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Browse Chesapeake Bay Boat Rentals.

All Chesapeake Bay Listings

Page 1 of 8175 listings

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
$175hour
$350 hr weekdays | $450 hr weekends | 15 ppl | Catamaran
Powerboats in Washington · 15 guests

$350 hr weekdays | $450 hr weekends | 15 ppl | Catamaran

5.0
Superowner
$350hour
🚤 Bonito Center Console Party Boat Rental Cheap Fishing Charter Tube FREE GAS⛽️
Powerboats in Virginia Beach · 4 guests

🚤 Bonito Center Console Party Boat Rental Cheap Fishing Charter Tube FREE GAS⛽️

5.0
$30-$83hour
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 2023
$225hour
Chesapeake Bay Sailing Charter - 33' Cape Dory sailing from Kilmarnock, Virginia
Sailing in Kilmarnock · 6 guests

Chesapeake Bay Sailing Charter - 33' Cape Dory sailing from Kilmarnock, Virginia

5.0
$73-$112hour
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
$180-$200hour
Come enjoy the DC view on the Potomac river aboard Sancha. $375HR to $450HR
Events in Washington · 12 guests

Come enjoy the DC view on the Potomac river aboard Sancha. $375HR to $450HR

5.0
$375hour
⚓️🛥️Premium Private Yachting Experience🍹☀️
Events in Washington · 6 guests

⚓️🛥️Premium Private Yachting Experience🍹☀️

4.9
Superowner
Best of 2023
$299-$329hour
23 Foot Grady White Gulfstream w/ twin Yamaha F150's
Powerboats in Virginia Beach · 6 guests

23 Foot Grady White Gulfstream w/ twin Yamaha F150's

New
$94hour
38' Mini-Yacht!! - Large "Ultra Luxury" Adventure Boat in Virginia Beach!
Events in Virginia Beach · 13 guests

38' Mini-Yacht!! - Large "Ultra Luxury" Adventure Boat in Virginia Beach!

5.0
Superowner
$199-$299hour
44ft ''Four Winds'' Fishing Yacht in Hampton, Virginia
Fishing in Hampton · 19 guests

44ft ''Four Winds'' Fishing Yacht in Hampton, Virginia

4.0
$225hour
38' Mini-Yacht!! - Large "Ultra Luxury" Adventure Boat in Hampton, Virginia!
Events in Hampton · 13 guests

38' Mini-Yacht!! - Large "Ultra Luxury" Adventure Boat in Hampton, Virginia!

5.0
Superowner
$199-$299hour
$150HR | 2-3 people | JetSki
Water Sports in Alexandria · 2 guests

$150HR | 2-3 people | JetSki

5.0
Superowner
$150hour
41' Lagoon Catamaran in Maryland
Sailing in Annapolis · 12 guests

41' Lagoon Catamaran in Maryland

5.0
Superowner
Best of 2023
$390hour
38' Hunter 376 Cruising Monohull in Annapolis, Maryland
Sailing in Annapolis · 6 guests

38' Hunter 376 Cruising Monohull in Annapolis, Maryland

5.0
Superowner
Best of 2023
$138-$150hour
Enjoy the sights of Colonial Beach, VA ! Come boat with us!
Events in Colonial Beach · 6 guests

Enjoy the sights of Colonial Beach, VA ! Come boat with us!

5.0
$160hour
Brand New Sea Ray SLX 310 Cruiser
Powerboats in Washington · 7 guests

Brand New Sea Ray SLX 310 Cruiser

5.0
Superowner
$300hour
Great Center Console for rent in Ocean City
Powerboats in Ocean City · 6 guests

Great Center Console for rent in Ocean City

4.8
$150hour
Pontoon Boat Rental in Virginia Beach | Party Cruise, Tubing, Fishing
Powerboats in Virginia Beach · 8 guests

Pontoon Boat Rental in Virginia Beach | Party Cruise, Tubing, Fishing

4.9
$54-$100hour
Charter 29ft Crownline Bowrider In Wildwood, NJ / Cape May, NJ
Powerboats in Wildwood · 6 guests

Charter 29ft Crownline Bowrider In Wildwood, NJ / Cape May, NJ

5.0
$250hour
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
$120hour
22' Bennington Pontoon | Best prices in DC + Jetski Add Ons
Powerboats in Washington · 6 guests

22' Bennington Pontoon | Best prices in DC + Jetski Add Ons

5.0
Superowner
Best of 2023
$185hour
Enjoy our World Class Service aboard Sea Ray 540 Sundancer
Events in Washington · 10 guests

Enjoy our World Class Service aboard Sea Ray 540 Sundancer

4.9
Superowner
Best of 2023
$400hour
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

5.0
Superowner
$150hour
31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD
Powerboats in Selby-on-the-Bay · 12 guests

31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD

5.0
$250hour
Brand New 25ft Crownline for Charter in Stone Harbor!
Powerboats in Stone Harbor · 6 guests

Brand New 25ft Crownline for Charter in Stone Harbor!

5.0
Snoozed - Active 26 Apr 2024
⭐️ 5-Star ⭐️ Cozy Up In Our Heated Outdoor Cockpit in Washington DC🔺ℕ𝕠 𝔸𝕕𝕕𝕚𝕥𝕚𝕠𝕟𝕒𝕝 𝔽𝕖𝕖𝕤🔺
Events in Washington · 6 guests

⭐️ 5-Star ⭐️ Cozy Up In Our Heated Outdoor Cockpit in Washington DC🔺ℕ𝕠 𝔸𝕕𝕕𝕚𝕥𝕚𝕠𝕟𝕒𝕝 𝔽𝕖𝕖𝕤🔺

5.0
Superowner
Snoozed - Active 03 Jun 2024
Experience the Serenity of Sailing SV Magic
Sailing in Mayo · 6 guests

Experience the Serenity of Sailing SV Magic

4.8
$165hour

Chesapeake Bay Reviews

  1. JA

    Jared

    Enjoy our World Class Service aboard Sea Ray 540 Sundancer

    I proposed to my girlfriend before the boat ride and we were running late. Captain Rod was extremely accommodating and added time to our boat ride so we had the full allotted time on the boat. When I book in the future I will book with Captain Rod again! It was perfect!

  2. JM

    Jancarlo

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

    Captain Troy was very respectful and friendly from start to end. My party and I had a wonderful time and loved his boat. I recommend captain Troy and his boat.

  3. JD

    Josiah

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

    Didn't believe we still have such wonderful people. Captain Dash and his co-captain are amongst the very best. Good service, friendly, timely, and most importantly, people Centered. My wife, kids, and I enjoyed riding with this team and we will always wish to ride with them.

  4. NC

    Nicki

    $350 hr weekdays | $450 hr weekends | 15 ppl | Catamaran

    My friends and I had THE BEST time boating with AJ’s team. They were all so accommodating, friendly and eager to ensure we had a great time. The communication from booking to boating was seamless and thorough. AJ was so responsive and helpful. I would 100% recommend anyone to book with them, they will go above and beyond to make sure you have an amazing time!

  5. DK

    Deanna

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

    Our group had the most amazing early evening trip! We went swimming, stopped for drinks and had the best day of summer so far! DuShawn and Carla took great care of us and cruising the bay at 4 pm was so peaceful, relaxing and the perfect temperature! It would be hard to top the fun we had especially crashing a 50th birthday party at the Rumor Reel! We all can’t wait to go out with DuShawn again!!

  6. SM

    Shabnam

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

    Dushaune was an incredibly wonderful and amazing captain! He has a fun, warm, welcoming personality! He was very easy to communicate with, and he answered all my questions in-depth! The whole boating tour experience was perfect - from start to finish! He is extremely knowledgeable about the history of the surrounding landmarks! My friends and I cannot stop raving about the boating experiences; we will hands down go back to Dushaune’s boating tour!! 5/5 stars for everything! :)