Holiday rentals in Shady Side

Perfect Stay in Deale, MD I had a fantastic stay at this beautiful waterfront home on Carr’s Creek. The hosts were incredibly attentive and made sure I was comfortable the entire time. We had snow during my stay, and they had the driveway and sidewalks cleared almost immediately after it stopped—such a thoughtful touch! The views here are stunning—pictures don’t do this place justice. It’s peaceful, quiet, and in a friendly neighborhood where I felt completely safe. It’s also super convenient, close to great food and anything else you might need. The house felt like home—spacious, welcoming, and fully stocked, especially the fantastic kitchen. Whether cooking, bird watching, soaking in the hot tub, or taking in the view, it was the perfect getaway. If you’re looking for a peaceful escape with family or loved ones, I can’t recommend this place enough!

Heather’s place is a little paradise on the water. Peaceful, quiet, and perfect for some real rest and relaxation. The house was exactly as described—spotless, all new, and super comfortable inside, with beautiful outdoor spaces to enjoy. Annapolis is just a short 25-minute drive away if you’re looking for great food and things to do. Communication with Heather was easy and fast. I’d come back anytime I’m in the area again!

Perfect location for a quiet, relaxing getaway. Everything about the stay was perfect and exactly as described/expected. We alternated between cooking in the AMAZING kitchen and eating at host recommended restaurants in North Beach. The house is located close enough to town if you choose to eat out (barely 5 minutes) and an acceptable drive to major grocery stores (15 minutes) if you opt to cook a few meals. The house was spotless. Hosts are super responsive and incredibly nice. Highly recommend staying at Bell Estates. Thank you, Daniel, for the perfect long weekend with my family!

The place is wonderful. We were down for Thanksgiving with my family and were travelling with our 2 dogs, Wally & Dolly. The location was perfect, close to Riviera Beach where our Family Thanksgiving Dinner was, very private, no noise or distractions for the dogs (that was great). The property was surrounded by water on three sides, great views! It is right next to Ft. Smallwood Park where we took the dogs for walks every day, they loved it. As for the house it was perfect for us, just about the size of our home, so that made it very comfortable for us. All one level, which made it great for us older people. It was furnished with very comfortable furniture. Lots of information about the local surroundings, things to do, and restaurants. Keith was wonderful to work with, very easy to communicate with which made the whole process very easy for us. We even had a conversation over the phone once we were in the house to make sure everything was to our liking, and we were happy !

It’s super cute, quaint and has such character. Something for the whole family we will be back.

Great place and nice host. Would stay again definitely worth the price. The property was awesome, great place for a fire pit and barbecue.

Most of the time I travel with just my family but sometimes we get to travel with our labor team also. Angel and Ryan offer great accommodations for all of us. Safe relaxing, spacious and great water pressure!!! We needed extra blanket because it was colder for April the night we were there and Ryan went out of his way to make it work for us. Our team was a mix of needs and they had something for all of us. They care for their house a little extra because it has a few live thriving plants what a great way to provide the true home feeling we so appreciate after hard work and long travels. The neighbor is great ! To accommodate all my teams needs I slept on the daybed and it was actually comfortable. All slept well. Thank you much Definitely worth the short drive out of DC.

Cheryl’s stay was so peaceful, comfortable and fun — even before pool season started. We could not believe how large the yard was and how quiet it was. Amazing wildlife. We saw bald eagles, heron, geese and lots of ducks! The house was squeaky clean and had everything we needed. We watched the stars at night and slept soundly. Downtown St. Michael’s is only about 10 minutes away and full of fun things to do. We’re so happy to be acquainted with the area after staying at Cheryl’s!

Excellent host! Great communicator and went out of her to make sure we didn't have any issues. Lovely place for a family get away!