Find Vacation Rentals in Winchester, Clark County

We have 92 properties to choose from
Winchester
Anytime
Guests

Popular Winchester Vacation Rentals

Find the perfect Winchester vacation rental

House Winchester
$116 per night
House ∙ 4 guests ∙ 1 bedroom
4.8
"Excellent" (5 ratings)
Winchester, Clark County, Kentucky, United States
Details
Vrbo
Details
Details
Condo Winchester
$262 per night
Condo ∙ 4 guests ∙ 2 bedrooms
4.5
"Outstanding" (2 ratings)
Winchester, Clark County, Kentucky, United States
Details
Vrbo
Details
Details
House Winchester
$194 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (19 ratings)
Winchester, Clark County, Kentucky, United States
Details
Vrbo
Details
Details
House Winchester
$285 per night
House ∙ 7 guests ∙ 4 bedrooms
4.5
"Outstanding" (2 ratings)
Winchester, Clark County, Kentucky, United States
Details
Vrbo
Details
Details
Farmhouse Winchester
$208 per night
Farmhouse ∙ 14 guests ∙ 4 bedrooms
Winchester, Clark County, Kentucky, United States
Details
Vrbo
Details
Details
Apartment Winchester
$110 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
4.7
"Outstanding" (6 ratings)
Winchester, Clark County, Kentucky, United States
Details
Vrbo
Details
Details
House Winchester
$262 per night
House ∙ 7 guests ∙ 4 bedrooms
4.5
"Outstanding" (2 ratings)
Winchester, Clark County, Kentucky, United States
Details
Expedia
Details
Details
Farmhouse Winchester
$167 per night
Farmhouse ∙ 14 guests ∙ 4 bedrooms
Winchester, Clark County, Kentucky, United States
Details
Expedia
Details
Details
Condo Winchester
$211 per night
Condo ∙ 4 guests ∙ 2 bedrooms
4.5
"Outstanding" (2 ratings)
Winchester, Clark County, Kentucky, United States
Details
Expedia
Details
Details
View more

Pet-Friendly Homes and Apartments

Apartment Pet-friendly Winchester
$99 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
4.7
"Outstanding" (3 ratings)
Winchester, Clark County, Kentucky, United States
Pet-friendly
Details
Expedia
Details
Details
Motel Pet-friendly Winchester
$76 per night
Motel ∙ 2 guests ∙ 1 bedroom
Winchester, Clark County, Kentucky, United States
Pet-friendly
Details
HomeToGo
Details
Details
Motel Pet-friendly Winchester
$86 per night
Motel ∙ 2 guests ∙ 1 bedroom
Winchester, Clark County, Kentucky, United States
Pet-friendly
Details
HomeToGo
Details
Details
View more

Vacation Homes With Terraces

House Balcony/Patio Winchester
$150 per night
House ∙ 4 guests ∙ 3 bedrooms
5.0
"Excellent" (24 ratings)
Winchester, Clark County, Kentucky, United States
Balcony/Patio
Details
Vrbo
Details
Details
View more

Frequently Asked Questions

What is the price of vacation rentals in Winchester?

The price per night in Winchester starts at $76.

Can I book a vacation rental in Winchester?

There are 88 vacation rental offers in Winchester available to book.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Winchester

Save hundreds with a vacation home rental from Tripping.com and forget the hotel room. For the ultimate getaway, Winchester offers 498 affordable vacation rentals with a price to match your budget and accommodation needs. Prices in Winchester start at an average price of $166 a night with long-term rentals averaging $3805 a month. These vacation rentals offer a range of amenities, so you’ll feel right at home. For those looking to stay in a corporate rental, 344 of Winchester’s rentals offer high speed WiFi Internet so you can easily keep in touch with your company or team. Go for a swim at one of the 163 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 319 vacation home rentals. Traveling with your dog or cat? Choose from 184 pet-friendly rentals in Winchester that allow you to bring your extended family along.Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your pets. Many properties allow you to book directly online, so once you find that perfect vacation rental, you’ll be all set to go! Search properties from 7 vacation rental sites in Winchester where the top providers in that area are HomeAway, HRS Holidays, and Booking.com. There are 170 HomeAway rentals, 126 HRS Holidays short term rentals and 80 Booking.com vacation rentals.

Popular Day Trips Near Winchester

image-tag