Vacation Rentals in Winchester, KY

2nd Story Historic Downtown 2BR with Modern Amenities
9.3

Excellent

·
Winchester
·
2 br
·
Sleeps 5
·
Lake · Waterfront · Mountains ·
From
$98/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Lake
Waterfront
Mountains
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Comfort Inn - Winchester
5.8

Good

·
Winchester
·
1 br
·
Sleeps 4
·
Pool · On Site Laundry · Smoking Allowed ·
From
$67/night
Check availability
Property
Hotel · 1 Bed
Amenities
Pool
On Site Laundry
Smoking Allowed
Carpet
Free Parking
Air Conditioning
Furnished
Wifi
Holiday Inn Express - Lexington East - Winchester, an IHG Hotel
8.5

Very good

·
Winchester
·
1 br
·
Sleeps 4
·
Pool · Workspace · On Site Laundry ·
From
$79/night
Check availability
Property
Hotel · 1 Bed
Amenities
Pool
On Site Laundry
Smoking Allowed
Carpet
Free Parking
Air Conditioning
Furnished
Wifi
Other spaces
Workspace
Best Western Winchester Hotel
8

Very good

·
Winchester
·
1 br
·
Sleeps 4
·
Assigned Parking · Workspace · On Site Laundry ·
From
$80/night
Check availability
Property
Hotel · 1 Bed
Amenities
Assigned Parking
On Site Laundry
Smoking Allowed
Carpet
Free Parking
Air Conditioning
Furnished
Wifi
Other spaces
Workspace
Hampton Inn Winchester KY
9.2

Excellent

·
Winchester
·
1 br
·
Sleeps 4
·
Pool · Workspace · On Site Laundry ·
From
$103/night
Check availability
Property
Hotel · 1 Bed
Amenities
Pool
On Site Laundry
Smoking Allowed
Carpet
Free Parking
Air Conditioning
Furnished
Wifi
Other spaces
Workspace
This house is a 3 bedroom(s), 2 bathrooms, located in Winchester, KY.
9

Excellent

·
Winchester
·
4 br
·
Sleeps 7
·
Dishwasher · Oven · In Unit Laundry ·
From
$212/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
House with all the amenities
10

Excellent

·
Winchester
·
3 br
·
Sleeps 6
·
Fireplace · Dishwasher · Oven ·
From
$175/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Garage Parking
Other spaces
Kitchen
Large Downtown Artist's Loft, 30 min to Lexington, Horse, Bourbon, R River Gorge
9

Excellent

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

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The Winchester Retreat
9.2

Excellent

·
Winchester
·
1 br
·
Outdoor Space · Fireplace · Oven ·
From
$100/night
Check availability
Property
House · 1 Bed · 2 baths
Amenities
Fireplace
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Showing 1 - 9 of 9 results
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1840 Historic Antibellum Estate in the heart of the Bluegrass

No reviews

·
Paris
·
8 br
·
Sleeps 20
·
Balcony · Private Pool · Fireplace ·
From
$1,952/night
Check availability
Property
House · 8 Beds · 9 baths
Amenities
Private Pool
Fireplace
Pool
Dishwasher
On Site Laundry
Oven
In Unit Laundry
Air Conditioning
Other spaces
Balcony, Kitchen
Welcome Hall 5 bedroom 1880’s home on 55 acres
10

Excellent

·
Paris
·
5 br
·
Sleeps 16
·
Fitness Center · Outdoor Space · Fireplace ·
From
$446/night
Check availability
Property
House · 5 Beds · 4 baths
Amenities
Fitness Center
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace, Kitchen
Loft Cabin on Stoner Creek - 3 minutes from Downtown Paris KY
10

Excellent

·
Paris
·
1 br
·
Sleeps 2
·
Furnished · Wifi ·
From
$161/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
Wifi
The Cabin at Denali Stud

No reviews

·
Paris
·
2 br
·
Sleeps 4
·
Hardwood Floor · Assigned Parking · Fireplace ·
From
$400/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Hardwood Floor
Assigned Parking
Fireplace
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Arlington's Oasis - 17 Miles to Lexington

No reviews

·
Paris
·
2 br
·
Sleeps 3
·
Outdoor Space · Oven · In Unit Laundry ·
From
$125/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Country getaway
10

Excellent

·
Winchester
·
3 br
·
Sleeps 6
·
Dishwasher · Oven · In Unit Laundry ·
From
$283/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Garage Parking
Other spaces
Kitchen
Hill 'n' Dale Kentucky Thoroughbred Horse Farm at Xalapa
10

Excellent

·
North Middletown
·
3 br
·
Sleeps 14
·
Fitness Center · Balcony · Outdoor Space ·
From
$2,044/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Fitness Center
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Balcony, Kitchen
Historic Paris Livery Home of Kentucky's Covered Bridge Tour
9.7

Excellent

·
Paris
·
1 br
·
Sleeps 4
·
Fitness Center · Outdoor Space · Fireplace ·
From
$195/night
Check availability
Property
House · 1 Bed · 2 baths
Amenities
Fitness Center
Fireplace
Smoking Allowed
In Unit Laundry
Air Conditioning
Furnished
Wifi

The best of Zumper, delivered

Be the first to hear about new listings matching your search.

Email
By clicking submit, I accept Zumper's Terms and Conditions, Privacy Policy, and Community Values.
In the Heart of Historic Downtown Paris KY
9.6

Excellent

·
Paris
·
1 br
·
Sleeps 2
·
Fitness Center · Balcony · Outdoor Space ·
From
$101/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Fitness Center
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Balcony, Kitchen
Unique Cabin in Kentucky Horse Country!
10

Excellent

·
Paris
·
1 br
·
Sleeps 2
·
Fitness Center · Outdoor Space · Waterfront ·
From
$275/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Fitness Center
Waterfront
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
The Honey Hut, Think of “ On Golden Pond"
10

Excellent

·
Mount Sterling
·
1 br
·
Sleeps 4
·
Balcony · Lake · Waterfront ·
From
$230/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Lake
Waterfront
Dishwasher
On Site Laundry
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
Farmhouse living within sight of Lexington - Horse Paddock available
10

Excellent

·
Winchester
·
3 br
·
Dishwasher · On Site Laundry · Oven ·
From
$250/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Dishwasher
On Site Laundry
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Storage
Other spaces
Kitchen
Contemporary One Bedroom Walk Up Apartment
9

Excellent

·
Paris
·
1 br
·
Sleeps 2
·
Fitness Center · Oven · In Unit Laundry ·
From
$110/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Fitness Center
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Charming & Inviting Apartment in Historic Downtown Paris, Ky.
9.6

Excellent

·
Paris
·
1 br
·
Sleeps 4
·
Fitness Center · Hardwood Floor · Central Heat ·
From
$110/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Fitness Center
Hardwood Floor
Central Heat
Fireplace
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
Best Western Paris Inn
7.9

Very good

·
Paris
·
1 br
·
Sleeps 4
·
Pool · Workspace · On Site Laundry ·
From
$90/night
Check availability
Property
Hotel · 1 Bed
Amenities
Pool
On Site Laundry
Free Parking
Air Conditioning
Furnished
Wifi
Swimming Pool
Business Center
Other spaces
Workspace
Home > Kentucky Vacation Rentals > Winchester Vacation Rentals
Updated: March 21, 2023

Learn about vacation rentals in

Winchester

Explore 9 vacation rentals near Winchester, Kentucky. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Winchester, you can see photos of Winchester vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Winchester vacation rentals in specific areas. Whether you’re looking for a Winchester staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Winchester is $67 per night and the highest price is $212 per night.
2 of the vacation rentals near Winchester are apartments or condos. The average bathroom count for this property type is 2. The median price for these vacation units is $154 per night. There are currently 1 vacation units under this price. 3 of the vacation rentals near Winchester are houses. The average bathroom count for a vacation house near Winchester is 2. The average price for vacation houses near Winchester is $162 per night. There are 1 vacation homes under this price. The most common amenities for vacation rentals near Winchester are: furnished, air conditioning, and wifi. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.

1 bed rentals

5 available

2 bed rentals

2 available

3 bed rentals

1 available

4+ bed rentals

1 available

Vacation Rentals in Winchester, KY FAQ

How many vacation rentals in Winchester are available?

There are currently 9 vacation rentals in Winchester available. Our vacation rentals in Winchester include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.

Are there any pet friendly vacation rentals in Winchester?

Yes, right now there are 4 pet friendly vacation rentals in Winchester. A pet friendly vacation rental in Winchester means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.

Are there any vacation rentals in Winchester with a pool?

Yes there are vacation rentals with a pool available in Winchester, KY. View more detailed vacation spots on Vacations by Zumper.

Are there any vacation rentals in Winchester with internet access?

As of March 21, 2023, there are vacation rentals with internet access available in Winchester, Kentucky. Check out more enjoyable destinations on Vacations by Zumper.

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