Boat vacation rentals near Chesapeake Bay

Boat BNB Luxury Accomadations Aboard a Catamaran

The most fun way to visit America's Sailing Capital, on the water accommodations aboard Zep Tepi! The spacious interior provides a fully stocked galley microwave, Nespresso, fridge, freezer & ice-maker. When the harbor has gone tranquil, & it's time for bed, we have a large stateroom w/ensuite bath & captain's office/walk-closet, & two comfortable aft queen bed cabins with a shared bath. Heat/AC, wifi & Apple TV, & just about all the creature comforts one could need for a vacation on the water!

Floating 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 mfancy marinas and restaurants nearby. Great for families, a romance trip, fishing charters, bike rental, boat life, and zen

Romantic Sailboat Experience by Seafood Restaurant

We can't adequately describe how romantic & carefree it feels to step aboard our sail boat. After a wonderful meal at the marina seafood restaurant our guests love to snuggle up together on deck and watch the sunset turn the sky pink & purple with a glass of bubbly. The marina atmosphere is simply magical & you'll love sleeping to the gentle sway of calm waters. Come enjoy a night aboard this amazingly cozy & romantic sail boat. Convenient to Norfolk & Virginia Beach, the location is prime!

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.

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!

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.

Serenity calls..

For lullaby dreams, nothing beats the lifestyle of your own private yacht for the sights of DMV or on the beautiful US Virgin Islands. These beautiful yachts sleep four to six adults comfortably and have the full amenities of a small condo. No winter cruises in DC. Not available December thru March.

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.

Mountains to Sea Hunter 356 sailboat

We are NOT currently offering over night stays on the boat. We do have other options available-please message for more info. **We do NOT allow children under the age of 5 on the boat.** Not suitable for children under the age of 5.