225+ Cressy Beach Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Cressy Beach

Discover more than 225 holiday rentals in Cressy Beach. PickleTrip™ holiday homes has everything you need to find a place to stay near Cressy Beach, MA.

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

Show more
Show less

Frequently Asked Questions About Cressy Beach Holiday Rentals

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

There are many holiday rentals available in Cressy Beach; however, here are a few of the most popular holiday homes listed in Cressy Beach on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Cressy Beach to find one that works for you.
Yes, there are 225 self-catering family homes and holiday rentals in Cressy Beach.
There are more than 225 luxury holiday homes in or near Cressy Beach, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 225 pet friendly rentals that are available in Cressy Beach.