Boat holiday rentals in Maryland

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Top-rated boat rentals in Maryland

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Guest favourite

A bright and welcoming dining saloon is visible, featuring a polished table surrounded by comfortable couches. Soft lighting highlights the rich wood finishes, and a television is mounted on the wall. Skylights above allow natural light to fill the space.

Boat in Annapolis

4.94 out of 5 average rating, 414 reviews

Stay aboard the S/V MY STUDIO on Annapolis Harbor

Discover life aboard a comfortably equipped sailing yacht. Great for couples on a weekend getaway, and child friendly for families looking to include their little pirates. Hands down this is a wonderful way to visit Historic Annapolis and Naval Academy. We love the opportunity to share our boat, and help create a memorable vacation. Weather permitting, Private Sailing Cruises can be arranged during your stay for an additional charge. Cheers, and I look forward to welcoming you aboard.

Top guest favourite

Boat in Annapolis

4.96 out of 5 average rating, 109 reviews

Welcome Aboard!

Unique accommodations on a comfortably equipped 43 foot Hatteras yacht, just a 5 minute drive to historic downtown Annapolis and the Naval Academy. 15 minute drive to the Navy Stadium, 15 minutes drive to Rt 50. THIS LISTING IS FOR ACCOMODATIONS ONLY; BOAT MAY NOT BE DRIVEN! Forward cabin has bunk beds. Aft cabin has a queen bed. Fully equipped galley (kitchen) with 2-burner cook top, microwave/oven, fridge, toaster oven and Keurig. Boat has WIFI, heat, AC and hot water!

Top guest favourite

A 33-foot C&C sailboat is anchored in calm waters, surrounded by other vessels. The sunset casts a soft glow over the scene, highlighting the boat's sleek lines and the gentle ripples of the water. A dinghy is tethered alongside, ready for exploration.

Boat in Annapolis

4.93 out of 5 average rating, 55 reviews

Sailboat Experience in Annapolis

Choosing this C and C 33 sailboat for your stay is opting for an experience over extravagance. It's about immersing yourself in the rhythm of the sea, understanding the sailor's way of life, and cherishing the simple joys that come with it. This is a sailboat and is like a camping experience in the water with peaceful and beautiful surroundings. Perfect for solo travelers, couples, or small groups, this sailboat promises a stay that's both unique and unforgettable.

A classic 34-foot trawler, Valentina, floats in Baltimore's harbor. The boat features a spacious top deck covered by an overhang, with a kayak secured on top. The hull displays a clean, white finish, reflecting the calm water surrounding the dock.

Boat in Baltimore

4.66 out of 5 average rating, 76 reviews

Charming Retreat on the Water—Walk to Fells Point

Welcome aboard Valentina, a 34-foot trawler docked in Baltimore’s harbor. Perfect for a couple’s getaway or solo retreat, this one-of-a-kind floating home is steps away from a quintessential Maryland crab house and walking distance from all the restaurants and bars in Fells Point and Canton.