Vacation rentals with a kayak in Worcester County

Two kayaks are positioned on the grassy shore, ready for use on the calm waterway. Bright paddles rest on each kayak, with the inviting waterfront location featuring docks and homes in the background. A propane grill is nearby, adding to the outdoor leisure atmosphere.

4.95 out of 5 average rating, 255 reviews

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

Superhost

Colorful armchairs with a fish pattern provide comfortable seating by large windows that offer views of the water and surrounding nature. A small green side table stands between the chairs, adorned with a vase of flowers.

4.82 out of 5 average rating, 28 reviews

The Oliver House

This property boasts breathtaking views of the Ocean City skyline and is nestled in a quiet neighborhood in West Ocean City. Bring your boat, paddle boards, kayaks and firewood for the most incredible vacation. Crabs and clams are plentiful and the kids can enjoy playing in the small beach area while splashing or swimming in the bay. Although you may never want to leave, it's a short drive to Ocean City's beaches and boardwalk, Assateague Island and the quaint must-see town of Berlin, Maryland.

A back deck features a seating area composed of a sofa and ottoman with soft cushions, facing a calm canal. A wooden table is positioned nearby. A red umbrella is closed and stands beside the seating, while a sunset casts gentle hues across the water.

4.94 out of 5 average rating, 104 reviews

3 BR Waterfront Home, Minutes to the Beach

Recently updated waterfront house located in the family-friendly Montego Bay community. Enjoy beautiful sunsets on the back deck or hop in one of the kayaks for a paddle around the wide-open canal. Try your hand at crabbing or fishing off the dock to catch your dinner. Within easy walking distance of the beach and Northside Park (about 10 minutes walk to both). Beach chairs, toys, boogie boards, and umbrellas are yours to use for fun in the sand and surf. The dock is available for boat tie-ups.

Guest suite in Ocean Pines

A cozy living area features a white couch and two accent chairs with a leaf pattern. A glass coffee table sits on a woven area rug. Large sliding doors provide a view of the outdoor patio, framed by greenery and water, enhancing the space's natural light.

4.95 out of 5 average rating, 377 reviews

Stunning private waterfront suite

Welcome to your cozy getaway with stunning water views from every room! This sweet 2-bedroom, 1-bath suite boasts a private entrance, a living room, and a cute kitchenette. Nestled in a peaceful, family-friendly neighborhood, you'll have year-round access to swimming pools, a golf course, tennis courts, a Yacht club, and lovely parks nearby. Only a quick 10-minute drive lands you on the sandy beaches and lively Boardwalk of Ocean City. Park in the driveway and step into your own private escape!

4.96 out of 5 average rating, 73 reviews

Two kayaks, one green and one red, rest against a tree near the water's edge. The grassy area features a stone path leading to a wooden pier, with trees providing shade in the background.

Home in Berlin

Private pool, waterfront, kayaks, bikes, firepits!

The Golden Quarter Farm is 150-acre waterfront, nature preserve, centrally located 5 miles from Assateague Island and its wild ponies, small town charm of Berlin, and OC Boardwalk. With a pool, kayaks, SUP, hiking trails, bikes, and birding, there's little reason to leave the property! Max of 8 adults. No parties. No Pets. Renters must sign a Rental Agreement & provide $250 refundable damage deposit. Pool open April-Sept 30th, NOT heated. 5% local room tax will be collected after booking.

An aerial view showcases a serene residential area surrounded by water and lush green landscapes. The neighborhood features a variety of homes, with canals and marshlands visible, hinting at a tranquil waterfront lifestyle. The horizon reflects soft colors of the sky, creating a peaceful scene.

4.97 out of 5 average rating, 59 reviews

Hot Tub Waterfront Home #1 Ocean City Skyline

Yes- Linens are included! (Bed sheets & bath towels) Experience the ultimate Ocean City getaway this year, with unbelievable water views from every room & a private two-story wrap-around balcony. Enjoy 4 comfy king beds. The home is perfect for groups seeking relaxation & home away from home. Only 4.2 miles from the Ocean City Boardwalk! What else is included? Bonfire pit Private Hot Tub Parking area Shampoo-Conditioner-Body Wash Soaps Laundry Detergent Kayak Beach chairs & umbrella

4.95 out of 5 average rating, 21 reviews

Peaceful, pet and family-friendly beach retreat

Escape the busy and hurried life in our Ocean Pines home. Nestled among the trees, enjoy your coffee peacefully, sitting on the wrap-around deck. Unwind in our open and bright family room with lots of natural light and huge windows. Equipped with fast WI-FI and lots of other essentials, we know your stay will be easy and relaxing. It's stocked with everything you need for a family vacation-games, puzzles, books, grilling supplies, kids supplies (pack-n-play, bibs, booster chair), and more!

5 out of 5 average rating, 19 reviews

The ranch-style house is situated on a spacious green lawn, surrounded by trees. Soft outdoor lighting highlights the front of the home as dusk approaches. A secondary building is visible to the right, with a clear area for parking and landscaping enhancing the natural setting.

Home in Snow Hill

The Puskar’s Landing

Centralized to the beaches of Assateague Island. In the heart of Worcester County. Off the country roads of Maryland’s Eastern Shore. This cute rancher sits one mile from Chincoteague Bay with public boat ramps, a beach and pier. You can boat or drive approximately thirty minutes to Ocean City or Chincoteague Island for food and fun. This spacious property has plenty of green space for kids to run and play and still have a peaceful evening. Bring your boats, campers, golf cart and bikes.

5 out of 5 average rating, 104 reviews

The exterior of a two-story house is framed by lush greenery and neatly arranged flower beds. A covered front porch with white railings invites guests, while the clean lawn extends towards the street. The sky above showcases a mix of clouds and blue.

Home in Berlin

Stay Salty OC Beach House

Welcome to your ultimate getaway near Assateague State Park & Ocean City! Our spacious retreat sleeps 14 guests and boasts resort-style amenities including pools, a gym, kayaks, and tennis courts. Located just moments from beaches, charming towns, and exciting attractions, you'll have everything you need for an unforgettable vacation. With a fully stocked kitchen, game rooms, cozy reading nooks, puzzles, and a balcony, there's something for everyone. Book now and let the relaxation begin!

Superhost

A spacious houseboat is docked securely along the water's edge, featuring large windows and a deck area. The surroundings include trees and a sandy space, creating a coastal atmosphere. The sky displays soft clouds illuminated by the setting sun.

Houseboat in Snow Hill

4.87 out of 5 average rating, 126 reviews

"Jolly"- Houseboat Getaway

#BoatLife! Jolly is a 42ft Holiday Mansion. Baywater Landing offers a laid back, coastal style. It buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & 3 outside deck areas to enjoy! Just 35 minutes from Ocean City, Assateague Island, and Chincoteague Island, this is the epicenter of everything coastal! A firepit in the sand just outside your door round out everything you'll need for a stress-free vacation.

4.99 out of 5 average rating, 122 reviews

Charming Waterfront Cottage w/2 King Suites + Dock

Newly renovated, sparkling, spacious house with room for seven and waterfront views is waiting for you. Perfect for a single or double family getaway, girls weekend, or quiet retreat. *Please note this is a No Smoking and No Pet Property. **We are located in a quiet, residential neighborhood with lovely neighbors in close proximity. Please consider this when booking. ***We do not supply sheets and towels. Rental License #2162

A vibrant pot of red flowers is positioned in the foreground, with a wooden deck leading to a clear blue pool in the background. The pool area features a white fence and steps, surrounded by greenery and a cloudy sky above.

4.98 out of 5 average rating, 135 reviews

Stunning Bayview Home with Own Private Pool

This home can be occupied by a max of 12 adults with a total of 15 including children. Come relax in this gorgeous bay view single-family home in the lovely Caine's Woods neighborhood of Ocean City, adjacent to Fenwick Island. Imagine lazy days spent on the beach followed by a dip in the pool outside the kitchen door! The pool is open from May 1- September 30. Obviously we can’t have it open during cold temperatures!

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Popular amenities for Worcester County kayak rentals

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Air conditioning

House rentals with a kayak

The front exterior of the house features a yellow facade with large windows and a welcoming doorway. A wooden deck is accessed by a set of stairs, and outdoor chairs are positioned for seating. Surrounding trees indicate a natural, wooded setting.

5 out of 5 average rating, 21 reviews

Salty Serenity

MiaRating, 5 stars1 week ago

Lovely home with great character and countless amenities. Such a perfect location! House was pretty clean and exactly as described. All the amenities were great, the backyard was incredible with a grill, fire pit, fairy lights, and screen-in-porch. Great for family or friends, would stay again! Accommodated our group incredibly well!

The image shows a balcony view overlooking a marina filled with boats. The calm water reflects the fluffy clouds above, and nearby buildings are visible along the shoreline. Green grass frames the balcony area, creating a serene outdoor space.

5 out of 5 average rating, 19 reviews

Marina Retreat | Relaxing Balconies & Pool

JonRating, 5 stars3 weeks ago

All around great place to stay! We felt right at home! Perfect layout and tons of space! Views from the back deck are amazing! Very walkable to anything you would need and easy 1.2 mile walk across the bridge to the boardwalk and beach! Would certainly stay again!!

5 out of 5 average rating, 11 reviews

A charming two-story home is surrounded by a white picket fence and shaded by trees. The house features a welcoming porch with multiple steps leading to the entrance, offering a sense of comfort and accessibility. A well-maintained lawn complements the serene atmosphere.

Home in Berlin

Waterfront Home & Golf Getaway

LashawnRating, 5 stars2 weeks ago

Christopher's house was absolutely beautiful with tons of space, it was perfrect for our family getaway. The photos online were great and definitely the reason I booked. However, the photos did the house no justice. It far exceeded my expectations after seeing the house in person. The space was super accommodating for my family. There were tons of boards games, fully equiped kitchen, and top of the line appliances, which made our stay even more comfortable. One of the best parts was being able to fish right in the backyard; such a peaceful and fun experience. The house was also very clean and included brand new washcloths, which was a nice touch and much appreciated. On top of all that, the location couldn't have been better, it was just minutes from the OC boardwalk. I am already forward to my next stay. Highly recommend!

A welcoming approach to a spacious home is depicted, framed by tall trees reaching towards a bright blue sky. A neatly paved driveway guides the eye towards the house, with manicured lawns and colorful foliage adding to the inviting landscape.

4.98 out of 5 average rating, 47 reviews

Coastal Oasis in Ocean Pines

ElvaRating, 5 stars2 weeks ago

My family and I had a wonderful time. The place was beautiful and very peaceful. Close to major attractions and the host was friendly. Would definitely come again. Thank you 😊

A bayfront home is depicted with a large deck featuring a wooden railing and an American flag. A private boat dock is visible alongside the home, accommodating several boats. Nearby properties are shown, with lush greenery and open spaces enhancing the waterfront view.

5 out of 5 average rating, 6 reviews

Bayside Home Grill Dock Bikes Kayaks

BrittanyRating, 5 stars2 weeks ago

Was a really beautiful house that had comfortable furnishings and great scenery. Hosts were very responsive and my family had an amazing time. Super awesome that it was pet friendly and we were able to bring our two dogs with us. Would definitely stay again!

Two kayaks, one yellow and one red, rest beside a calm waterway. Lush green grasses line the bank, with a wide expanse of sky filled with soft clouds overhead. The scene conveys a peaceful outdoor setting, ideal for leisurely exploration.

4.93 out of 5 average rating, 14 reviews

Entire House+Yard+Kayaks •Walk2Beach• 2 Living Rms

SierraRating, 5 stars1 week ago

The place was amazing had a lot of space, close to a bunch of restaurants and a quick walk to the beach

A spacious living area features comfortable seating arrangements, including a large sectional sofa and recliners. A flat-screen television is positioned on an entertainment unit, and ample natural light is provided by multiple windows and a sliding door leading to the sunroom. Wooden flooring enhances the open atmosphere.

4.95 out of 5 average rating, 88 reviews

Spacious 4 bedroom waterfront home & boat access!

MartinRating, 5 stars1 day ago

Convenient location for lacrosse tournament. Home was well-maintained and host very communicative, instructions were detailed/straightforward. Will stay again if needed.

An open living space is showcased with warm wood flooring that leads to a cozy seating area featuring a leather sofa adorned with colorful cushions. Natural light floods through sliding doors that offer access to outdoor views. A staircase leads to the upper level.