Historic Annapolis Home with Waterfront Views & Pool Access | House in Annapolis, MD

9.8 (31 Reviews) |   5 Bedrooms  2 Bathrooms  10 Guests
Hillsmere House | Historic Annapolis Home with Waterfront Views & Pool Access

5 Bedroom House with View, Bedding and Barbecue

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.

Historic Annapolis Home with Waterfront Views & Pool Access is located in Hillsmere. Historic Annapolis Home with Waterfront Views & Pool Access provides accommodation, featuring Guest Services, Parking, Balcony/Terrace, among other amenities. This House features Guest Services, Parking, Balcony/Terrace, to make your stay a comfortable one.

Historic Annapolis Home with Waterfront Views & Pool Access has 5 Bedrooms , 2 Bathrooms, and max occupancy of 10 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Hillsmere has interesting places to visit. If you want to learn more about the House in Hillsmere, such as places to visit and things to do nearby, you can check below to learn more.

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Annapolis, 21403, United States

Amenities

Air Conditioner
Parking
TV
View
Ocean View
Balcony/Terrace
Security/Safety
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Toiletries
Guest Services
Barbecue/Outdoor Cooking
Child Friendly
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Heating
  • Air conditioning
Bathrooms
  • Hair dryer
  • Shower
  • Towels provided
  • Free toiletries
  • 2 bathrooms
  • Shampoo
  • Toilet paper
  • Soap
Bedroom
  • 5 bedrooms
  • Sofa bed
  • Bed sheets provided
  • Dining table
  • Living room
  • Fireplace
  • Wood stove
  • Dining room
Kitchen
  • Dishwasher
  • Blender
  • Coffee/tea maker
  • Stovetop
  • Microwave
  • Oven
  • Refrigerator
  • Cookware/dishes/utensils
  • Electric kettle
Laundry
  • Near laundromat
  • Washing machine and dryer
  • Laundry facilities
Ocean view
  • Beach sun loungers
Parking
  • Onsite parking
Pet Friendly
  • No pets allowed
Accessibility
  • Smoke-free property
Activities
  • Fitness facilities nearby
  • Golfing on site
  • Birdwatching nearby
  • Horse riding nearby
  • Hiking/biking trails nearby
  • Sailing nearby
  • Water sports equipment
  • Ice skating nearby
  • Winery tours nearby
  • Basketball nearby
  • Golf nearby
  • Hiking nearby
  • Kayak on site
Entertainment
  • Smart TV
General
  • Recycling
  • Energy-saving switches
  • At least 80% lighting from LEDs
  • English
  • Near a health or beauty spa
  • Near the bay
  • Near a hospital
  • On the waterfront
  • On the river
  • Desk
  • Desk chair
Guest Services
  • Iron/ironing board
  • Housekeeping (on request)
Internet
  • Free WiFi
Outdoors
  • Patio
  • Terrace
  • Outdoor furniture
  • Gas grill
  • Garden
Security/Safety
  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

Policies

Check-in
Check-in time starts at 4:00 pm minimum check-in age: 25
Check-out
Check-out before 11:00 am
Child Policy
Children are welcome.
Event Policy
No events allowed
Pet Policy
Pets not allowed
Smoking Policy
Smoking is not permitted
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 host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip host has not indicated whether there is a smoke detector on the property onsite parties or group events are strictly prohibited special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation

Reviews

jerome r.
Mar 7, 2025 11:28:53 PM
Review Score:   10
Summary: 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.
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FAQ's

Is this Hillsmere house pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Hillsmere house have a swimming pool?

No, this Hillsmere house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Hillsmere house?

Best-rates for the Hillsmere house starts from $1,056 per night with includes Ocean View, Child Friendly, Kitchen, Guest Services, Parking, Balcony/Terrace, Wellness Facilities, Fireplace/Heating, Toiletries, Internet, View, Bedding/Linens, Barbecue/Outdoor Cooking, Laundry, Air Conditioner, TV, Security/Safety with all other facilities. Casai matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

Is Hillsmere house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Hillsmere house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Hillsmere house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Hillsmere house?

Based on the information reported by the owner or manager, the Hillsmere house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Hillsmere house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Hillsmere house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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