127+ James Madison Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near James Madison

Discover more than 127 holiday rentals in James Madison. PickleTrip™ holiday homes has everything you need to find a place to stay near James Madison, VA.

Whether you are looking for luxury villas in James Madison, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartment for family holidays, or stylish accommodation for a business trip, we can help you find the perfect place with private pickleball courts or nearby facilities. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, Internet connectivity, and more.

If you are planning to travel to James Madison with a whole family or group, PickleTrip™ holiday accommodations can make your trip more memorable. We have plenty of places to stay in James Madison for families, large parties, or private owner accommodations for long or short trips. Pet-friendly holiday rentals are available as well. Book your favorite vacation rentals in James Madison with PickleTrip™. Stay and play pickleball when you travel.

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Frequently Asked Questions About James Madison Holiday Rentals

There are a lot of options in James Madison. If you plan on staying in the James Madison 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 James Madison:

There are many holiday rentals available in James Madison; however, here are a few of the most popular holiday homes listed in James Madison on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in James Madison to find one that works for you.
Yes, there are 127 self-catering family homes and holiday rentals in James Madison.
There are more than 127 luxury holiday homes in or near James Madison, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 127 pet friendly rentals that are available in James Madison.