Tucked between the Chesapeake Bay and 500 acres of state park, this round house sits on a peninsula with panoramic views to indulge the senses. Listen to and photograph eagles, ospreys, and songbirds just to name a few. Less than an hour from DC, and 35 minutes to Annapolis, this get away is great for adventures in the city, or as an idyllic space for teleworking. Relax, play, and take it all in.
Enjoy our 2 story, 3 bedroom, 2 bath, and wrap around deck with panoramic views of the Chesapeake Bay. We have two outdoor security cameras overlooking the house entrance and parking.
Our prices include all fees. No hidden fees.
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Lovely bay views with kayaks, bikes, fire pit, crabbing & more
Shady Side
Lovely bay views with kayaks, bikes, fire pit, crabbing & more
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 indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
About the neighborhood
Shady Side
Located in Shady Side, this vacation home is on the waterfront. Chesapeake Bay and Franklin Point State Park reflect the area's natural beauty and area attractions include Chesapeake Beach Water Park and Chesapeake Beach Railway Museum. Wild Bird Center and Maryland Hall for Creative Arts are also worth visiting. Kayaking, motor boating, and sailing offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails nearby.
Galesville Heritage Museum - 14 min drive - 15.1 km
Getting around
Easton, MD (ESN-Easton - Newnam) - 80 min drive
Restaurants
Bayside Bull - 19 min drive
7-Eleven - 11 min drive
Jesse Jay’s - 8 min drive
Dunkin' - 19 min drive
Skippers Pier Restaurant and Dock Bar - 14 min drive
Frequently asked questions
Is Round House -- Panoramic Views -- Chesapeake Bay pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Round House -- Panoramic Views -- Chesapeake Bay?
As of Jun 27, 2026, prices found for a 1-night stay for 2 adults at Round House -- Panoramic Views -- Chesapeake Bay on Jun 28, 2027 start from $632, 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?
Onsite parking is available at the property.
What time is check-in at Round House -- Panoramic Views -- Chesapeake Bay?
Check-in begins at 3:00 PM.
What time is check-out at Round House -- Panoramic Views -- Chesapeake Bay?
Check-out is at 10:00 AM.
Where is Round House -- Panoramic Views -- Chesapeake Bay located?
Situated on the waterfront, this vacation home is steps from Chesapeake Bay and Northern Chesapeake Bay. Franklin Point State Park and Shadyside Park are also within 3 mi (5 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
We had a wonderful spring break 3 day getaway at this hidden gem. Sarah was so accommodating and sweet. The house was spotless and beautifully kept! No complaints at all.
We look forward to visiting again soon!
We celebrated our daughter’s 30th bday at this beautiful home. The view and wildlife sightings did not disappoint. Our host was very helpful in providing recommendations on food and activities that made our trip great. This is a great house, inside and out!
Susan M.
Stayed 2 nights in Jun 2022
Response from VrboOwner on Jun 26, 2022
So glad you all had a good time celebrating!! You all are welcome back anytime!
The Round house is tranquil and relaxing. Everything you need for a quiet get away with amazing views of the bay. Beds are comfy and well appointed. We have 4 kids ages 6-10 and they all enjoyed the games and books and riding their bikes around the gated community.
Friends since childhood, we are all turning 50 this year. This home has an amazing view, is great for hanging out and catching up. The rooms and layout were really comfortable. The deck was great. We really enjoyed our stay. Great restaurants in Deale are 15 minutes away. Highly recommend. Host was great.
Andrew M.
Stayed 2 nights in Jun 2022
Response from VrboOwner on Jun 23, 2022
So glad you all enjoyed your stay! You all are welcome back anytime!
In a quiet community, this place has wonderful marsh and bay views, and great rooms and outdoor deck space to view from. Bird life was fun to watch (Osprey, geese, ducks, blackbirds, bluebirds, etc.) Well furnished, with comfortable beds, and well-equipped kitchen. Heating was quiet and well controlled. Plenty of good work spaces if you need to work from "home." Sarah was quick and helpful in her communications with us. Wonderful getaway from DC (only an hour drive) for the four of us (though the house would also be comfortable for more than four).
Enjoy views of the bay from the amazing deck! We were able to see eagles and osprey fish for their meals.
The gated community offers a park with 2 piers and a playground for your children. We had the opportunity to watch a pod of dolphins swimming and a fisherman catch a stingray.
The deck is a great way to start your day sitting and sipping on your coffee.
This home won’t let you down. It checks off everything on your vacation list.
Ann Marie H.
Stayed 5 nights in Jul 2022
Response from VrboOwner on Jul 26, 2022
So glad yall had such a lovely time! Please visit us again!
We had a wonderful stay at this lovely house! The neighborhood is charming and quiet and the house itself is situated at the end of the street, with beautiful views. It looks exactly like the photos online and was very clean - plus it had tons of stuff already there for us (like soap, detergent, etc. and spices and some condiments in the kitchen). Loved that there are multiple sitting areas, and the bathrooms are huge, so it never felt cramped. Sarah quickly responded when we had a few questions leading up to our stay. Several friends and I wanted a house where we could just chill and enjoy the views and this fit the bill perfectly, we're already talking about returning in the future :) Thank you!
A wonderful light filled home with spectacular views out over the Chesapeake Bay. The resident fox, birds and bunnies were a nature lovers delight. Peaceful quiet neighborhood. The house was updated and comfortable with a Zen vibe. Enjoyed our stay here very much.
It was lovely to strategically schedule a weekend oasis of peace by the bay in the middle of our bustling DC vacation. It allows those of us who wanted the excitement of the city to have it and those of us who needed the peace of beauty and relaxation to experience it. We are grateful for the space and time and location. All was lovely.
This house was everything we could have asked for and more. It was beautiful inside and had gorgeous views. It was quiet and you feel like you are alone on an island but with every amenity you’d like. We will definitely return! Thank you!
My wife and I enjoyed our wedding anniversary weekend in Shady Side. The property was just as described. Very nice furnishings and all essentials (kitchen, bath, etc.) were taken care of by the owner. The best part of the property is the unique building design which grants you wonderful views of the Bay and wildlife. Special place!
We had a great time and thoroughly enjoyed the house. The views and location were amazing. We had many bald eagle sightings along with a fox and her kits playing in the neighbor's yard. Would highly recommend.
Love to travel and spend time on the water. Spouse and I spilt our time between D.C. and Shady Side. Hope to share our love and appreciation of the Chesapeake Bay with others!
Why they chose this property
Instantly fell in love with the views through the windows!
What makes this property unique
Offers stunning 180 views of the bay. House is on stilts so the view from up here is phenomenal!