Serene Sunsets at Historic Waterfront Home

Annapolis, Maryland
$1101 avg/night Minimum Stay 2 Nights
Bed 4

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Night 2 nights

Min Stay

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.



Somehistory: 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.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Beach Sun Loungers
  • DINING

    Dining Table
  • 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

    4 Bedrooms Bed Sheets Provided Sofa Bed
  • GENERAL

    Energy-saving Switches Recycling Unit Size: 2187 Sq Ft (203 Sq M) Uses Some LED Lighting
  • KITCHEN

    Cookware/dishes/utensils Dishwasher Electric Kettle Ice Maker Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Garden Gas Grill Outdoor Furniture Patio Terrace
  • BATHROOMS

    2 Bathrooms Free Toiletries Hair Dryer Shampoo Shower Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk Desk Chair
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Kayak On Site Water Sports Equipment
  • ENTERTAINMENT

    Smart TV
  • LIVING SPACES

    Fireplace Living Room Wood Stove
  • 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 Availability

Review Review

  • Suzan C.

    Submitted Oct 27, 2025

    Stayed Oct 16, 2025

    Beautiful outdoor area, open floorplan and spacious dining area were great for our group. Kitchen could use some additional plates and cookware but we made do with what was there.

  • Patricia D.

    Submitted Aug 7, 2025

    Stayed Jul 18, 2025

    The location was great, convenient to Annapolis & the surrounding area. It was the perfect gathering place for family to celebrate my birthday. The water view was spectacular as we sat outside having morning coffee or gathered for an afternoon drink. It was a great place to welcome my family to Annapolis as we enjoyed the serenity of the home.

  • Valentina S.

    Submitted Jul 27, 2025

    Stayed Jul 24, 2025

    Perfect place for a family long weekend getaway! Very relaxing location, clean, comfortable, and beautiful.

  • jerome r.

    Submitted Mar 7, 2025

    Stayed Mar 1, 2025

    We were looking for a house, large enough to accommodate a small gathering for my father’s 90th birthday. This was the perfect place. The views were gorgeous. The house had the perfect flow. We were all able to gather and mingle without being cut off from one another. The bedrooms were spacious and the beds were extremely comfortable. We can’t say enough good things about this place. Management was excellent and responsive. They were very helpful. They are the best management company we’ve ever dealt with renting homes.

  • Dana E.

    Submitted Dec 29, 2024

    Stayed Nov 23, 2024

    Gorgeous neighborhood and a very cool house. The view is amazing and the sunsets were incredible. The house could have been cleaner, there were stains on some of the furniture, and the kitchen was a mess -- we had to wash every pot or pan before using it and the cabinets above the stove were grimy. There was only 1 dish towel in the house. Most of the towels and sheets were pretty old and threadbare and needed to be replaced. Overall very good but not 5 star which is what they are striving for,

  • Laura G.

    Submitted Nov 23, 2024

    Stayed Dec 31, 1969

    HIGHLY RECOMMEND! Our stay was a bit unusual. We were a group of 7 women who needed to spend a day in a comfortable location AWAY FROM THE OFFICE where we could share, brainstorm and work on our Business Plan for the coming year. Sunset Serenity was the PERFECT location. As we are all Realtors, the location location location of the property as well as the inviting, comfortable furnishings , as well as plenty of seating, really made this home ideal. We ALL remarked how we didn't want to leave. In fact, I was the last to leave, bc I just wanted 20 minutes to sit on the porch, look at the water and just breathe! What a wonderful spot!

  • Gail F.

    Submitted Sep 27, 2024

    Stayed Sep 23, 2024

    What a spot to take a break. We ended up here after the wash out of another accommodation. The location is delightful & the house charming, more than we could have wished for. Thank you Cathy for your effort in saving the the annual venture of four ladies in their eighties.

  • Allison B.

    Submitted Aug 7, 2024

    Stayed Aug 1, 2024

    We were in town for a Lacrosse tournament. Perfect house for two families. Thank you.

  • Elizabeth C.

    Submitted Jun 21, 2024

    Stayed Jun 14, 2024

    We had such a wonderful Father’s Day weekend, at this lovely property! The views are beautiful, the house was laid out perfectly for our large family, and everyone enjoyed fishing off the dock.

  • Douglas H.

    Submitted Apr 6, 2024

    Stayed Mar 27, 2024

    Sunset serenity is the perfect description

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Total

Includes taxes and fees
$1,101+
View details