Compare Winchester Guest House Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Guest Houses in Winchester

$134 nightly

$148 total

Feb 24 - Feb 25

Total with taxes and fees

At this guesthouse, guests have access to features like laundry facilities. This guesthouse also has barbecue grills.

Pet friendly

Air conditioning

At this guesthouse, guests have access to features like laundry facilities.

Pet friendly

Air conditioning

"The Guest House", Located on a 300 acre horse farm.

At this guesthouse, guests have access to features like laundry facilities.

Air conditioning

Parking available

Don't see what you're looking for?

See all available properties in Winchester

View all properties

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.

Hotel Options in Winchester

Hampton Inn Winchester

1025 Early Dr Winchester KY

$106 nightly

$117 total

Mar 1 - Mar 2

Total with taxes and fees

The Manchester

941 Manchester St Lexington KY

$201 nightly

$234 total

Mar 22 - Mar 23

Total with taxes and fees

9.6/10 Exceptional! (1,169 reviews)

Hilton Lexington/Downtown

369 West Vine Street Lexington KY

$150 nightly

$174 total

Mar 8 - Mar 9

Total with taxes and fees

8.4/10 Very Good! (1,002 reviews)

Winchester Guest Houses essential information

Accommodation	3 Guest Houses
Lowest Price	$117
Highest Price	$234
Popular accommodation	Luxury on Main / North, College Park Bungalow, "The Guest House", Located on a 300 acre horse farm.