MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings

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Check prices for these dates

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

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 SAR 428
SAR 1,106 total
includes taxes & fees
11 Jun - 12 Jun
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 SAR 300
SAR 530 total
includes taxes & fees
14 Jun - 15 Jun
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 SAR 285
SAR 527 total
includes taxes & fees
15 Jun - 16 Jun
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 SAR 428
SAR 762 total
includes taxes & fees
14 Jun - 15 Jun
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 SAR 364
SAR 691 total
includes taxes & fees
22 Jun - 23 Jun
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 SAR 172
SAR 510 total
includes taxes & fees
20 Jun - 21 Jun
‘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 SAR 422
SAR 847 total
includes taxes & fees
17 Jun - 18 Jun
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 SAR 338
SAR 981 total
includes taxes & fees
15 Jun - 16 Jun
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 SAR 429
SAR 785 total
includes taxes & fees
14 Jun - 15 Jun
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 SAR 358
SAR 704 total
includes taxes & fees
7 Jul - 8 Jul
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 SAR 429
SAR 556 total
includes taxes & fees
11 Jun - 12 Jun
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 SAR 357
SAR 683 total
includes taxes & fees
2 Jul - 3 Jul
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 SAR 387
SAR 716 total
includes taxes & fees
14 Jun - 15 Jun
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 SAR 259
SAR 737 total
includes taxes & fees
15 Jun - 16 Jun
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 SAR 276
SAR 756 total
includes taxes & fees
11 Jun - 12 Jun
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 SAR 323
SAR 686 total
includes taxes & fees
6 Jul - 7 Jul
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 SAR 297
SAR 668 total
includes taxes & fees
16 Jun - 17 Jun
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 SAR 534
SAR 879 total
includes taxes & fees
15 Jun - 16 Jun
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 SAR 422
SAR 652 total
includes taxes & fees
11 Jun - 12 Jun
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.
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

Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"Great place to stay. Bed was comfy. Parking was excellent."
Pamela 1-night trip
Posted 1 hour ago
Elwood Hotel & Suites

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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