Cookies!

We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.

Map View

Chester, Maryland Boat Rentals

Page 1 of 1 • 24 listings

Powerboats in Stevensville · 6 guests

32' Center Console - up to 6 Guests from Stevensville, MD

5.0

$375/hour

Powerboats in Kent Narrows · 11 guests

Come take a cruise on the Annapolis Jet Boat

New

$360/hour

Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New

$250/hour

Sailing in Annapolis · 10 guests

DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!

New

$232+/hour

Sailing in Annapolis · 12 guests

SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

5.0

$400+/hour

Sailing in Annapolis · 13 guests

STARZ -Lagoon 42 Catamaran in Chesapeake Bay

5.0

Snoozed - Active 02 Oct 2025

Sailing in Annapolis · 12 guests

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

5.0

$250+/hour

Sailing in Annapolis · 12 guests

SLOWDOWN - DUFOUR 430

New

$250+/hour

Sailing in Annapolis · 13 guests

Sail in Style Aboard the 2024 Seawind 1160 Lite – Your Perfect Charter Escape

New

$350+/hour

Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

5.0

$325/hour

Sailing in Annapolis · 13 guests

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

5.0

$1,100/hour

Events in Annapolis · 8 guests

Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

5.0

$250/hour

Events in Annapolis · 128 guests

Enjoy the best views of Annapolis, MD aboard the Island Princess

New

$600+/hour

Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0

Superowner

$138+/hour

Instant Book

Events in Annapolis · 6 guests

Relaxing Excitement of the Chesapeake Bay and tributaries on our Yacht

New

$300/hour

Sailing in Rock Hall · 4 guests

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

4.6

$275+/night

Powerboats in Annapolis · 6 guests

Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis

4.8

$95+/hour

Instant Book

Sailing in Rock Hall · 6 guests

43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

5.0

$150+/hour

Sailing in Rock Hall · 6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

5.0

$150/hour

Events in Selby-on-the-Bay · 6 guests

Maxum 30ft Yacht! Escape for a day on the Chesapeake

New

$350/hour

Events in Selby-on-the-Bay · 8 guests

43ft Cruiser Express Yacht for Daily Charter

5.0

$400/hour

Powerboats in Selby-on-the-Bay · 10 guests

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

5.0

$275/hour

Events in Selby-on-the-Bay · 10 guests

Private Yacht Charter: On 40ft Regal Commodore

5.0

$350/hour

Instant Book

Sailing in Saint Michaels · 6 guests

Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail

5.0

$325/hour

Top Destinations Nearby

Chester Reviews

ET
Eris

Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
This is everything you could want. Great boat and captain. McCoy has everything you need for a great trip. Plenty of space onboard for all your food and drink and all the toys you could want for a fun day on the water. We count thank him enough fro a such great experience and a great price! We will be booking again for sure!
DC
Donte

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
From start to finish, the entire experience was seamless and professional. There was zero chaos—everything ran like clockwork. The crew was exceptional: friendly, attentive, and incredibly knowledgeable about the Chesapeake Bay and Annapolis. The yacht itself was spotless and in pristine condition. From the moment we arrived, the crew went above and beyond—helping us load in, beautifully setting up our catering, keeping our group refreshed with drinks and snacks, and later packing up leftovers and loading them into our car. Every detail was handled with care. If you’re considering a yacht rental, don’t hesitate—this experience was truly top-notch. We’re already looking forward to booking again!
GA
Giselle

38-ft Hunter 376 Sailing Adventure in Annapolis
Capt. Alberto and Graciela, the best! We had a great time and enjoyed learning about sailing with them. Everything was as described and much better. You’ll have a great time too! ⛵️☀️🩵
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!
martine

Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
Our Trip with McCoy was great! He was very accommodating and knew the good swimming spots. Boat came with floaties and was very nice and clean.
Sam

38-ft Hunter 376 Sailing Adventure in Annapolis
Captain Alberto is a wonderful Captain. Handles the boat with an expert confidence and was also a willing and kind teacher to my two kids who had millions of questions.