Vacation rentals with a kayak in Somerset County

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Top-rated kayak rentals in Somerset County

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Home in Smith Island

5 out of 5 average rating, 8 reviews

Double H Ranch on Smith Island

Relax in this 1910 era Smith Island home. Has one large upstairs bedroom with second twin bed separate from main bedroom. Comfortable family room with seating for 5. Enclosed patio is ideal in the summer. Large kitchen fully stocked to cook your meals. Large bathroom with newly installed shower. Also new washer/dryer. Easy access to the water. Kayaks and bikes are available in the shed. Island is only accessible by boat. Enjoy the tranquility of this unique place. Truly a special place.

Superhost

Home in Crisfield

4.79 out of 5 average rating, 109 reviews

Home of the Terrapin King

The LaVallette House is where the Maryland terrapin originated! Albert Tallmadge LaVallette Jr. launched the terrapin soup industry from this very site in 1887 (you can still see the old terrapin pins beside the driveway). In addition to the property’s historic charm, the location just can’t be beat. The five-bedroom house is completely private. Guests have to drive through wetlands to get to it, and the only neighbors in close proximity are the gulls and the fish in the Chesapeake Bay.

Guest favorite

Home in Smith Island

4.96 out of 5 average rating, 52 reviews

Island Time (whole house rental)

3 story home with 2 wrap around porches. One first floor room and three second floor rooms-including a master suite. The third floor is a loft with sleeping for 5 and a full bath. Breathtaking views of sunrises and sunsets. Life on the island is laid back. Visit us to get away from the fast pace life. We offer complimentary bikes, kayaks, fishing poles, crab nets, porch swings, hammock, hot tub, etc. Golf Carts available for rent. Breakfast and STEAMED CRABS are available for a charge.

Guest favorite

Cottage in Westover

4.99 out of 5 average rating, 205 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

Winter time is a great time at Rumbley! Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all window. Look out to the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Wifi, Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

Guest favorite

Farm stay in Westover

5 out of 5 average rating, 57 reviews

The Homestead at Sugar Water Manor Farm Stay

The Homestead at Sugar Water Manor sits on nearly 70 acres of farm and woods on the Manokin River. Guests have full access to the property including kayaks, the pool and can make arrangements to enjoy the farm crew, collect eggs & harvest for your meals. A breakfast treat will be delivered for your breakfast. It has the best sunset views from it’s screened in porch. With views of the river, garden and farm you will not know where to look first. No WiFi/TV or smoking on property

Cottage in Westover

4.94 out of 5 average rating, 17 reviews

Dog-Friendly Westover Cottage w/ River Access!

Located on the shores of the Big Annemessex River, this charming Westover vacation rental cottage offers expansive views of the water and access to local adventure! The riverfront deck is perfect for grilling up a meal, while the screened-in porch is an ideal spot to unwind with your crew. Ready to explore? Check out local parks or take your boat out on the water. Featuring 2 bedrooms, 1 bathroom, a loft, and a fireplace, this Maryland property is the perfect retreat!

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Home in Saxis

4.77 out of 5 average rating, 39 reviews

Beautiful Bayfront with Sanctuary Private Beach

Seaside Sanctuary welcomes you to your own private hideaway. Scenic, stylish & SO well stocked: This listing includes parking, WIFI, smart TV, a PRIVATE BEACH, board GAMES, books, BEACH CHAIRS+UMBRELLA, and a fire pit. Enjoy being AWAY FROM CROWDS, but only 23 miles to popular Chincoteague Island. Seaside Sanctuary provides everything you could ever need for a great vacation! Let your stress go away with a beautiful sunset and sunrise; a stroll on the beach.

Guest favorite

Cottage in Westover

4.93 out of 5 average rating, 171 reviews

Heaven on the Bay - A Peaceful Waterfront Retreat

This Chesapeake Bayfront cottage has spectacular views to take you away from everything in any season. It boasts more than 120 feet of waterfront, and you can dangle your feet off the 70 ft “dock of the bay”. Launch kayaks from the small sandy beach in summer, or cozy up to the wood stove in the winter. Inside, you’ll find wood floors throughout, modern kitchen & baths with bay views from every room. Kayaks, SUP, bicycles & crab traps too!

Guest favorite

Cottage in Smith Island

5 out of 5 average rating, 50 reviews

IDLEHOUR, 3 BEDROOMS 2 BATHS W/ DOCK

Unwind and relax after a busy life in the city. Get comfortable and enjoy plenty of extra room at this spacious place. Awake refreshed and ready for a day of kayaking, bicycling and or exploring the island. We have a deep water dock (4 houses down from the house) for crabbing, launch the kayaks, boat mooring or just relaxing. A large hot & cold outdoor shower for that nature experience.

Guest favorite

Home in Westover

5 out of 5 average rating, 10 reviews

Rumbley Retreat

**Fisherman Welcome!!! Private dock/ minute boat ride to good fishing in the Manokin!! (We now have WiFi!! ) Welcome to our peaceful retreat on Goose Creek. Relax and unplug with family and friends, while enjoying beautiful waterfrontage. House comes with private dock across the street which allows you to dock your boat and truly enjoy being on the water!

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Home in Westover

4.94 out of 5 average rating, 31 reviews

Private beach with comfort

Relax with the whole family at this peaceful place to stay. Fantastic waterfront home.Your own very private location with your own sand beach. Perfect for family get away with water activities, swim,fish,Kayak etc.This home has a Handicap ramp and a Walk in shower with small curb for anyone who needs.

Guest favorite

Guest suite in Deal Island Historic District

4.9 out of 5 average rating, 105 reviews

Private guest suite near Deal Island Maryland

Nothing extraordinary here. What I have available, at a reasonable rate is a clean private suite. With self check-in using kwikset smart code touchpad electronic deadbolt. Private driveway with plenty of room for your truck and boat. Room and deck are handicap accessible using entry ramp or steps.