Vacation rentals with a kayak in Assateague Island

Find and book unique kayak rentals on Airbnb

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Popular amenities for Assateague Island kayak rentals

House rentals with a kayak

Guest favorite
A serene waterfront view is presented, featuring a wooden dock extending over still water. Lush green grass fills the foreground, while trees line the opposite bank, creating a natural backdrop under a partly cloudy blue sky.
Home in Woolford
4.93 out of 5 average rating, 145 reviews

Waterfront Getaway with Dock

TysheraRating, 5 stars1 month ago
Went to location as a family get-away. The views were breathtaking, who knew we would find such peace so close to home. Literally sat on the couch and stared outside for hours. The home was small enough to enjoy each other's company but large enough to allow everyone the time and space to do their own thing. The price was more than reasonable and we can't wait to return.
Guest favorite
Home in Preston
4.96 out of 5 average rating, 94 reviews

River House on the Choptank

JimRating, 5 stars4 days ago
Great place! very charming, relaxing, peaceful! No problem feeling right at home. We would stay here again in a heartbeat. Here are a few pointers for those who are planning to stay here: - Its pretty far from grocery / convenience stores - about 30 minutes one way. Do your homework before you get to the place, and try to get all the supplies you will need ahead of time. - The bathrooms are Jack and Jill's so if you're going to a big event - in our case a wedding, make sure that you have a bathroom plan in place as you will have to make sure both sides of the door are ready for who is going to take their time first. No biggie if you're used to j&j bathroom arrangements. I totally recommend this place for a group of 4 - 6 who want together time to relax!
Top guest favorite
The exterior of the retreat is showcased, featuring a grassy area leading to a dock with colorful kayaks. A charming blue building with a fish mural is visible, providing access to outdoor amenities. Surrounding trees offer a natural backdrop, enhancing the waterfront setting.
Home in Reedville
5 out of 5 average rating, 55 reviews

Fresh Air, Waterfront Views, & Pet Friendly

HeatherRating, 5 stars6 days ago
We spent a lovely few days at this home and highly recommend it! The location is fantastic -- right on the water on a quiet creek -- with all the things you need to enjoy yourself. We were very happy to have a fully fenced yard since we brought our dogs. If anything, I think the photos undersell the house: for instance, the furniture in the living room is larger and nicer than it appears in the pics, so you can really spread out and relax in there. A note to EV drivers: we brought our EV and there's conveniently an outdoor 110v outlet on the side of the house next to the driveway.
Top guest favorite
Two green kayaks are positioned on a wooden dock overlooking a calm body of water. Lush trees line the far shore, and the sky is filled with soft blue hues and gentle clouds, creating a serene outdoor environment.
Home in Reedville
5 out of 5 average rating, 60 reviews

Spacious waterfront family retreat. Dogs welcome!

JanetRating, 5 stars6 days ago
Dawn’s place is the nicest Airbnb we have ever found! I never experienced a house where there are so many extras to make your visit special! Dawn and her husband have gone above and beyond to create this peaceful dog-friendly oasis. The game room was a blast, the dock and patios were comfortable with chairs, cushions, lounges and a fire pit. Dawn even supplied graham crackers, marshmallows and chocolate to make Smores! The beds were super comfortable and there were tons of towels for people and pets. We also enjoyed the deep bathtub, bubble bath and shower. It was go great not to have to bring shampoo, body wash and all this much need toiletries that fill your suitcase. My family had a relaxing fun week there and will definitely be back. I wish we could give a ten star rating because that’s what this place deserves! Thanks Dawn 😇
Guest favorite
An aerial view captures the house positioned near the peaceful waterfront, with the nearby public boat ramp and Rumbley Pit & Pub clearly marked. Lush green marshland surrounds the area, highlighting the relaxing atmosphere of this scenic retreat.
Home in Westover
5 out of 5 average rating, 16 reviews

Rumbley Retreat

ChadRating, 5 stars3 months ago
Came down for a duck hunting trip! The place was perfect! Very clean and cozy! Hope the owner was very attentive and quick to respond with any questions! If in the area again I will definitely book again!
Guest favorite
Home in Cambridge
4.96 out of 5 average rating, 112 reviews

Gorgeous, waterfront home - Perfect for Families.

Leslie RogersRating, 5 stars5 months ago
We had the most beautiful Thanksgiving gathering at Casey’s Porch on the bay for an extended family reunion. The house is lovely - spacious, gorgeous and cozy at the same time. The views on the water were amazing. There were plenty of beds and ‘hang out’ spots for our tweens and teens, and 3 private baths for the adult couples were much appreciated. And our hosts could not have been more helpful and friendly. Thank you for giving us this opportunity to make more happy memories together!
Top guest favorite
Home in Oxford
5 out of 5 average rating, 53 reviews

Stunning Chesapeake waterfront home

Karina And ClintRating, 5 stars2 weeks ago
Where should we begin? Lucas and Heather were wonderful hosts. Excellent and quick communication. Their home has been thoughtfully curated with top notch, kitchen appliances, bed and bath linens, entertainment amenities, and more. Even on a cool and rainy day, you can sit around the fireplace, listen to music, play games and look out the window to a stunning view of the water. No stone was left unturned. This is indeed a special place in the lovely little town of Oxford. We hope to stay again. Thank you, Lucas and Heather for the exceptional hospitality.
Guest favorite
Two kayaks, one red and one blue-green, are positioned on a wooden platform near a tranquil waterway. In the background, a small, weathered shed is partially visible among the trees, surrounded by lush greenery and reflecting the peaceful surroundings.
Home in Onancock
4.8 out of 5 average rating, 141 reviews

Charming Waterfront Cottage on Cedar Creek

SteveRating, 5 stars1 week ago
My family and I came down for Easter weekend to visit family. We LOVED the property and can't wait to return when it's warm. The location is top notch. Beautiful creek to kayak, dock to fish or crab from and a spacious backyard and fire pit. Would highly recommend.

Cottage rentals with a kayak

Top guest favorite
A sandy patch leads to the water’s edge, where a small beach area is outlined by natural stone. A covered structure houses kayaks, and lush greenery surrounds the scene, with tall grass and trees providing a serene backdrop.
Cottage in Oxford
5 out of 5 average rating, 12 reviews

Sailor's Cottage - Private Waterfront

RobertRating, 5 stars7 months ago
Jessica and Richard were very welcoming and friendly. Place was great right on water. Very private. Grandson and I fished off dock with good success. J&R lent us a crab pot and we had a blast.
Top guest favorite
Two kayaks rest on a wooden deck, with one in red and the other in yellow. A paddle lies alongside them. In the background, the fenced backyard leads to the water, and a small shed can be seen beside a grassy area.
Cottage in Woolford
5 out of 5 average rating, 62 reviews

Waterfront! Hot Tub! w/Guest House, Pier, Kayaks

MalgorzataRating, 5 stars2 months ago
A fantastic weekend getaway! Natalie’s home is beautifully located, offers spectacular views, and is incredibly well appointed with thoughtful touches like extra plush towels and spices and coffee. We enjoyed everything and even though the weather did not cooperate we had days of exploring the natural beauty, history, and local towns.
Superhost
A covered deck offers seating with wicker chairs and colorful cushions overlooking the calm waters of the Chesapeake Bay. The decking is made of warm-colored wood, and a gentle view of the shoreline can be seen in the distance, enhancing the serene atmosphere.
Cottage in Reedville
4.88 out of 5 average rating, 203 reviews

Private point on the Bay🌤hammock, hot tub, kayaks❤️

HeatherRating, 5 stars2 weeks ago
With 180 degree water views, what could be better?! We saw birds, incredible sunrises over the bay, and enjoyed sunset in the hot tub. It’s just right for a long weekend getaway to relax and unwind!
Guest favorite
Two green kayaks are positioned on a wooden dock overlooking a calm waterway. The sunlit scene features clear blue skies and a serene reflection in the water, enhancing the natural beauty of the surrounding area.
Cottage in Cambridge
4.98 out of 5 average rating, 49 reviews

Cozy Cottage on the Bay

SarahRating, 5 stars5 months ago
My husband, dog, and I enjoyed a wonderful Thanksgiving break at this very nice and beautifully situated cottage! The views from the back deck and kitchen are as gorgeous as the listing photos suggest and, while the house is right next door to another one, we heard not a peep from the neighbors during our 5 days there. Everything was very attractive and well thought out - the kitchen was well appointed with everything we needed; the chairs, sofa, and bed were super comfy, the bathroom was clean and cheerful. Maxine was great host, answering all our questions quickly and helpfully. It's a 15-20 minute drive to downtown Cambridge, where we had nice dinners out in town at Blue Ruin and Bombay Social. We also took good day trips to Easton, St. Michaels, the Blackwater National Wildlife Refuge, and the impressive Harriet Tubman Underground Railroad Park and Visitor Center. The whole area is full of beauty and history, and this cottage was a great home base!
Guest favorite
Cottage in Onancock
4.96 out of 5 average rating, 160 reviews

A "True" Chesapeake Bay Waterfront Experience!

JenniferRating, 5 stars1 week ago
I truly wish I could put into words just how beautiful and peaceful this home and property were. It is truly a place that was so inviting and well maintained it made me miss the eastern shore of Virginia and start looking at properties in the area. The land is so cool to walk and explore and the bay at this home is just serene. To be able to wake up and see the view this home has is just spectacular. Matt is spot on with the description of his home and you truly can't find one thing wrong with this home or the property surrounding it and having a dog,it is so key with the wash station outside because our lab puppy could not get enough of the bay or going out in the kayaks with us. I truly wish they had more stars to rate this home. Thank you for being so gracious and allowing us to visit your spectacular home!
Superhost
An outdoor dining area features a round table surrounded by six floral-patterned chairs, set on a wooden deck. The space is enclosed by large windows, providing views of the serene green landscape and trees, ideal for enjoying meals in a tranquil setting.
Cottage in Painter
4.89 out of 5 average rating, 89 reviews

Cottage by the bay (private peaceful surroundings)

SharonRating, 5 stars1 week ago
Lovely clean, everything needed provided cottage in a peaceful neighborhood with a short walk to the Bay. Kids loved the little beach and the sandbar when the tide went down. No bugs in April;)
Top guest favorite
A charming cottage is positioned by the water's edge, surrounded by trees and lush greenery. The structure features large windows that allow natural light to illuminate the interior. A clear blue sky is visible above, reflecting on the calm water.
Cottage in East New Market
4.95 out of 5 average rating, 62 reviews

Cottage on Cabin Creek

JenniferRating, 5 stars3 weeks ago
We would highly recommend this peaceful and relaxing cottage. We especially loved the views, the dock for fishing, & the views from the bedroom. Janelle was very helpful with places to visit as well as working out an issue that came up at the property. She was quick to respond & made every effort to make sure we were comfortable. Would definitely stay here again! 😊
Top guest favorite
A spacious kitchen with a large central island is featured, complemented by white cabinetry and stainless steel appliances. Natural light fills the room through the window, illuminating the dining area with a wooden table and blue chairs nearby, creating an inviting space for gatherings.
Cottage in Lewes
4.99 out of 5 average rating, 183 reviews

Ebb & Flow Beach House - Lewes Bay Beach Retreat

AmyRating, 5 stars6 days ago
We had a great stay! The house is spacious and inviting. The beds were very comfortable. The kitchen is super well stocked, probably the best we have ever encountered at an airbnb. The location is great- just a few blocks from the beach and bike path and easy walking or biking into town. A great place for a large group, and nice that there are bedrooms on the first floor for older folks who appreciate avoiding stairs. Host was very flexible with us when we needed to change dates.

Cabin rentals with a kayak

Guest favorite
A peaceful view of a two-story cabin located by a serene pond, with lush greenery surrounding the property. Reflections of the cabin and trees are visible on the calm water's surface, creating a tranquil atmosphere. A blue sky with scattered clouds completes the scene.
Cabin in Saint Michaels
4.99 out of 5 average rating, 108 reviews

True St. Michaels 6 Acre Waterfront w/heated pool

KyleRating, 5 stars3 months ago
Marissa’s home was beautiful and had everything we needed - plus some. Plenty of clean/comfort space and restrooms for our party of 6. We had such a relaxing, warm stay during a snowy January weekend - even smores! Marissa was always responsive and provided suggestions for shopping and dining in St. Michael’s. It was lovely all the way around! Highly recommend this home and working with these owners. Top notch!
Superhost
A calm waterfront scene depicts a tranquil bay under a clear blue sky, with a single kayak gliding across the still water. The horizon is lined with trees, providing a natural backdrop. A crescent moon is visible in the sky.
Cabin in Reedville
4.71 out of 5 average rating, 21 reviews

"Elderberries" Chesapeake Bayfront Cottage

MarkRating, 5 stars6 months ago
Had a great time at the Elderberries cottage! The views were spectacular, and you could take them in from the enclosed porch, the open deck, and even the living room. The entire setup was perfect for a vacation/remote work getaway, and the kitchen has everything you need. WiFi worked great, and the smart TV supported pretty much any streaming service you'd want. Rachel was friendly and super responsive; we hope to stay there again sometime.
Guest favorite
A bright blue kayak rests on the shallow water, showcasing its two green paddles secured on top. The kayak is designed for stability, featuring seating areas and multiple storage compartments, with the sandy bottom visible beneath the clear water.
Cabin in Reedville
4.97 out of 5 average rating, 252 reviews

Dinna Fash-3 BR Waterfront Log Cabin

AshleyRating, 5 stars2 weeks ago
Great air bnb! The view was even better than I imagined
Guest favorite
A wooden deck extends from the house towards the water, framed by leafy trees. A serene view of the lake is visible, with a gentle slope leading to the water's edge. Decorative elements, including garden plants and a wind chime, enhance the tranquil setting.
Cabin in Reedville
4.95 out of 5 average rating, 84 reviews

Waterfront Cabin: beach, kayaks, hot tub & firepit

JacobRating, 5 stars2 weeks ago
This is a wonderful place on a large creek off the Chesapeake Bay. This place oozes with charm and ambiance and feels so peaceful. We spent the first day just relaxing and doing nothing but looking at the water and chilling on the front porch. The house is updated on the inside and has a large lot with kayaks and a fishing pier. Great hiking at the natural preserves in the area too. We're grateful to the hosts for opening their home to us and we'll definitely come back.
Superhost
A quaint cottage is presented with a welcoming porch and a light blue door. Lush greenery surrounds the structure, and a seating area with colorful chairs is visible on the lawn, providing a relaxed outdoor space for guests.
Cabin in Saint Michaels
4.75 out of 5 average rating, 80 reviews

Cottage #4 Chesapeake Blue down the drive way.

DavidRating, 5 stars8 months ago
I recently had the pleasure of staying at Alexander and his wife's charming cottage, and we couldn't be happier with the experience. From the moment we arrived, Alex and his wife were incredibly accommodating and helpful, ensuring we had everything needed for a comfortable stay. The cottage itself was cozy and well-maintained, offering everything we required for a relaxing getaway. One of the highlights of our stay was the breathtaking sunset views. Watching the sun dip below the horizon from the dock was simply mesmerizing. The location is also ideal—just a short 10-minute drive to downtown St. Michaels, where we enjoyed exploring the local shops and restaurants. The hosts truly go above and beyond to make their guests feel welcome, and it shows in every aspect of their hospitality. I highly recommend this place for anyone looking for a peaceful and memorable retreat.
Guest favorite
A rustic cabin is surrounded by tall pine trees, featuring a spacious deck with multiple seating areas. An American flag is displayed, while a grill is positioned nearby. Large windows allow natural light into the interior, creating a welcoming exterior view.
Cabin in Onancock
4.94 out of 5 average rating, 49 reviews

Awesome private off grid cabin with creek view.

JayneRating, 5 stars1 week ago
Great place to stay for rest, relaxation, peace and quiet. In my short time there, I saw a wild turkey, a fox, an otter, red wing black birds, a woodpecker, and cardinals. And at night, I heard tree frogs and an owl was really close by. Terri is wonderful as a host!

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