Photo by Hyelsinta

Search Apartments 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 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

Compare 123 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!
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
Lexington Apt. with parking & private entrance Preview listing
Exterior

Lexington Apt. with parking & private entrance Preview listing

10.0 out of 10, Exceptional, (125)
"This is a very clean and comfortable place to stay when visiting Lexington . "
The price is AED 268
AED 545 total
includes taxes & fees
21 Apr - 22 Apr
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, (56)
"This unit is my favorite and my preferred stay in Georgetown. Lots of stairs going up, just FYI, very close to great restaurants and Irish Pub. Georgetown is a wonderful small town and so close to Lexington. This unit is very close to grocery shopping and very walkable."
Chic Main Street Retreat < 7 Mi to KY Horse Park!
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 AED 311
AED 788 total
includes taxes & fees
16 Apr - 17 Apr
This apartment is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
Quaint Apartment in Historic Georgetown!
Fridge, microwave, stovetop, coffee/tea maker

Quaint Apartment in Historic Georgetown!

9.8 out of 10, Exceptional, (42)
"We really enjoyed our stay. It is on the 2nd floor with a light of stairs to access the unit. It was definitely not an issue for us but could be for some people. If I'm in the Lexington area again I would definitely stay here. "
Quaint Apartment in Historic Georgetown!
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
9.6 out of 10, Exceptional, (5)
"Our children had an adventure planned with their cousins, so we came down for the day and needed a place to stay and this was perfect. Good beds for everyone and an easy check-in. The host reached out to make sure we had everything we needed and everything was perfect."
The price is AED 477
AED 1,028 total
includes taxes & fees
20 Apr - 21 Apr
Amazing Beds, Fast WiFi - Walk to EKU & Downtown Venues - 5 minutes to I-75
Luxury on Main / South
Fridge, microwave, oven, stovetop

Luxury on Main / South

10.0 out of 10, Exceptional, (38)
"Came to visit our daughter at EKU to spend a few days of relaxation."
The price is AED 349
AED 668 total
includes taxes & fees
16 Apr - 17 Apr
Luxury on Main / South
Treetops Solar Sanctuary
Property grounds

Treetops Solar Sanctuary

10.0 out of 10, Exceptional, (72)
"We loved feeling like we were surrounded by trees in the midst of the burbs. The stay was cozy and fun, the decor was whimsical and made me feel more at home than the usual sterile beige everything that comes with rental stats. "
The price is AED 253
AED 633 total
includes taxes & fees
21 Apr - 22 Apr
Treetops Solar Sanctuary
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
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, (33)
"Very nice place, right in heart of Lexington!"
Newly Renovated 2BR Apartment w/ Free Parking in Downtown
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
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, (90)
"Good place. Beds a little hard for older people"
The price is AED 441
AED 846 total
includes taxes & fees
20 Apr - 21 Apr
Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena
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)
"Beautiful remodeled older house into apartments. I love this place. Second time I stayed there!! Only issue is that it's hard to work the dead bolt on entry door. Great hosts. Great accomodations!"
The price is AED 367
AED 750 total
includes taxes & fees
6 May - 7 May
The Colonels Apartment is a freshly renovated 3bedroom 1bath downtown Richmond apartment
Springside Equine Getaway
Smart TV, books

Springside Equine Getaway

10.0 out of 10, Exceptional, (9)
"Great way to spend a night close to my college daughter at Georgetown College. Great location and walking distance to the college and downtown!"
The price is AED 514
AED 850 total
includes taxes & fees
28 Apr - 29 Apr
Springside Equine Getaway
Location location location-#15015318-1
Exterior

Location location location-#15015318-1

10.0 out of 10, Exceptional, (26)
"The property was warm and convenient to everything around town . It was super clean, warm, and spacious for us. It had all of the amenities that we needed. The beds were very comfortable. "
Location location location-#15015318-1
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, (29)
"Staying in area due to family medical issues. Very convenient and close to hospital. Nice to have a restful area after long days of stress. "
The price is AED 312
AED 526 total
includes taxes & fees
17 Apr - 18 Apr
Comfy Upstairs 2 bed/1 bath near EKU in Richmond
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 AED 349
AED 668 total
includes taxes & fees
16 Apr - 17 Apr
Luxury On Main / East
Peaceful Location in walking distance to the University & Hospitals
Microwave, oven, stovetop, coffee/tea maker

Peaceful Location in walking distance to the University & Hospitals

9.0 out of 10, Wonderful, (2)
"The apartment was clean and ready, easy to find, and an 8 minute drive to where I was working on campus at University of Kentucky. Great price."
Peaceful Location in walking distance to the University & Hospitals
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 AED 349
AED 668 total
includes taxes & fees
27 Apr - 28 Apr
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.
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 AED 444
AED 490 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 AED 416
AED 858 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 AED 386
AED 547 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

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 951 lodging choices including 167 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. Treetops Solar Sanctuary: Located 16.7 mi/26.9 km away in Lexington. Free WiFi, private balconies, and sofa beds are included. 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. The Scholars Apartment is a freshly renovated 2bedroom 1bath downtown Richmond apartment: 17.6 mi/28.3 km away in Richmond. Free WiFi and private patios are included. Amazing Beds, Fast WiFi - Walk to EKU & Downtown Venues - 5 minutes to I-75: It’s located in Richmond, 18 mi/29 km from Winchester. Includes private patios, fireplaces, and Smart TVs.
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.