Westchester Family Rentals & Large Homes

Find Family-Friendly Vacation Rentals Near Westchester

About Westchester Family Rental on PickleTrip

Looking to stay in Westchester and play pickleball with your family in your downtime? Look no further than PickleTrip™! We offer a variety of affordable pickleball-friendly accommodations including vacation rentals, resorts, and hotels with private courts on-site or nearby.

While we are known for our premium pickleball stays, we also offer a variety of other great properties for your stay. Choose from boutique hotels, cozy cottages, lakefront villas, and more. Many of our properties are located in prime pickleball destinations so you can spend your days playing the sport you love.

Traveling with your family or a group of pickleball enthusiasts? No problem! We have the perfect accommodations for you. From spacious villas to comfortable condos, we have plenty of room for your family and friends to stay and play. Stay and play pickleball when you travel with PickleTrip™!

Show more
Show less

Frequently Asked Questions About Westchester Family Rentals

The average price per night for a family holiday rental in Westchester is $369. Check the list of kid-friendly accommodations in Westchester.
There are 1061 2-bedroom rental properties that are available in Westchester. You can book for your next trip with PickleTrip.
Yes, here are some top-rated family vacation rentals in Westchester that have a private swimming pool:

Check all holiday rentals with a pool in Westchester on PickleTrip.

Yes, We have 1061 direct by owner rentals in Westchester.
Yes, Of course! There are many luxury rental properties in or near Westchester. Use our search filter to discover all of our luxury homes with your favorite amenities. Sorting by price is another way to find the luxury holiday rentals in Westchester, though more expensive is not always better.