Holiday rentals with a kayak in Worcester County

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

4.83 out of 5 average rating, 29 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.

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

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, 74 reviews

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.

4.93 out of 5 average rating, 27 reviews

Cottage on the water

We are located right off of Route 90 and minutes to the beach. Ocean Pines is filled with amenities. We have a public access yacht club and golf course are close to the town of Berlin for dining and a visit to the famous Burley Oak Brewery. The family will enjoy Ocean City for fun at Jolly Rogers or the Boardwalk for the rides. West Ocean city has the famous Orange Crush at the Harborside restaurant and don't forget Assateague Island and the horses. We are also 2 miles from the local winery.

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!

4.98 out of 5 average rating, 50 reviews

Coastal Oasis in Ocean Pines

Coastal sanctuary is a private mother-in-law suite with a private entrance, just 15 minutes from Ocean City MD. 2 bedrooms, spa like bath, family room, w/sleeper sofa, kitchenette overlooking a marsh and bay. You will have the entire floor. 1000 sq feet. Daily visitors include deer, heron, birds and duck. Follow the deer path and use our stand-up paddle boards and/or Kayaks. Assateague wild ponies and Ocean City boardwalk are an close by. Berlin voted the coolest small town in America.

5 out of 5 average rating, 19 reviews

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, 105 reviews

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

Houseboat in Snow Hill

4.87 out of 5 average rating, 131 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, 124 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

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Holiday House Rentals with a Kayak

5 out of 5 average rating, 22 reviews

Salty Serenity

CoraRating, 5 stars2 weeks ago

Dan and Heather's place was quite lovely with all the amenities of home. The kitchen was stocked with miscellaneous items one may sometimes forget to pack. The instruction manual was quite useful as well as having access to WiFi, the Ocean Pines Beach Club, etc. If you enjoy a rustic outdoor fire pit area, you'll be in for a treat. The Ocean Pines vibe is memorable, peaceful and continually pulls me back for more! The listing for this home is accurate and my husband and I would love to come back again in the future.

4.83 out of 5 average rating, 6 reviews

4 BR/3.5 Bath w/Community Pool, Hot Tub, Gym

ShaniqueRating, 5 stars6 days ago

I would highly recommend, this home is very comfortable and have literally everything you need there to feel at home. You think of it they have it which is greatly appreciated especially when I have children. So clean and comfortable

4.85 out of 5 average rating, 20 reviews

Marina Retreat | Relaxing Balconies & Pool

JonRating, 5 stars1 month 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

Waterfront Home & Golf Getaway

LashawnRating, 5 stars3 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!

4.94 out of 5 average rating, 36 reviews

Pet Friendly -Spacious Coastal Cape-Explore WestOC

McKenzieRating, 5 stars2 weeks ago

We throughly enjoyed our trip, even though it rained all weekend the house offers a lot of amenities to keep you occupied. Location is great and with lots of hidden gem restaurants nearby.

4.94 out of 5 average rating, 16 reviews

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

WarrenRating, 5 stars1 week ago

Very clean and nice place to stay! Plenty of space inside and looks just like the pictures. Host was super responsive and made check in and out extremely easy.

4.96 out of 5 average rating, 89 reviews

Spacious 4 bedroom waterfront home & boat access!

MartinRating, 5 stars1 week ago

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