House in Anne Arundel County, MD
10 guests · 5 bedrooms · 3 baths
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About this house rental
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
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
Amenities at Experience the Chesapeake Bay Lifestyle at the Historic and Waterfront Bay Dreams
Non-smoking
Pets allowed
Family friendly
Map of Anne Arundel County, MD
Ratings and reviews
8 / 10Excellent·Jan 2026
The location was very nice. Overall it was a good house for our needs. The layout is really odd. No bathroom on the first floor, which was very inconvenient after a couple days. Tons of closet space. The heating needs me to be figured out. We were dying if heat in our bedroom while the main areas were very cold.
8 / 10Excellent·Apr 2025
We booked Bay dreams as extended family for a local wedding. Great location and only wish the weather was nicer so we could use some outdoor space. Right on the water amazing views. 3rd floor bedrooms are more kids rooms than suited for adults. Master suite is amazing and other 2 bedrooms nice as well. Living room and dining are has plenty of space as well. Kitchen is tiny wouldn’t want more than a couple 2-3 people in at same time a little congested but worked just fine for us.
10 / 10Outstanding·Dec 2024
This property is perfectly situated with incredible water views, fabulous walks by the bay and great retail and restaurant options in town. The porch off the master suite is an incredible retreat to watch the sunrise and just enjoy the water views. The house is a little bit more unique layout than the pictures imply but certainly does largely add to the charm. It was close to perfect for my intended fwnjjandmmmmm
6 / 10Average·Oct 2025
The house was clean, towels were provided and beautiful views.
There was no sponge, dish detergent or dishwasher soap and just a few trash bags for us to use. We rent a condo in NJ and always provide these to our renters to help them keep our place tidy. It would have been nice to have a roll of paper towels and a box of tissues as well. Everything else was fine.
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Top rated by guests
8Excellent
(7 Ratings)
"This property is perfectly situated with incredible water views, fabulous walks by the bay and great retail and restaurant options in town. The porch off the master suite is an incredible retreat to w..."
Catherine G.Don't miss out! Price and availability may change
