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

North Beach, Maryland
$822 avg/night
Bed 5

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

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

Read More Expand
  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    5 Bedrooms
  • GENERAL

    At Least 80% Lighting From LEDs Recycling Unit Size: 2800 Sq Ft (260 Sq M)
  • KITCHEN

    Coffee/tea Maker Dishwasher Microwave Oven Refrigerator Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Firepit
  • BATHROOMS

    3 Bathrooms Hair Dryer Shampoo Shower
  • LANGS SPOKEN

    English
  • ENTERTAINMENT

    TV
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Games
  • LOCATION HIGHLIGHTS

    On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Rates & Availability

Review Review

  • Kelly H.

    Submitted Jan 6, 2026

    Stayed Nov 26, 2025

    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.

  • Janet G.

    Submitted Oct 8, 2025

    Stayed Sep 24, 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.

  • Michael M.

    Submitted Apr 12, 2025

    Stayed Apr 11, 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.

  • Catherine G.

    Submitted Dec 11, 2024

    Stayed Nov 25, 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

  • Stacey R.

    Submitted Oct 9, 2024

    Stayed Oct 2, 2024

    The view and location was the highlight as well as dog friendly. The master bed is very low and uncomfortable. The home needs some TLC but they consider it charm.

  • Tom R.

    Submitted Aug 21, 2024

    Stayed Aug 14, 2024

    We just returned from our vacation and must say what a great time we had! This home was very comfortable for our family - lots of comfortable beds, big table for dining, lots of outdoor seating options and great porches. Highly recommended!

Your dates are Available!

Total

Includes taxes and fees
$822+
View details