Winchester, Lexington holiday accommodation: short-term house rentals & properties

Discover a selection of 7 homes and other holiday rentals in Winchester that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the amenities that you expect for your stay, which might include cable TV and a washer and dryer. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Winchester

Surrounded by farmland & 5 min. from downtown Winchester

Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.

Sleeps 12 · 4 bedrooms · 3 bathrooms

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

Sleeps 8 · 4 bedrooms · 2+ bathrooms

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Head to the friendly city of Winchester

Learn about the unique charm of Winchester with a stay in a holiday home rental. Travellers to this welcoming city praise the restaurants, hiking and shopping. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Winchester

Are you searching for attractions to visit during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Winchester a fun spot to go on holiday. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Claiborne Farm (14.5 mi / 23.4 km)
Talon Winery (15.5 mi / 24.9 km)
Kearney Hills Golf Links (21.3 mi / 34.2 km)
Cassell Creek Golf Course (4.1 mi / 6.6 km)
Paradise Cove Aquatic Center (17.8 mi / 28.7 km)
Southwind Golf Course (2.2 mi / 3.5 km)

Exploring the natural features in Winchester

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Winchester is a great place to spend some time outside. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

Kentucky River (12.5 mi / 20.1 km)
Raven Run Nature Sanctuary (13.3 mi / 21.3 km)
Lake Reba (18 mi / 29 km)
Kentucky Horse Park (21.3 mi / 34.3 km)
Masterson Station Park (21.7 mi / 34.9 km)
Lykins Park (2 mi / 3.3 km)

Travelling to and around Winchester

The nearest airport is in Lexington, KY (LEX-Blue Grass), located 23 mi (37.1 km) from the city centre.

Frequently asked questions

How much does it cost to rent a holiday home in Winchester?

A number of things influence what you’ll pay for a holiday home in Winchester, like the season, length of stay and type of property. Still, all of our holiday homes have one thing in common — incredible value. Simply enter your travel dates to find your ideal fit.

How much does it cost to rent a beach house in Winchester?

The average price for a holiday home near the beach in Winchester will depend on when you’re going and the style and size of property you’re searching for. You can quickly and easily find prices on Stayz by entering your destination and preferred travel dates. Then use the handy filters to select the number of bedrooms and amenities that you need, like air conditioning, WiFi and a hot tub.

What are the top attractions for families in Winchester?

You’ll find loads of fabulous things to do and see with the family in Winchester, such as:

Bluegrass Heritage Museum
Lykins Park
Southwind Golf Course

How old do you have to be to rent a holiday home in Winchester?

The minimum required age is usually 16, 18 or 21. It can vary from property to property on Stayz, so look at the rules of your preferred Winchester holiday home before booking your stay.

How long can I rent a holiday home in Winchester for?

The amount of time you can rent a Winchester holiday home for is down to each property. Simply tap in your travel dates to find available options offering longer term stays. They come with all you need to make your extended getaway more comfortable like kitchens and laundries. Some holiday homes might also offer weekly or monthly discounts, so you can stay longer for less money.