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Oxford, Maryland Boat Rentals

Page 1 of 124 listings

Experience the Charm of St. Michaels Aboard the 41ft Sail Selina 2hr Boat Tour
Sailing in Saint Michaels · 6 guests

Experience the Charm of St. Michaels Aboard the 41ft Sail Selina 2hr Boat Tour

New
$350/hour
Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours
Sailing in Saint Michaels · 6 guests

Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours

New
$400/hour
Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail
Sailing in Saint Michaels · 6 guests

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

5.0
$325/hour
Sailing Adventures on the Choptank River
Sailing in Cambridge · 6 guests

Sailing Adventures on the Choptank River

New
$100/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
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
$400/hour
 VIKO S 35 Sailboat in Deale
Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

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

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$250+/hour
COME CRUISE THE BEAUTIFUL CHESAPEAKE BAY!
Powerboats in Deale · 6 guests

COME CRUISE THE BEAUTIFUL CHESAPEAKE BAY!

5.0
$200/hour
Luxurious 51’ SeaRay Flybridge Yacht With Twin 600 Hp Cummins Engine
Events in Deale · 10 guests

Luxurious 51’ SeaRay Flybridge Yacht With Twin 600 Hp Cummins Engine

5.0
$500/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
VIKO 30 Premium Sailing Yacht In Deale, MD
Sailing in Deale · 5 guests

VIKO 30 Premium Sailing Yacht In Deale, MD

New
$925/day
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
$350/hour
31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD
Powerboats in Selby-on-the-Bay · 10 guests

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

5.0
Snoozed - Active 02 Sep 2025
43ft Cruiser Express Yacht for Daily Charter
Events in Selby-on-the-Bay · 8 guests

43ft Cruiser Express Yacht for Daily Charter

5.0
$400/hour
Private Yacht Charter: On 40ft Regal Commodore
Events in Selby-on-the-Bay · 10 guests

Private Yacht Charter: On 40ft Regal Commodore

5.0
$350/hour
Instant Book
Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.
Sailing in Mayo · 6 guests

Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.

5.0
$175+/hour
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
SLOWDOWN - DUFOUR 430
Sailing in Annapolis · 12 guests

SLOWDOWN - DUFOUR 430

New
$250+/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
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
 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
50ft Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

5.0
$325/hour

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Oxford Reviews

  1. LA

    Lashaia

    43ft Cruiser Express Yacht for Daily Charter

    Here’s a polished version of your review: --- We had an incredible time on our sunset cruise around Annapolis! Captain Rob was the perfect host—welcoming, accommodating, and thoroughly professional. The boat was immaculate and just right for our group, offering plenty of space and comfort. Rob made sure we caught the best views of the sunset and always prioritized our safety. It was a smooth, relaxing experience from start to finish. We would absolutely book again and highly recommend this tour to anyone looking for a scenic and memorable way to enjoy Annapolis from the water. It was absolutely perfect!

  2. JS

    Jen

    STARZ -Lagoon 42 Catamaran in Chesapeake Bay

    I highly recommend Chronic Sailing! We did a 4 hour charter out of Annapolis as a bachelorette party. Captain Steve and Sarah were so accommodating and made our time so memorable. We are so appreciative. They made everything so easy- from booking to sailing and making memories with us. The STARZ catamaran boat was incredible! It fit our big group comfortably and gave us a little bit of luxury as we lounged and enjoyed on the bay. Again, this was a great experience for all of us and I would love to use them again!

  3. MS

    Michael

    Private Yacht Charter: On 40ft Regal Commodore

    Our boat ride with Dennis was awesome. His boat is very well maintained with plenty of space to make sure everyone always has a good seat and view. He took us to two great spots he knew about, one for swimming, and one for sunset viewing. During the ride he was always asking questions to make sure everyone was taken care of and having a good time. The kids (ages 7-8) were giggling non stop the first time he went full throttle, so this experience is definitely recommended for families.

  4. JH

    Jessica

    Luxurious 51’ SeaRay Flybridge Yacht With Twin 600 Hp Cummins Engine

    This was such a great trip! The boat is Beautiful and Michael & Norma were wonderful! We felt right at home. If you are looking for a boat trip, I would 110 recommend Michael! It was such a great experience. We will be returning.

  5. JR

    Jordan

    Private Yacht Charter: On 40ft Regal Commodore

    We had a great day with Dennis. He was easy to work with and has a fantastic boat. He let us make decisions while being attentive to all of our concerns. It was a great time! 10/10 recommend!

  6. JV

    Javier

    Private Yacht Charter: On 40ft Regal Commodore

    Captain Dennis was an amazing host. We came with a group of 10 and everyone had an amazing experience. The boat is amazing and Captain Dennis will make sure you have a great time!