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.

4.94 out of 5 average rating, 251 reviews

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

CassieRating, 5 stars2 weeks ago

We had a wonderful stay! The house is conveniently located close to everything we needed- shops, restaurants, and attractions, especially the huge playground park just a short drive away. The space was clean, cozy, and very comfortable. I especially appreciated how family-friendly the home was. They had a crib already set up for our 9-month-old, which made things so much easier for us. We felt right at home and would definitely come back again!

A vibrant green kayak rests on a wooden dock, which extends over calm water. The dock is lined with poles and residential homes are visible in the background, along with a clear sky dotted with wispy clouds.

4.96 out of 5 average rating, 101 reviews

3 BR Waterfront Home, Minutes to the Beach

JenRating, 5 stars4 months ago

My family visited with adults and children, and the house suited us perfectly. The house was very clean, it had all amenities and housewares listed, and everything was in good condition, plus the kids appreciated the toys at the house. The view of the bay out back is wonderful! We visited OC for the Winterfest of Lights at Northside Park, and the house was conveniently located for that, and anything else we wanted (restaurants, quick trip up to Rehoboth, trip to the boardwalk). We had an issue initially getting into the house when we first arrived, but the host was very quick to respond and help us trouble shoot, and found a solution that served us for the entirety of our stay. I highly recommend this home and would love to visit again!

4.92 out of 5 average rating, 12 reviews

A serene view of marshland and water under a pastel sky reflects soft pink and blue hues. The calm water is bordered by grass and stretches towards distant houses, creating a tranquil coastal landscape.

Townhouse in Ocean City

Bayfront sunset view, 3 decks, dock & boat slip!

JamirRating, 5 stars7 months ago

This place was better than anything around by far especially for this price it’s a nice spot with warm welcoming views from the porch out back and it’s in an amazing location about 10 minutes from the boardwalk 10/10 would recommend

5 out of 5 average rating, 102 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

JackRating, 5 stars3 months ago

The place was great and we (four kids) all enjoyed their stay! There was a lot of toys and amenities for both the adults and kiddos and the neighborhood was lovely. We utilized the indoor pool, playground and walked the community. Would definitely stay again and try out the kayaks and more outdoor amenities when it's not so cold. Thank you for everything Linda - including the communication, flexibility and comforts of home.

4.99 out of 5 average rating, 119 reviews

Charming Waterfront Cottage w/2 King Suites + Dock

AngelinaRating, 5 stars2 weeks ago

My friends and I had a wonderful stay at Jennifer’s home. It was well equipped, spacious, with a beautiful view. We felt very comfortable due to all of the thoughtful touches/amenities. The location was excellent, with many bars, restaurants, and shops close by and a quick drive to Ocean City and Asseatague Island. We would most definitely return.

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, 131 reviews

Stunning Bayview Home with Own Private Pool

MaggieRating, 5 stars4 months ago

Terrific house for a multi-family get together! Super spacious with lots of spots for groups to hang out separately or all together. Great location - near restaurants and attractions. We stayed in the off season but would love to come back in the summertime to enjoy the pool.

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Popular amenities for Worcester County kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5 out of 5 average rating, 18 reviews

Salty Serenity

CharlesRating, 5 stars5 months ago

Our stay at Salty Serenity was great lots of things to do in just a short drive, House was clean and comfortable, Area was quiet. First time using Roku TV different from what I have at home.

5 out of 5 average rating, 15 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

House near Chincoteague Bay w/space for toys

BethanneRating, 5 stars7 months ago

Perfect home to enjoy this beautiful area of MD! The hosts were proactively responsive and so easy to communicate with and flexible. The home itself is gorgeous, I felt like I was staying in something from the pages of Better Homes & Gardens. They keep it absolutely lovely and they think of the little things - like plenty of soft blankets for snuggling on the couch. Even though the temp in the house was perfect - it's always nice to have a soft blanket. If you have small children there is a room that already has a crib & changing table - a godsend when you're traveling with littles!!! The location is close to the Assateague Island National Seashore & other beautiful places. My only regret is that we didn't get to stay longer.

5 out of 5 average rating, 16 reviews

Marina Retreat | Relaxing Balconies & Pool

LaurieRating, 5 stars4 months ago

Edward and owner were very responsible and even went out of their way to help us when we have to make some change to our plans. Very nice place. Would definitely recommend.

4.97 out of 5 average rating, 58 reviews

Hot Tub Waterfront Home #1 Ocean City Skyline

RasheemRating, 5 stars4 weeks ago

Most peaceful stay I’ve had at an airbnb, it was cozy and had beautiful scenery day and night, we had a little mishap with the hot tub but it was resolved and the rest of the house more than made up for it. Great stay, definitely recommend!

Superhost

A waterfront property is presented, featuring a spacious deck with multiple white chairs and expansive glass windows. The well-kept lawn surrounds the house, and a fire pit area is visible in the foreground, all under a clear blue sky.

4.78 out of 5 average rating, 23 reviews

The Oliver House

ChrisRating, 5 stars7 months ago

Stayed for Ocean’s calling festival 2024. Would do it again. Great place!

4.98 out of 5 average rating, 44 reviews

Coastal Oasis in Ocean Pines

AngelaRating, 5 stars2 months ago

This place was spotless and beautiful 🥰 I would definitely go back.

4.94 out of 5 average rating, 17 reviews

Peaceful, pet and family-friendly beach retreat

ChrisRating, 5 stars6 months ago

Sara's house was clean and full of all amenities and then some. Our kids had a blast with all of the toys and games, and our dogs were at peace and comfortable. The house has plenty of space inside anoutut, and it is just a short drive from OCMD. Thank you!

A clear view of shimmering water extends towards the horizon, reflecting sunlight under a bright blue sky. The image captures a portion of the home's exterior, with white railings framing the scene, emphasizing the waterfront's proximity.