 total
includes taxes & fees
15 Apr - 16 Apr
Springside Equine Getaway
Luxury on Main / South
Fridge, microwave, oven, stovetop

Luxury on Main / South

10.0 out of 10, Exceptional, (36)
"Our third time to stay for EKU event. Our tradition. "
The price is SAR 356
SAR 682 total
includes taxes & fees
19 Mar - 20 Mar
Luxury on Main / South
Luxury on Main / West
Fridge, microwave, oven, stovetop

Luxury on Main / West

9.6 out of 10, Exceptional, (47)
"My son relocated to Richmond for a job so we make frequent trips to visit. I love staying here and booked my next stay before I checked out! Great value for such wonderful accommodations. "
The price is SAR 356
SAR 682 total
includes taxes & fees
18 Mar - 19 Mar
Luxury on Main / West
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
Seasonal outdoor pool

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1503)
"Really clean and convenient!!! "
The price is SAR 472
SAR 521 total
includes taxes & fees
18 Mar - 19 Mar
Natural Bridge State Resort Park
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 SAR 386
SAR 800 total
includes taxes & fees
30 Mar - 31 Mar
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!
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, (282)
"Had an excellent stay, but departure was horrific in the snow. Rolled our car down the side of the mountain."
The price is SAR 347
SAR 736 total
includes taxes & fees
15 Apr - 16 Apr
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - 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 938 lodging choices including 169 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. This apartment is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.: 16.5 mi/26.6 km away in Lexington. Free WiFi and Smart TVs are included. Lexington Apt. with parking & private entrance Preview listing: It’s located in Lexington, 21.1 mi/34 km from Winchester. Includes free WiFi and private patios.
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 Cassell Creek Golf Course.
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.