49+ Boston Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Boston

Discover more than 49 holiday rentals in Boston. PickleTrip™ holiday homes has everything you need to find a place to stay near Boston, .

Whether you are looking for luxury villas in Boston, 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 Boston with a whole family or group, PickleTrip™ holiday accommodations can make your trip more memorable. We have plenty of places to stay in Boston 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 Boston with PickleTrip™. Stay and play pickleball when you travel.

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Frequently Asked Questions About Boston Holiday Rentals

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

There are many holiday rentals available in Boston; however, here are a few of the most popular holiday homes listed in Boston on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Boston to find one that works for you.
Yes, there are 49 self-catering family homes and holiday rentals in Boston.
There are more than 49 luxury holiday homes in or near Boston, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 49 pet friendly rentals that are available in Boston.