Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
42 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.
-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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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. The area's natural beauty can be seen at Chesapeake Bay and Jonas Green State Park, while Ballet Theater of Maryland and Annapolis Civil Rights Plaque are cultural highlights. Wild Bird Center and Maryland Hall for Creative Arts are also worth visiting.
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 9 May 2026, prices found for a 1-night stay for 2 adults at Serene Sunsets at Historic Waterfront Home on 15 June 2026 start from AU$1,213, 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).
Reviews
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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.
Suzan C.
Stayed 3 nights in Oct 2025
Response from VrboOwner on 4 Nov 2025
Thanks, Suzan! We’re delighted to hear that Sunset Serenity provided a beautiful outdoor area and spacious dining experience for your group. It’s fantastic that the open floorplan suited your needs. We appreciate your feedback regarding the kitchenware and will look into adding more plates and cookware. We hope to host you again in the future!
Melissa~iTrip Annapolis
From a partner site
8/10 Good
Peter W.
6 Apr 2026
Easter Weekend
Amazing location, great space, equipped kitchen that allowed our families to enjoy each other. The kayaks were awesome to have at our disposal.
Just a safety warning that the wooden steps into the house front and out of the back of the house are falling apart. I wouldn’t say anything about this except for the large loose and exposed nail heads could hurt someone unaware of them. Full trash cans upon arrival made for extra clean up bc we couldn’t contain our trash bags which led to deep digging by local animals.
Overall a great house, clean, and organized and any of these small items didn’t interfere with our fun, thank you!
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.
Patricia D.
Stayed 3 nights in Jul 2025
Response from VrboOwner on 8 Aug 2025
Thank you for staying with us Patricia & we welcome you back anytime! Melissa~iTripAnnapolis
This is a special place. If you want to feel relaxed and have great water views and magnificent sunsets this is the place.
vicki n.
Stayed 3 nights in Aug 2023
Response from VrboOwner on 20 Sept 2023
Thank you Vicki for the kind review of Sunset Serenity. We hope to have the opportunity to host you again. Safe Travels!
-Tiffany
From a partner site
10/10 Excellent
Sharon G.
6 Dec 2023
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.
Diane we are so happy to hear you enjoyed your stay at Sunset Serenity. Thank you for your kind review. Please come back and stay with us again. Safe Travels!
-Tiffany
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.
Elizabeth C.
Stayed 2 nights in Jun 2024
Response from VrboOwner on 22 June 2024
Hi Elizabeth! Thank you for your positive feedback & I am happy to hear you enjoyed tour stay! We welcome you back anytime!
Enjoyed our stay here for a girls weekend. Only complaint is that the house needed to be deep cleaned—spider webs!
Anna H.
Stayed 2 nights in Jan 2024
Response from VrboOwner on 15 Feb 2024
So sorry you saw cobwebs, Anna. Our cleaner at this home is normally great, but sometimes things get missed. The problem has been fixed! We strive to deliver ONLY 5-star reviews to our guests. We hope you’ll give us another chance next time you’re coming back to Annapolis.
Sean, iTrip Annapolis
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!
Aparna P.
Stayed 5 nights in Oct 2022
Response from VrboOwner on 20 Sept 2023
Thank you Aparna! We truly hope you will come back and stay at Sunset Serenity again very soon! - Cathy
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.
Steve & Kay N.
Stayed 3 nights in Dec 2023
Response from VrboOwner on 30 Dec 2023
Thanks, Steve and Kay! We welcome you back any time. Please reach out next time you’re planning a trip to Annapolis.
Sean, iTrip Annapolis
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.
Joan N.
Stayed 3 nights in Jul 2023
Response from VrboOwner on 20 Sept 2023
Thank you Joan for the kind review of Sunset Serenity. We are so happy to hear you enjoyed your stay. Please come back and stay with us again. Safe Travels!
-Tiffany
From a partner site
10/10 Excellent
Carol S.
3 July 2023
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.
Carol S.
From a partner site
10/10 Excellent
Allison B.
7 Aug 2024
Family Fun
We were in town for a Lacrosse tournament. Perfect house for two families. Thank you.
Allison B.
Stayed 3 nights in Aug 2024
Response from VrboOwner on 13 Aug 2024
Hi Allison! Thank you for allowing us to host your stay & we are thrilled to know you enjoyed your time in the home! We welcome you back anytime, Melissa~iTripAnnapolis
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.
Joe E.
Stayed 4 nights in May 2023
Response from VrboOwner on 20 Sept 2023
Thank you Joe! We are so happy to hear you enjoyed your stay. Please come back and stay with us again. Safe Travels!
-Tiffany
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.
lori v.
Stayed 3 nights in Oct 2023
Response from VrboOwner on 19 Oct 2023
Lori we are pleased to hear you enjoyed your stay at Sunset Serenity. We look forward to hosting you again. Safe Travels!
-Tiffany
From a partner site
10/10 Excellent
Carrie w.
1 Aug 2023
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.
Carrie w.
Stayed 3 nights in Jul 2023
Response from VrboOwner on 20 Sept 2023
Thank you Carrie for the kind review of Sunset Serenity. We are so happy to hear you enjoyed your stay. We hope to have the opportunity to host you again. Safe Travels! -Tiffany
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.
Patricia C.
Stayed 8 nights in May 2023
Response from VrboOwner on 20 Sept 2023
Thank you so much for your review of Sunset Serenity. We are so happy you enjoyed your stay. Please come back and stay with us again. Safe Travels!
-Tiffany
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.
Caitlin M.
Stayed 2 nights in Sep 2022
Response from VrboOwner on 20 Sept 2023
Thank you Caitlin! We were so happy to host you and your group at Sunset Serenity! Join us again for another stay! - Cathy
From a partner site
10/10 Excellent
Gail F.
27 Sept 2024
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.
Gail F.
Stayed 3 nights in Sep 2024
Response from VrboOwner on 3 Oct 2024
Hi Gail! Thank you for being a great guest & we welcome you back anytime! Thank you for sharing your positive feedback, we sincerely appreciate knowing you enjoyed your time in the home, Melissa~iTripAnnapolis
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!
Kate G.
Stayed 2 nights in Nov 2022
Response from VrboOwner on 20 Sept 2023
Thank you Kate! We hope you come back and stay with us again at Sunset Serenity! - Cathy
From a partner site
10/10 Excellent
jerome r.
7 Mar 2025
Amazing stay
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.
jerome r.
Response from VrboOwner on 10 Mar 2025
Hi Jerome! Thank you for allowing us to host your stay & we are thrilled to know you enjoyed your time in the home! We welcome you back anytime, Melissa~iTripAnnapolis
About the host
Hosted by iTrip Vacations Annapolis - Sean Degnan
Languages:
English
Premier Host
They consistently provide great experiences for their guests