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Browse Chesapeake Bay Boat Rentals.

Page 3 of 9205 listings

$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
Best of 2025
$285/hour
Instant Book
Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis
Powerboats in Annapolis · 6 guests

Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis

4.8
$95+/hour
Instant Book
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
$180/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 Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia
Sailing in Kilmarnock · 4 guests

Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia

5.0
$15+/hour
$250 hr | 6 ppl | Grill and BBQ Family & Friends Boat
Powerboats in Washington · 8 guests

$250 hr | 6 ppl | Grill and BBQ Family & Friends Boat

5.0
Superowner
Best of 2025
$250/hour
Instant Book
Chaparral 350 Signature Motor Yacht Rental in Washington, District of Columbia
Events in Washington · 9 guests

Chaparral 350 Signature Motor Yacht Rental in Washington, District of Columbia

5.0
$300/hour
41' Meridian Yacht for Charter in Washington, D.C.
Events in Washington · 13 guests

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

5.0
$288+/hour
Chaparral SSX 27ft - Captained Private Charter - Watersports Included!!
Powerboats in Edgewater · 6 guests

Chaparral SSX 27ft - Captained Private Charter - Watersports Included!!

5.0
$225/hour
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
$225/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
Cruise The Potomac River From Fort Washington to National Harbor and surrounding
Powerboats in Fort Washington · 11 guests

Cruise The Potomac River From Fort Washington to National Harbor and surrounding

5.0
$169/hour
Instant Book
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
45' Sea Ray Luxury Yacht Stewardess, Crew and Captain Provided
Events in Washington · 10 guests

45' Sea Ray Luxury Yacht Stewardess, Crew and Captain Provided

5.0
Superowner
Best of 2025
$600/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
Yamaha SX210 Bowider w/Swim Platform 6 Passengers w/Captain
Powerboats in Annapolis · 6 guests

Yamaha SX210 Bowider w/Swim Platform 6 Passengers w/Captain

5.0
$115/hour
Escape the Ordinary! 42' Sea Ray Sundancer
Events in Washington · 6 guests

Escape the Ordinary! 42' Sea Ray Sundancer

4.9
$250/hour
18ft Bayliner - View the city from the water
Powerboats in Washington · 6 guests

18ft Bayliner - View the city from the water

4.3
$100/hour
Instant Book
Wakeboarding & Tubing | $300hr | 8 PPL
Powerboats in Arlington · 8 guests

Wakeboarding & Tubing | $300hr | 8 PPL

5.0
Superowner
Best of 2025
$300/hour
Instant Book
$350hr|11 people| Luxury Yacht
Events in Washington · 11 guests

$350hr|11 people| Luxury Yacht

5.0
Superowner
Best of 2025
$350/hour
Instant Book
Largest Yacht in DC | $1200 HR | 65ft Viking Flybridge Yacht
Events in Washington · 13 guests

Largest Yacht in DC | $1200 HR | 65ft Viking Flybridge Yacht

New
Superowner
Best of 2025
$1,200/hour
Instant Book
Adventure Awaits on the DC Wake Boat!
Powerboats in Washington · 12 guests

Adventure Awaits on the DC Wake Boat!

New
$200/hour
Instant Book
 SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN
Sailing in Annapolis · 12 guests

SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

5.0
$400+/hour
$275 HR | 8 people + Water Activities
Events in Washington · 9 guests

$275 HR | 8 people + Water Activities

5.0
Superowner
Best of 2025
$275/hour
Instant Book

Chesapeake Bay Reviews

  1. John

    John

    Wakeboarding & Tubing | $300hr | 8 PPL

    AJ is fantastic! He worked at finding us the perfect match for a boat and driver. We had a great day with Ryan wakeboarding, wake surfing and tubbing. AJ was prompt, accurate and pleasant, it’s clear he likes people and working hard! Thank you AJ and Ryan! We will book again!

  2. KC

    Kassidy

    Wakeboarding & Tubing | $300hr | 8 PPL

    AJ was quick to communicate and make the trip happen for us. Had a blast wake surfing on the Potomac with the monuments behind us. Quite a way to celebrate the 4th! The captain and first mate were kind and hospitable as well. Overall a great experience.

  3. VC

    Veronica

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

    5 stars! We had an amazing time on the boat with our group of friends! The crew was super friendly and made sure everything ran smoothly from start to finish. The boat was clean, spacious, and had everything we needed to relax and enjoy the day. We danced and enjoyed beautiful views — definitely one of the highlights of our summer. Highly recommend for anyone looking to have a great time on the water!

  4. ZF

    Zachary

    18ft Bayliner - View the city from the water

    Fernando is a joy to work with. He’s prompt on his responses extremely fair on pricing and he will be where he says he’s going to be When he says he’s gonna be there. Equipment in all working order, Clean and full of fuel!

  5. PP

    Philip

    Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis

    A squal popped out of bo where and william was very helpful with getting me and my friends to safety. Highly recommend rent from him

  6. AU

    Ami

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

    Imrul and his team are great to work with, the boat was in great shape and the crew was super friendly and so fun to be around. We look forward to many more trips together.