
Holiday rentals with a kayak in Somerset County
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Top-rated rentals with kayak in Somerset County
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House rentals with a kayak

The Hideaway
This is really a beautiful house, with a great location and with lovely views of the water, fully outfitted, comfortable beds, and lots of special spaces to relax. The perfect place for a holiday weekend for us and our friends. Stephen has thought the whole thing through. We had a lovely time and would return any time.

Beautiful Bayfront with Sanctuary Private Beach
This home was the ideal setting for our bachelorette getaway. We thoroughly enjoyed the serene waterfront, and having access to the kayaks added a unique touch to our stay. The living room, with its expansive and open layout, was perfect for gathering and enjoying board games together. Thank you for the warm hospitality and for sharing your beautiful home with us!

The Salt Marsh Shanty
A very comfortable home in a gorgeous setting. The marsh out back is like a small private nature preserve. I spent lots of time watching the bird life and the changing light, as well as the easy kayaking at the doorstep. No noise save for birdsong, and I saw hummingbirds, bald eagles, and lots in between. The house is new and very clean with a well-stocked kitchen and room to unwind. The hosts are thoughtful and provide equipment/supplies to enjoy the water and related activities.

Creek House - Luxury Waterfront on Holden's Creek
We all really enjoyed our stay. We had a great time making and eating our meals, sitting on the various porches watching the creek and all the birds, exploring the grounds, and using the canoe. The peace of the place was wonderful. We especially enjoyed watching the two ospreys nesting across the creek. Allysin stopped by to check on us and was very friendly and welcoming. She was very appreciative of the feedback we provided about a relatively minor issue with the water pressure on the main floor. If we visit the area again, we will definitely consider staying again.

Historic Hoopersville Getaway on Chesapeake Bay!
Our group of eight had a very lovely weekend. It is an older house with a few quirks here and there but was overall clean and comfortable in a terrific remote setting. Good kitchen with an amazing view of the water. The owner Marc was extremely responsive and accommodating, and gave us several suggestions for things to do in the area.

Private Beach & Fishing Pier: Wicomico River House

5 bedroom waterfront retreat with private dock

Heaven on the Bay - A Peaceful Waterfront Retreat
Cottage rentals with a kayak

Dog-Friendly Westover Cottage w/ River Access!
we enjoyed a lovely stay at this charming riverside cottage. We loved the beautiful surroundings, privacy and stocked accommodation. It was a great spot to get away and also visit Chincoteague and Assateague. Kelly was an amazing host, attentive and responsive throughout to ensure we had an enjoyable stay. We hope to visit again and highly recommend.

Levering Creek Cottage with Private Dock
The house was wonderful -- clean, simply furnished, a more-than-adequate kitchen and bathroom. Beds extremely comfortable. The pictures suggest the back yard is on the water....there is actually a house behind Janet's house. BUT, there is an easy-to-access dock that was just wonderful. The single negative? The bugs!! Not anything controllable by others, of course, but did discourage us from the walking of the island we hoped to do. The end of the dock was our refuge -- and the view was just wonderful. Birds plentiful. The people of Smith Island were welcoming, gracious, patient. No exceptions. I am grateful they offer such hospitality.

IDLEHOUR, 3 BEDROOMS 2 BATHS W/ DOCK
This was our 2nd stay on the island , but first time at Mary Kim's. Great hospitality including home cooked egg rolls that made the long journey even more worth it. The only downfall would be the dock and kayak spot is a couple doors down, but Mary Kim was very communicative. lastly, I highly recommend the golf cart service on the island, gives you more of an ability to explore the island.

Private Beachfront Cottage with 2 Bedrooms + Loft
Our family had such a lovely vacation in a great location. We made so many memories and enjoyed the beach and water everyday. Chelsea was a very responsive and accommodating host. So happy to have chosen their place for our vacation. The only draw back was the bugs but we were fully aware that they would be there as it was made very clear in the listing and in the reviews and it wouldn’t have changed our minds and we would love to visit again.

Waterfront Cottage in Mt. Vernon
We had an amazing stay at Melanie’s waterfront home! The location was absolutely perfect right on the water with stunning views and peaceful surroundings. We loved having access to the kayaks, grill, and outdoor furniture it made it easy to relax and enjoy the beautiful setting. The house was fully equipped with everything we needed for a comfortable stay, and the neighborhood was quiet with super friendly neighbors. Melanie was a fantastic host thoughtful, responsive, and even left us a list of local restaurant recommendations, which turned out to be excellent! This spot was exactly what we were looking for, and we’re already looking forward to coming back. Highly recommend!

Rumbley Cottage on the Tangier Sound-Private Beach
Very nice house with beautiful views. Would highly recommend anyone renting this location. Multiple options for water activities located right at the house (kayaks, stand up paddle boards, etc.).
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- Chesapeake Bay
- Ocean City Beach
- Assateague Island National Seashore
- Ocean City Boardwalk
- Jolly Roger Amusement Park
- Bayside Resort Golf Club
- Northside Park
- Jolly Roger at the Pier
- Assateague Beach
- Haven Beach
- Snead Beach
- Heritage Shores
- Ragged Point Beach
- Plantation Lakes Golf and Country Club
- Gerry Boyle Park
- Wallops Beach
- Trimper Rides of Ocean City
- Oxford Beach
- Assateague State Park
- Piney Point Beach
- Lane Beach
- Gargathy Beach
- Guard Shore
- Parramore Beach