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.

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Winchester apartments

A kitchen with white cabinets, a black countertop, and a patterned rug.

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

‘Edith’ Carriage House Getaway - Hamburg/I-75!
Lexington
9.6 out of 10, Exceptional, (5 reviews)
"A great one night stay! Plenty of room. Nice kitchen area and outside deck."
United States
Kevin P.
‘Edith’ Carriage House Getaway - Hamburg/I-75!
A hotel lobby with a flat-screen TV, a coat rack, a table with chairs, and a view of the outside through large glass doors.

2. 2 Full Beds | Non-Smoking, Micfridge

2 Full Beds | Non-Smoking, Micfridge
Lexington
9.8 out of 10, Exceptional, (353 reviews)
"It felt like home during our stay! Friendly staff made us feel welcome."
United States
Anonymous traveller
The price is HK$458
HK$504 total
includes taxes & fees
1 Nov - 2 Nov
2 Full Beds | Non-Smoking, Micfridge
A modern kitchen with teal cabinets, a black stove, and a black microwave. There is a black and white rug on the floor.

3. Modern Studio - Stylish Apartment in Downtown Lexington

Modern Studio - Stylish Apartment in Downtown Lexington
Lexington
9.6 out of 10, Exceptional, (13 reviews)
"Nice, clean and pet friendly place to stay! Close to downtown!"
United States
Ruthie C.
The price is HK$537
HK$1,544 total
includes taxes & fees
20 Oct - 21 Oct
Modern Studio - Stylish Apartment in Downtown Lexington
A wooden structure with a sign that reads 'TREETOPS ON GARDEN.'

4. Treetops Solar Sanctuary

Treetops Solar Sanctuary
Chevy Chase
10.0 out of 10, Exceptional, (92 reviews)
"Great place to stay!"
United States
Anna C.
The price is HK$622
HK$1,395 total
includes taxes & fees
19 Oct - 20 Oct
Treetops Solar Sanctuary
A modern living room with a glass coffee table, leather armchair, dining area with chairs, and a chandelier.

5. Luxury on Main / South

Luxury on Main / South
Richmond
10.0 out of 10, Exceptional, (58 reviews)
"Clean, well stocked and comfortable. I always enjoy my stay here. "
United States
Robert T.
The price is HK$746
HK$1,428 total
includes taxes & fees
19 Oct - 20 Oct
Luxury on Main / South
A bedroom with a bed, bedside tables, a ceiling fan, a mirror, and a door.

6. Westfield Blue

Westfield Blue
Richmond
9.4 out of 10, Exceptional, (12 reviews)
"Nice and easy lil spot"
United States
ZACHARY W.
The price is HK$579
HK$1,244 total
includes taxes & fees
12 Nov - 13 Nov
Westfield Blue
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

7. 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, (92 reviews)
"The place was just the right size and very convenient to where we had to go to!"
United States
Julie W.
The price is HK$1,059
HK$2,044 total
includes taxes & fees
15 Nov - 16 Nov
Modern 2bd 2ba - Near I75, No Steps, Free Wifi
A modern kitchen with a central island, a dining area with a gray sofa, and a ceiling fan.

8. 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$1,500 total
includes taxes & fees
19 Oct - 20 Oct
Charming studio apartment in Richmond, just minutes away from EKU
A living room with a wooden coffee table, a sofa, a lamp, and a potted plant.

9. Luxury on Main / West

Luxury on Main / West
Richmond
9.6 out of 10, Exceptional, (58 reviews)
"Wonderful place to stay. Would gladly return."
United States
Joshua N.
The price is HK$746
HK$1,428 total
includes taxes & fees
4 Nov - 5 Nov
Luxury on Main / West
A room with a wooden floor, a dining table with chairs, a sofa, and a television.

10. Seabiscuit Loft - Studio Stay in Downtown Lexington

Seabiscuit Loft - Studio Stay in Downtown Lexington
Lexington
9.0 out of 10, Wonderful, (4 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$673
HK$1,719 total
includes taxes & fees
18 Oct - 19 Oct
Seabiscuit Loft - Studio Stay in Downtown Lexington
A kitchen with a stove, microwave, black cabinets, a marble countertop, and a coffee maker.

11. 'Ralph' Comfortable Downtown/UK Apartment

'Ralph' Comfortable Downtown/UK Apartment
Downtown Lexington
8.2 out of 10, Very good, (27 reviews)
"Great location for what I needed. Loved the old house."
United States
Bill
The price is HK$400
HK$1,139 total
includes taxes & fees
18 Oct - 19 Oct
'Ralph' Comfortable Downtown/UK Apartment
A hallway with a white wall, a door with a black handle, and a white shelf with black hooks.

12. Charming Modern Studio Stay - Walk to Chevy Chase

Charming Modern Studio Stay - Walk to Chevy Chase
Lexington
10.0 out of 10, Exceptional, (3 reviews)
"This unit is exactly as described! Great communication, great location!! Will definitely be back!!!"
United States
Wendy s.
The price is HK$1,058
HK$2,275 total
includes taxes & fees
20 Oct - 21 Oct
Charming Modern Studio Stay - Walk to Chevy Chase
A bedroom with a fireplace, a bed with a patterned bedspread, a large painting on the wall, and a chandelier.

13. The Kenwick Pied-à-terre - Lexington Apartment with Historic Charm

The Kenwick Pied-à-terre - Lexington Apartment with Historic Charm
Kenwick
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful stay and great location! The grocery store below was wonderful. The property was spacious and close to everything! As well as lots of great dining and coffee shops. It was a beautiful neighborhood for evening walks as well."
United States
Miranda M.
The Kenwick Pied-à-terre - Lexington Apartment with Historic Charm
A modern kitchen with white cabinets, a black stove, and a central island with stools.

14. Morning Glory - Cozy Apartment in Downtown Lexington

Morning Glory - Cozy Apartment in Downtown Lexington
Lexington
Morning Glory - Cozy Apartment in Downtown Lexington
A bedroom with a bed, a nightstand, a desk, a chair, a door, and a rug.

15. Stay Central in Style - UK/DT/Keeneland/Rupp

Stay Central in Style - UK/DT/Keeneland/Rupp
Lexington
10.0 out of 10, Exceptional, (2 reviews)
"Worked well for a short term stay."
United States
Tom L.
The price is HK$665
HK$2,020 total
includes taxes & fees
22 Oct - 23 Oct
Stay Central in Style - UK/DT/Keeneland/Rupp
A living room with a flat-screen TV mounted on a wooden beam, a white console table with a plant, and a blue patterned rug.

16. 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, (3 reviews)
"Very convenient to downtown Lexington"
United States
Chad C.
The price is HK$561
HK$1,936 total
includes taxes & fees
19 Oct - 20 Oct
Charming 2-bedroom apartment with AC, WiFi in brilliant Lexington
A spacious loft with high ceilings, a large living area with a dark leather sofa, a coffee table, and a dining area with a brick wall and large windows.

17. Bourbon Trail - Loft in Downtown Lexington

Bourbon Trail - Loft in Downtown Lexington
Lexington
9.6 out of 10, Exceptional, (5 reviews)
"Great stay! Very convenient to all the must see places. Would stay here again "
United States
Taylor L.
The price is HK$635
HK$1,666 total
includes taxes & fees
20 Oct - 21 Oct
Bourbon Trail - Loft in Downtown Lexington
A room with wooden flooring, a ceiling fan, a white door, a blue rug, a wooden cabinet, and a microwave.

18. The Loft at Kettlestone with Hot Tub in the RRG

The Loft at Kettlestone with Hot Tub in the RRG
Powell County
10.0 out of 10, Exceptional, (3 reviews)
"The Loft was a great place to relax. It was well equipped and had everything we needed for our stay. Location was perfect for us. The hot tub was a nice touch. We loved being greeted by the dog. He was super friendly."
United States
Mary C.
The price is HK$704
HK$1,212 total
includes taxes & fees
11 Nov - 12 Nov
The Loft at Kettlestone with Hot Tub in the RRG
A wooden deck with a table and chairs, surrounded by a house and greenery.

19. Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington

Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington
Downtown Lexington
10.0 out of 10, Exceptional, (46 reviews)
"Great little place"
United States
Maria J.
The price is HK$820
HK$1,225 total
includes taxes & fees
25 Oct - 26 Oct
Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington
A spacious living area with a brown leather sofa, white fluffy chairs, and a coffee table. A kitchen is visible in the background with white cabinets and a flat-screen TV mounted on the wall.

20. Modern Loft - Parking Included, Walk to Downtown

Modern Loft - Parking Included, Walk to Downtown
Downtown Lexington
10.0 out of 10, Exceptional, (10 reviews)
"Clean, comfortable apartment. Walkable to downtown restaurants and bars. Great stay!"
United States
Stu
The price is HK$938
HK$2,073 total
includes taxes & fees
21 Oct - 22 Oct
Modern Loft - Parking Included, Walk 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.
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Top Winchester Hotel Reviews

Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

8/10 Good
"All good."
Gary 1-night trip
Posted less than an hour ago
Fairfield Inn & Suites by Marriott Lexington North

Find out more about Winchester

Winchester Apartments information

Number of reviews
717
Accommodation
115 Apartments
Lowest Price
HK$504
Highest Price
HK$2,275

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 1025 accommodation choices including 161 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 . Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington: Located 18 mi/29 km away in Lexington . Amenities include a Smart TV . Access to on-site laundry facilities is available on site . Modern Studio - Stylish Apartment in Downtown Lexington: It's situated in Lexington , 17 mi/27.3 km away. Includes a Smart TV . 'Edith' Carriage House Getaway - Hamburg/I-75!: 10.9 mi/17.6 km away in Lexington . Bourbon Trail - Loft in Downtown Lexington: It's situated in Lexington , 17 mi/27.3 km from Winchester.
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. College Park and GRCHS Baseball Field 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 Cassell Creek Golf Course and Winchester Opera House.
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.

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