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Compare 98 Vacation Homes in Henderson with updated reviews, rates, and availability.
![Exterior](https://images.trvl-media.com/lodging/68000000/67330000/67326000/67325935/782a7e19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Captain's Quarters
Captain's Quarters
9.8 out of 10, Exceptional, (84)
![Terrace/patio](https://images.trvl-media.com/lodging/63000000/62580000/62578000/62577978/41ca91c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
10.0 out of 10, Exceptional, (46)
![Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier](https://images.trvl-media.com/lodging/62000000/61640000/61633900/61633861/5294047c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
10.0 out of 10, Exceptional, (51)
![Chestertown Vacation Rental | 4BR | 4.5BA | 6 Steps Required | 3,232 Sq Ft](https://images.trvl-media.com/lodging/110000000/109330000/109326900/109326847/5d64b793.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Pet-Friendly Home on Chester River w/ Dock!
Pet-Friendly Home on Chester River w/ Dock!
9.6 out of 10, Exceptional, (4)
![Waterfront with private pier and great views](https://images.trvl-media.com/lodging/95000000/94840000/94839700/94839681/29cc8f41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
10.0 out of 10, Exceptional, (24)
![Beach](https://images.trvl-media.com/lodging/95000000/94340000/94339600/94339545/w1284h966x0y656-8b907b0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Wind Song Getaway on the Beach
Wind Song Getaway on the Beach
9.8 out of 10, Exceptional, (25)
![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101080000/101073900/101073809/a6fbe8f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf
10.0 out of 10, Exceptional, (5)
![Living area](https://images.trvl-media.com/lodging/88000000/87680000/87670600/87670535/474ab76d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Stylish Home on the Choptank River (with Tidal Beach)
Stylish Home on the Choptank River (with Tidal Beach)
10.0 out of 10, Exceptional, (31)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Henderson
![Exterior](https://images.trvl-media.com/lodging/68000000/67330000/67326000/67325935/782a7e19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Captain's Quarters
Captain's Quarters
9.8 out of 10, Exceptional, (84)
![Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier](https://images.trvl-media.com/lodging/62000000/61640000/61633900/61633861/5294047c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
10.0 out of 10, Exceptional, (51)
![Terrace/patio](https://images.trvl-media.com/lodging/63000000/62580000/62578000/62577978/41ca91c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
10.0 out of 10, Exceptional, (46)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Recent reviews of Henderson hotels
Recent reviews of Henderson hotels
![Bally's Dover Casino Resort](http://images.trvl-media.com/lodging/2000000/1580000/1573000/1572988/w1000h664x0y0-4dc8e6eb_y.jpg)
Bally's Dover Casino Resort
5/5 Excellent
"Great place to stay"
A verified traveler from Chesterfield stayed at Bally's Dover Casino Resort
Posted 1 day ago