Entire home

Serene waterfront sunsets in this sprawling historic Annapolis home

Escape to this serene haven where you can kayak across the creek or unwind in an Adirondack chair under wisteria pergola shade.

Photo gallery for Serene waterfront sunsets in this sprawling historic Annapolis home

Interior
Point of interest
Smart TV, fireplace
5 bedrooms, desk, iron/ironing board, free WiFi
Terrace/patio

Reviews

9.6 out of 10
Exceptional

Entire home

5 bedrooms2 bathroomsSleeps 10

Popular amenities

  • Washer
  • Barbecue grill
  • Parking available
  • Outdoor Space
  • Air conditioning
  • Kitchen

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Serene waterfront sunsets in this sprawling historic Annapolis home

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.

Property manager

iTrip Vacations Annapolis - Sean Degnan

Languages

English

Property amenities

Beach

  • Beach sun loungers

Internet

  • Free WiFi

Parking and transportation

  • Onsite parking

Kitchen

  • Refrigerator
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Toaster
  • Paper towels
  • Kitchen island
  • Blender

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bed sheets provided
  • Sofa bed

Bathrooms

  • 2 bathrooms
  • Shower
  • Free toiletries
  • Towels provided
  • Shampoo
  • Soap
  • Hair dryer
  • Toilet paper

Living spaces

  • Fireplace
  • Living room
  • Dining room
  • Wood stove

Entertainment

  • Smart TV

Outdoor areas

  • Patio
  • Terrace
  • Gas grill
  • Garden
  • Outdoor furniture

Laundry

  • Washing machine and dryer
  • Near laundromat

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Housekeeping (on request)
  • Iron/ironing board

Location highlights

  • On the river
  • On the waterfront
  • Near a health or beauty spa
  • Near a hospital
  • Near the bay

Things to do

  • Water sports equipment
  • Fitness facilities nearby
  • Kayak on site
  • Golfing on site
  • Ice skating nearby
  • Golf nearby
  • Winery tours nearby
  • Basketball nearby
  • Fishing nearby
  • Hiking nearby
  • Marina nearby
  • Birdwatching nearby
  • Water skiing nearby

Safety features

  • 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)

General

  • At least 80% lighting from LEDs
  • Recycling
  • Energy-saving switches

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

Guests can access their accommodation through a private entrance
You will receive an email from the host with check-in and check-out instructions

Access methods

Private entrance

Pets

Pets not allowed

Children and extra beds

Children are welcome

Important information

You need to know

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
Onsite parties or group events are strictly prohibited
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
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

Property is also known as

11125

About the neighborhood

Map
Annapolis, MD

What's nearby

  • Maryland Quiet Waters Park - 1 min drive
  • Navy-Marine Corps Memorial Stadium - 8 min drive
  • Anne Arundel Medical Center - 10 min drive
  • Annapolis City Dock - 11 min drive
  • U.S. Naval Academy - 11 min drive

Getting around

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

Restaurants

  • ‪McDonald's - ‬8 min drive
  • ‪Little Italy - ‬5 min drive
  • ‪Shika Sushi and Ramen - ‬7 min drive
  • ‪Senor's Chile - ‬13 min drive
  • ‪Starbucks - ‬7 min drive

Frequently asked questions

Is Serene waterfront sunsets in this sprawling historic Annapolis home pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Serene waterfront sunsets in this sprawling historic Annapolis home?

Check-in begins at 4:00 PM.

What time is check-out at Serene waterfront sunsets in this sprawling historic Annapolis home?

Check-out is at 11:00 AM.

Where is Serene waterfront sunsets in this sprawling historic Annapolis home located?

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

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Serene waterfront sunsets in this sprawling historic Annapolis home Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 24 out of 28 reviews
Rating 8 - Good. 2 out of 28 reviews
Rating 6 - Okay. 2 out of 28 reviews
Rating 4 - Poor. 0 out of 28 reviews
Rating 2 - Terrible. 0 out of 28 reviews

9.4/10

Cleanliness

Reviews

10/10 Excellent

Elizabeth C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful Father’s Day weekend
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.
Stayed 2 nights in Jun 2024

10/10 Excellent

Alan P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Charming house on great property
Wonderful location on the water with well maintained property and great views. Will be glad to stay here again.
Stayed 4 nights in Oct 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Gail F.

WOW!
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.
Stayed 3 nights in Sep 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Allison B.

Family Fun
We were in town for a Lacrosse tournament. Perfect house for two families. Thank you.
Stayed 3 nights in Aug 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Sharon G.

Recent Stay
Good Morning, We are enjoying our stay at Sunset Serenity and will definitely return again. All of the accommodations are nice and the house is very nice.

10/10 Excellent

vicki n.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely place
This is a special place. If you want to feel relaxed and have great water views and magnificent sunsets this is the place.
Stayed 3 nights in Aug 2023

8/10 Good

Douglas H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
sunset serenity
Sunset serenity is the perfect description
Stayed 6 nights in Mar 2024

6/10 Okay

Anna H.

Liked: Check-in, communication, location, listing accuracy
Beautiful House and Location
Enjoyed our stay here for a girls weekend. Only complaint is that the house needed to be deep cleaned—spider webs!
Stayed 2 nights in Jan 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Laura G.

Perfect Off-Site getaway
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!

10/10 Excellent

Dianne D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Peaceful and beautiful
Comfortable and enjoyable in a beautiful setting
Stayed 6 nights in Apr 2023

10/10 Excellent

Steve & Kay N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Chesapeake Bay retreat
We enjoyed this lovely home and setting along the Chesapeake Bay / South River. Well equipped home with a beautiful yard, and views of the Bay. Quiet neighborhood, yet accessible to Quiet Waters Park, historic Annapolis, and Sandy Point State Park.
Stayed 3 nights in Dec 2023

10/10 Excellent

Tara K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Thanks for a great time
We had a lovely three nights in this beautiful home. The spacious home had everything we needed for a great girls weekend.
Stayed 3 nights in Jun 2023

10/10 Excellent

Joan N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
a wonderful house/property
My friends and I had a great time at the house, which had everything we'd hoped for: a great outdoor space, a super functional kitchen, a comfortable living room and even really comfortable beds.
Stayed 3 nights in Jul 2023

10/10 Excellent

Aparna P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Getaway!
We had a lovely stay at Sunset Serenity House! The house was beautifully decorated as well as comfortable and cozy. The views were breathtaking and we had plenty of space to work and explore the grounds! Will definitely recommend to friends and family!
Stayed 5 nights in Oct 2022
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Carol S.

Breathtaking views and gorgeous home!
The sunset views from this gorgeous house are stunning! The setting is like a fairytale, with amazing water views and magical gardens. And the layout of the house is so inviting. And it’s all so close to downtown Annapolis! I would rent this place again in a heartbeat.

10/10 Excellent

lori v.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family celebration
Such a stunning property with a beautiful view. The landscaping and dwellings were perfect for our family. We appreciate the history of the home. It had everything this family needed and I would rent it again. The location to downtown and necessary stores were also perfect. Quiet and Elegant.
Stayed 3 nights in Oct 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Cristina F.

Beautiful Lakeside Escape
Loved staying at Sunset Serenity, the house is large and beautiful, comfortable and has great kitchen and all the comforts a family needs. From the little ones to the teens everyone loved the time spent here. The only thing is distance, make su to have transportation and watch out for deers at night when driving. But overall 5/5.

10/10 Excellent

Joe E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Quick Annapolis Visit
What a gorgeous space!! Beautiful and clean inside. The neighborhood was quiet and very nice... not too far from the Great Frogs Winery. Getting to sit in the outside space and watch the sunset and kayak a little bit w the kids was such a fun and relaxing time. We're looking forward to staying again when we're in the area.
Stayed 4 nights in May 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Carrie w.

Sunset Serenity - Superb!
Our stay at Sunset Serenity was magical. Our two families, young and old alike, loved the property. While the parents enjoyed the sunset, the kids were able to master kayaking in a safe and fun environment. The proximity to the city made it a perfect location for a getaway. As frequent VRBO families, this is by far our favorite spot. We look forward to returning again.
Stayed 3 nights in Jul 2023

10/10 Excellent

Patricia C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Peace and Serenity
This property is warm and inviting from the minute you arrive. It has everything you need for your stay. Large open space for family and beautiful country charm. The sunsets are a gift from God!!! The nature is also amazing. Another treat is the Green Frog Winery a short walk from the home.
Stayed 8 nights in May 2023

10/10 Excellent

Elizabeth H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
College Reunion
The property was absolutely perfect. The views alone made it perfect with sunsets that take your breath away. Plenty of space for our group. Well appointed throughout, especially the kitchen. Sean at iTrip was very quick to respond to any question. Very easy to work with.
Stayed 3 nights in Nov 2023

10/10 Excellent

Caitlin M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful, relaxing home
We had the most amazing time staying at this wonderful property. Despite poor weather all weekend, the views of the water from the living/dining areas were spectacular, and the accommodations very comfortable. The home is beautiful, with a great balance of historic charm and modern comfort. We divided our time between the house and taking advantage of Annapolis and the surrounding area. A perfect weekend getaway for our group of friends.
Stayed 2 nights in Sep 2022

10/10 Excellent

Kate G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Spectacular Views!
What a wonderful weekend with friends in this charming home. We could have just sat on the patio all weekend relaxing and enjoying the spectacular views. Easy ride into Downtown Annapolis, make sure to visit Great Frogs Winery just down the road and take a walk in this lovely neighborhood. It doesn’t get much better than this!
Stayed 2 nights in Nov 2022

10/10 Excellent

Michael Q.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A special, special place
BEAUTIFUL setting, lovely house... it was really perfect for a family get-together for my dad's birthday. The property has a big property, for running around or hanging out. You're right on the water, which means beautiful sunsets. You're a short drive from town. The great room is a perfect place for hanging. One small gripe: they could better stock the kitchen, but still plenty of stuff available for cooking. And the management team is responsive and helpful. We're already planning our trip back. It's a great, great place.
Stayed 3 nights in Feb 2024

10/10 Excellent

Jamila W., Fort Lauderdale, Florida

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Sunsets, Cozy Stay
I don't have a single complaint. This was the perfect home for my family. We had 3 generations stay (all adults) and found the home had everything we needed. We are the type of family that makes our morning coffee time a ritual. The open kitchen/dining/living room had more than enough space for us to have coffee, talk, laugh, and look over the water. Everyone got a ton of pictures in the evening watching the sunset. We would love to come back when the weather gets a bit warmer. Highly recommend this property to anyone looking.
Stayed 3 nights in Mar 2023