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
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Winchester apartments

Living area

Eclectic Luxury Loft

Eclectic Luxury Loft
Richmond
The price is SAR 551
SAR 914 total
includes taxes & fees
4 Aug - 5 Aug
Eclectic Luxury Loft
Interior

Retro Studio: Romantic Getaway in Frenchburg

Retro Studio: 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 537
SAR 1,286 total
includes taxes & fees
5 Jul - 6 Jul
Retro Studio: Romantic Getaway in Frenchburg
House (0 Bedroom) | Interior

Retro Studio: Romantic Getaway in Frenchburg

Retro Studio: Romantic Getaway in Frenchburg
4.0 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 SAR 702
SAR 1,275 total
includes taxes & fees
5 Jul - 6 Jul
Retro Studio: Romantic Getaway in Frenchburg
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, (2 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 SAR 280
SAR 521 total
includes taxes & fees
5 Jul - 6 Jul
The Loft at Kettlestone with Hot Tub in the RRG
2 bedrooms, WiFi

Muddy Boots HideoutI Cozy 2BR I 15m to RRG I Wi-Fi

Muddy Boots HideoutI Cozy 2BR I 15m to RRG I Wi-Fi
Stanton
The price is SAR 360
SAR 624 total
includes taxes & fees
5 Jul - 6 Jul
Muddy Boots HideoutI Cozy 2BR I 15m to RRG I Wi-Fi
2 bedrooms, WiFi

The Lazy Hiker I Cozy 2BR I 15m to RRG I Wi-Fi

The Lazy Hiker I Cozy 2BR I 15m to RRG I Wi-Fi
Stanton
The price is SAR 360
SAR 624 total
includes taxes & fees
5 Jul - 6 Jul
The Lazy Hiker I Cozy 2BR I 15m to RRG I Wi-Fi
TV

Yeti Escape I Cozy 2BR I 15m to RRG I Wi-Fi

Yeti Escape I Cozy 2BR I 15m to RRG I Wi-Fi
Stanton
The price is SAR 360
SAR 624 total
includes taxes & fees
5 Jul - 6 Jul
Yeti Escape I Cozy 2BR I 15m to RRG I Wi-Fi
TV

The Wanderers Nest I Cozy 2BR I 15m to RRG I Wi-Fi

The Wanderers Nest I Cozy 2BR I 15m to RRG I Wi-Fi
Stanton
The price is SAR 360
SAR 624 total
includes taxes & fees
5 Jul - 6 Jul
The Wanderers Nest I Cozy 2BR I 15m to RRG I Wi-Fi
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 360
SAR 624 total
includes taxes & fees
12 Jul - 13 Jul
Ruppside Retreat I Cozy 2BR I 15m to RRG I Wi-Fi
2 bedrooms, WiFi

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

The Swish & Stay I 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 324
SAR 583 total
includes taxes & fees
5 Jul - 6 Jul
The Swish & Stay I Cozy 2BR I 15m to RRG I Wi-Fi
TV

Nature's Nook I Cozy 2BR I 15m to RRG I Wi-Fi

Nature's Nook I Cozy 2BR I 15m to RRG I Wi-Fi
Stanton
The price is SAR 459
SAR 748 total
includes taxes & fees
19 Jul - 20 Jul
Nature's Nook I 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
10.0 out of 10, Exceptional, (1 review)
"Everything was perfect!"
United States
Miguel
The price is SAR 351
SAR 470 total
includes taxes & fees
5 Jul - 6 Jul
The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling
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 429
SAR 659 total
includes taxes & fees
6 Jul - 7 Jul
Charming studio in fabulous Berea near Pinnacles, Berea College, Hospital & 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, (89 reviews)
"Everything was fantastic!!"
United States
Leah Anne G.
The price is SAR 426
SAR 868 total
includes taxes & fees
15 Jul - 16 Jul
Modern 2bd 2ba - Near I75, No Steps, Free Wifi
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 749 total
includes taxes & fees
4 Aug - 5 Aug
Charming studio apartment in Richmond, just minutes away from EKU
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 375
SAR 1,122 total
includes taxes & fees
2 Aug - 3 Aug
1200 sf Apt -3 BR-Amazing Beds-Walk to EKU & Downtown Venues - 5 minutes to I-75
1 bedroom, iron/ironing board, WiFi, bed sheets

Westfield Blue

Westfield Blue
Richmond
9.8 out of 10, Exceptional, (7 reviews)
"Close to EKU and downtown Richmond. Very nice space to stay and relax in."
United States
Chris P.
The price is SAR 331
SAR 655 total
includes taxes & fees
12 Jul - 13 Jul
Westfield Blue
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 484
SAR 824 total
includes taxes & fees
4 Aug - 5 Aug
Westfield Green
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
12 Jul - 13 Jul
Luxury on Main / West
Dining

Luxury On Main / East

Luxury On Main / East
Richmond
10.0 out of 10, Exceptional, (8 reviews)
"Great location near downtown Richmond. This apartment is very clean and large for your stay. I will be back again when we come to town to visit family. "
United States
Trent W.
Luxury On Main / East
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

Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG

10/10 Excellent
"Clean, accessible room did not disappoint"
Aderonke 1-night trip
Posted 10 hours ago
Holiday Inn Express Lexington Horse Park Area by IHG

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 1001 lodging choices including 150 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. 1 King Bed | Non-Smoking, Micfridge: Located 18.1 mi/29.1 km away in Lexington. Free WiFi and Smart TVs are included. Treetops Solar Sanctuary: It's situated in Lexington, 16.7 mi/26.9 km away. Includes free WiFi, private balconies, and sofa beds. Modern Studio - Stylish Apartment in Downtown Lexington: 17 mi/27.3 km away in Lexington. Amenities include Smart TVs. Lexington Apt. with parking & private entrance Preview listing: Located in Lexington, 21.1 mi/34 km from Winchester. Includes free WiFi and private patios. Access to onsite laundry facilities is available on site.
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 Wiseman 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 Lykins Park 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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