An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

Search Apartments in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Winchester apartments

1 bedroom, iron/ironing board, WiFi, bed sheets

Westfield Blue

Westfield Blue
Richmond
9.0 out of 10, Wonderful, (8 reviews)
"This is a fantastic property. Incredible comfort, walkable to all of the historic downtown, and delightfully and tastefully decorated. I even took ideas for a home I am designing."
United States
Keith G.
The price is HK$691
HK$1,367 total
includes taxes & fees
19 Jul - 20 Jul
Westfield Blue
Private kitchen

‘Edith’ Carriage House Getaway - Hamburg/I-75!

‘Edith’ Carriage House Getaway - Hamburg/I-75!
Lexington
9.6 out of 10, Exceptional, (5 reviews)
"Had difficulties checking in other than that felt right at home!"
United States
Kaydance
The price is HK$447
HK$1,164 total
includes taxes & fees
14 Aug - 15 Aug
‘Edith’ Carriage House Getaway - Hamburg/I-75!
Dining

1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Lexington
10.0 out of 10, Exceptional, (47 reviews)
"The property is misrepresented in the listing. It is not a non-smoking apartment but is a sketchy motel room that has definitely been smoked in. The smoke detector was wrapped in plastic wrap. It was dirty and we couldn’t stay there. We had to book another room for the night which was amazing."
United States
Tracy
The price is HK$510
HK$561 total
includes taxes & fees
16 Jul - 17 Jul
1 King Bed | Non-Smoking, Micfridge
Private kitchen

The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling

The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling
Mount Sterling
10.0 out of 10, Exceptional, (1 review)
"Everything was perfect!"
United States
Miguel
The price is HK$896
HK$1,160 total
includes taxes & fees
16 Jul - 17 Jul
The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling
Dining

Luxury on Main / South

Luxury on Main / South
Richmond
10.0 out of 10, Exceptional, (52 reviews)
"Great amenities"
United States
Michael C.
The price is HK$745
HK$1,426 total
includes taxes & fees
22 Jul - 23 Jul
Luxury on Main / South
Interior

Charming studio apartment in Richmond, just minutes away from EKU

Charming studio apartment in Richmond, just minutes away from EKU
Richmond
9.0 out of 10, Wonderful, (2 reviews)
"The property was nice and clean. Easy access to shops close by and food. "
United States
Tyler C.
The price is HK$607
HK$1,490 total
includes taxes & fees
16 Jul - 17 Jul
Charming studio apartment in Richmond, just minutes away from EKU
Living area

Bourbon Trail - Loft in Downtown Lexington

Bourbon Trail - Loft in Downtown Lexington
Lexington
9.6 out of 10, Exceptional, (5 reviews)
"We had a great stay at this location. It was clean, cozy, and nice. The property owner was very nice and was very easy to communicate with. If I ever stay in Lexington again it will be here. "
United States
Awntavio W.
The price is HK$577
HK$1,589 total
includes taxes & fees
19 Jul - 20 Jul
Bourbon Trail - Loft in Downtown Lexington
Smart TV, fireplace

Luxury on Main / West

Luxury on Main / West
Richmond
9.6 out of 10, Exceptional, (58 reviews)
"The cleanliness of the apartment, very spacious and the easy check-in."
United States
Kassy B.
The price is HK$745
HK$1,426 total
includes taxes & fees
15 Aug - 16 Aug
Luxury on Main / West
Interior

Seabiscuit Loft - Studio Stay in Downtown Lexington

Seabiscuit Loft - Studio Stay in Downtown Lexington
Lexington
9.4 out of 10, Exceptional, (3 reviews)
"We got this apartment for much needed rest while my husband was taking treatments. We were able to rest and enjoyed our stay."
United States
April S.
The price is HK$541
HK$1,537 total
includes taxes & fees
16 Jul - 17 Jul
Seabiscuit Loft - Studio Stay in Downtown Lexington
Exterior detail

Treetops Solar Sanctuary

Treetops Solar Sanctuary
Chevy Chase
10.0 out of 10, Exceptional, (92 reviews)
"Such a wonderful little hidden gem! The host was fantastic and was perfect for a trip up to Lexington! Would use again and would highly recommend!"
United States
Matthew Y.
The price is HK$621
HK$1,394 total
includes taxes & fees
29 Jul - 30 Jul
Treetops Solar Sanctuary
Exterior

Safe & Secure 2br near UKPD in Lex - Rest easy, walk 2 UK

Safe & Secure 2br near UKPD in Lex - Rest easy, walk 2 UK
Downtown Lexington
9.8 out of 10, Exceptional, (10 reviews)
"Great host. Walkable to other places "
United States
Anonymous traveller
The price is HK$517
HK$1,856 total
includes taxes & fees
16 Jul - 17 Jul
Safe & Secure 2br near UKPD in Lex - Rest easy, walk 2 UK
Interior

Charming 2-bedroom apartment with AC, WiFi in brilliant Lexington

Charming 2-bedroom apartment with AC, WiFi in brilliant Lexington
Downtown Lexington
10.0 out of 10, Exceptional, (1 review)
"Very convenient to downtown Lexington"
United States
Chad C.
The price is HK$560
HK$1,906 total
includes taxes & fees
20 Jul - 21 Jul
Charming 2-bedroom apartment with AC, WiFi in brilliant Lexington
Interior

Westfield Green

Westfield Green
Richmond
10.0 out of 10, Exceptional, (17 reviews)
"So nice I did not want to leave! Beautifully decorated and an amazing layout. Will definitely stay here again next time I am in Richmond! We felt right at home. "
United States
Christina P.
The price is HK$910
HK$1,608 total
includes taxes & fees
18 Jul - 19 Jul
Westfield Green
TV

Yeti Escape I Cozy 2BR I 15m to RRG I Wi-Fi

Yeti Escape I Cozy 2BR I 15m to RRG I Wi-Fi
Stanton
The price is HK$836
HK$1,445 total
includes taxes & fees
16 Jul - 17 Jul
Yeti Escape I Cozy 2BR I 15m to RRG I Wi-Fi
1 bedroom, iron/ironing board, WiFi, bed sheets

Big Blue - Stylish Studio in Downtown Lexington

Big Blue - Stylish Studio in Downtown Lexington
Lexington
The price is HK$541
HK$1,547 total
includes taxes & fees
19 Jul - 20 Jul
Big Blue - Stylish Studio in Downtown Lexington
Coffee/tea maker, fridge, microwave, oven

Modern 2bd 2ba - Near I75, No Steps, Free Wifi

Modern 2bd 2ba - Near I75, No Steps, Free Wifi
Richmond
9.8 out of 10, Exceptional, (90 reviews)
"Everything was fantastic!!"
United States
Leah Anne G.
The price is HK$872
HK$1,793 total
includes taxes & fees
2 Aug - 3 Aug
Modern 2bd 2ba - Near I75, No Steps, Free Wifi
Interior

Central Stay! Near UK/Downtown/Campus.

Central Stay! Near UK/Downtown/Campus.
Lexington
10.0 out of 10, Exceptional, (2 reviews)
"Nice quiet apartment conveniently located near the University and fun restaurants. Hosts were great and responded quickly to any questions."
United States
Alison T.
Central Stay! Near UK/Downtown/Campus.
Living area

Modern Loft - Parking Included, Walk to Downtown

Modern Loft - Parking Included, Walk to Downtown
Downtown Lexington
10.0 out of 10, Exceptional, (7 reviews)
"Our stay was perfect. Very clean, the bed was amazing. "
United States
Haylee W.
Modern Loft - Parking Included, Walk to Downtown
Exterior

1200 sf Apt -3 BR-Amazing Beds-Walk to EKU & Downtown Venues - 5 minutes to I-75

1200 sf Apt -3 BR-Amazing Beds-Walk to EKU & Downtown Venues - 5 minutes to I-75
Richmond
9.8 out of 10, Exceptional, (14 reviews)
"We enjoyed our stay. Location was amazing for our trip!"
United States
Deanna E.
The price is HK$784
HK$2,342 total
includes taxes & fees
26 Jul - 27 Jul
1200 sf Apt -3 BR-Amazing Beds-Walk to EKU & Downtown Venues - 5 minutes to I-75
Smart TV

Central Location! Walk 2 UK campus/Chandler Hospital, Mins to Downtown

Central Location! Walk 2 UK campus/Chandler Hospital, Mins to Downtown
Lexington
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was very clean and nice. We were staying for the music festival Railbird at the Red Mile, so it was a very easy walk making the weekend nice not having to worry with parking or taxis service. Traffic was a mess and we just walked right on by. Thanks for a great weekend"
United States
Mark B.
The price is HK$957
HK$2,366 total
includes taxes & fees
14 Aug - 15 Aug
Central Location! Walk 2 UK campus/Chandler Hospital, Mins to Downtown
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

GuestHouse Lexington

GuestHouse Lexington

10/10 Excellent
"It's great for an overnight stay while traveling and the location to places to eat. The only suggestion I have is the housekeepers need to refill the soap, shower gel and shampoo/conditioner dispensers."
Patti 1-night trip
Posted less than an hour ago
GuestHouse Lexington

Find out more about Winchester

Winchester Apartments information

Number of reviews
416
Accommodation
127 Apartments
Lowest Price
HK$561
Highest Price
HK$2,366

Frequently asked questions

What's it like to stay at an apartment in Winchester?
There are plenty of places to stay in the larger Lexington area, with 1004 accommodation choices including 146 apartments. Any visit to a new destination can be a culinary trip, so why not visit the area's restaurants?
How do you know if an apartment is the right 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 couples who want to live like locals, but also for families who want the conveniences of home.
What's a favourite apartment I should consider for a stay in Winchester?
Listed below are some of the more popular apartments in the area to choose from: 2 Full Beds | Non-Smoking, Micfridge: Situated in Lexington , 18.1 mi/29.1 km from the heart of Winchester. Includes free WiFi and a Smart TV . 1 King Bed | Non-Smoking, Micfridge: Located 18.1 mi/29.1 km away in Lexington . Free WiFi and a Smart TV are included . Treetops Solar Sanctuary: It's situated in Lexington , 16.7 mi/26.9 km away. Includes free WiFi, a balcony and a sofa bed . Modern Studio - Stylish Apartment in Downtown Lexington: 17 mi/27.3 km away in Lexington . Amenities include a Smart TV . Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington: Located in Lexington , 18 mi/29 km from Winchester. Includes a Smart TV . Access to on-site laundry facilities is available on site .
What can I expect from the weather when I travel to 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 temperature of 22°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Winchester is 1426 mm.
What should I see and do in Winchester?
Winchester is known for its restaurants. Wiseman Park and Lykins 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 Winchester Opera House and Clark County Courthouse.
What's the best way to get to and around Winchester?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Lexington, KY (LEX-Blue Grass), which is located 23 mi (37.1 km) from the heart of the city. If you'd like to venture out around the area, consider renting a car to explore more sights.

Explore a world of travel with Expedia