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The Best Sailboat Rentals in Chesapeake Bay

Browse, book, and get out onto the water with local captains and boat owners.

Our Favorite Sailboat Rentals in Chesapeake Bay

4.9 (443 reviews)

•

Sailing in Annapolis · 6 guests
AnnapolisBoatExperiences presents an Exclusive Sail on its Classic 37' Ketch
5.0
$200+/hour
Sailing in Annapolis · 6 guests
38-ft Hunter 376 Sailing Adventure in Annapolis
5.0
Superowner
$100+/hour
Events in Washington · 13 guests
$650hr | 12 Guests | SLX400
4.5
Superowner
$700/hour
Instant Book
Sailing in Rock Hall · 6 guests
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
5.0
$150/hour
Sailing in Gloucester Point · 6 guests
Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
5.0
Superowner
$125/hour
Sailing in Mayo · 6 guests
Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay
5.0
$150+/hour
Sailing in Washington · 49 guests
$4400 | 49 Guests | 2hrs | Sailing Catamaran
5.0
Superowner
$2,200/hour
Sailing in Rock Hall · 4 guests
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
4.6
$275+/night
Sailing in Gloucester Point · 6 guests
Let's Go Sail in Gloucester Point, Virginia
4.9
Superowner
$117+/hour
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
Sailing in Saint Michaels · 6 guests
Private Sail on 44ft Leopard Catamaran | 6 People | Gratuity & Tax Included
New
$585/hour
Sailing in Kilmarnock · 4 guests
Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia
5.0
$15+/hour

Suggested Searches

This weekend $100-$300 trips 2-4 people Captained

Types of Boats Popular in Chesapeake Bay

Top Sailboat Rental Locations Near Chesapeake Bay

Most Popular Yacht Rentals in Chesapeake Bay

Events in Arnold · 12 guests
$1250 2hrs| 12 Guests | 39ft Regal
5.0
Superowner
$600/hour
Events in Washington · 12 guests
50' Come enjoy the DC view on the Potomac river aboard Sancha
5.0
Superowner
$375+/hour
Events in Washington · 11 guests
$350hr|11 Guests | Water Toys
5.0
Superowner
$350/hour
Events in Edgewater · 12 guests
$375hr | 12 Guests | Annapolis Area
New
Superowner
$375/hour

Most Popular Boat Tours in Chesapeake Bay

Events in Washington · 13 guests
$350 | 13 Guests | Wharf | Double Deck Boat
New
Superowner
$375/hour
Powerboats in Washington · 12 guests
32' Yacht w/all black interior & red seats
5.0
$400/hour
Events in Washington · 8 guests
Luxury Chris-Craft Charter | Washington, DC | Captain Included | Up to 8 Guest
New
Superowner
$400/hour
Powerboats in Edgewater · 6 guests
Chaparral SSX 27ft - Captained Private Charter - Watersports Included!!
5.0
$225/hour

Most Popular Pontoon Rentals in Chesapeake Bay

Powerboats in Annapolis · 12 guests
27' Godfrey Tritoon Pontoon Boat - Perfect for Cruising and Entertaining
New
$175+/hour
Powerboats in Fort Washington · 12 guests
Luxury 23ft Bennington Pontoon with Captain - DMV Events, Cruises & Parties!
New
$200/hour
Powerboats in Washington · 12 guests
Amazing 22' Pontoon in Washington D.C.
5.0
$250+/hour
Powerboats in Cape May · 18 guests
The Big Kahuna 18 Passenger Tiki Boat
5.0
$250/hour

Recent Reviews in Chesapeake Bay

Top Sailboat Rental Locations in the United States

How To Book on Getmyboat

4.9 out of 5! • 500,000+ reviews

Browse
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Inquire & Book
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Enjoy
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!

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