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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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.
The price is CA $64
CA $190 total
includes taxes & fees
Oct 4 - Oct 5
‘Edith’ Carriage House Getaway - Hamburg/I-75!

2. 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)
"Clean, unexpected amenities provided in case you forgot something. Ceiling fans in living room and bedroom. Recently renovated. The sweet treats in the fridge upon check in, both local, were a nice touch and paired well with coffee in the morning. Walkable to a nice local bar and grill, downtown area, was a bonus. 5 minutes to I-64. About a half an hour or less to Red River Gorge/ Natural Bridge if you are going hiking. Pet friendly. WiFi. We would definitely stay here again!"
United States
Dan S.
The price is CA $162
CA $209 total
includes taxes & fees
Sep 28 - Sep 29
The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling
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)
"very clean & great location"
United States
BJ F.
The price is CA $92
CA $271 total
includes taxes & fees
Sep 27 - Sep 28
Modern Studio - Stylish Apartment in Downtown Lexington
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.

4. 2 Full Beds | Non-Smoking, Micfridge

2 Full Beds | Non-Smoking, Micfridge
Lexington
10.0 out of 10, Exceptional, (348 reviews)
"It felt like home during our stay! Friendly staff made us feel welcome."
United States
Anonymous traveller
The price is CA $87
CA $96 total
includes taxes & fees
Oct 4 - Oct 5
2 Full Beds | Non-Smoking, Micfridge
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, (55 reviews)
"Clean, well stocked and comfortable. I always enjoy my stay here. "
United States
Robert T.
The price is CA $130
CA $253 total
includes taxes & fees
Sep 28 - Sep 29
Luxury on Main / South
A wooden structure with a sign that reads 'TREETOPS ON GARDEN.'

6. 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 CA $112
CA $251 total
includes taxes & fees
Sep 27 - Sep 28
Treetops Solar Sanctuary
A bedroom with a bed, bedside tables, a ceiling fan, a mirror, and a door.

7. Westfield Blue

Westfield Blue
Richmond
9.4 out of 10, Exceptional, (11 reviews)
"Nice and easy lil spot"
United States
ZACHARY W.
The price is CA $104
CA $224 total
includes taxes & fees
Sep 27 - Sep 28
Westfield Blue
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.

8. 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 CA $123
CA $309 total
includes taxes & fees
Sep 27 - Sep 28
Modern Loft - Parking Included, Walk to Downtown
A bedroom with a fireplace, a bed with a patterned bedspread, a large painting on the wall, and a chandelier.

9. 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 price is CA $169
CA $459 total
includes taxes & fees
Sep 28 - Sep 29
The Kenwick Pied-à-terre - Lexington Apartment with Historic Charm
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
9.4 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 CA $102
CA $283 total
includes taxes & fees
Sep 27 - Sep 28
Seabiscuit Loft - Studio Stay in Downtown Lexington
A hallway with a white wall, a door with a black handle, and a white shelf with black hooks.

11. Charming Modern Studio Stay - Walk to Chevy Chase

Charming Modern Studio Stay - Walk to Chevy Chase
Lexington
10.0 out of 10, Exceptional, (2 reviews)
"Will absolutely be back!!! So convenient, clean and one of the best ky virbos I’ve had. Thank you!!"
United States
Rebecca S.
The price is CA $131
CA $331 total
includes taxes & fees
Sep 28 - Sep 29
Charming Modern Studio Stay - Walk to Chevy Chase
A hot tub on a wooden deck with a barbecue grill.

12. 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 CA $99
CA $190 total
includes taxes & fees
Oct 1 - Oct 2
The Loft at Kettlestone with Hot Tub in the RRG
A living room with a wooden coffee table, a sofa, a lamp, and a potted plant.

13. 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 CA $130
CA $253 total
includes taxes & fees
Oct 12 - Oct 13
Luxury on Main / West
A kitchen with a stove, microwave, black cabinets, a marble countertop, and a coffee maker.

14. 'Ralph' Comfortable Downtown/UK Apartment

'Ralph' Comfortable Downtown/UK Apartment
Downtown Lexington
8.2 out of 10, Very good, (26 reviews)
"Great location for what I needed. Loved the old house."
United States
Bill
The price is CA $72
CA $200 total
includes taxes & fees
Sep 27 - Sep 28
'Ralph' Comfortable Downtown/UK Apartment
A modern kitchen with white cabinets, a black stove, and a central island with stools.

15. Morning Glory - Cozy Apartment in Downtown Lexington

Morning Glory - Cozy Apartment in Downtown Lexington
Lexington
The price is CA $102
CA $285 total
includes taxes & fees
Sep 29 - Sep 30
Morning Glory - Cozy Apartment in Downtown Lexington
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 CA $91
CA $334 total
includes taxes & fees
Sep 28 - Sep 29
Charming 2-bedroom apartment with AC, WiFi in brilliant Lexington
A bedroom with a bed, bedside table, lamp, and a ceiling fan.

17. Green Oasis - Studio Apartment in Downtown Lexington

Green Oasis - Studio Apartment in Downtown Lexington
Lexington
6.0 out of 10, (2 reviews)
"Me and my girl had a very enjoyable time staying at the Green Oasis. The property was clean and just as listed on VRBO. The around back parking spots made for easy parking and unloading of any luggage or groceries we had."
United States
Noah C.
The price is CA $102
CA $283 total
includes taxes & fees
Sep 27 - Sep 28
Green Oasis - Studio Apartment in Downtown Lexington
A living room with a sofa, a wooden coffee table, a TV on a stand, a striped rug, a potted plant, and a window with curtains.

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

Central Location! Walk 2 UK campus/Chandler Hospital, Mins to Downtown
Lexington
9.6 out of 10, Exceptional, (4 reviews)
"Overall was a nice place to stay a little smaller than expected. Older property appliances were updated everything worked as it should would have preferred a unit on 1st floor since there was no elevator and we are in our 60s but all in all well worth the price."
United States
david h.
The price is CA $66
CA $290 total
includes taxes & fees
Sep 27 - Sep 28
Central Location! Walk 2 UK campus/Chandler Hospital, Mins to Downtown
A two-story brick house with a front porch, a garage, and a driveway.

19. 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, (17 reviews)
"We enjoyed our stay. Location was amazing for our trip!"
United States
Deanna E.
The price is CA $141
CA $429 total
includes taxes & fees
Sep 28 - Sep 29
1200 sf Apt -3 BR-Amazing Beds-Walk to EKU & Downtown Venues - 5 minutes to I-75
A modern kitchen with a central island, a dining area with a gray sofa, and a ceiling fan.

20. 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 CA $122
CA $285 total
includes taxes & fees
Oct 19 - Oct 20
Charming studio apartment in Richmond, just minutes away from EKU
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

Hyatt Regency Lexington

Hyatt Regency Lexington

10/10 Excellent
"Nice clean room great location"
Brian 1-night trip
Posted 1 hour ago
Hyatt Regency Lexington

Find out more about Winchester

Winchester Apartments information

Number of reviews
655
Accommodation
116 Apartments
Lowest Price
CA $96
Highest Price
CA $459

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 1019 lodging choices including 155 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 favorite 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 Smart TVs. Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington: Located 18 mi/29 km away in Lexington. Amenities include Smart TVs. Access to onsite laundry facilities is available on site. Treetops Solar Sanctuary: It's situated in Lexington, 16.7 mi/26.9 km away. Includes free WiFi, private balconies, and sofa beds. '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 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. 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 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.

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