Chestertown Overwater Villas & Floating Home Rentals

Find villas near Chestertown - We found 65 exact matches

About Chestertown Villa on Float Homes

Explore a wide selection of luxurious floating homes and overwater villas near Chestertown. These unique water-based accommodations provide an exceptional experience, featuring top-tier amenities such as private swimming pools, WiFi, hot tubs, and stunning water views, and more.

Whether you're planning a romantic escape, a family vacation, or a getaway with friends, Float Homes offers thousands of floating homes and overwater villas to meet your needs. Each rental is designed with comfort and relaxation in mind, offering its own distinctive style and amenities.

Float Homes' floating homes and overwater villas are located in some of the most sought-after destinations, including Chestertown. Choose from a range of settings such as beachfront, mountain, or seaside retreats, many of which come with private pools, luxurious bedrooms, and additional amenities like fitness centers and direct water access.

Booking your perfect floating home or overwater villa in Chestertown is easy with Float Homes. Browse our collection and take advantage of special offers and deals, available directly through our platform as well as on leading vacation rental sites like Airbnb and VRBO. Make your next trip truly unforgettable with Float Homes' exceptional water-based accommodations.

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Frequently Asked Questions About Chestertown Rental Villas

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 Villa Rentals in Chestertown:

At Float Homes, the average rental fee for standard villas in Chestertown is $522 per night. FloatHomes.com has a large database of quality villas near Chestertown that are suitable for families, a romantic getaway, or a solo trip with single or multiple bedrooms.
Yes, here are the top villas rentals in Chestertown that are pet friendly:See all pet-friendly vacation rentals in Chestertown on Float Homes
Most of our listed villas are suitable for families. The number of rooms varies, and you can check out the complete list of villas in Chestertown to find what works for you.
Based on the 2025 data from our Float Homes site, there are more than 65 private swimming pools or villas with indoor pools in or near Chestertown.
There are 65 villas in or near Chestertown that have hot tubs. The most popular places to stay with hot tubs include:See all holiday vacation rentals in Chestertown on Float Homes
Most definitely! There are many luxury villas in Chestertown. Use our search filter to discover all of our luxury villas, and choose the one that matches your taste. Sorting by price is another way to find the most expensive villas in Chestertown.