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Holiday 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

Holiday House Rentals with a Kayak

Guest favourite
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.
Top Guest favourite
Home in Dameron
5 out of 5 average rating, 105 reviews

Peace Point - Waterfront, Secluded, Home w/hot tub

RayRating, 5 stars1 week ago
I don’t know if I can express how much I loved our stay at Rich and Yumi’s place. The property is very beautiful, private and very peaceful. We enjoyed fishing and taking in all of the sights and sounds of nature surrounding us. The fire pit area and hot tub were very nice additions to the property. The house was very clean and comfortable. The house was very well stocked. Rich and Yumi pay great attention to detail. We were greeted by a nice welcome basket and card to welcome us. After departing we realized that my daughter had forgotten a few items. Rich was very responsive and helpful in locating the items and arranging to ship them to us. I absolutely fell in love with this place and definitely plan to return in the future. Thank you very much Rich and Yumi for sharing your amazing property with us!
Top Guest favourite
Home in Ocean Pines
4.99 out of 5 average rating, 120 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.
Guest favourite
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!
Guest favourite
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!
Top Guest favourite
Home in Belle Haven
4.96 out of 5 average rating, 103 reviews

Bay Breeze Home on private waterfront

BrettRating, 5 stars4 days ago
The host's communication was excellent from start to finish, and I was so impressed by how immaculately clean the house was. Tucked away off the beaten path, it offered the peaceful escape I was craving, and the views were simply amazing, providing a breathtaking backdrop to my getaway. I highly recommend this spot for anyone seeking tranquility and cleanliness in a beautiful setting – I would definitely book it again.
Guest favourite
Home in Chincoteague
4.95 out of 5 average rating, 21 reviews

Fiddler On The Creek-Kayaks, Canoe & Shared Pier!

AlanaRating, 5 stars2 weeks ago
We absolutely loved our stay on Chincoteague Island! Sherry was a truly exceptional host—welcoming, thoughtful, and incredibly accommodating from start to finish. The townhouse was everything we hoped for and more: impeccably clean, beautifully decorated, and perfectly equipped with everything we could possibly need. The view was stunning—waking up to the peaceful beauty of the island was a dream—and the beds were so comfortable after a day of exploring. It was the perfect home base for enjoying all that Chincoteague has to offer. We’re already looking forward to our next visit!
Guest favourite
Home in Seaford
4.9 out of 5 average rating, 30 reviews

Hidden Gem of the Eastern Shore on Gravelly Creek

SalRating, 5 stars1 week ago
This place was great. The backyard space was peaceful. We had a great time fishing and kayaking in the river. The house is in a quiet area that feels very remote (in a good way), but is in close proximity to Seaford. Host was a good communicator. The laundry onsite was very convenient and we enjoyed the ping pong and the variety of table games. Kitchen has all the necessities and multiple options for coffee. House is even more spacious than it appears in the photographs.

Cottages with a kayak

Superhost
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 favourite
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 favourite
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!
Top Guest favourite
Cottage in Kilmarnock
5 out of 5 average rating, 83 reviews

Cottage on Prentice Creek, PA

BeverlyRating, 5 stars5 months ago
I cannot find the words to express our families stay. When I say this was the best stay at an ABNB we have had thus far it was. The outside itself from the landscaping to the scenery was breathtaking. Checking in was a breeze. Once inside pictures cannot begin to show the beauty of this property. The hosts have really thought through a guest experience. They went over and beyond hosts duties adding extreme attention to details. Anything and everything you may need or want for your stay was there. Even with all the extra amenities and the beauty of the home our family instantly felt at home. We loved our stay so much we have already booked our next stay.
Top Guest favourite
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 favourite
Cottage in Gwynn
4.96 out of 5 average rating, 209 reviews

Mystic Seahorse Cottage & game room

MegRating, 5 stars8 months ago
We love staying here! It’s so peaceful, quiet, and calm. The house is always clean and well stocked. Our favorite features are the kayaks/canoe and the private beach access!! Thank you for another wonderful weekend by the water!
Top Guest favourite
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.
Guest favourite
Cottage in Wittman
4.89 out of 5 average rating, 159 reviews

"Wittman Cottage"

JeanRating, 5 stars4 weeks ago
This was my 2nd visit to Lace’s home and would return again! I greatly enjoyed the private, quiet and peaceful surroundings, with views of Harris Creek from both the front and rear of the home, yet just a short drive to the shops & restaurants of St. Michaels and only 30 minutes to Easton. My favorite part? The huge screened in porch with lots of comfy furniture facing the water. With a dock, fire pit, outdoor eating spaces & included kayaks you, relatives & friends will enjoy yourselves at this spacious home.

Cabin rentals with a kayak

Superhost
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 favourite
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 favourite
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.
Cabin in White Stone
4.85 out of 5 average rating, 115 reviews

Two Bedroom + Loft Cabin on the Bay

ColinRating, 5 stars9 months ago
This cabin was the perfect getaway for my family. The waterfront location is absolutely stunning, and my sons had a fantastic time playing in the water. The cabin is exceptionally well-equipped, providing everything we could possibly need. It's a true escape from civilization, offering a profound sense of peace and tranquility. We're grateful to Justin for sharing his beautiful cabin with us. We're already looking forward to returning in the near future!​​​​​​​​​​​​​​​​
Superhost
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 favourite
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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