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Browse Chesapeake Bay Boat Rentals.

Page 1 of 9202 listings

Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise
Sailing in Oxon Hill · 6 guests

Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise

5.0
$240/hour
50' Come enjoy the DC view on the Potomac river aboard Sancha
Events in Washington · 12 guests

50' Come enjoy the DC view on the Potomac river aboard Sancha

5.0
$375+/hour
Pro line Center Console Magothy River - Perfect for fishing exploring cruising
Powerboats in Severna Park · 12 guests

Pro line Center Console Magothy River - Perfect for fishing exploring cruising

5.0
$65+/hour
Instant Book
$400/hr Weekday & $750/hr Weekend
Events in Washington · 13 guests

$400/hr Weekday & $750/hr Weekend

4.8
Superowner
Best of 2025
$750/hour
Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.
Events in Washington · 6 guests

Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.

5.0
$220+/hour
Bugatti JetBoat - $300Hr - DC
Powerboats in Washington · 4 guests

Bugatti JetBoat - $300Hr - DC

5.0
Superowner
Best of 2025
$300/hour
26′ BENNINGTON PONTOON | Adventure Awaits | Seats 12
Powerboats in Annapolis · 12 guests

26′ BENNINGTON PONTOON | Adventure Awaits | Seats 12

5.0
$194+/hour
Private Yacht Charter: On 40ft Regal Commodore
Events in Selby-on-the-Bay · 10 guests

Private Yacht Charter: On 40ft Regal Commodore

5.0
$300/hour
Luxurious Godfrey SweetWater Tritoon
Powerboats in Fort Washington · 10 guests

Luxurious Godfrey SweetWater Tritoon

4.9
$175/hour
The Fantastic Voyage
Powerboats in Alexandria · 10 guests

The Fantastic Voyage

5.0
$225/hour
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
Best of 2025
$225/hour
50’ Sea Ray Luxury Yacht on the Potomac. Experience luxury!
Events in Washington · 12 guests

50’ Sea Ray Luxury Yacht on the Potomac. Experience luxury!

4.7
Best of 2025
$450+/hour
Luxurious 51’ SeaRay Flybridge Yacht With Twin 600 Hp Cummins Engine
Events in Deale · 10 guests

Luxurious 51’ SeaRay Flybridge Yacht With Twin 600 Hp Cummins Engine

5.0
$500/hour
JEHM of the SEA 2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!
Sailing in Annapolis · 12 guests

JEHM of the SEA 2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!

5.0
$250+/hour
$200hr M-Th | $350hr F-Su | 12 ppl | Luxury Yacht SLX 350
Events in Washington · 12 guests

$200hr M-Th | $350hr F-Su | 12 ppl | Luxury Yacht SLX 350

5.0
Superowner
Best of 2025
$350/hour
Paint, party and yacht with us! Climb aboard the 45ft Sea Ray
Events in Washington · 12 guests

Paint, party and yacht with us! Climb aboard the 45ft Sea Ray

4.7
Superowner
$425+/hour
Instant Book
$250hr M-Th | $350 F-Su | 13 ppl | Luxury Boat
Powerboats in Washington · 13 guests

$250hr M-Th | $350 F-Su | 13 ppl | Luxury Boat

5.0
Superowner
Best of 2025
$350/hour
2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland
Powerboats in Severna Park · 4 guests

2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland

5.0
$120/hour
38-ft Hunter 376 Sailing Adventure in Annapolis
Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0
Superowner
$138+/hour
Instant Book
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
Party on Catamaran |15 People | $300hr
Powerboats in Washington · 15 guests

Party on Catamaran |15 People | $300hr

5.0
Superowner
Best of 2025
$400/hour
The Commodore Yacht | 13PPL | $500hr
Events in Washington · 13 guests

The Commodore Yacht | 13PPL | $500hr

5.0
Superowner
Best of 2025
$500/hour
Party Boat Rental Virginia Beach Charter 8 Seat Pontoon Boat Oceanfront FREE GAS
Powerboats in Virginia Beach · 8 guests

Party Boat Rental Virginia Beach Charter 8 Seat Pontoon Boat Oceanfront FREE GAS

5.0
$75+/hour
Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
Events in Annapolis · 8 guests

Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

5.0
$250/hour

Chesapeake Bay Reviews

  1. AP

    Alysha

    50’ Sea Ray Luxury Yacht on the Potomac. Experience luxury!

    We had an amazing experience with Captain in Yacht 17! He was incredibly flexible and accommodating throughout the booking process. Friendly and professional from start to finish, he made sure we had everything we needed. My guests had a fantastic time and haven’t stopped talking about it since. Highly recommend booking this yacht!

  2. GG

    Gbo

    Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.

    Capt Troy is really a nice person he and his wife went the extra mile to plan a special surprise for my wife. They very welcoming. I will recommend them for anyone that wants to plan a surprise or special occasion to go with him.

  3. LC

    Laura

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

    Amazing! I went with my family, ages 5 and up, and everyone had a fantastic time. Captain Dushaune is a gem - personable, patient, funny, prepared. His boat is beautiful and well maintained. He was laid back while also keeping us safe and happy. He knew the waterways well, took us to a perfect cove for swimming and relaxing. The marina where his boat is located is ideal - clean, easy parking, great views, great water access. I cannot wait to book with him again. Highest possible recommendation!

  4. Marie

    Marie

    38-ft Hunter 376 Sailing Adventure in Annapolis

    We thoroughly enjoyed our time with Alberto and his wife, Grace. Alberto is a delight to sail with - we learned so much from him. Grace is so lovely and gracious. We sailed around Annapolis during Memorial Day weekend and the weather was perfect. Alberto was very accommodating and friendly. We hope to see you again soon!

  5. JC

    John

    Pro line Center Console Magothy River - Perfect for fishing exploring cruising

    Robert is a great host and provided us with an awsome experience. Boat was very good for our 4 hour trip around the bay and handled the rough weather that kicked up with no problem. We had 5 adults and a dog.

  6. Jose

    Jose

    $250hr M-Th | $350 F-Su | 13 ppl | Luxury Boat

    A+ experience despite some challenges with scheduling. AJ helped me secure a boat to help my mom experience a day on the water despite her limited mobility. The team was extremely communicative the day of the booking, keeping us apprised of updates to the schedule throughout. The boat was very comfortable for our party of eight and I would consider booking again, even for a larger party.