Chestertown Houseboat Rentals
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Book a Last Minute Place to Stay in Chestertown
About Chestertown Vacation Rentals
Explore over 63 floating homes in Chestertown. From luxurious floating houses to unique water chalets and houseboats, each offers premium amenities designed for families, groups, and adventurers. Enjoy exceptional comfort and a one-of-a-kind water experience with these incredible water-based accommodations. Perfect for relaxing retreats, vibrant escapes, or waterfront adventures, these floating homes provide style and comfort in Chestertown.
Looking for last-minute deals or the best offers on floating homes, houseboats, or floating cabins? With Float Homes, comparing available options in Chestertown is simple. Find spacious family-friendly accommodations, cozy water chalets, or luxurious houseboats—all designed for maximum comfort and convenience during your stay.
On average, floating homes in Chestertown offer approximately 935.77 ft² of space, giving you and your group plenty of room to relax and enjoy the stunning waterfront.
The average nightly rate for floating homes in Chestertown typically ranges around US $528.
Float Homes offers a secure and convenient platform to compare and book the best floating homes in Chestertown. Explore a wide range of properties at competitive rates, and enjoy a unique stay on the water with us.
Top Floating Accommodation Types in Chestertown
| Type | Count |
|---|---|
| Vacation Homes | 41 |
| Holiday Apartments | 9 |
| Cottages | 3 |
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★ Pro Tip: Float Homes makes it easy to compare the best floating home listings from top vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature to effortlessly flip between floating homes, houseboats, luxury overwater villas, eco-friendly floating houses, and various accommodation types. Filter by availability, prices, cancellation policies, and unique amenities to find the perfect floating home for your next water escape in Chestertown.
Weather in Chestertown, MD
View the weather forecast for Chestertown before booking your Chestertown Vacation Rentals to confirm your best time to go.
Top Attractions Around Chestertown, MD
Float Homes offers a diverse selection of top floating homes and water retreats around the world. Chestertown. Research things to do on your vacation before you visit Chestertown.
Other Places to Stay in Chestertown, MD
Frequently Asked Questions About Chestertown?
What are the top floating home rentals in Chestertown?
Planning to stay in Chestertown? Consider booking your stay at one of these top-rated floating homes for a unique and unforgettable water escape:
- Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
- Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
- Carriage House Hideaway in Middle of Chestertown
- Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!
- Circa 1900 Home in the Heart of Historic Downtown Chestertown
- Country Estate in Historic District
- Contemporary waterfront house with private dock & kayaks!
- 350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
- Historic Downtown Garden Oasis with Private Patio
- Breathtaking waterfront home on the Chester River
How many floating home rentals are available in Chestertown?
As of 2025, FloatHomes offers over 63 floating homes and water-based accommodation in Chestertown. Discover a wide selection of houseboats, water chalets, and more, with new listings added regularly.
In 2025, FloatHomes showcases over 63 properties in Chestertown, sourced from multiple platforms. Find the perfect floating home for your next getaway.
Float Homes offers more than 63 premier floating accommodations in Chestertown for 2025. Explore unique, water-based accommodations today.
