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

Top Guest favourite
Home in Snow Hill
5 out of 5 average rating, 19 reviews

The Puskar’s Landing

CandaceRating, 5 stars1 week ago
Such a beautiful home! It also was very cozy and peaceful. The beach and pier is a nice walk away and the hot tub was perfect for relaxing. Host was very friendly and responsive if we needed anything. I will most definitely be staying here again!
Guest favourite
Home in Cambridge
4.98 out of 5 average rating, 128 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

AnneRating, 5 stars1 month ago
This was a great house for our teammates to stay in for the weekend!
Superhost
Home in Ocean City
4.89 out of 5 average rating, 18 reviews

Bayfront Sunset Sanctuary @ Stone Harbor

KenyettaRating, 5 stars1 week ago
They how was very clean and was not far from local attractions and the views was tranquil
Guest favourite
Home in White Stone
4.94 out of 5 average rating, 111 reviews

Coastal Farmhouse Getaway

SeanRating, 5 stars1 month ago
My wife is a bit of a planner so scheduling a last-minute getaway is not something I do often, but I'm so glad I did. This was exactly what we needed, A few days away from the stresses of life and family. This home met all of those needs. It was quiet, secluded and overall a very beautiful location and home. It had everything we needed and more. The small towns of White Stone and Kilmarnock offered many fantastic food options which we definitely took advantage of. I would definitely recommend this place to friends and family. We have already started looking to see if we can plan a trip here with the whole family. Thanks again to our host who was very responsive and helped answer all of our questions.
Guest favourite
Home in Onancock
5 out of 5 average rating, 18 reviews

Leave your paw prints by the bay

MaryRating, 5 stars3 weeks ago
First of all, this house and the views are STUNNING. This was the first vacation that I have taken with my fiancé and our 2 pups, and we had the best time--it was such a sad day when we had to leave lol. We basically ordered Doordash and Walmart Pickups the entire time we were there and never left the property during our stay. The kitchen was very well stocked with all the cookware you could need, there are kayaks and paddle boards for entertainment, and plenty of floats for relaxing in the bay. There is a little private beach within 1 min walking distance from the house and there is access to the water from the backyard. It had everything we wanted for a relaxing vacation with our pups. I am already working on convincing my fiancé that we need to go back in the near future. 10/10 would recommend.
Top Guest favourite
Home in Chincoteague
4.96 out of 5 average rating, 27 reviews

Fiddler On The Creek-Kayaks, Canoe & Shared Pier

JasonRating, 5 stars2 weeks ago
Fiddler on the Creek exceeded all expectations. The house was impeccably clean, tastefully furnished, and well-equipped with everything you could possibly need—including kayaks, paddles, two adult life vests, fishing rods, bug spray, a crabbing pot, etc., etc. The waterfront views are stunning, especially in the evening when you’re out on the kayaks (just be sure to check the tides so you don’t get stranded!). It was very peaceful to sit out on the deck and watch the lighthouse. It’s just a short drive to both Assateague Island and downtown Chincoteague, making it a perfect home base. I'd also highly recommend taking the pony tour with Captain Dan's Around the Island Tours—he was incredibly friendly and knowledgeable, and the tour was a highlight of our trip. We’d absolutely recommend this place to others and look forward to returning ourselves!
Top Guest favourite
Home in Ocean Pines
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 😊
Guest favourite
Home in Greenbackville
4.91 out of 5 average rating, 86 reviews

Stunning waterfront panoramic view getaway house

AlanaRating, 5 stars3 weeks ago
We loved our stay in Captain’s Cove! Nick was a very responsive host with wonderful local suggestions. Do be aware that there is really not much in the way of gas stations, grocery stores or restaurants in the immediate area. We knew that going in, though, and it wasn’t an issue for us. Just know you will need to drive a bit or prepare with those items on your way in (which Nick told us in advance as well!) The view is beautiful! The Airbnb is exactly as pictured. It was very quiet as well. Loved that it was pet friendly so we could bring our dog! Would definitely stay again!

Cottages with a kayak

Top Guest favourite
Cottage in Oxford
5 out of 5 average rating, 15 reviews

Sailor's Cottage - Private Waterfront

KathleenRating, 5 stars1 week ago
A peaceful and charming place to stay! It was more than I hoped it would be.
Guest favourite
Cottage in Lewes
4.84 out of 5 average rating, 114 reviews

'Cottage by the bay', sleeps 8 near Rehoboth beach

ChrisRating, 5 stars6 days ago
Needed a clean, quiet place for a long weekend for a local wedding. Very few options willing to accomodate us. The property and Tim were wonderful
Guest favourite
Cottage in Onancock
4.9 out of 5 average rating, 50 reviews

Peaceful 5 bedroom cottage on the Eastern Shore...

HannaRating, 5 stars1 week ago
Took my adult siblings and parents to Taryn’s property & everyone has already asked “can we go back next year?” The seclusion, water views, and acreage to explore was incredible. We were excited to take our dogs who loved running through the marsh out to the beach. Yes, there’s a lot of flies and ticks due to the marshy area, but we brought plenty of bug spray and checked the dogs each evening for ticks. Definitely recommend catching a sunset on the beach. No frills, no fuss..lots of fun & no-phone-service family bonding time.
Top Guest favourite
Cottage in Woolford
5 out of 5 average rating, 64 reviews

Waterfront Cottage, Pier, Sunsets, Hot Tub,Kayaks

TheresaRating, 5 stars4 days ago
Natalie was a wonderful host - the cottage was clean and welcoming and looked just like the photos. Natalie was very responsive, flexible and friendly. The river was peaceful and we enjoyed kayaking and fishing off the dock. We are very thankful we found such a perfect spot for our weekend trip to Maryland.
Guest favourite
Cottage in Cambridge
4.98 out of 5 average rating, 49 reviews

Cozy Cottage on the Bay

SarahRating, 5 stars6 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!
Superhost
Cottage in Painter
4.89 out of 5 average rating, 93 reviews

Cottage by the bay (private peaceful surroundings)

JorgeRating, 5 stars1 week ago
Very secluded but I don't mind that all. The home is beautiful and the host is very attentive.
Top Guest favourite
Cottage in Smith Island
5 out of 5 average rating, 51 reviews

IDLEHOUR, 3 BEDROOMS 2 BATHS W/ DOCK

MelissaRating, 5 stars8 months ago
This was our 2nd stay on the island , but first time at Mary Kim's. Great hospitality including home cooked egg rolls that made the long journey even more worth it. The only downfall would be the dock and kayak spot is a couple doors down, but Mary Kim was very communicative. lastly, I highly recommend the golf cart service on the island, gives you more of an ability to explore the island.
Top Guest favourite
Cottage in East New Market
4.95 out of 5 average rating, 64 reviews

Cottage on Cabin Creek

MicheleRating, 5 stars1 month ago
It was a great stay. Host was responsive and home was calm and clean. Loved seeing the osprey from bed! Those windows highlighted the beautiful view. The weather was a bit dumpy but the space provided everything we needed.

Cabin rentals with a kayak

Superhost
Cabin in Reedville
4.73 out of 5 average rating, 22 reviews

"Elderberries" Chesapeake Bayfront Cottage

JoelRating, 5 stars3 weeks ago
We enjoyed our stay here. Very quiet area, nice comfortable space. The gravel road leading in (maybe a half-mile long) and driveway gave us a good area for morning and evening dog walks. We did not end up doing any fishing but the pond looked like a great place for kayak fishing. Not specific to the house but in the area: Rita's Cafe in Weems was great (food truck on a small road)--Chef Craige usually has a special and some regular menu items. Leadbellys (at Fairport Marina) had good oysters and hush puppies and was convenient for our first night. River Market in White Stone has good food to be ordered at the rear counter and prepared items in the coolers. Out of the Oven Bakery (White Stone) had great bread Miss Mary's seafood, also in White Stone had great fresh fish and prepared items. The three places in White Stone are very close to each other so convenient when running out.
Cabin in Sussex County

The Boathouse on the Creek

AlyssaRating, 5 stars1 week ago
Lea and Skip were wonderful hosts. The place is beautiful and peaceful, surrounded by nature - the pictures didn’t do it justice! We were pleasantly surprised to find a fire pit, Adirondack chairs, crab traps and even kayaks to use during our stay (it was too windy during our visit, so we hope to come back to use those!) The towns are really cute with shops and restaurants, and we visited a winery and a distillery in our adventures. Close to the beach towns, but off the beaten path. Thank you again for the great accommodations! We will be back!
Superhost
Cabin in Tangier
4.67 out of 5 average rating, 3 reviews

Beach Road Oasis, Tangier Island, VA

Luke-N-MelissaRating, 5 stars1 week ago
Our experience at Ted and Jen's house by the beach was amazing. We enjoyed it so much! The house was clean and comfortable, with all the little touches like a basket of snacks and a can of bug spray. Ted and Jen were amazing hosts. From meeting us at the ferry, to showing us a little tour of the island on the way to the house, to giving us pointers on how to enjoy the area, Ted and Jen gave us the full Tangier Island experience. We expect to make this a yearly summer tradition!
Guest favourite
Cabin in Onancock
4.94 out of 5 average rating, 50 reviews

Awesome private off grid cabin with creek view.

DanielRating, 5 stars2 weeks ago
This place was as described. Very peaceful get away for my family and totally worth the price we paid. Teresa was quick to respond and recommended some place to eat. We will be back to experience the fall weather.

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