Holiday rentals in Shady Side

Such a beautiful location with a wonderful view, I came for a staycation just for the night and it was absolutely worth it and exactly what I was looking for. I can’t wait to come back in the warmer months!

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!

The house was quaint and comfortable. It would be perfect for a family with younger children. It was easy to find and so nice to wake up so close to the beach.

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!

We thoroughly enjoyed our stay at this AIRBNB. It was walking distance to a nice Mexican Restaurant as well as to a brewery. We spent hours on the front porch in the nice rocking chairs. The back of the property overlooked the water which was beautiful! It was close to everything in town! The house was clean and had all of the necessities. We also enjoyed the front sitting area during the morning. The owner was responsive and helpful! We would definitely recommend this property.

Michael's place was perfect for our spring break getaway. I really liked the laid back beach vibe and how kid friendly the house was. The kids were able to walk to beach themselves and had a great time on the trampoline! We loved seeing who could find the most shark teeth.

This apartment was perfect for our family get together. Although we had a short stay, every detail made us feel very welcome. Michelle was very helpful and promptly mer our needs.