A historic downtown area with a prominent clock tower and a green-roofed building.

Search Apartment Rentals in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Winchester apartments

Outdoor spa tub

Meadowview Guest House

Meadowview Guest House
Hillsboro
10.0 out of 10, Exceptional, (26 reviews)
"I was out there for a wedding and this place was great for a weekend trip."
United States
L
The price is CA $142
CA $250 total
includes taxes & fees
Jun 28 - Jun 29
Meadowview Guest House
Smart TV

Bourbon Getaway - Walk to Distillery & Riverfront

Bourbon Getaway - Walk to Distillery & Riverfront
Augusta
10.0 out of 10, Exceptional, (4 reviews)
"This space is as clean and well done as any we’ve ever stayed in! We love Augusta. You will too!"
United States
Anthony A.
The price is CA $162
CA $264 total
includes taxes & fees
Jun 29 - Jun 30
Bourbon Getaway - Walk to Distillery & Riverfront
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Spacious 3-bedroom apartment with WiFi, AC in charming Ripley

Spacious 3-bedroom apartment with WiFi, AC in charming Ripley
Ripley
9.6 out of 10, Exceptional, (5 reviews)
"Nicely decorated property. This was perfect for our family and we’d definitely stay hear again when in Ripley. "
United States
John and Chris S.
The price is CA $235
CA $325 total
includes taxes & fees
Jun 28 - Jun 29
Spacious 3-bedroom apartment with WiFi, AC in charming Ripley
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Countryside Inn & Suites

Countryside Inn & Suites

8/10 Good
"Nice water pressure. The only bad thing it doesn't have elevators. It's got two levels, but no elevator. The staff was nice enough to give us the bottom floor because it would be hard to climb stairs for me."
Theresa 2-night trip
Posted 19 hours ago
Countryside Inn & Suites

Find out more about Winchester

Winchester Apartments information

Number of reviews
35
Accommodation
11 Apartments
Lowest Price
CA $250
Highest Price
CA $325

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You might have as many choices centrally in Winchester, but Expedia can help you find accommodations in the area similar to apartments. When you search on Expedia, you can filter by amenities you might find in an apartment such as a kitchen. You can also search for similar properties such as condos, vacation homes, or cottages.
Why would you choose an apartment over a traditional hotel room?
Often offering more space than a traditional hotel room, an apartment includes a kitchen, so you can have some home-cooked meals. Apartments are ideal for families who want the conveniences of home, and also for couples who want to stay away from the tourist areas.
What's the best apartment I should consider for a stay in Winchester?
Here are some of the top apartments in the area: Meadowview Guest House: Located in Hillsboro, 14.8 mi/23.8 km from the heart of Winchester. Includes free WiFi. Access to a hot tub is available on site. Home away from Home! - 1BR apartment in Maysville: Located 21.2 mi/34.1 km away in Maysville. Amenities include Smart TVs. Bourbon Getaway - Walk to Distillery & Riverfront: Located in Augusta, 22.1 mi/35.6 km away. Includes free WiFi and Smart TVs. Access to onsite laundry facilities is available on site. Spacious 3-bedroom apartment with WiFi, AC in charming Ripley: Located 17.2 mi/27.6 km away in Ripley. Free WiFi and Smart TVs are included. Access to onsite laundry facilities is available on site. Beautiful studio in historic downtown Maysville: Located in Maysville, 21.3 mi/34.2 km from Winchester. Includes free WiFi and Smart TVs. Access to onsite laundry facilities is available on site.
What can I expect from the weather when I travel to Winchester?
Though weather is just one factor, 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 37°F. Average annual precipitation for Winchester is 50 inches.
What are the must-see places to visit in Winchester?
While you're exploring the area, Rocky Fork Lake and Ripley Lions Club Community Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you'll find Adams Lake State Park and Serpent Mound.
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 Cincinnati, OH (LUK-Cincinnati Municipal - Lunken Field), which is located 43.2 mi (69.6 km) from the city center. Otherwise, you can search for flights to Cincinnati-Northern Kentucky Int'l Airport (CVG), which is 54.6 mi (87.9 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

Explore a world of travel with Expedia