Holiday houses in Taylors Island

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!

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!

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.

This cabin was everything we wanted and more! It’s in the perfect location, just a short drive to so many activities but also tucked away offering privacy. The house was so cozy it put us at ease as soon as we walked in. The owner was proactive and very quick to respond, including sending a great packing and local activity list a couple days in advance of our trip which came in very handy. Activities: This rental comes with guest passes to the private Shark Tooth Beach where our kids had so much fun finding real shark and manta ray teeth in the sand! Westmorland State Park and George Washington’s Birthplace both had great hiking and beaches for the kids. We visited Garners Produce twice where the kids fed animals and pedaled toy tractor’s while we picked up farm fresh milk and eggs. We spent our afternoons kayaking on the quiet lake soaking up the sunshine. We will definitely book another vacation at this cabin. You will not be disappointed with your stay at this little gem!

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

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!

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.