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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

Our top choices for Winchester apartments

Interior

Hot Tub & Fire Pit: Romantic Getaway in Frenchburg

Hot Tub & Fire Pit: Romantic Getaway in Frenchburg
Frenchburg
9.6 out of 10, Exceptional, (5 reviews)
"This place was very nice and clean. Perfect for a weekend getaway."
United States
JACOB F.
The price is CA $198
CA $480 total
includes taxes & fees
Jun 14 - Jun 15
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, (149 reviews)
"Great place and so clean. Host was great and will stay here again"
United States
Eric D.
The price is CA $112
CA $226 total
includes taxes & fees
Jun 10 - Jun 11
Lexington Apt. with parking & private entrance Preview listing
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
10.0 out of 10, Exceptional, (1 review)
"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 $107
CA $197 total
includes taxes & fees
Jun 15 - Jun 16
The Loft at Kettlestone with Hot Tub in the RRG
Hair dryer, towels, soap, toilet paper

Luxury On Main / East

Luxury On Main / East
Richmond
10.0 out of 10, Exceptional, (7 reviews)
"I truly enjoyed my stay in this beautiful apartment. "
United States
Robert T.
The price is CA $132
CA $255 total
includes taxes & fees
Jun 10 - Jun 11
Luxury On Main / East
Bathroom

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 CA $140
CA $261 total
includes taxes & fees
Jun 22 - Jun 23
Luxury on Main / South
Private kitchen

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

‘Edith’ Carriage House Getaway - Hamburg/I-75!
Lexington
9.6 out of 10, Exceptional, (4 reviews)
"Had difficulties checking in other than that felt right at home!"
United States
Kaydance
The price is CA $60
CA $185 total
includes taxes & fees
Jun 15 - Jun 16
‘Edith’ Carriage House Getaway - Hamburg/I-75!
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, (88 reviews)
"Everything was fantastic!!"
United States
Leah Anne G.
The price is CA $157
CA $325 total
includes taxes & fees
Jun 15 - Jun 16
Modern 2bd 2ba - Near I75, No Steps, Free Wifi
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, (13 reviews)
"We enjoyed our stay. Location was amazing for our trip!"
United States
Deanna E.
The price is CA $125
CA $404 total
includes taxes & fees
Jun 10 - Jun 11
1200 sf Apt -3 BR-Amazing Beds-Walk to EKU & Downtown Venues - 5 minutes to I-75
Smart TV, fireplace, books

Ruppside Retreat I Cozy 2BR I 15m to RRG I Wi-Fi

Ruppside Retreat I Cozy 2BR I 15m to RRG I Wi-Fi
Stanton
The price is CA $125
CA $253 total
includes taxes & fees
Jun 10 - Jun 11
Ruppside Retreat I Cozy 2BR I 15m to RRG I Wi-Fi
Towels, toilet paper

The Swish & Stay l Cozy 2BR I 15m to RRG I Wi-Fi

The Swish & Stay l Cozy 2BR I 15m to RRG I Wi-Fi
Stanton
10.0 out of 10, Exceptional, (1 review)
"The room was newly renovated and really nice! The host's communication was top notch! I'll definitely stay here again the next time that I'm in the area!"
United States
Clint H.
The price is CA $133
CA $261 total
includes taxes & fees
Jul 7 - Jul 8
The Swish & Stay l Cozy 2BR I 15m to RRG I Wi-Fi
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 $159
CA $206 total
includes taxes & fees
Jun 10 - Jun 11
The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling
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 CA $159
CA $286 total
includes taxes & fees
Jul 2 - Jul 3
Luxury on Main / West
Smart TV

Westfield Gold

Westfield Gold
Richmond
8.8 out of 10, Excellent, (10 reviews)
"Great place to stay!"
United States
Melissa H.
The price is CA $118
CA $238 total
includes taxes & fees
Jun 10 - Jun 11
Westfield Gold
Living area

Bourbon Trail - Loft in Downtown Lexington

Bourbon Trail - Loft in Downtown Lexington
Lexington
10.0 out of 10, Exceptional, (3 reviews)
"Great stay! Very convenient to all the must see places. Would stay here again "
United States
Taylor L.
The price is CA $79
CA $254 total
includes taxes & fees
Jun 10 - Jun 11
Bourbon Trail - Loft in Downtown Lexington
Hair dryer, towels, soap, toilet paper

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 $87
CA $262 total
includes taxes & fees
Jun 10 - Jun 11
Modern Studio - Stylish Apartment in Downtown Lexington
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 CA $120
CA $281 total
includes taxes & fees
Jul 6 - Jul 7
Charming studio apartment in Richmond, just minutes away from EKU
Exterior detail

Treetops Solar Sanctuary

Treetops Solar Sanctuary
Chevy Chase
10.0 out of 10, Exceptional, (87 reviews)
"Great location with kindest host! "
United States
Tiffany S.
The price is CA $110
CA $248 total
includes taxes & fees
Jun 10 - Jun 11
Treetops Solar Sanctuary
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 CA $162
CA $292 total
includes taxes & fees
Jun 15 - Jun 16
Westfield Green
Exterior

Charming studio in fabulous Berea near Pinnacles, Berea College, Hospital & I-75

Charming studio in fabulous Berea near Pinnacles, Berea College, Hospital & I-75
Berea
10.0 out of 10, Exceptional, (2 reviews)
"Great experience and thoughtfulness of owner … excellent communication!Spacious in and around home and this is an extension of home! Private tho !Close to all we wanted and did in the Berea area ! Highly recommend!"
United States
sally s.
The price is CA $157
CA $242 total
includes taxes & fees
Jun 10 - Jun 11
Charming studio in fabulous Berea near Pinnacles, Berea College, Hospital & I-75
1 bedroom, iron/ironing board, free WiFi, bed sheets

Springside Equine Getaway

Springside Equine Getaway
Georgetown
10.0 out of 10, Exceptional, (17 reviews)
"Located close to small shops and restaurants."
United States
Melissa S.
The price is CA $220
CA $409 total
includes taxes & fees
Jul 1 - Jul 2
Springside Equine Getaway
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

21c Museum Hotel Lexington

21c Museum Hotel Lexington

10/10 Excellent
"Loved the heated bathroom floors!"
Angela 1-night trip
Posted 1 hour ago
21c Museum Hotel Lexington

Find out more about Winchester

Winchester Apartments information

Number of reviews
517
Accommodation
126 Apartments
Lowest Price
CA $197
Highest Price
CA $480

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 998 lodging choices including 153 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: Treetops Solar Sanctuary: Situated in Lexington, 16.7 mi/26.9 km from the heart of Winchester. Includes free WiFi, private balconies, and sofa beds. 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. Newly Renovated 2BR Apartment w/ Free Parking in Downtown: Located in Lexington, 17.8 mi/28.7 km away. Includes sofa beds and Smart TVs. Access to onsite laundry facilities is available on site. The Loft at Kettlestone with Hot Tub in the RRG: Located 20.8 mi/33.5 km away in Stanton. Free WiFi, private balconies, and fireplaces are included. Onsite laundry facilities and a hot tub are on site. 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. Community Park and The Holler 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 Wiseman Park and Winchester Traveling Trail.
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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