Best Apartments in Winchester, KY for Your Vacation from $67

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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Our top choices for Winchester apartments

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

Lexington

Kevin P.

$116 nightly

Sep 15 - Sep 16

Total with taxes and fees

2. The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling

Mount Sterling

Miguel

$134 nightly

Sep 7 - Sep 8

Total with taxes and fees

3. Westfield Blue

Richmond

Keith G.

$124 nightly

Sep 3 - Sep 4

Total with taxes and fees

4. 2 Full Beds | Non-Smoking, Micfridge

Lexington

Anonymous traveler

$61 nightly

Sep 16 - Sep 17

Total with taxes and fees

5. Treetops Solar Sanctuary

Chevy Chase

Matthew Y.

$138 nightly

Sep 3 - Sep 4

Total with taxes and fees

6. Luxury on Main / South

Richmond

Robert T.

$166 nightly

Sep 8 - Sep 9

Total with taxes and fees

7. Bourbon Trail - Loft in Downtown Lexington

Lexington

Taylor L.

$172 nightly

Sep 3 - Sep 4

Total with taxes and fees

8. Modern 2bd 2ba - Near I75, No Steps, Free Wifi

Richmond

Leah Anne G.

$237 nightly

Sep 23 - Sep 24

Total with taxes and fees

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Top Winchester Hotel Reviews

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent

"Nice room breakfast was average Food at bar was good They did not replace coffee service in room Would stay there again"

Elwood Hotel & Suites

10/10 Excellent

"This is a truly unique hotel, from the entrance with patio and dining seating into the charming lobby that made me feel like i had arrived in New Orleans! The very elegant indoor dining areas are backed with a magnificent bar that looked like it came out of a glamorous 1930's movie! And the food! We were only there for one night, wish it had been more, but both our dinner and brunch meals were absolutely delicious. The servers at both meals were excellent, and very cheerful and friendly. Actually, everyone on staff that we encountered there seemed to enjoy their job and interacting with the guests. Our corner room was quite large, clean, nicely furnished, and quiet. The Elwood has a very high satisfaction rating, which is well-deserved, and is very reasonably priced for such a lovely experience. I hope to be back in Lexington soon to stay there again. Even if you don't need a place to stay, I highly recommend enjoying a meal there!"

GuestHouse Lexington

10/10 Excellent

"A comfortable space, clean, friendly staff, and great for the price. Hotel is smoking free, so you don’t have that wandering smoke smell you sometimes get in hotels that allow both. I was meeting people for breakfast at a different location, so I didn’t eat their breakfast, but the offerings were worthy."

Holiday Inn Express Lexington - Horse Park Area by IHG

10/10 Excellent

"The hotel is clean, easily accessible from major highways, and in a safe area. The front desk staff was helpful, quick with check in, and polite. The week we stayed, we were in a number of different hotels and this was by far the best. Rooms are clean, supplied fully, and quiet. Excellent property."

Find out more about Winchester

Winchester Apartments information

Number of reviews	785
Accommodation	114 Apartments
Lowest Price	$67
Highest Price	$342

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 1015 lodging choices including 154 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. Modern Studio - Stylish Apartment in Downtown Lexington: Located 17 mi/27.3 km away in Lexington. Amenities include Smart TVs. Treetops Solar Sanctuary: It's situated in Lexington, 16.7 mi/26.9 km away. Includes free WiFi, private balconies, and sofa beds. Luxury on Main / South: Located 17.9 mi/28.7 km away in Richmond. Private balconies, fireplaces, and separate dining areas are included. Access to onsite laundry facilities is available on site. Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington: Located in Lexington, 18 mi/29 km from Winchester. Includes Smart TVs. 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. Winchester Traveling Trail and College 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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Winchester Vacation Rentals

Apartments in Winchester for Rent

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Check prices for these dates

Our top choices for Winchester apartments

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

2. The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling

3. Westfield Blue

4. 2 Full Beds | Non-Smoking, Micfridge

5. Treetops Solar Sanctuary

6. Luxury on Main / South

7. Bourbon Trail - Loft in Downtown Lexington

8. Modern 2bd 2ba - Near I75, No Steps, Free Wifi

9. The Kenwick Pied-à-terre - Lexington Apartment with Historic Charm

10. Charming Modern Studio Stay - Walk to Chevy Chase

11. Seabiscuit Loft - Studio Stay in Downtown Lexington

12. Westfield Green

13. Charming 2-bedroom apartment with AC, WiFi in brilliant Lexington

14. Safe & Secure 2br near UKPD in Lex - Rest easy, walk 2 UK

15. 1200 sf Apt -3 BR-Amazing Beds-Walk to EKU & Downtown Venues - 5 minutes to I-75

16. Luxury on Main / West

17. Big Blue - Stylish Studio in Downtown Lexington

18. Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington

19. 'Ralph' Comfortable Downtown/UK Apartment

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

Find vacation rentals that suit your style

Top Winchester Hotel Reviews

Embassy Suites by Hilton Lexington/UK Coldstream

Find out more about Winchester

Winchester Apartments information

Frequently asked questions

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