Winchester vacation rentals

KAYAK searches hundreds of travel sites at once for vacation home deals in Winchester

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Useful Info
Recommended by KAYAK

Best Winchester vacation rentals

Most recommended vacation rentals in Winchester

Show all
2nd Story Historic Downtown 2BR with Modern Amenities - Winchester - Building
2nd Story Historic Downtown 2BR with Modern Amenities
Winchester, KY
Free Wi-Fi
Pet friendly
$238+
Check availability
The Winchester - Winchester - Living room
The Winchester
Winchester, KY
Parking
Free Wi-Fi
$185+
Check availability
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min. - Winchester - Bedroom
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
Winchester, KY
$359+
Check availability
Farmhouse living within sight of Lexington - Horse Paddock available - Winchester - Patio
Farmhouse living within sight of Lexington - Horse Paddock available
Winchester, KY
Free Wi-Fi
$389+
Check availability
New Serene Country Refuge At The Right Angle - Winchester - Living room
New Serene Country Refuge At The Right Angle
Winchester, KY
Free Wi-Fi
$222+
Check availability
The Perch - New / Downtown! - Winchester - Bedroom
The Perch - New / Downtown!
Winchester, KY
Free Wi-Fi
$365+
Check availability
Large Downtown Artist's Loft, 30 min to Lexington, Horse, Bourbon, R River Gorge - Winchester - Living room
Large Downtown Artist's Loft, 30 min to Lexington, Horse, Bourbon, R River Gorge
Winchester, KY
$293+
Check availability
Romance, Convenience With Hiking Nearby! Jacuzzi Tub Large Space. Pet Friendly! - Winchester
Romance, Convenience With Hiking Nearby! Jacuzzi Tub Large Space. Pet Friendly!
Winchester, KY
10Wonderful(1)
Free Wi-Fi
Pet friendly
$160+
Check availability
House with all the amenities - Winchester
House with all the amenities
Winchester, KY
Free Wi-Fi
$224+
Check availability
Barnwood Hideaway, Winchester. Near Red River Gorge, Natural Bridge,Lexington - Winchester
Barnwood Hideaway, Winchester. Near Red River Gorge, Natural Bridge,Lexington
Winchester, KY
Free Wi-Fi
Pet friendly
$160+
Check availability
The Winchester 2 - Winchester
The Winchester 2
Winchester, KY
10Wonderful(1)
Parking
Free Wi-Fi
$169+
Check availability
Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

$0 - $98$98 - $195$195 - $292$292 - $389$389+ per night

Property Types

ApartmentCondoHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet
Useful Info

Good to know

Low season

December

High season

April

Average price (weeknight)

$200

Average price (weekend night)

$162
Cheapest month to stay with an average 67% drop in price.
Most expensive month to stay with an average 29% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Winchester vacation rental deals

  • Vacation rentals in Winchester are around 50% more expensive than hotels on average. Search here to compare prices for all accommodation types in Winchester.
  • The best vacation rental property in Winchester is Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min. (9.9, 21 reviews), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Winchester, you should consider visiting during the low season. The cheapest vacation homes in Winchester can be found in December and October.
  • The cheapest night for renting a vacation home in Winchester is Friday. In contrast, the most expensive is Sunday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Winchester for 2 days.

FAQs when booking a vacation home in Winchester

  • What types of vacation rentals are available in Winchester?

    There are loads of different property types that you can make your vacation home in Winchester. You’ll find cabins and houses.

  • Are there any pet-friendly vacation rentals in Winchester?

    There are a number of dog and pet-friendly Winchester vacation rentals, with around 16% allowing you to bring your pet along with you.

  • How can I find vacation rentals near me in Winchester?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Winchester?

Our map will help you find the perfect place to stay in Winchester by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Winchester

Winchester vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Winchester. Find cheap vacation homes to rent in Winchester. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Winchester that suits you best.

Not what you’re looking for? Find thousands of other hotels, airline tickets, car rentals and package deals with KAYAK.