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Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Winchester apartments

Smart TV

Cozy upstairs 2 bed/1 bath Richmond apt near EKU

Cozy upstairs 2 bed/1 bath Richmond apt near EKU
Richmond
10.0 out of 10, Exceptional, (34 reviews)
"Always a great stay. We’ve stayed here several times, and will continue to do so when we visit our daughter at EKU. "
United States
Angela B.
The price is CA $104
CA $183 total
includes taxes & fees
Apr 23 - Apr 24
Cozy upstairs 2 bed/1 bath Richmond apt near EKU
Outdoor spa tub

The Loft at Kettlestone with Hot Tub in the RRG

The Loft at Kettlestone with Hot Tub in the RRG
Powell County
The price is CA $187
CA $280 total
includes taxes & fees
May 7 - May 8
The Loft at Kettlestone with Hot Tub in the RRG
Apartment (0 Bedroom) | Interior

Hot Tub & Fire Pit: Romantic Getaway in Frenchburg

Hot Tub & Fire Pit: Romantic Getaway in Frenchburg
3.5 star property
Frenchburg
6.0 out of 10, (1 review)
"Stay was okay. Building was clean and everything worked well. Location was much further from red river gorge than expected, about 45 minutes to 1 hour 15 minutes one way to a trail. Bed was very hard. Hot tub was nice. Overall, decent if you dont mind the sleeping conditions and the drive but for us it wasnt worth the cost "
United States
Michael
The price is CA $134
CA $374 total
includes taxes & fees
Apr 28 - Apr 29
Hot Tub & Fire Pit: Romantic Getaway in Frenchburg
Exterior

Lexington Apt. with parking & private entrance Preview listing

Lexington Apt. with parking & private entrance Preview listing
Copperfield
10.0 out of 10, Exceptional, (143 reviews)
"Great place and so clean. Host was great and will stay here again"
United States
Eric D.
The price is CA $109
CA $222 total
includes taxes & fees
May 3 - May 4
Lexington Apt. with parking & private entrance Preview listing
Fridge, microwave, oven, stovetop

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, (86 reviews)
"Really comfortable, clean place to stay, and the location is very convenient. I really like the secure entry system used, and the host is extremely responsive. Great VRBO experience."
United States
Peggy C.
The price is CA $146
CA $306 total
includes taxes & fees
Apr 26 - Apr 27
Modern 2bd 2ba - Near I75, No Steps, Free Wifi
1 bedroom, iron/ironing board, WiFi, bed sheets

Westfield Blue

Westfield Blue
Richmond
9.8 out of 10, Exceptional, (6 reviews)
"Very cute and clean place, excellent communication by host. The neighborhood was very nice and the property was filled with large and beautiful potted plants. Cute gazebo in the back yard, and ample parking both on and off street. Would definitely stay here again. "
United States
Lori K.
The price is CA $101
CA $216 total
includes taxes & fees
Apr 29 - Apr 30
Westfield Blue
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
The price is CA $156
CA $202 total
includes taxes & fees
Apr 23 - Apr 24
The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling
Smart TV, fireplace

Luxury on Main / South

Luxury on Main / South
Richmond
10.0 out of 10, Exceptional, (49 reviews)
"Well maintained units, best kept secret...Love this location and unit, will be my go to location"
United States
Michael W.
The price is CA $117
CA $234 total
includes taxes & fees
Apr 26 - Apr 27
Luxury on Main / South
Microwave, oven, stovetop

Modern Studio - Stylish Apartment in Downtown Lexington

Modern Studio - Stylish Apartment in Downtown Lexington
Lexington
9.6 out of 10, Exceptional, (5 reviews)
"Had a great stay! Kevin was very communicative, helpful, and reasonable throughout the whole process. The place itself was cozy, clean, and felt like home. Will definitely stay again!"
United States
Malik
The price is CA $141
CA $332 total
includes taxes & fees
Apr 27 - Apr 28
Modern Studio - Stylish Apartment in Downtown Lexington
TV, offices

The Colonels Apartment is a freshly renovated 3bedroom 1bath downtown Richmond apartment

The Colonels Apartment is a freshly renovated 3bedroom 1bath downtown Richmond apartment
Richmond
7.8 out of 10, Good, (12 reviews)
"Great location. Walking distance to downtown Richmond. A little rough around the edges but overall good stay for our family of 4. "
United States
Josh B.
The price is CA $136
CA $282 total
includes taxes & fees
Apr 23 - Apr 24
The Colonels Apartment is a freshly renovated 3bedroom 1bath downtown Richmond apartment
Fridge, microwave, oven, stovetop

Bluegrass Getaway

Bluegrass Getaway
Georgetown
10.0 out of 10, Exceptional, (17 reviews)
"The place was spotless, bed was comfortable 1 mile from Georgetown. Would stay again. "
United States
Chris B.
The price is CA $170
CA $386 total
includes taxes & fees
Apr 28 - Apr 29
Bluegrass Getaway
Interior

Westfield Green

Westfield Green
Richmond
10.0 out of 10, Exceptional, (15 reviews)
"Very nice place. We will definitely stay again. "
United States
Sue C.
The price is CA $101
CA $216 total
includes taxes & fees
Apr 23 - Apr 24
Westfield Green
1 bedroom, iron/ironing board, WiFi, bed sheets

Green Oasis - Studio Apartment in Downtown Lexington

Green Oasis - Studio Apartment in Downtown Lexington
Lexington
10.0 out of 10, Exceptional, (1 review)
"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 $139
CA $326 total
includes taxes & fees
Apr 26 - Apr 27
Green Oasis - Studio Apartment in Downtown Lexington
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
10.0 out of 10, Exceptional, (11 reviews)
"Everything was perfect, we had to make a change to the reservation and the host responded immediately and was very helpful in getting that taken care of. It is a great place and a fantastic location if you need to be near the university and downtown."
United States
James o.
The price is CA $122
CA $316 total
includes taxes & fees
Apr 28 - Apr 29
1200 sf Apt -3 BR-Amazing Beds-Walk to EKU & Downtown Venues - 5 minutes to I-75
Dining

Luxury On Main / East

Luxury On Main / East
Richmond
10.0 out of 10, Exceptional, (6 reviews)
"Great renovation on an older building. "
United States
Tim S.
The price is CA $82
CA $195 total
includes taxes & fees
Apr 23 - Apr 24
Luxury On Main / East
Private kitchen

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

‘Edith’ Carriage House Getaway - Hamburg/I-75!
Lexington
9.0 out of 10, Wonderful, (2 reviews)
"Had a pleasant stay ! Thanks "
United States
brenda s.
The price is CA $65
CA $188 total
includes taxes & fees
May 10 - May 11
‘Edith’ Carriage House Getaway - Hamburg/I-75!
Microwave, oven, stovetop

Travelers Cove upstairs 1-bedroom apartment Richmond near EKU with WiFi, AC

Travelers Cove upstairs 1-bedroom apartment Richmond near EKU with WiFi, AC
Richmond
9.4 out of 10, Exceptional, (3 reviews)
"It was the best hotel I have ever stayed in. Must say it’s the best Richmond hotel "
United States
Ujwal T.
The price is CA $107
CA $185 total
includes taxes & fees
Apr 23 - Apr 24
Travelers Cove upstairs 1-bedroom apartment Richmond near EKU with WiFi, AC
Microwave, oven, stovetop, dishwasher

Earl Grey - Studio Space in Downtown Lexington

Earl Grey - Studio Space in Downtown Lexington
Lexington
The price is CA $118
CA $329 total
includes taxes & fees
Apr 27 - Apr 28
Earl Grey - Studio Space in Downtown Lexington
Interior

Solar Sanctuary

Solar Sanctuary
Chevy Chase
10.0 out of 10, Exceptional, (11 reviews)
"Perfect for a weekend with 3 of us. Quaint neighborhood and very clean place. Has everything u need for a short weekend trip. "
United States
Jeff K.
The price is CA $108
CA $235 total
includes taxes & fees
May 4 - May 5
Solar Sanctuary
Outdoor dining

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
9.8 out of 10, Exceptional, (24 reviews)
"Great location. Super clean. "
United States
paula A.
The price is CA $130
CA $199 total
includes taxes & fees
Apr 29 - Apr 30
Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington
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

Natural Bridge State Resort Park

Natural Bridge State Resort Park

10/10 Excellent
"A wonderful place to stay. Quite and peaceful. Parking very accessible to the room."
Sandi 2-night trip
Posted 2 hours ago
Natural Bridge State Resort Park

Find out more about Winchester

Winchester Apartments information

Number of reviews
375
Accommodation
125 Apartments
Lowest Price
CA $183
Highest Price
CA $441

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 1014 lodging choices including 166 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: Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington: Located in Lexington, 18 mi/29 km from the heart of Winchester. Includes Smart TVs. Access to onsite laundry facilities is available on site. Treetops Solar Sanctuary: Located 16.7 mi/26.9 km away in Lexington. Free WiFi, private balconies, and sofa beds are included. Private One Bedroom Apartment in Downtown Lexington near Rupp Arena: Located in Lexington, 18.3 mi/29.4 km away. Includes free WiFi, private patios, and fireplaces. Access to onsite laundry facilities is available on site. Modern Studio - Stylish Apartment in Downtown Lexington: 17 mi/27.3 km away in Lexington. Amenities include Smart TVs. 'Ralph' Comfortable Downtown/UK Apartment: It's situated in Lexington, 17.7 mi/28.4 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. Winchester Traveling Trail 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 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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