Boat holiday rentals in Maryland

Floating yacht home with private beach

A truly unique experience, Enjoy the stunning view of the bay and nature staying on this 40 ft yacht moored at a fishing Marina. Sleeps 8 snuggly with 2 bedrooms and 2 bathrooms. Newly renovated with full kitchen and all the amenities. Small beach with grill, steps away from a tiki bar for cocktails and full menu including seafood. Mins drive from historical Annapolis and fancy marinas and restaurants nearby. Great for families, a romance trip, fishing charters, bike rental, boat life, and zen

Location · Family · Hospitality

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.

Family · Value · View

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!

Family · Value · Kitchen

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.

Location · Family · Hospitality

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.

Location · Value · Quiet

Fells Point Noble Pirate

Comfortable 42 foot cabin cruiser yacht with secure dock. Located in Canton close to Fells Point. Many bars, restaurants and attractions within walking distance. Harbor cruises available from the same pier for an additional fee.

Value · Family · Solo travel

On the WATER mini studio boat

25f overnighter boat. Simply an experience on a budget. No recommend if you are over 6f tall.

Location · Value · Quiet

LEO on the WATER

Get cozy and settle into this rustic space. Spacious 40f boat for two people.

Location · Family · Cleanliness