Boat holiday rentals near Chesapeake Bay

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 + Seafood Restaurant

We can't adequately describe how romantic & carefree it feels to step aboard our sail boat. The perfect stay begins by treating yourselves to dinner at the marina's seafood restaurant, then snuggle up together on deck to watch the sunset turn the sky pink & purple. The marina atmosphere is simply magical & you'll love rocking with the gentle sway of calm waters. Come enjoy a weekend aboard this amazingly cozy & romantic sail boat. Convenient to Norfolk & Virginia Beach, the location is prime!

Miss Tryst! A 41’ sailing yacht

Come escape to our little patch of paradise on Gwynns island. Stay on a spacious 41 foot sailboat with room to sleep 8! Note, this is an experience, sort of like glamping, it’s not for everyone. At the end of the day it is a boat. There is also a full bathroom and an outdoor shower on the property just steps from the dock. Docked at a small marina and oyster farm you can purchase oysters for your stay. Also just a very short walk from a Gwynns island gem, The Hole in the Wall restaurant!

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.

The "Cookie B", Private, Cozy and One of a Kind

The "Cookie B" is easily accessible from our adjacent parking lot via our newly lighted stairs and ramp and her position in the marina offers maximum indoor and outdoor privacy. Her bow deck is huge so catch some rays by day and star gaze by night. Then enjoy morning coffee on a covered aft deck. And the view!!!The "Cookie B" enjoys one of the most beautiful, unobstructed and unique sights to be found at any place along the James River.

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.

The Radius

In the peaceful and calm end of Sue creek, in the most premium slip Baltimore Boating Center marina has to offer, your 2 bed, 2 bath boat is amazing retreat. Incredible decks and access to Charlys waterfront restaurant and mini golf and games. This boat is the perfect getaway.

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.

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.