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  3. Windham County
  4. Holiday Homes

1745+ Windham County Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Windham County

Discover more than 1745 holiday rentals in Windham County. Rent By Owner holiday homes has everything you need to find a place to stay near Windham County, VT.

Whether you are looking for luxury villas in Windham County, 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. 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 Windham County with a whole family or group, RBO holiday accommodations make your trip memorable. We have plenty of places to stay in Windham County for families, large parties, or private owner accommodations for long or short trips. Windham County Pet-friendly holiday rentals are available. Book your favorite vacation rentals in Windham County with Rent By Owner. RBO makes it easy to compare and book holiday rentals today.

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Frequently Asked Questions About Windham County Holiday Rentals

There are a lot of options in Windham County. If you plan on staying in the Windham County 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 Windham County:

There are many holiday rentals available in Windham County; however, here are a few of the most popular holiday homes listed in Windham County on our website:
At Rent By Owner most of our places to stay are perfect for families. Check out the complete list of holiday homes in Windham County to find one that works for you.
Yes, there are 1745 self-catering family homes and holiday rentals in Windham County.
There are more than 1745 luxury holiday homes in or near Windham County, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: