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Vacations by Zumper

Vacation Rentals in Winchester, KY

PRICE PER NIGHT

ACCOMMODATION TYPES

Top-Rated Vacation Rentals in Winchester, KY

Book a vacation rental in Winchester that has the highest visitor rating. Here are 6 of the best vacation rentals in Winchester.
2nd Story Historic Downtown 2BR with Modern Amenities
10

Excellent

·
Winchester
·
2 br
·
Sleeps 5
·
Lake · Air Conditioning · In Unit Laundry ·
From
$98/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Lake
Air Conditioning
In Unit Laundry
Oven
Wifi
Mountains
Furnished
Waterfront
Other spaces
Kitchen
This house is a 3 bedroom(s), 2 bathrooms, located in Winchester, KY.
10

Excellent

·
Winchester
·
3 br
·
Sleeps 7
·
Kitchen · Wifi · Dishwasher ·
From
$212/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Wifi
Dishwasher
Air Conditioning
Oven
Furnished
In Unit Laundry
Other spaces
Kitchen
House with all the amenities
10

Excellent

·
Winchester
·
3 br
·
Sleeps 6
·
Wifi · Dishwasher · Air Conditioning ·
From
$175/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Wifi
Dishwasher
Air Conditioning
Oven
Fireplace
Garage Parking
Furnished
In Unit Laundry
Other spaces
Kitchen
Large Downtown Artist's Loft, 30 min to Lexington, Horse, Bourbon, R River Gorge
10

Excellent

·
Winchester
·
2 br
·
Sleeps 4
·
Furnished · Dishwasher · Air Conditioning ·
From
$210/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Furnished
Dishwasher
Air Conditioning
Wifi
In Unit Laundry
Other spaces
Kitchen
The Winchester Retreat
10

Excellent

·
Winchester
·
1 br
·
Sleeps 5
·
Wifi · Kitchen · Furnished ·
From
$100/night
Check availability
Property
House · 1 Bed · 2 baths
Amenities
Wifi
Furnished
Smoking Allowed
Fireplace
Air Conditioning
Oven
In Unit Laundry
Other spaces
Kitchen
Hampton Inn Winchester KY
9.2

Excellent

·
Winchester
·
1 br
·
Sleeps 4
·
Storage · Carpet · Business Center ·
From
$103/night
Check availability
Property
Hotel · 1 Bed
Amenities
Storage
Carpet
Business Center
Fitness Center
Residents Lounge
Wifi
Furnished
Pool
Other spaces
Workspace

Our Recommended Vacation Rentals in Winchester, KY

We analyzed vacation rentals in Winchester from many property providers including but not limited to VRBO, Booking.com, Evolve, Blueground and more. We're providing our top recommended offers on the best vacation rentals in Winchester to help you find a deal for your next trip.
Baymont by Wyndham Winchester
7

Very good

·
Winchester
·
1 br
·
Sleeps 4
·
Carpet · On Site Laundry · Swimming Pool ·
From
$60/night
Check availability
Property
Hotel · 1 Bed · 1 bath
Amenities
Carpet
On Site Laundry
Swimming Pool
Pool
Free Parking
Air Conditioning
Fitness Center
Wifi
Other spaces
Workspace
Best Western Winchester Hotel
8.1

Very good

·
Winchester
·
1 br
·
Sleeps 4
·
Smoking Allowed · Free Parking · Furnished ·
From
$80/night
Check availability
Property
Hotel · 1 Bed
Amenities
Smoking Allowed
Free Parking
Furnished
Assigned Parking
Wifi
On Site Laundry
Air Conditioning
Carpet
Other spaces
Workspace
Comfort Inn - Winchester
5.7

Good

·
Winchester
·
1 br
·
Sleeps 4
·
Pool · Carpet · Air Conditioning ·
From
$67/night
Check availability
Property
Hotel · 1 Bed
Amenities
Pool
Carpet
Air Conditioning
Free Parking
Wifi
Smoking Allowed
On Site Laundry
Business Center
Holiday Inn Express - Lexington East - Winchester, an IHG Hotel
8.6

Very good

·
Winchester
·
1 br
·
Sleeps 4
·
Air Conditioning · Business Center · Wheelchair Accessible ·
From
$79/night
Check availability
Property
Hotel · 1 Bed
Amenities
Air Conditioning
Business Center
Wheelchair Accessible
On Site Laundry
Free Parking
Wifi
Smoking Allowed
Swimming Pool
Other spaces
Workspace
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Home > Kentucky Vacation Rentals > Winchester Vacation Rentals
Updated: October 2, 2023