Chestertown Family Rentals & Large Homes

Find Family-Friendly Vacation Rentals Near Chestertown

About Chestertown Family Rental on Float Homes

Discover 162 in Chestertown, perfect for your group's reunion or family retreat.

Float Homes offers thousands of water-based accommodations, including spacious houseboats, overwater villas, floating cabins, and overwater bungalows ideal for large families or groups. Whether you're hosting a family reunion with kids, parents, cousins, aunts, uncles, grandparents, and even pets, our Chestertown rentals provide plenty of space and savings compared to traditional hotels.

Renting a floating home in Chestertown through Float Homes gives you access to a wide range of options, ensuring the perfect accommodation for your family getaway. Our properties are equipped with essential amenities such as comfortable beds, outdoor seating areas, Wi-Fi, kitchenettes, private decks, and even swimming pools, ensuring a memorable experience for your entire group.

Explore thousands of floating home rentals with Float Homes, including spacious houseboats, overwater villas, and water chalets, perfect for accommodating large groups or multiple families. Many of our rentals feature private pools, offering you the best value for your budget.

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Frequently Asked Questions About Chestertown Family Rentals

There are a lot of options in Chestertown. If you plan on staying in the Chestertown area, consider making a reservation for a few nights at one of these properties as these have been rated the top Family Rentals in Chestertown:

The average price per night for a family holiday rental in Chestertown is $373. Check the list of kid-friendly accommodations in Chestertown.
There are 162 2-bedroom rental properties that are available in Chestertown. You can book for your next trip with Float Homes.
Yes, here are some top-rated family vacation rentals in Chestertown that have a private swimming pool:

Check all holiday rentals with a pool in Chestertown on Float Homes.

Yes, We have 162 direct by owner rentals in Chestertown.
Yes, Of course! There are many luxury rental properties in or near Chestertown. 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 Chestertown, though more expensive is not always better.