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Serene Sunsets at Historic Waterfront Home

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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 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.
A covered outdoor deck with a view of a lake and grassy area.

Reviews

9.6 out of 10
Exceptional

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

Popular amenities

  • Balcony or patio
  • Barbecue grill
  • Free internet
  • Air-conditioning
  • Kitchen
  • Refrigerator

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

Add dates for prices

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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.
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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
  • Navy-Marine Corps Memorial Stadium - 16 min drive - 7.9 km
  • U.S. Naval Academy - 17 min drive - 7.6 km
  • Annapolis City Dock - 18 min drive - 7.9 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
  • ‪Grump's Cafe - ‬7 min drive
  • ‪Adam's Grille & Taphouse - Edgewater - ‬13 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 24 Oct, 2026, prices found for a 1-night stay for 2 adults at Serene Sunsets at Historic Waterfront Home on 1 Dec, 2026 start from S$1,669, 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 Spa Creek. Dr. Aris T. Allen Memorial and People's Brewer Hill Cemetery 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 33 out of 39 reviews
Rating 8 - Good. 4 out of 39 reviews
Rating 6 - Okay. 2 out of 39 reviews
Rating 4 - Poor. 0 out of 39 reviews
Rating 2 - Terrible. 0 out of 39 reviews

9.4/10

Cleanliness

9.8/10

Check-in

9.6/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful and unique heritage home with amazing outdoor patio and views! Lots of grass for little ones to crawl and run around.
Stayed 3 nights in Sep 2026
Response from VrboOwner on 15 Sept, 2026
Thanks, Rick! Please come back soon and stay with us again.
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy
Property was great, the floors were slightly
Stayed 4 nights in Aug 2026
Response from VrboOwner on 21 Sept, 2026
Thanks, Christelle. We hope we can host you again soon.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had an amazing stay at Serene Sunsets. Perfect getaway for our girl trip. This place has a lot of old charm with some updates. Beds are comfortable. Sunsets are to die for. Giant Frog winery within walking distance was a fun bonus. If they added a hot tub to this property it would take it over the top. It can be a little tricky to find the house in the dark since there is no clear marking on the road. Would totally stay again.
Stayed 5 nights in Sep 2026
Response from VrboOwner on 2 Oct, 2026
Thanks, Liv. We are so glad you enjoyed everything a d we hope we can host you again soon.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
This is a little piece of heaven
Stayed 3 nights in May 2026
Response from VrboOwner on 9 Jun, 2026
Thanks, Kat! Hope you’ll come back and stay with us again. Sean, iTrip Annapolis
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect place for a family long weekend getaway! Very relaxing location, clean, comfortable, and beautiful.
Stayed 3 nights in Jul 2025
Response from VrboOwner on 30 Jul, 2025
Thanks, Valentina! We welcome you back again any time! Sean, iTrip Annapolis
Verified review

10/10 Excellent

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
Response from VrboOwner on 3 Nov, 2023
Thanks, Alan. We look forward to hosting you again! Sean
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
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
Verified review

10/10 Excellent

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
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
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
From a partner site

10/10 Excellent

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.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Peaceful and beautiful

Comfortable and enjoyable in a beautiful setting
Stayed 6 nights in Apr 2023
Response from VrboOwner on 20 Sept, 2023
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
Verified review

6/10 Okay

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
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
Verified review

10/10 Excellent

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
Response from VrboOwner on 22 Jun, 2024
Hi Elizabeth! Thank you for your positive feedback & I am happy to hear you enjoyed tour stay! We welcome you back anytime!
Verified review

10/10 Excellent

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
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
Verified review

10/10 Excellent

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
Response from VrboOwner on 20 Sept, 2023
Thank you Tara for the kind review of Sunset Serenity. Please come back and stay with us again. Safe Travels! -Tiffany
Verified review

10/10 Excellent

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
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
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

sunset serenity

Sunset serenity is the perfect description
Stayed 6 nights in Mar 2024
Response from VrboOwner on 11 Apr, 2024
Hi Douglas! Thank you for your positive feedback. We welcome you back anytime, thank you, Melissa~iTripAnnapolis
Verified review

10/10 Excellent

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
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

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.
From a partner site

10/10 Excellent

Family Fun

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

10/10 Excellent

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
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
From a partner site

10/10 Excellent

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
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
Verified review

10/10 Excellent

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
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
Verified review

10/10 Excellent

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
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
Verified review

10/10 Excellent

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
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
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