Holiday rentals in Caroline County

Harold and Ashley were a peach to work with. Pleasure to stay in the home and most definitely would revisit if applicable.

We really enjoyed our stay at Steven’s River house on the Choptank River. I appreciated the beautiful, peaceful atmosphere while sitting on the back deck! The home is clean, open and very comfortable. Steven was always quick to answer emails and we would love to stay again should we come back to the area!

If you are staying in the area, Cindy’s place is absolutely the place. Cindy is a friendly, gracious host who lives nearby, is willing to chat, but is not the least bit intrusive. The house is as clean as could be, beautifully furnished, comfortable, excellent bedding and linens. It is decorated with some of Cindy’s beautiful quilts — she is far too modest about them, they are lovely. I hope to stay there again!

This historic property in Maryland is an amazing find. The property is a lovely two plus acres with many cozy retreats to stop and take in the wonderful trees. If you want a more rigorous outdoor experience, there is a lovely park 5 minutes away and a larger area with an arboretum about 15 minutes away. It is an easy walk into downtown which has several restaurants. The hosts have thought of everything, and I do mean everything. The character of the house is exceptional, but it is comfortable not stuffy. Lots of amazing artwork and books throughout. The kitchen is fully stocked and comfortable to eat or cook in. The rain shower in the bathroom was delightful and the beds are comfortable. It was a perfect place to have a mini family reunion for a few days. We will be visiting the house again

Relaxing retreat vibes. A beautiful place to getaway and disconnect from everything. The hot tub was wonderful and the house is gorgeous. Exactly as pictured! Took a trip to Rehobeth beach and it was so fun!!

We stayed in January 2025 for a family gathering with 6 adults and 6 kids (ages 5 months to 8 years). The house is lovely and we enjoyed cooking in the beautiful kitchen and sitting by the fireplace. Although the yard and play structure were covered in snow, the kids enjoyed it all anyway including roller skating and scootering on the long driveway. Our host was very responsive to a few issues we encountered. Something to know about the bunk room--you must go through the garage to get to it. It was fine for our purposes. The beds and linens were all very comfortable. The shower and bath in the primary bedroom was a treat.

This place is a must stay for any hunters coming to the area to take advantage of the great waterfowl and deer season. I’ve been hunting in Centreville for over 10 years and will stay here every year moving forward if the property is available. My group loves to cook and the kitchen here is perfect to make (and eat) a large meal as a group. I couldn’t be happier with my stay and will be coming back again.

Carrie’s house was beautiful, peaceful and everything we were looking for!!! We will definitely stay there again.