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

Home in Deal Island Historic District
New place to stayThe Hideaway
WilliamRating, 5 stars2 weeks ago
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.

Home in Deal Island Historic District
4.67 out of 5 average rating, 3 reviewsReel Relaxation-Waterfront
ChristineRating, 5 stars1 month ago
Our stay at Reel Relaxation was nothing short of wonderful. Our family of 5 had such a relaxing and enjoyable spring break there and the home exceeded our expectations. Not only was the home location beautiful because it was right on the water but Holly had kayaks for us to use, crab traps (which my kids were enthralled with), bikes, a fire pit (that was already filled with wood and read to go!), a hot tub, and lots of board games in the house. The home itself was spotless and had all of the amenities (and more!) that you would want/need. The only drawback is it is a solid 30-40 minutes to get to any type of food store, restaurant, etc. but that is just a result of the location itself. We would go back in a heartbeat though because it was the perfect remote get-away and the view/access to the water right off the dock was amazing. Highly recommend!

Home in Westover
New place to stayThe Salt Marsh Shanty
NicoleRating, 5 stars2 weeks ago
This is a special house and my kids and I felt immediately at home. The marsh is otherworldly beautiful and we appreciated the access to the kayaks, crabbing equipment, and grill. The sun rise and sunset alone were worth every penny. We gave already decided we want to make it a place we go to throughout the year!

Home in Temperanceville
Creek House - Luxury Waterfront on Holden's Creek
RebeccaRating, 5 stars1 month ago
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.

Home in Hoopersville
4.57 out of 5 average rating, 23 reviewsHistoric Hoopersville Getaway on Chesapeake Bay!
JenniferRating, 5 stars9 months ago
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.

Home in Princess Anne
Private Beach & Fishing Pier: Wicomico River House

Home in Westover
5 bedroom waterfront retreat with private dock

Home in Westover
New place to stayHeaven on the Bay - A Peaceful Waterfront Retreat
Cottage rentals with a kayak
Guest favorite

Cottage in Westover
4.83 out of 5 average rating, 35 reviewsDog-Friendly Westover Cottage w/ River Access!
MarthaRating, 5 stars1 week ago
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.
Top guest favorite

Cottage in Smith Island
4.97 out of 5 average rating, 228 reviewsLevering Creek Cottage with Private Dock
kathyRating, 5 stars3 days ago
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.
Top guest favorite

Cottage in Smith Island
5 out of 5 average rating, 51 reviewsIDLEHOUR, 3 BEDROOMS 2 BATHS W/ DOCK
MelissaRating, 5 stars7 months ago
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.
Guest favorite

Cottage in Deal Island Historic District
4.95 out of 5 average rating, 85 reviewsPrivate Beachfront Cottage with 2 Bedrooms + Loft
SuzanneRating, 5 stars3 days ago
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.
Top guest favorite

Cottage in Princess Anne
5 out of 5 average rating, 7 reviewsWaterfront Cottage in Mt. Vernon
ChristinaRating, 5 stars1 week ago
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!
Top guest favorite

Cottage in Westover
4.99 out of 5 average rating, 226 reviewsRumbley Cottage on the Tangier Sound-Private Beach
PattyRating, 5 stars1 week ago
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
- Parramore Beach
- Gargathy Beach
- Guard Shore