Airbnb, Cabins, Vacation Rentals in Winchester, KY

Compare 544 available, short term vacation home properties, starts from $15

Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.

Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.

Find the best vacation rental

ACCOMMODATION TYPES

Save Up To 72%

Airbnb, Vacation rentals and hotel deals in Winchester, KY

Days Inn by Wyndham Lexington Southeast
Days Inn by Wyndham Lexington Southeast
Days Inn by Wyndham Lexington Southeast
Days Inn by Wyndham Lexington Southeast
6.9 (140 reviews)
Days Inn by Wyndham Lexington Southeast
Hotel · 2 Guests · 1 Bedroom
$60 /night
View deal
Clarion Hotel Lexington
Clarion Hotel Lexington
Clarion Hotel Lexington
Clarion Hotel Lexington
7.0 (283 reviews)
Clarion Hotel Lexington
Hotel · 2 Guests · 1 Bedroom
$90 /night
View deal
Bluegrass Extended Stay
Bluegrass Extended Stay
Bluegrass Extended Stay
Bluegrass Extended Stay
7.2 (196 reviews)
Bluegrass Extended Stay
Hotel · 2 Guests · 1 Bedroom
$54 /night
View deal
Days Inn & Suites by Wyndham Lexington
Days Inn & Suites by Wyndham Lexington
Days Inn & Suites by Wyndham Lexington
Days Inn & Suites by Wyndham Lexington
6.6 (397 reviews)
Days Inn & Suites by Wyndham Lexington
Hotel · 2 Guests · 1 Bedroom
$64 /night
View deal
Best Western Winchester Hotel
Best Western Winchester Hotel
Best Western Winchester Hotel
Best Western Winchester Hotel
8.3 (195 reviews)
Best Western Winchester Hotel
Hotel · 2 Guests · 1 Bedroom
$89 /night
View deal
Econo Lodge Lexington
Econo Lodge Lexington
Econo Lodge Lexington
Econo Lodge Lexington
7.2 (149 reviews)
Econo Lodge Lexington
Motel · 2 Guests · 1 Bedroom
$48 /night
View deal
Super 8 by Wyndham Richmond
Super 8 by Wyndham Richmond
Super 8 by Wyndham Richmond
Super 8 by Wyndham Richmond
8.0 (187 reviews)
Super 8 by Wyndham Richmond
Hotel · 2 Guests · 1 Bedroom
$64 /night
View deal
Quality Quarters Inn
Quality Quarters Inn
Quality Quarters Inn
Quality Quarters Inn
5.2 (146 reviews)
Quality Quarters Inn
Motel · 2 Guests · 1 Bedroom
$55 /night
View deal
Private bedroom in peaceful home, located 15 minutes from University of Kentucky
Private bedroom in peaceful home, located 15 minutes from University of Kentucky
Private bedroom in peaceful home, located 15 minutes from University of Kentucky
Private bedroom in peaceful home, located 15 minutes from University of Kentucky
10 (1 review)
Private bedroom in peaceful home, located 15 minutes from University of Kentucky
Holiday home · 2 Guests · 1 Bedroom
$58 /night*
View deal
Sleep Inn Lexington
Sleep Inn Lexington
Sleep Inn Lexington
Sleep Inn Lexington
7.5 (160 reviews)
Sleep Inn Lexington
Hotel · 2 Guests · 1 Bedroom
$79 /night
View deal
La Quinta Inn Lexington-Horse Park
La Quinta Inn Lexington-Horse Park
La Quinta Inn Lexington-Horse Park
La Quinta Inn Lexington-Horse Park
6.4 (296 reviews)
La Quinta Inn Lexington-Horse Park
Hotel · 2 Guests · 1 Bedroom
$87 /night
View deal
Comfort Inn & Suites Mount Sterling
Comfort Inn & Suites Mount Sterling
Comfort Inn & Suites Mount Sterling
Comfort Inn & Suites Mount Sterling
6.2 (143 reviews)
Comfort Inn & Suites Mount Sterling
Hotel · 2 Guests · 1 Bedroom
$83 /night
View deal
This apartment is a 0 bedroom(s), 1 bathrooms, located in Lexington, KY.
This apartment is a 0 bedroom(s), 1 bathrooms, located in Lexington, KY.
This apartment is a 0 bedroom(s), 1 bathrooms, located in Lexington, KY.
This apartment is a 0 bedroom(s), 1 bathrooms, located in Lexington, KY.
7.2 (7 reviews)
This apartment is a 0 bedroom(s), 1 bathrooms, located in Lexington, KY.
Apartment · 2 Guests · 1 Bedroom
$52 /night*
View deal
Clarion Pointe Richmond North near University
Clarion Pointe Richmond North near University
Clarion Pointe Richmond North near University
Clarion Pointe Richmond North near University
8.3 (140 reviews)
Clarion Pointe Richmond North near University
Hotel · 2 Guests · 1 Bedroom
$76 /night
View deal
Motel 6-Lexington, KY - Airport
Motel 6-Lexington, KY - Airport
Motel 6-Lexington, KY - Airport
Motel 6-Lexington, KY - Airport
5.8 (241 reviews)
Motel 6-Lexington, KY - Airport
Hotel · 2 Guests · 1 Bedroom
$57 /night
View deal
Arlington's Oasis is a Charming Townhuse located in Paris Kentucky
Arlington's Oasis is a Charming Townhuse located in Paris Kentucky
Arlington's Oasis is a Charming Townhuse located in Paris Kentucky
Arlington's Oasis is a Charming Townhuse located in Paris Kentucky
8.0 (2 reviews)
Arlington's Oasis is a Charming Townhuse located in Paris Kentucky
Holiday home · 2 Guests · 1 Bedroom
$89 /night*
View deal
Countryside Inn Motel
Countryside Inn Motel
Countryside Inn Motel
Countryside Inn Motel
5.2 (84 reviews)
Countryside Inn Motel
Motel · 2 Guests · 1 Bedroom
$57 /night
View deal
avid hotels - Lexington - Hamburg Area, an IHG Hotel
avid hotels - Lexington - Hamburg Area, an IHG Hotel
avid hotels - Lexington - Hamburg Area, an IHG Hotel
avid hotels - Lexington - Hamburg Area, an IHG Hotel
9.0 (56 reviews)
avid hotels - Lexington - Hamburg Area, an IHG Hotel
Hotel · 2 Guests · 1 Bedroom
$73 /night
View deal
Private Studio Downtown - UK Campus/Downtown/Rupp
Private Studio Downtown - UK Campus/Downtown/Rupp
Private Studio Downtown - UK Campus/Downtown/Rupp
Private Studio Downtown - UK Campus/Downtown/Rupp
Private Studio Downtown - UK Campus/Downtown/Rupp
Apartment · 2 Guests · 1 Bedroom
$72 /night*
View deal
Quality Inn Lexington - Horse Park
Quality Inn Lexington - Horse Park
Quality Inn Lexington - Horse Park
Quality Inn Lexington - Horse Park
4.6 (27 reviews)
Quality Inn Lexington - Horse Park
Hotel · 2 Guests · 1 Bedroom
$86 /night
View deal
Search all

Vacation Destinations Near Winchester, KY

Airbnb, Log Cabin Rentals with Fireplace, and Other Rental Options in Winchester, KY

Secluded, 2 bedroom, cabin in a beautiful mountain setting.
Secluded, 2 bedroom, cabin in a beautiful mountain setting.
Secluded, 2 bedroom, cabin in a beautiful mountain setting.
Secluded, 2 bedroom, cabin in a beautiful mountain setting.
Fireplace
10 (1 review)
Secluded, 2 bedroom, cabin in a beautiful mountain setting.
Chalet · 2 Guests · 1 Bedroom
$141 /night*
View deal
Kentucky River Cottages ~ Featured on the Live Well Network's Sweet Retreats!
Kentucky River Cottages ~ Featured on the Live Well Network's Sweet Retreats!
Kentucky River Cottages ~ Featured on the Live Well Network's Sweet Retreats!
Kentucky River Cottages ~ Featured on the Live Well Network's Sweet Retreats!
Fireplace
9.8 (46 reviews)
Kentucky River Cottages ~ Featured on the Live Well Network's Sweet Retreats!
Cottage · 2 Guests · 1 Bedroom
$375 /night*
View deal
Inviting Lexington Home: 2 Miles to University!
Inviting Lexington Home: 2 Miles to University!
Inviting Lexington Home: 2 Miles to University!
Inviting Lexington Home: 2 Miles to University!
Fireplace
Inviting Lexington Home: 2 Miles to University!
Cottage · 2 Guests · 1 Bedroom
$150 /night
View deal
Search all
What Are The Best Rental Amenities in Winchester, KY?
Best Amenities in Winchester, KY
+
Check above for the most common and the least popular rental amenities in Winchester, and pick the one that fits your preference easily. In Winchester, 255 rentals offer Internet or Wifi, 252 rentals offer Air Conditioning, 239 rentals offer TV. So, if you need Internet or Wifi during your vacation, use the Internet or Wifi filter to compare these properties. Two amenities that are not typical are Hot Tub, Pool.
Which Price Range Is Considered As A Good Deal in Winchester, KY Area?
Vacation House & Condo Rental Price Information in Winchester, KY
+
The graph shows the percentages of vacation homes in each price bucket. Winchester has the largest percentage (25.00%) of homes in $100 - $150 price range.
$0 to 50
$0 to 50
$50 to 100
$50 to 100
$100 to 150
$100 to 150
$150 to 200
$150 to 200
$200 to 250
$200 to 250
$250 to 300
$250 to 300
$300 to 350
$300 to 350
$350 to 400
$350 to 400
$400 to 450
$400 to 450
$450 to 500
$450 to 500
$500 +
$500 +
What Are The Popular Property Types in Winchester, KY?
Rental Property Types in Winchester, KY
+
Before visiting Winchester, it is a good idea to explore all the accommodation types in this area, and pick the one that fits your group well. All the available accommodation types are: House, Condo, Apartment, Cabin, Townhome, Cottage, Studio, Hotel, Farmhouse, Chateau / Country House, Bed And Breakfast, Guest House, Lodge, Chalet, Campground. House is the most-liked rental type, with the largest percentage of 42.28%. The biggest home in this area available for rent is around 12500 square feet.The least popular accommodation in Winchester is Campground rentals
How Many Accommodations Are Not Pets Friendly in Winchester, KY?
Percentage of Pet Friendly Rental Properties in Winchester, KY
+
32.72% of vacation homes in Winchester are pet friendly. If you have pet allergies, make sure to check the home property and see whether it is a pet-friendly vacation home or not.
Must-Visit Trails in Winchester, KY?
Top Trails In Winchester, KY
+
Here are the trails we recommend in Winchester: Fort Boonesborough Campground Loop Trail, Raven Run Red Trail, Raven Run Nature Sanctuary Trail, McConnell Springs Trail, Shillito Park Trail, Veterans Park Trail, Veterans Park Outer Loop, John Holder Trail, Winchester Walking Trail, Pilot Knob Trail.
Where Are The Campgrounds in Winchester, KY Area?
Campgrounds Recommendations In Winchester, KY
+
If you love outdoors or travel with an RV, here are the campgrounds in Winchester: Three Springs Campground, Taylorsville Lake Campground, Renfro Valley KOA, Fort Boonesborough Campground, Natural Bridge State Resort Park Campground, Elkhorn Campground, Twin Knobs Campground, Zilpo - Daniel Boone Nat. For. Campground, Boat Gunnel Group Campground, Buckhorn Campground.
What are the Airports in Winchester, KY?
Airports Options in Winchester, KY
+

1 airport(s) close to Winchester are:

Other Vacation Rentals Ideas

Airbnb, Vacation House with Full Kitchen, and Other Rental Options in Winchester, KY

Stay in a newly renovated home in the heart of Dtown Lexington
Stay in a newly renovated home in the heart of Dtown Lexington
Stay in a newly renovated home in the heart of Dtown Lexington
Stay in a newly renovated home in the heart of Dtown Lexington
Full Kitchen
9.6 (8 reviews)
Stay in a newly renovated home in the heart of Dtown Lexington
Holiday home · 2 Guests · 1 Bedroom
$100 /night*
View deal
VERY PRIVATE 3BR HOUSE W/ POOL TABLE & AWESOME PORCHES. DOGS WELCOME!
VERY PRIVATE 3BR HOUSE W/ POOL TABLE & AWESOME PORCHES. DOGS WELCOME!
VERY PRIVATE 3BR HOUSE W/ POOL TABLE & AWESOME PORCHES. DOGS WELCOME!
VERY PRIVATE 3BR HOUSE W/ POOL TABLE & AWESOME PORCHES. DOGS WELCOME!
Full Kitchen
10 (5 reviews)
VERY PRIVATE 3BR HOUSE W/ POOL TABLE & AWESOME PORCHES. DOGS WELCOME!
Holiday home · 2 Guests · 1 Bedroom
$300 /night*
View deal
Luxury Home | Hot Tub | Game Room | Downtown | Patio & Firepit
Luxury Home | Hot Tub | Game Room | Downtown | Patio & Firepit
Luxury Home | Hot Tub | Game Room | Downtown | Patio & Firepit
Luxury Home | Hot Tub | Game Room | Downtown | Patio & Firepit
Full Kitchen
9.6 (25 reviews)
Luxury Home | Hot Tub | Game Room | Downtown | Patio & Firepit
Holiday home · 2 Guests · 1 Bedroom
$280 /night*
View deal
Search all
* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
See all offers