270+ Winchester Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Winchester

Explore a diverse selection of more than 270 holiday rentals in Winchester with SunSki Resorts. Our holiday homes offer everything you need for a comfortable stay near Winchester, TN.

Whether you're in search of luxurious villas, furnished homes, unique condos, cozy cottages for a romantic escape, spacious apartments for family vacations, or stylish accommodations for business trips, we've got you covered. Our holiday rentals boast top-notch amenities including indoor/outdoor swimming pools, fully-equipped kitchens, gyms, hot tubs, high-speed Internet, and more.

Planning a trip to Winchester with your family or a group? Our holiday accommodations ensure a memorable experience for all. With plenty of options available for families, large groups, or private owner accommodations for short or long trips, you'll find the perfect fit. We also offer pet-friendly holiday rentals, catering to all members of your travel party. Book your preferred vacation rental in Winchester with SunSkiResorts and enjoy a seamless booking experience today.

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Frequently Asked Questions About Winchester Holiday Rentals

There are a lot of options in Winchester. If you plan on staying in the Winchester area, consider making a reservation for a few nights at one of these properties as these have been rated the top Holiday Home Rentals in Winchester:

There are many holiday rentals available in Winchester; however, here are a few of the most popular holiday homes listed in Winchester on our website:
At SunSkiResorts most of our places to stay are perfect for families. Check out the complete list of holiday homes in Winchester to find one that works for you.
Yes, there are 270 self-catering family homes and holiday rentals in Winchester.
There are more than 270 luxury holiday homes in or near Winchester, according to 2025 data from SunSkiResorts. Consider these homes for your next holiday:
Yes, there are 270 pet friendly rentals that are available in Winchester.