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Chesapeake Bay, US Boat Rentals & Yacht Charters

Page 2 of 10220 listings

High Demand
The Play Station-23 Foot Pontoon With Lights, Bluetooth, Charging Ports, Cooler
Powerboats in Fort Washington · 10 guests

The Play Station-23 Foot Pontoon With Lights, Bluetooth, Charging Ports, Cooler

4.9
Superowner
Best of 2026
$225/hour
Amazing 22' Pontoon in Washington D.C.
Powerboats in Washington · 12 guests

Amazing 22' Pontoon in Washington D.C.

5.0
$250+/hour
DMV’s Cleanest 6 passenger Party Deck Boat
Powerboats in Washington · 6 guests

DMV’s Cleanest 6 passenger Party Deck Boat

5.0
$175/hour
Luxe Party Boat Washington D.C.
Powerboats in Washington · 12 guests

Luxe Party Boat Washington D.C.

5.0
Superowner
$275/hour
Limited Availability
$350/hr | 12 PPL | SLX 350
Events in Washington · 12 guests

$350/hr | 12 PPL | SLX 350

4.9
Superowner
$350/hour
Instant Book
18ft Bayliner - View the city from the water
Powerboats in Arlington · 6 guests

18ft Bayliner - View the city from the water

4.8
$100/hour
$285 HR | 10 people | Sea Ray 330 Sundancer Yacht
Events in Washington · 10 guests

$285 HR | 10 people | Sea Ray 330 Sundancer Yacht

5.0
Superowner
$285/hour
Your Aquatic Escape: Bayliner 180 | Fast, Fun & Ready to Cruise!
Powerboats in Arlington · 6 guests

Your Aquatic Escape: Bayliner 180 | Fast, Fun & Ready to Cruise!

5.0
$100+/hour
2023 Yamaha AR190 - Perfect Day on the Water!
Powerboats in Virginia Beach · 7 guests

2023 Yamaha AR190 - Perfect Day on the Water!

5.0
$200/hour
Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay
Sailing in Mayo · 6 guests

Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay

5.0
$150+/hour
Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
Sailing in Gloucester Point · 6 guests

Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

5.0
Superowner
$125/hour
Limited Availability
Private Yacht Charter: On 40ft Regal Commodore
Events in Selby-on-the-Bay · 10 guests

Private Yacht Charter: On 40ft Regal Commodore

5.0
$400/hour
Limited Availability
$650 hr | 14 ppl | Luxury Yacht
Events in Washington · 14 guests

$650 hr | 14 ppl | Luxury Yacht

5.0
Superowner
$650/hour
Instant Book
Bayliner Small boat | 6 ppl | $150hr
Events in Washington · 6 guests

Bayliner Small boat | 6 ppl | $150hr

5.0
Superowner
$175/hour
Cruise in Comfort Aboard "Chill Time" – 31ft Cabin Cruiser in Solomons Island
Powerboats in Solomons · 6 guests

Cruise in Comfort Aboard "Chill Time" – 31ft Cabin Cruiser in Solomons Island

5.0
$200/hour
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
Sailing in Rock Hall · 4 guests

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

4.6
$275+/night
Limited Availability
Sanpan 2500 RE Pontoon in Washington, Living room comfort on the water!
Powerboats in Washington · 10 guests

Sanpan 2500 RE Pontoon in Washington, Living room comfort on the water!

5.0
$200/hour
Limited Availability
2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island
Powerboats in Annapolis · 8 guests

2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island

4.9
$225/hour
$350hr|11 people| Luxury Yacht
Events in Washington · 11 guests

$350hr|11 people| Luxury Yacht

5.0
Superowner
$350/hour
$300hr | National Harbor| 10 Guests | 30 Min Free
Events in Oxon Hill · 8 guests

$300hr | National Harbor| 10 Guests | 30 Min Free

New
Superowner
$300/hour
2022 Chaparral 23' SSI  - Get up to 6 captained up and down the Potomac River
Powerboats in Fort Washington · 6 guests

2022 Chaparral 23' SSI - Get up to 6 captained up and down the Potomac River

5.0
$150+/hour
High Demand
41' Meridian Sedan Yacht for Charter in Washington, D.C.
Events in Washington · 13 guests

41' Meridian Sedan Yacht for Charter in Washington, D.C.

5.0
$300+/hour
Amazing SeaRay 260 Sundancer for Charter in DC
Powerboats in Washington · 6 guests

Amazing SeaRay 260 Sundancer for Charter in DC

5.0
$160/hour
Let's Go Sail in Gloucester Point, Virginia
Sailing in Gloucester Point · 6 guests

Let's Go Sail in Gloucester Point, Virginia

5.0
Superowner
$117+/hour

Chesapeake Bay Reviews

  1. Geoffrey

    Geoffrey

    34' Hunter Cruising Monohull In Rock Hall, Maryland United States

    Icarus is a great boat and very well equipped. The sails and everything else on the vessel are in great shape and the fact it only draws 4' 6" is perfect for the Chesapeake. I spent a week on Icarus and everything worked well. The value of chartering Icarus is undeniable. I plan to charter Icarus again. Icarus has a lot of sail area, so if the winds are strong douse the headsail early.

  2. JC

    Janna

    Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay

    We had a wonderful time on Captain Bill's boat! We booked a 2-hour charter and it was the perfect quick escape for our family of 6. The crew was friendly and welcoming. The boat had plenty of space to relax. It was a smooth, stress-free experience ideal for families or friends needing a taste of the water.

  3. Elizabeth

    Elizabeth

    DMV’s Cleanest 6 passenger Party Deck Boat

    I booked this boat for my birthday! It was a great experience Ed was our captain he was so nice, efficient and fun to ride the boat! We took bathroom breaks with no problem! I’ll deff recommend Terrance and Ed for a booking with them! Great people!

  4. KK

    Kara

    $350/hr | 12 PPL | SLX 350

    We had a fantastic experience with 24 people across two boats! Coordinating a group this size could have easily been complicated, but the team made everything feel seamless. Captain Chip, Captain Todd and Muhammad were all friendly, helpful and easy to communicate with, and they did a great job coordinating both boats so our group could spend the day together on the water. The boats were clean, spacious, and comfortable, and there was plenty of room for everyone to relax and enjoy themselves.We had a beautiful day on the Potomac and would absolutely book with them again for a large group event. One thing I'd recommend for larger groups booking multiple boats is confirming pickup locations in advance. Our boats ended up boarding from two different marinas before meeting up, which wasn't a problem in the end, but it's helpful information to have ahead of time when coordinating a larger group. Overall, we had an amazing experience and would absolutely book again. Highly recommend.

  5. AM

    Adriana

    The Play Station-23 Foot Pontoon With Lights, Bluetooth, Charging Ports, Cooler

    I booked it for my bach party and it was so worth it! The boat was so nice and spacious. Troy was communicative, direct, and on time! We danced, partied, ate and sang! Recommend 100%

  6. RK

    Richard

    34' Hunter Cruising Monohull In Rock Hall, Maryland United States

    Our group of four had a great three days onboard the Icarus. The boat was easy to sail and operate. No problems motoring around in the marinas, steers easy in reverse too. Jim was a great host, very responsive and knowledgeable. Highly recommend his boat to sail the Chesapeake!