Find Vacation Rentals in Winchester, Clark County

We have 81 properties to choose from
Winchester
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Winchester
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Popular Winchester Vacation Rentals

Find the perfect Winchester vacation rental

House Winchester
$109 per night
House ∙ 5 guests ∙ 1 bedroom
4.8
Outstanding (23 ratings)
Winchester, Clark County, Kentucky, United States
Details
Vrbo
Details
Details
Farmhouse Winchester
$262 per night
Farmhouse ∙ 14 guests ∙ 4 bedrooms
5.0
Outstanding (38 ratings)
Winchester, Clark County, Kentucky, United States
Details
Vrbo
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Details
House Winchester
$178 per night
House ∙ 8 guests ∙ 4 bedrooms
4.0
Very good (1 rating)
Winchester, Clark County, Kentucky, United States
Details
Vrbo
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Details
House Winchester
$339 per night
House ∙ 7 guests ∙ 3 bedrooms
4.7
Excellent (16 ratings)
Winchester, Clark County, Kentucky, United States
Details
Vrbo
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Details
House Winchester
$176 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (1 rating)
Winchester, Clark County, Kentucky, United States
Details
Vrbo
Details
Details
Cottage Winchester
$241 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
Winchester, Clark County, Kentucky, United States
Details
Vrbo
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Condo Winchester
$239 per night
Condo ∙ 4 guests ∙ 2 bedrooms
4.7
Excellent (6 ratings)
Winchester, Clark County, Kentucky, United States
Details
Vrbo
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Details
Apartment Winchester
$101 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
4.9
Outstanding (13 ratings)
Winchester, Clark County, Kentucky, United States
Details
Vrbo
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Details
House Winchester
$1,546 per night
House ∙ 20 guests ∙ 8 bedrooms
5.0
Outstanding (16 ratings)
Winchester, Clark County, Kentucky, United States
Details
Vrbo
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Vacation rentals and apartments with air conditioning

House  Winchester
$174 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (28 ratings)
Winchester, Clark County, Kentucky, United States
Air conditioning
Details
Vrbo
Details
Details
Resort  Winchester
$96 per night
Resort ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding (4 ratings)
Winchester, Clark County, Kentucky, United States
Air conditioning
Details
Vrbo
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Frequently Asked Questions

What is the price of vacation rentals in Winchester?

The price per night in Winchester starts at $77.

Can I book a vacation rental in Winchester?

There are 81 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

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