Winchester Villa Rentals & RBO Homes

Find villas near Winchester - We found 152 exact matches

About Winchester Villa on Rent By Owner

Rent By Owner has more than 152 villas near Winchester. These rentals have all the luxury accoutrements to give you comfort, including amenities such as - private swimming pools, WIFI, spas, hot tubs, and more.

Rent By Owner has a wide range of villa rentals near Winchester, and there are different options for families, friends, or even couples. These rentals come in unique styles or sizes that would definitely suit your needs.

Rent By Owner offers expectational rental villas that are out of the ordinary and not found elsewhere, whether you are traveling on a beachfront, seaside, mountain, or any destination. RBO is an all-in-one travel platform that matches you with the perfect rental villa in Winchester for your dream vacation, including top travel locations in the USA & the Rest of the World. Many have private pools, luxury bedrooms, and even features like tennis courts, beach volleyball, spas, fitness clubs & more.

RBO Villas are available for last-minute bookings and may include special offers for Airbnb, VRBO & RBO-style villas. So find your last-minute getaway today with RBO in Winchester, and get ready to enjoy maximum comfort on your next holiday.

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Frequently Asked Questions About Winchester Rental Villas

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 Villa Rentals in Winchester:

At Rent By Owner, the average rental fee for standard villas in Winchester is $358 per night. RBO has a large database of quality villas near Winchester that are suitable for families, a romantic getaway, or a solo trip with single or multiple bedrooms.
Yes, here are the top villas rentals in Winchester that are pet friendly:See all pet-friendly vacation rentals in Winchester on Rent By Owner
Most of our listed villas are suitable for families. The number of rooms varies, and you can check out the complete list of villas in Winchester to find what works for you.
Based on the 2025 data from our Rent By Owner site, there are more than 152 private swimming pools or villas with indoor pools in or near Winchester.