Find Vacation Rentals in Winchester

We have 14 properties to choose from
Winchester

Popular Winchester Vacation Homes and Apartments

Find the perfect Winchester vacation accommodation

Pet-friendly
Motel ∙ 4 guests
Winchester, Clark County, Kentucky, United States
Check rates
synthetic
4.4
Details
Pet-friendly
Bed & Breakfast ∙ 3 guests ∙ 1 bedroom
Winchester, Clark County, Kentucky, United States
from $56
Airbnb
5.0
Details
Pet-friendly
Cottage ∙ 5 guests ∙ 2 bedrooms
Winchester, Clark County, Kentucky, United States
from $102
Airbnb
5.0
Details
View more

Recommended Rentals With Pools

Pool
Motel ∙ 4 guests
Winchester, Clark County, Kentucky, United States
Check rates
synthetic
4.4
Details
Pool
Hotel
Winchester, Clark County, Kentucky, United States
Check rates
synthetic
4.8
Details
Pool
Bed & Breakfast ∙ 3 guests ∙ 1 bedroom
Winchester, Clark County, Kentucky, United States
from $56
Airbnb
5.0
Details
View more

Pet-Friendly Homes and Apartments

Pet-friendly
Motel ∙ 4 guests
Winchester, Clark County, Kentucky, United States
Check rates
synthetic
4.4
Details
Pet-friendly
Cottage ∙ 5 guests ∙ 2 bedrooms
Winchester, Clark County, Kentucky, United States
from $102
Airbnb
5.0
Details
Pet-friendly
Bed & Breakfast ∙ 3 guests ∙ 1 bedroom
Winchester, Clark County, Kentucky, United States
from $56
Airbnb
5.0
Details
View more
Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Winchester

Save hundreds with a vacation home rental from Tripping.com and forget the hotel room. For the ultimate getaway, Winchester offers 498 affordable vacation rentals with a price to match your budget and accommodation needs. Prices in Winchester start at an average price of €166 a night with long-term rentals averaging €3805 a month.

These vacation rentals offer a range of amenities, so you’ll feel right at home. For those looking to stay in a corporate rental, 344 of Winchester’s rentals offer high speed WiFi Internet so you can easily keep in touch with your company or team. Go for a swim at one of the 163 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 319 vacation home rentals.

Traveling with your dog or cat? Choose from 184 pet-friendly rentals in Winchester that allow you to bring your extended family along.Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your pets. Many properties allow you to book directly online, so once you find that perfect vacation rental, you’ll be all set to go!

Search properties from 7 vacation rental sites in Winchester where the top providers in that area are HomeAway, HRS Holidays, and Booking.com. There are 170 HomeAway rentals, 126 HRS Holidays short term rentals and 80 Booking.com vacation rentals.

Top Destinations in Kentucky

Destinations Close to Winchester