222+ Wellesley Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Wellesley

Discover more than 222 holiday rentals in Wellesley. Rent By Owner holiday homes has everything you need to find a place to stay near Wellesley, MA.

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

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Frequently Asked Questions About Wellesley Holiday Rentals

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

There are many holiday rentals available in Wellesley; however, here are a few of the most popular holiday homes listed in Wellesley 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 Wellesley to find one that works for you.
Yes, there are 222 self-catering family homes and holiday rentals in Wellesley.
There are more than 222 luxury holiday homes in or near Wellesley, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: