Compare Winchester Guest House Rentals

Start date: Check-in selected.
To Date
End date: Check-out

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

Luxury on Main / North

Luxury on Main / North

Richmond KY
$144 nightly
The price is $159 total per night
$159 total
Jan 11 - Jan 12
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
College Park Bungalow

College Park Bungalow

Winchester KY
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.

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

Lexington KY
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

    Best Western Winchester Hotel

    Best Western Winchester Hotel

    1307 W Lexington Ave Winchester KY
    $72 nightly
    The price is $80 total per night from Jan 13 to Jan 14
    $80 total
    Jan 13 - Jan 14
    Total with taxes and fees
    8.4/10 Very Good! (999 reviews)
    Hampton Inn Winchester

    Hampton Inn Winchester

    1025 Early Dr Winchester KY
    $124 nightly
    The price is $136 total per night from Jan 25 to Jan 26
    $136 total
    Jan 25 - Jan 26
    Total with taxes and fees
    9.2/10 Wonderful! (454 reviews)
    Baymont by Wyndham Winchester

    Baymont by Wyndham Winchester

    960 Interstate Dr Winchester KY
    $80 nightly
    The price is $88 total per night from Jan 14 to Jan 15
    $88 total
    Jan 14 - Jan 15
    Total with taxes and fees
    7/10 Good! (772 reviews)

Winchester Guest Houses essential information

Accommodation
3 Guest Houses
Lowest Price
$80
Highest Price
$159
Popular accommodation
Luxury on Main / North, College Park Bungalow, "The Guest House", Located on a 300 acre horse farm.

More to Explore