Entire home

Serene Sunsets at Historic Waterfront Home

Photo gallery for Serene Sunsets at Historic Waterfront Home

A spacious living room with a large sofa, a dining area, and a view of the outdoors.
A large property with a red barn, multiple houses, and a lake.
A covered outdoor deck with a view of a lake and grassy area.
A hallway with glass doors, a chandelier, and a view of the backyard.
A bedroom with a bed, a ceiling fan, a window, and a door leading outside.

Reviews

9.6 out of 10
Exceptional
Located at the waterfront, this 4-bedroom vacation home accommodates 10 guests. It features 2 separate living rooms and offers water views from multiple areas. Enjoy outdoor spaces including a balcony, patio, and porch. Nearby attractions include Great Frogs Winery and Maryland Quiet Waters Park.

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Maryland Quiet Waters Park
4 bedrooms2 bathroomsSleeps 10

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue grill
  • Balcony or patio

Explore the area

View in a map
Annapolis, MD
  • Place, Great Frogs Winery
    ‪12 min walk‬
  • Place, Maryland Quiet Waters Park
    ‪17 min walk‬
  • Place, U.S. Naval Academy
    ‪17 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪44 min drive‬

Rooms & beds

4 bedrooms (sleeps 10)

Loft

3 Single Beds

Main Floor King

1 King Bed

Main Floor Queen

1 Queen Bed

Main Floor Twin

1 Single Bed

Milk House Living Room

1 Double Sofa Bed

Waterview Milk House Suite

1 Queen Bed

2 bathrooms

Main Floor Queen

Toilet · Shower only

Upstairs Hall

Bathtub · Toilet · Shower only

Spaces

Deck or patio
Kitchen
Number of living rooms
Garden

About this property

Serene Sunsets at Historic Waterfront Home

Experience the Difference: Professionally Managed by iTrip Annapolis

Enjoy stunning western-facing views across the river and a natural tidal pond from this sprawling historic home that sits on 1.5+ acres. The light-filled farmhouse is located on Persimmon Point, which is positioned between Harness Creek and the South River. It is a peninsula rich in local lore that includes Native American oysters mounds, pirate hideouts, tobacco farming and world champion cows.



Some history: Once the home was part of the original Wimbledon Farm. From the 1930’s, Wimbledon Farm grew abundant produce and tobacco. The last magnificent tobacco barn in Annapolis is on the property next to the house. Wimbledon was also famous for their dairy. Their dairy cows and bulls attracted breeders from around the world and famously started the “Carnation” milk herd. The dairy barn was immense and the milk came into the small milk house, which is now the charming "Milkhouse Suite". Here the milk was chilled and sent out to be bottled and delivered.



Today: The house offers a special, very private family retreat just minutes to downtown Annapolis. The home was renovated to its current beauty by opening the entire back of the house to the water with windows and connecting the main house to the "milk house". All of the living space, and 4 of the 5 bedrooms, are on the main floor. The lofted upstairs bedroom is perfect for the younger crowd with 3 twin beds and room to enjoy each other's company. The open floor plan, deck and terrace provide multiple living spaces inside and out. There are 2 full baths and room for 10 guests to sleep comfortably.



Enjoy the outdoors on stone patio with fountain and dining tables, a pair of Adirondack chairs on the back deck under the shady wisteria pergola, and a BBQ grill. Inside, the dining table seats 8 with room for 3 more at the breakfast bar. Across the lush lawn, there is also a small pier on the pond for kayak launching or fishing fun for small anglers. Guests can also get away from the day by lounging on the creek side on the front porch swing.



Local activities: Great Frogs Winery (less than ½ mile away down the street), Quiet Waters Park (hiking trails, ice skating, SUP rentals) and kayaking or biking.



SLEEPING ARRANGEMENTS 5 BR / 2 BA / Sleeps 10 adults (2 children):

Milk House Suite:

-Main Floor

-Queen Bed

-Living room with Full sofa sleeper

-Private en-suite bathroom large tile shower

-Private entrance and water views



Main Floor King:

-King bed

-Private entrance to front porch



Main Floor Queen:

-Queen bed



Main Floor Twin

-Built-in Twin Bed



Upstairs Loft

-3 Twin beds



-Full Hall Bath with stand-up Shower and clawfoot Tub



HIGHLIGHTS:

-Outdoor waterfront furnished terrace and deck - access to decks or porch from main entries

-Small fishing and boat launch pier on the pond

-Kayaks

-Mulitple living spaces: family room, living room and loft

-BBQ Gas grill (propane tank provided)

-Dining room table with seating for 8

-Breakfast bar with seating for 3

-Vermont casting gas stove

-High Speed Internet and WiFi

-Flatscreen TV's

-Luxury Westin Heavenly mattress in milk house, fine linens, complimentary toiletries Starter Kit, and boutique-level service

-Parking for multiple cars in driveway

-Full-size washers/dryers located on the main floor



Property Distance to:

-Downtown Annapolis – 4 miles

-U.S. Naval Academy – 4 miles

-Washington, DC – 33 miles

-Baltimore - 33 miles

-Great Frogs Winery - .4 miles

-Quiet Waters Park - 4.2 miles by land - closer by sea!



*Amenity & Supplies starter pack, coffees and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid.

* All beds are made for you with freshly-laundered sheets & towels.



House Rules

Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the house at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Be respectful of the house and contents - it is someone's home and the owners live in the home when not renting it. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind.

Add dates for prices

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

No pets allowed
default

Smoking

Smoking is not permitted

Important information

You need to know

Property # 2947314vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Annapolis

Located on the waterfront, this holiday home is in Hillsmere, a neighbourhood in Annapolis. Shoppers can check out Annapolis City Dock, while everyone can enjoy the natural beauty of Chesapeake Bay and Sandy Point State Park. Wild Bird Center and Maryland Hall for Creative Arts are also worth visiting.
Map
Annapolis, MD

What's nearby

  • Great Frogs Winery - 12 min walk - 1.1 km
  • Maryland Quiet Waters Park - 17 min walk - 1.5 km
  • U.S. Naval Academy - 17 min drive - 7.6 km
  • Annapolis City Dock - 18 min drive - 7.9 km
  • Sandy Point State Park - 27 min drive - 23.5 km

Getting around

  • Odenton Station - 25 min drive
  • Fort Meade, MD (FME-Tipton) - 28 min drive

Restaurants

  • ‪McDonald's - ‬7 min drive
  • ‪Royal Farms - ‬13 min drive
  • ‪Shika Sushi & Ramen - ‬7 min drive
  • ‪The Beacon Restaurant - ‬11 min drive
  • ‪Señor Chile - ‬12 min drive

Frequently asked questions

Is Serene Sunsets at Historic Waterfront Home pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Serene Sunsets at Historic Waterfront Home?

As of 28 Aug, 2026, prices found for a 1-night stay for 2 adults at Serene Sunsets at Historic Waterfront Home on 30 Aug, 2026 start from S$2,949, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Serene Sunsets at Historic Waterfront Home?

On-site parking is available at the property.

What time is check-in at Serene Sunsets at Historic Waterfront Home?

Check-in begins at 4:00 PM.

What time is check-out at Serene Sunsets at Historic Waterfront Home?

Checkout is at 11:00 AM.

Where is Serene Sunsets at Historic Waterfront Home located?

Located in Hillsmere, this holiday home is 0.6 mi (1 km) from Great Frogs Winery and within 3 miles (5 km) of Wild Bird Center and Kunta Kinte–Alex Haley Memorial. St John's College and Spa Creek are also within 3 miles (5 km).

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback