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Deale, Maryland Boat Rentals

Page 1 of 124 listings

 VIKO S 35 Sailboat in Deale
Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

New
$298hour
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$2,600day
Catalina 445 Sailboat
Sailing in Deale · 6 guests

Catalina 445 Sailboat

New
$298hour
Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland
Events in North Beach · 8 guests

Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland

5.0
$400hour
Experience the Serenity of Sailing SV Magic
Sailing in Mayo · 6 guests

Experience the Serenity of Sailing SV Magic

4.8
$165hour
Charter this 42ft Sailboat, for up 6 persons to enjoy the middle Chesapeake Bay
Sailing in Mayo · 6 guests

Charter this 42ft Sailboat, for up 6 persons to enjoy the middle Chesapeake Bay

5.0
$175hour
Maxum 30ft Yacht! Escape for a day on the Chesapeake
Events in Selby-on-the-Bay · 6 guests

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

New
$365hour
43ft Cruiser Express Yacht for Daily Charter
Events in Selby-on-the-Bay · 8 guests

43ft Cruiser Express Yacht for Daily Charter

5.0
$400hour
31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD
Powerboats in Selby-on-the-Bay · 12 guests

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

5.0
$250hour
Pristine Hooligan Departs from a Private Pier with a Captain and Fuel INCLUDED
Powerboats in Annapolis · 5 guests

Pristine Hooligan Departs from a Private Pier with a Captain and Fuel INCLUDED

New
$200hour
Bentley 220 Cruise Pontoon for rent in Edgewater
Powerboats in Edgewater · 10 guests

Bentley 220 Cruise Pontoon for rent in Edgewater

New
$400hour
Relax in the Sun in Edgewater and Annapolis
Powerboats in Edgewater · 10 guests

Relax in the Sun in Edgewater and Annapolis

New
$200hour
Charter 42' Lagoon Catamaran in Annapolis, MD
Sailing in Edgewater · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

New
$400hour
Enjoy a Day on the Bay and Cruise the South River
Powerboats in Annapolis · 6 guests

Enjoy a Day on the Bay and Cruise the South River

New
$130-$150hour
Cruise on the Shannon Brendan
Fishing in Annapolis · 6 guests

Cruise on the Shannon Brendan

New
$350hour
Come take a cruise on the Annapolis Jet Boat
Powerboats in Annapolis · 11 guests

Come take a cruise on the Annapolis Jet Boat

New
$500hour
30ft Bowrider! Enjoy a day on the water around the Chesapeake Bay in Maryland!
Powerboats in Annapolis · 8 guests

30ft Bowrider! Enjoy a day on the water around the Chesapeake Bay in Maryland!

3.7
Snoozed - Active 02 Jan 2025
Fully Crewed Annapolis Sailing Cruises
Sailing in Annapolis · 6 guests

Fully Crewed Annapolis Sailing Cruises

New
$175person
Historical Annapolis Private Boat Cruise onboard a beautiful Swift Trawler!
Events in Annapolis · 6 guests

Historical Annapolis Private Boat Cruise onboard a beautiful Swift Trawler!

5.0
Snoozed - Active 02 Jun 2024
Sail the Sea on the Pintita
Sailing in Annapolis · 20 guests

Sail the Sea on the Pintita

New
$500-$750hour
41' Lagoon Catamaran in Maryland
Sailing in Annapolis · 12 guests

41' Lagoon Catamaran in Maryland

5.0
Superowner
Best of 2023
$390hour
50ft Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

New
$425hour
38' Hunter 376 Cruising Monohull in Annapolis, Maryland
Sailing in Annapolis · 6 guests

38' Hunter 376 Cruising Monohull in Annapolis, Maryland

5.0
Superowner
Best of 2023
$138-$150hour
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
$250hour

Deale Reviews

  1. Danika

    Danika

    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    We had the best time! Everything was perfect! Rob communicated well! The boat looked exactly like the pictures. It was enough space for my 10 guest party! We sailed out for 7hrs and it still didn’t feel like enough time! I’m so glad I went with this boat and will be using it again in the future. Best birthday ever!!!

  2. JH

    Jennifer

    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    Rob was so communicative and helpful throughout the entire booking process, and our experience on the boat was even better! Not only was it a beautifully appointed vessel, but our captain Adam took such wonderful care of our group. We can never outdo this day-- just plan when we can do it again!

  3. GE

    Gerard

    Experience the Serenity of Sailing SV Magic

    Had a fantastic day sailing with Josh! He was great with communications and was ready to go when we got there. The boat is very comfortable and while we only did a 3 hour sail, the boat has a good galley and bathroom and would be great for a longer sail. The marina location is excellent and we were in the Chesapeake in 15 to 20 minutes. Josh was a great captain - we enjoyed chatting with him and he made us very comfortable. Highly recommended.

  4. WC

    Whitney

    Experience the Serenity of Sailing SV Magic

    We had an awesome trip with Josh. He was very flexible with timing and knowledgeable about sailing. We were able to take our engagement photos on Josh’s boat with his help and input on lighting/backgrounds. It was a wonderful experience we will never forget!

  5. WB

    Winnie

    Charter this 42ft Sailboat, for up 6 persons to enjoy the middle Chesapeake Bay

    Capt. Bill was so accommodating and great with his communication. We had an emergency and he was very understanding. He gave my nine year old great information about the boat and the waters. He and Jonathan were very kind during our charter. It was a great first sail for our family!

  6. AH

    Angela

    Charter this 42ft Sailboat, for up 6 persons to enjoy the middle Chesapeake Bay

    Captain Bill was absolutely marvelous!! The trip was amazing!! My guest and I chartered a three hour venture and had the wonderful adventure! We celebrated my cousin’s birthday and everyone was elated to ride with such a great captain! He went above and beyond to make sure we had a joyous occasion! His personality was second to none!! I extremely recommend you charter him for your next boat ride!! You will not be disappointed!!