Vacation rentals with a kayak in Somerset County

Excellent, beautiful and clean house, we recommend to anyone who’s looking for a high end stay. Our host was amazing, friendly and very supportive.

This house is truly a hidden gem on the island. It’s fully stocked and beautifully furnished, catering to all types of travelers—whether you’re an adventurer looking to explore or someone like me who enjoys relaxing at home. Everything you could possibly need is right here, making it perfect for a peaceful getaway or an unforgettable vacation. I absolutely loved my stay and can’t wait to return in the near future!

Our stay at Dominic’s place was absolutely fantastic. The house was spotless, had incredible views, and included everything we needed to enjoy our stay. Dominic was very responsive and provided suggestions on local area activities and restaurants.

Beautiful home on Tangier Sound. Equipped with so many extras…kayaks, paddle boards, beach chairs, etc, etc and a nice crab steamer! Hosts thought of everything. Lots of little extras . Nature lovers who appreciate the Eastern Shore of Maryland and the Chesapeake Bay with its beautiful marshes, beaches and quiet solitude will love it here. There is a great little restaurant 1.3 miles away with great crab cakes and orange crushes. Pit and Pub at Goose Creek Marina. Our weather was perfect and the beach was delightful! Hope to visit again!

Cozy, quiet, cute and super clean, I loved Homestead Cottage. I became incredibly spoiled by a fresh baked treat being left at my door each morning. I loved walking in the cool shade of the giant, ancient magnolias imagining what it would have been like approaching Clifton, through the brick gates, 200 years ago. I spent quite a bit of time at Racoon's Point, a little bit of local bay beach 1/4 mile away. I think the pool setting is so lovely and many days after a swim, in the golden light of the late afternoon I would walk to a spot just on the water where a group of Adirondacks have thoughtfully been placed and bask (with a glass of wine & little snack) in the magic hours of fading light. Very nice reset. I loved talking with the burros, and saying good mornings with the hens and geese. I loved the comfort of my bed and many thoughtful things. I so appreciate all that must happen, all the work that goes into creating such a soothing to the soul, place and I thank you.

Have been to Smith Island many times and always rave about t. Locals are very helpful to visitors. Great kayaking ! Will return again next year! Michelle and John are terrific hosts !

The place was beautiful, inside and out! Chris was very helpful and responsive. Lots of fun games to play. The kids loved the loft. Everything in the house worked and functioned well. It was clean, comfortable and well-stocked. Can't beat that view!!

It's sometimes difficult to find a place that accepts dogs & is reasonably priced. Tim allowed us a very early check-in to accommodate our needs and we truly appreciate d it. I'd readily recommend his place. One of the better airbnb places AND they accept dogs. A winner all around!!

I think this'll become an annual retreat. The cottage is lovely, the location gorgeous and quiet, all the amenities we could want in the kitchen. Chelsea is a wonderful host, communicating about all the details of access and amenities. it's a hidden gem, perfect for a romantic weekend, family holiday or solo retreat. The sunrise and sunsets are unparalleled.