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Browse Chesapeake Bay Boat Rentals.

4.9(Average of 1,623 reviews in this area)
Learn more about boating in Chesapeake Bay

All Chesapeake Bay Listings

1 - 24 of 182 listings
38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
Sailing in Potomac River · 6 guests

38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

5.0
Superowner
Best of 2022
$150hour
BEST DAY EVER! CLEAN BOAT! HIGHLY EXPERIENCED CAPTAIN! $325/hr WEEKENDS $275 WEEKDAYS
Events in Potomac River · 6 guests

BEST DAY EVER! CLEAN BOAT! HIGHLY EXPERIENCED CAPTAIN! $325/hr WEEKENDS $275 WEEKDAYS

5.0
Superowner
Best of 2022
$325hour
⭐️ 5-Star ⭐️ cozy up in our heated outdoor cockpit in Washington DC🔺ℕ𝕠 𝔸𝕕𝕕𝕚𝕥𝕚𝕠𝕟𝕒𝕝 𝔽𝕖𝕖𝕤🔺
Events in Potomac River · 6 guests

⭐️ 5-Star ⭐️ cozy up in our heated outdoor cockpit in Washington DC🔺ℕ𝕠 𝔸𝕕𝕕𝕚𝕥𝕚𝕠𝕟𝕒𝕝 𝔽𝕖𝕖𝕤🔺

5.0
Superowner
Best of 2022
$350hour
$150 HR | 8 people | Bayliner Deck Boat Rental in Washington, District of Columbia
Powerboats in Potomac River · 8 guests

$150 HR | 8 people | Bayliner Deck Boat Rental in Washington, District of Columbia

5.0
Superowner
Best of 2022
$150hour
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
Sailing in Chesapeake Bay · 6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

5.0
Superowner
$150hour
41' Lagoon Cruising Catamaran in Maryland, United States
Sailing in Potomac River · 12 guests

41' Lagoon Cruising Catamaran in Maryland, United States

5.0
Superowner
Best of 2022
$349hour
☀️🛥🔺No Extra Fees🔺$225hr Weekdays / $300hr Weekends Premium Private Yachting🍹🏝
Powerboats in Potomac River · 6 guests

☀️🛥🔺No Extra Fees🔺$225hr Weekdays / $300hr Weekends Premium Private Yachting🍹🏝

4.9
Superowner
Best of 2022
$300hour
Instant Book
Enjoy the scenic routes of Washington DC on the Upper Potomac on this luxurious yacht with Captain Rod Patterson
Events in Potomac River · 10 guests

Enjoy the scenic routes of Washington DC on the Upper Potomac on this luxurious yacht with Captain Rod Patterson

4.9
Superowner
Best of 2022
$375hour
💎🛥1️⃣of a Kind Luxury Cruisers Sports Yacht‼️🍹☀️
Events in Potomac River · 6 guests

💎🛥1️⃣of a Kind Luxury Cruisers Sports Yacht‼️🍹☀️

5.0
Superowner
Best of 2022
$500hour
$ 375 | 10 people | Luxury Yacht in Washington, District of Columbia
Events in Potomac River · 16 guests

$ 375 | 10 people | Luxury Yacht in Washington, District of Columbia

5.0
Superowner
Best of 2022
$375hour
$275 HR | 8 people + Water Activities with Sea ray 300 Motor Yacht in Washington, District of Columbia
Events in Potomac River · 8 guests

$275 HR | 8 people + Water Activities with Sea ray 300 Motor Yacht in Washington, District of Columbia

5.0
Superowner
Best of 2022
$275hour
SeaRay Sundancer 320 Motor Yacht Rental in Washington, District of Columbia | $275 HR | 8 people
Events in Potomac River · 8 guests

SeaRay Sundancer 320 Motor Yacht Rental in Washington, District of Columbia | $275 HR | 8 people

5.0
Superowner
Best of 2022
$275hour
32ft Cruiser Motor Yacht in Washington, District of Columbia| 8 people | $250 HR
Events in Potomac River · 8 guests

32ft Cruiser Motor Yacht in Washington, District of Columbia| 8 people | $250 HR

5.0
Superowner
Best of 2022
$250hour
''3 BuOYS'' Regal 38 SAV Motor Yacht Rental in Arnold, Maryland
Events in Potomac River · 10 guests

''3 BuOYS'' Regal 38 SAV Motor Yacht Rental in Arnold, Maryland

5.0
Superowner
$575hour
''Imi Ola'' Seawind 1260 Cruising Catamaran Charter in Edgewater, Maryland
Sailing in Potomac River · 12 guests

''Imi Ola'' Seawind 1260 Cruising Catamaran Charter in Edgewater, Maryland

5.0
Superowner
$716hour
Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
Sailing in Chesapeake Bay · 6 guests

Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

5.0
Superowner
$125hour
"Stress Free" Four Winns Vista 348
Events in Potomac River · 8 guests

"Stress Free" Four Winns Vista 348

New
Superowner
$599hour
Wakeboarding | Cruising $150hr - 8 PPL
Powerboats in Potomac River · 7 guests

Wakeboarding | Cruising $150hr - 8 PPL

New
Superowner
Best of 2022
$150hour
"Arabella" Meridian 341
Events in Potomac River · 6 guests

"Arabella" Meridian 341

New
Superowner
$671hour
SpeedBoat | $275 Hr | 10 People
Events in Potomac River · 10 guests

SpeedBoat | $275 Hr | 10 People

New
Superowner
Best of 2022
$275hour
"Allon-Z" Jeanneau MC11 Motor Yacht Rental in Reedville, Virginia
Events in Chesapeake Bay · 8 guests

"Allon-Z" Jeanneau MC11 Motor Yacht Rental in Reedville, Virginia

New
Superowner
$398hour
''ADDIS'' Wellcraft 260 SE Motor Yacht Rental in Washington, District of Columbia
Events in Potomac River · 6 guests

''ADDIS'' Wellcraft 260 SE Motor Yacht Rental in Washington, District of Columbia

New
Superowner
$278hour
Luxury Yacht - $200 hr - 2 People
Events in Potomac River · 7 guests

Luxury Yacht - $200 hr - 2 People

New
Superowner
Best of 2022
$200hour
Double Deckers Boat | $450 HR | 14 People
Events in Potomac River · 14 guests

Double Deckers Boat | $450 HR | 14 People

New
Superowner
Best of 2022
$450hour

Chesapeake Bay Reviews

  1. CR
    Chad
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    For our wedding anniversary, I wanted to try to do something that we'd never done before. Getting a chartered boat for a day cruise along the Chesapeake Bay was certainly a memorable way to spend the day, in no small part due to the efforts of Cap'n Joe. The weather was wonderful, which he had nothing to do with, but he took us on a wonderful round trip on the Bay so we could get back to our son on-time in the evening. The vessel was magnificent! It was well worth the expense and was honestly impressive. I'd definitely do this again with friends. Simply outstanding.

  2. AW
    Alan
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Perfect for a few hours or the whole day. The captain made it easy as he knew all the trick of the area so we just needed to sit back and enjoy or man the helm to steer Down wind is the perfect time for light fair and another beverage. We will keep Capt Albert on our short list if we want to get away for an after noon Thanks Alberto

  3. VF
    Vanessa
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    We loved our day with Alberto and Grace! A great boat, and such a fun outing on the water. Even with lighter wind today, we had an amazing time. Alberto was helpful and responsive in our initial communications and planning. We would absolutely head back out with Captain Alberto again. Thank you!

  4. MC
    Matthew
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Capt. Alberto and his wife were super hosts for us today. We had a wonderful time, it was easy to get to and on the boat, got to pull some lines and steer the boat. Good stories and sailing pointers as well! It was a beautiful day with the right amount of sun and wind! Best way to celebrate my 40th Birthday! thanks so much Capt!

  5. Michelle
    Michelle
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Loved everything about this experience, and it blew our group’s expectations out of the water! It was a big enough boat for 6 of us, and we had drinks and snacks brought onboard. Alberto and his wife were very accommodating when we wanted to go swimming and allowed one of us to man the ship (with tips and supervision of course). Would definitely book again!

  6. JC
    Jason
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    We signed up for a three hour tour with Captain Alberto and had an outstanding experience. From timeliness and preparation to his extensive knowledge of sailing the and Annapolis sailing community, he provided a great morning. We were able to help as much or as little as we wanted and able to simply enjoy a wonderful morning on the water. Many thanks for a wonderful time, hope to catch up with you again soon! Jason

Boating Guide - Chesapeake Bay

Chesapeake Bay Boat Rentals

One of the best experiences you can have on the east coast of the United States is a boat rental on the Chesapeake Bay. Book a sailboat charter for an all-encompassing tour of the bay and see the stunning shoreline from the water. Boat tours and fishing on the Chesapeake Bay are not only great for tourists but are also fabulous experiences for life-long locals to enjoy in the summer. There are many water tours and types of boating experiences you can have on the Chesapeake Bay. Choose from pontoon rentals, sailboat rentals, bareboat rentals, yacht charters and even houseboat rentals.

GetMyBoat has 182 listings for boating experiences in Chesapeake Bay with 1,623 reviews.

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