Caroline County Holiday Rentals

"We sought a large home for a special family birthday, with multiple bedrooms, roomy eating and living areas, and water access for recreation. This house met all our requirements and more. Our grandchildren, from teen to preschool, loved the multiple kayaks, the crab traps, roasting marshmallows at the fire pit, swimming in the heated pool, finding oyster shells along the shoreline. We visited Annapolis for a sail and sightseeing, even though it meant driving back over the Bay bridge, and we...

"Great location. House is old and therefore a little quirky, but overall comfortable. "

"The room and location were perfect. Very clean and comfortable space to stay and right in the heart of town. "

"Born and raised in this area. Just back to visit friends and family. Staying at grandmas cottage felt like just that. Thanks. "

"Comfortable beds, meticulous details of EA Poe throughout, walking distance to adorable Dolce’ for coffee and pastries, and lovely Milford charm are a few of the outstanding qualities of this home away from home. "

"Great House "

"Gorgeous views and location. "

"This our second time staying here and we absolutely love it! Looking forward to staying here again in May 2026. "

"Wonderful home in excellent location!!"

"I booked this house for the property, the backyard, the dock, and it didn't disappoint. It's also about 20 mins from the main town (Cambridge) which was exactly what we wanted - a break from crowds and the bustle. We had such a relaxing few days just reading, fishing from the dock, and kayaking. We were four people, but this would easily fit two families. A wonderful stay overall."

"My kids and I absolutely loved our stay at the Outlook! So peaceful and relaxing. We spent a lot of time walking around the trails spotting deer and toads. We did a good amount of fishing on the dock, catching catfish. I hope to stay here again in the future."

"This is a beautiful property, well appointed, but not too formal for families wanting to be in the pool or on the water all day. We were a party of 12 including six grandchildren. There was plenty to do for the adults and the grandchildren and plenty of space in the home to not feel like you were on top of each other. The sunsets were spectacular. Marissa is an extremely responsive host, and all our questions were answered in a timely fashion. Saint Michaels is very close by and an absolutely...