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Elkton, Maryland Boat Rentals

Page 1 of 124 listings

Keywest 2000wa w/ brand new reliable motor
Maryland · 5 guests

Keywest 2000wa w/ brand new reliable motor

New
$400/day
Up to six (6) kayaks for rent near Brandywine River
Adventures in Pennsylvania · 6 guests

Up to six (6) kayaks for rent near Brandywine River

New
$89+/day
PHILLY FIRST LUXURY PARTY PONTOON BOAT IS FINALLY HERE!!! VOTE BEST OF 2022
Powerboats in Philadelphia · 10 guests

PHILLY FIRST LUXURY PARTY PONTOON BOAT IS FINALLY HERE!!! VOTE BEST OF 2022

5.0
$275/hour
Sail out of Middle River onboard Hunter 41 AC Sailboat!!
Sailing in Essex · 6 guests

Sail out of Middle River onboard Hunter 41 AC Sailboat!!

5.0
$175/hour
"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
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
$140+/hour
Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD
Sailing in Rock Hall · 4 guests

Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD

5.0
$150/hour
Timber Creek Tour with a USCG Licensed Captain
Powerboats in Philadelphia · 6 guests

Timber Creek Tour with a USCG Licensed Captain

New
$215/hour
Philly Schuylkill River Tour with a USCG Licensed Captain
Powerboats in Philadelphia · 6 guests

Philly Schuylkill River Tour with a USCG Licensed Captain

5.0
$215/hour
Philly Delaware River Tour with a USCG Licensed Captain
Powerboats in Philadelphia · 6 guests

Philly Delaware River Tour with a USCG Licensed Captain

5.0
$215/hour
Cruise the Chesapeake on Bay Lady
Powerboats in Essex · 5 guests

Cruise the Chesapeake on Bay Lady

New
Snoozed - Active 18 May 2025
Sunset Sail - Philadelphia Waterfront with O'Day 322 Sailing Yacht
Sailing in Philadelphia · 6 guests

Sunset Sail - Philadelphia Waterfront with O'Day 322 Sailing Yacht

5.0
$350/hour
STARCRAFT LUXURY PARTY PONTOON IS FINALLY HERE!!BEST OF BALTIMORE WINNER 2022...
Powerboats in Baltimore · 10 guests

STARCRAFT LUXURY PARTY PONTOON IS FINALLY HERE!!BEST OF BALTIMORE WINNER 2022...

5.0
$275/hour
 42ft Party Yacht Best of Baltimore 2022-23 Winner!
Events in Baltimore · 12 guests

42ft Party Yacht Best of Baltimore 2022-23 Winner!

5.0
$400/hour
Stunning!!! Smooth 26ft Larson Party Cabin Cruiser for Baltimore, Maryland
Powerboats in Baltimore · 6 guests

Stunning!!! Smooth 26ft Larson Party Cabin Cruiser for Baltimore, Maryland

5.0
$190/hour
30 ft sailboat with highly experienced Captain in Baltimore Inner Harbor
Sailing in Baltimore · 5 guests

30 ft sailboat with highly experienced Captain in Baltimore Inner Harbor

5.0
$150/hour
Cruise the Inner Harbor and beyond on a Monterey 350 Sport Yacht
Powerboats in Baltimore · 6 guests

Cruise the Inner Harbor and beyond on a Monterey 350 Sport Yacht

5.0
$275/hour
Instant Book
Fishing Charter in Pasadena, Maryland
Fishing in Riviera Beach · 6 guests

Fishing Charter in Pasadena, Maryland

5.0
$840/day
Instant Book
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
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
Pershing 65 Power Mega Yacht Rental in Stevensville, Maryland
Events in Stevensville · 6 guests

Pershing 65 Power Mega Yacht Rental in Stevensville, Maryland

New
$550/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

Elkton Reviews

  1. DD

    Danuta

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    What an enjoyable experience! Captain Joe was always attuned to our wishes, making an extra effort to make this afternoon pleasant for all. His company is very agreeable. We wish we could relive yesterday's feeling of complete relaxation over and over!

  2. CM

    Catherine

    PHILLY FIRST LUXURY PARTY PONTOON BOAT IS FINALLY HERE!!! VOTE BEST OF 2022

    Captain Brian was AMAZING. He was so generous and kind with our guests. The boat was beautiful and very clean. He even trailered his boat and brought it to the location where our event was taking place. He worked non-stop for 5 hours giving boat tours of our reservoir to over 150 people. Our guests had a wonderful time and the boat ride was a highlight. We would definitely use Captain Brian again.

  3. FC

    Francesco

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

    We simply loved our three days sailing excursion of the Chesapeake bay. The boat Icarus is very comfortable to maneuver and to live in for a family of four. The bay has numerous nice coves and spots were to stay for the night. Mr James help has been crucial for maximizing our time and energies on these limited days. Thank you Jiim!

  4. MI

    Maria

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

    One of the best sailing weekends we have ever experienced! The boat is manageable and in great shape! James is a great host, he explained everything when we got there, suggested an amazing route and was there when we got back to make sure everything went well. 100% recommended, we’ll definitely rent it again!

  5. George

    George

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

    Great value! Excellent sailing gear!! If you are an experienced sailor with at least one other person, you won't find a better value for day or overnight sailing near Annapolis. I will definitely be renting this boat again either with my family for the day or some buddies overnight. Took Icarus on a two night late-October trip from Rock Hall, overnight in Annapolis then St. Michaels with a couple buddies. James made the process VERY easy - very communicative and willing to go the extra mile for our convenience. This Hunter 34 sails really well (especially upwind.) It is set up that one experienced sailor and one other person can easily manage it. Comfort-wise it is probably better dockside on shore power in order to be able to utilize the cabin climate control system and power outlets for charging your phones (bring portable chargers if you won't be on shore power.) Returning the boat into the slip was a little tricky and James offered to be there to "coach us" in but we managed it on our own. The diesel was very reliable and fuel efficient - recommend you listen very carefully to James when he explains how to start it because can be a little tricky (as of Oct 2023.) Recommend you bring a handheld (or phone) GPS because as of Oct 23 the GPS is in the cabin. Bottom line - this is a great value - don't hesitate to book!!

  6. Janessa

    Janessa

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

    We had a wonderful experience chartering Jim’s sailboat over Labor Day weekend. Jim was very accommodating, walking through the boat with us and making sure everything was in great shape before we began our charter. We sailed from Rock Hall to Annapolis and back, spending two nights aboard Icarus. His upgrades to the boat really helped make it easier to sail and more comfortable to relax in, and Jim was always readily available if we had any questions. Could not recommend this more highly, and we don’t think there’s a better charter out there for the price in the Chesapeake.