Experience the Chesapeake Bay Lifestyle at the Historic and Waterfront Bay Dreams

Experience the Difference: Professionally Managed by iTrip Annapolis

Experience the Difference: Professionally Managed by iTrip Annapolis

Welcome to Bay Dreams, a beautifully-restored historic home once known as the "Waterfront Inn of Holland Point." Nestled on the western shore of the Chesapeake Bay, and located just a mile from the Inn and Marina at Herrington Harbour, this charming retreat offers breathtaking views and a rich history, seamlessly blending historic charm with modern luxuries. Ideal for families and couples, Bay Dreams promises an unforgettable getaway.



Property Highlights:

Expansive Bay Views: Enjoy stunning sunrises and refreshing bay breezes from the impressive new waterfront porch.

Spacious Living Areas: Relax in the grand family room, formal dining room, updated eat-in kitchen, and multiple outdoor living spaces.

Outdoor Fun: Walk or bike to one of two local beaches: Rose Haven Memorial Park, less than a mile away and the North Beach boardwalk, beach (requires paid daily passes), fishing pier, shops, and more. Also nearby is the Inn at Herrington Harbour.



Sleeping Arrangements (Sleeps 6 adults, 4 kids, and a toddler):



2nd Floor King Suite:

King Bed

Separate stand-up shower, bathtub, and large vanity

Attached waterfront sunroom



2nd Floor King Garden Bedroom:

King Bed



Family Bedroom:

Queen Bed and Toddler bed



Two shared baths on the 2nd floor: One full bath with stand-up shower and a half bath with laundry



Top Floor Full Bedroom:

Full Bed with Full Trundle

Half bath



Top Floor Twin Bedroom:

2 Twin beds over Twin trundles (4 Twin beds total)

Half bath



Additional Features:

Outdoor Spaces: Waterfront covered porch, yard with loungers, wrap-around sofa, and Adirondack chairs around a gas firepit

Furnished Sunporch: Ideal for relaxing and enjoying the views

Updated Kitchen: Equipped with appliances big and small

Modern Amenities: WiFi, flat-screen TVs, and luxury linens

Complimentary Starter Kit: Includes coffee, toiletries, paper goods, and cleaning supplies

Convenient Parking: Room to accommodate multiple cars

Family-Friendly: Washer and dryer in the home

Pet-Friendly: Small dogs (under 40 lbs) welcome with a $150 pet fee

Keyless Entry: Easy access with an electronic lock code



Convenient Location:

- Annapolis - 26 miles

- Washington, DC - 36 miles

- Baltimore - 51 miles



Amenity & Supplies Starter Pack: Includes coffee, sweeteners, soap, shampoo, conditioner, lotion, hand sanitizer, paper towels, toilet paper, dish soap, sponge, and dishwashing liquid.

Fresh Linens: All beds are made with freshly-laundered sheets and towels.



House Rules

House Rules:

No smoking or parties

Must be 25+ to rent, with an adult present at all times

For your security, we have one door camera facing the outside of the home and a noise decibel monitor that is compliant with the law.

Check-in: 4:00 PM, Check-out: 11:00 AM