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Find The Best Boat Rentals in Rock Hall

Page 1 of 124 listings

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
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
$150/hour
43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

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

5.0
$150+/hour
Come take a cruise on the Annapolis Jet Boat
Powerboats in Kent Narrows · 11 guests

Come take a cruise on the Annapolis Jet Boat

New
$360/hour
32' Center Console - up to 6 Guests from Stevensville, MD
Powerboats in Stevensville · 6 guests

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

5.0
$375/hour
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 2025
$225/hour
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$250/hour
Fishing Charter in Pasadena, Maryland
Fishing in Riviera Beach · 6 guests

Fishing Charter in Pasadena, Maryland

5.0
$840/day
Instant Book
Enjoy your day on the water with a Yamaha Waverunner EX Jet ski!
Water Sports in Riviera Beach · 6 guests

Enjoy your day on the water with a Yamaha Waverunner EX Jet ski!

New
$65+/hour
Pro line Center Console Magothy River - Perfect for fishing exploring cruising
Powerboats in Severna Park · 12 guests

Pro line Center Console Magothy River - Perfect for fishing exploring cruising

5.0
$65+/hour
Instant Book
"RENT ME" Spacious 38' Cruiser- plenty of room for celebrating or relaxing!!!
Powerboats in Essex · 6 guests

"RENT ME" Spacious 38' Cruiser- plenty of room for celebrating or relaxing!!!

5.0
$150/hour
Instant Book
Still Crazy II - Cruise the Chesapeake in luxury! (Captain Included)
Powerboats in Pasadena · 10 guests

Still Crazy II - Cruise the Chesapeake in luxury! (Captain Included)

New
Snoozed - Active 02 Aug 2025
Cruise the Chesapeake on Bay Lady
Powerboats in Essex · 5 guests

Cruise the Chesapeake on Bay Lady

New
Snoozed - Active 02 Sep 2025
Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese
Sailing in Essex · 6 guests

Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese

5.0
$150/hour
Watch July 4th. fireworks from the water in Annapolis Harbor.
Events in Annapolis · 12 guests

Watch July 4th. fireworks from the water in Annapolis Harbor.

New
$320/hour
Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
Events in Annapolis · 8 guests

Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

5.0
$250/hour
38-ft Hunter 376 Sailing Adventure in Annapolis
Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0
Superowner
$138+/hour
Instant Book
New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
Sailing in Annapolis · 13 guests

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

5.0
$1,100/hour
Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis
Powerboats in Annapolis · 6 guests

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

4.8
$95+/hour
Instant Book
 Sail in Style Aboard the 2024 Seawind 1160 Lite – Your Perfect Charter Escape
Sailing in Annapolis · 13 guests

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

New
$350+/hour
STARZ -Lagoon 42 Catamaran in Chesapeake Bay
Sailing in Annapolis · 13 guests

STARZ -Lagoon 42 Catamaran in Chesapeake Bay

5.0
Snoozed - Active 02 Oct 2025
DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!
Sailing in Annapolis · 10 guests

DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!

New
$232+/hour
 SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN
Sailing in Annapolis · 12 guests

SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

5.0
$400+/hour
JEHM of the SEA 2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!
Sailing in Annapolis · 12 guests

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

5.0
$250+/hour

Rock Hall Reviews

  1. AI

    Amy

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

    Dushaune was amazing! The best boat ride we have ever had. He is extremely nice and drove us to a swimming area that was amazing. We enjoyed just hanging in the water, talking with him. We lost track of time because we were having so much fun. Would definitely love to go on a ride with him again.

  2. 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!

  3. HT

    Hien

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

    Dushaune is a great captain and great host, he is down to earth, knowledgeable, funny. We are a group of 6 with very different characters and age (from 7-50) but all of us had fun. We felt great after the ride. Thanks Dushaune. Highly recommended

  4. 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! ⛵️☀️🩵

  5. LC

    Laura

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

    Amazing! I went with my family, ages 5 and up, and everyone had a fantastic time. Captain Dushaune is a gem - personable, patient, funny, prepared. His boat is beautiful and well maintained. He was laid back while also keeping us safe and happy. He knew the waterways well, took us to a perfect cove for swimming and relaxing. The marina where his boat is located is ideal - clean, easy parking, great views, great water access. I cannot wait to book with him again. Highest possible recommendation!

  6. Marie

    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!