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64 boats in Chestertown, US
1 / 7
$100+/hour
Oxford, MD
5.0
(59 bookings)
3 - 8 hours rental • No captain
1 / 24
$245+/hour
TOP OWNER
Pasadena, MD
5.0
(45 bookings)
3 - 8 hours rental • Captained
1 / 15
$119+/hour
INSTANT BOOK
1 / 4
$88+/hour
Easton, MD
5.0
(14 bookings)
2 - 8 hours rental • Captain optional
1 / 17
$72+/hour
Stevensville, MD
4.9
(176 bookings)
2 - 8 hours rental • No captain
1 / 7
$335+/hour
1 / 5
$81+/hour
Easton, MD
5.0
(6 bookings)
2 - 8 hours rental • No captain
1 / 5
$59+/hour
Galena, MD
5.0
(2 bookings)
2 - 8 hours rental • No captain
1 / 10
$281+/hour
Annapolis, MD
5.0
(4 bookings)
2 - 8 hours rental • Captained
1 / 20
$304+/hour
1 / 13
$265+/hour
1 / 10
$670+/hour
INSTANT BOOK
1 / 4
$120+/hour
INSTANT BOOK
Glen Burnie, MD
5.0
(54 bookings)
2 - 8 hours rental • Captain optional
1 / 17
$86+/hour
TOP OWNER
Edgewater, MD
5.0
(24 bookings)
3 - 8 hours rental • Captain optional
1 / 10
$125+/hour
1 / 10
$106+/hour
Sparrows Point, MD
2 - 8 hours rental • No captain
1 / 22
$144+/hour
1 / 17
$47+/hour
TOP OWNER
Edgewater, MD
4.9
(67 bookings)
2 - 8 hours rental • Captain optional
Search as I move the map
$100
2013 20' Sweetwater Sunrise Pontoon - Oxford - Tred Avon in comfort
5.0
(59 bookings)
$100+
/hour
$245
Still Crazy II - Cruise the Chesapeake in luxury! (Captained)
TOP OWNER
5.0
(45 bookings)
$245+
/hour
$119
24ft Proline
4.9
(42 bookings)
$119+
/hour
$88
Spacious Deckboat-Stingray 212SC (Delivery Available)
5.0
(14 bookings)
$88+
/hour
$72
Fun and Sporty 20' Sea Hunt 207 Triton - Kenn Point Farm
4.9
(176 bookings)
$72+
/hour
$335
Sea to Sky - Lagoon 42
$335+
/hour
$81
High end boat with the smooth, dry ride! Eastern Shore Boat Vacation!
5.0
(6 bookings)
$81+
/hour
$59
Explore the beautiful Sassafras River on a Center Console
5.0
(2 bookings)
$59+
/hour
$281
Blue Angel | Private Annapolis Water Tours & Cruises | 11 ppl
5.0
(4 bookings)
$281+
/hour
$304
Spacious House-Yacht Perfect for Relaxing on the Water
$304+
/hour
$265
24’ Chaparral sport boat with open bow
5.0
(9 bookings)
$265+
/hour
$670
12 PPL | $600hr | Luxury Yacht SLX 400
$670+
/hour
$120
Tahoe T16: Your Ticket to Fun on the Water!
5.0
(54 bookings)
$120+
/hour
$86
23' Grady White-Perfect Family Fishing Boat!
TOP OWNER
5.0
(24 bookings)
$86+
/hour
$125
Fish Cruise Fun aboard Good Stuff
$125+
/hour
$106
22’ Bayliner Cruiser - 5 Persons - Fishing- Onboard Water and Toilet
$106+
/hour
$144
Bayliner VR6 at Kent Narrows!
4.9
(115 bookings)
$144+
/hour
$47
Excellent Chesapeake sailing onboard Windsnap
TOP OWNER
4.9
(67 bookings)
$47+
/hour