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

Superhost

Home in Onancock

4.91 out of 5 average rating, 34 reviews

The Quarter Deck/Spacious home with water views!

KimRating, 5 stars4 weeks ago
This house was perfect for our Christmas family gathering. There was plenty of space in the house and the kitchen had everything we needed. The neighborhood is lovely and the neighbors that we met were all friendly and welcoming. Thank you for creating such a peaceful and beautiful space for families to enjoy.
Superhost

Home in Selbyville

5 out of 5 average rating, 4 reviews

Luxury home by the bay

JamesRating, 5 stars8 months ago
Great house and the community was very well maintained. My kids loved the amenities that came with the community, including the pool and the small, but kid friendly beach. Overall, this was the nicest Airbnb house we have stayed in. We’d love to come back.
Guest favourite

Home in Westover

5 out of 5 average rating, 14 reviews

Rumbley Retreat

KatieRating, 5 stars1 week ago
Accurately listed place! Nice & updated. Very clean. Convenient location for guided duck hunting trip. Very nice place!
Superhost

Home in Bethany Beach

4.93 out of 5 average rating, 45 reviews

Georgo Family Beach House

DonaldRating, 5 stars4 months ago
We had a great vacation. The house was well-appointed and very comfortable. We walked to the beach everyday, which we basically had to ourselves. Our dog Willie Boy gives it 4 paws up and one waggly tail (highest rating possible). James is a great host - responsive and informative. Stay well, Don 🎺, Liz 🙏 and Willie Boy 🐾
Guest favourite

Home in Cambridge

4.89 out of 5 average rating, 19 reviews

Waterfront & Hot Tub! 4 BR/4 BA - Central Location

VincentRating, 5 stars3 weeks ago
David’s place was great! It was better than we expected and was perfect for my group of nine to bring in the new year!
Guest favourite

Home in Oxford

5 out of 5 average rating, 50 reviews

Stunning Chesapeake waterfront home

PrudenceRating, 5 stars2 months ago
This home was lovely to spend time in and out! I believe the best parts were the screened-in porch, the beautiful kitchen, the backyard by the private dock, the neighborhood kitties, the birds (including water fowl), the nearby walk to quaint Oxford, and much more! Lucas and Heather are fast at responding and enjoyable individuals. You will not be disappointed with this gem of a house! 5 star!
Superhost

Home in Cambridge

4.92 out of 5 average rating, 13 reviews

Three Creeks Point - Waterfront family estate

RonRating, 5 stars6 months ago
The house is beautiful, it is in a beautiful setting, and it is very well equipped. The kitchen was well stocked and had a full complement of cooking basics and condiments. The house had most everything we might have wanted: kayaks, bikes, ping pong, table games, telescope, and more. The house was spotless, the wi-fi was strong, and all instructions were clear and easily available. Though a 15-20 minutes drive to the nearby town, that is the tradeoff for a property with an extensive waterfront. We would be happy to return there in the future.
Guest favourite

Home in Cambridge

5 out of 5 average rating, 10 reviews

"Goose Landing" Waterfront Retreat

JohnRating, 5 stars5 months ago
This was a great vacation. This place has it all from the pool to the kayaking, fishing, crabbing and the late night fires were we all just sat around the fire and enjoyed the time together. The house was awesome, plenty of room for all. The family had a great time. Definitely would rent this place again.

Cottages with a kayak

Guest favourite

Cottage in Chincoteague

4.96 out of 5 average rating, 148 reviews

Waterfront-CI Bay sunsets-Amazing views

MaureenRating, 5 stars2 months ago
We were looking for a peaceful off season rental and got exactly that. The weather was nice enough to walk into town and go kayaking. We love to cook and the kitchen was very well equipped. It is decorated like a magazine. Everything is beautiful and comfortable. The host was communicative and helpful. We loved that things were labeled! We’d definitely return.
Guest favourite

Cottage in Oxford

5 out of 5 average rating, 12 reviews

Sailor's Cottage - Private Waterfront

RobertRating, 5 stars3 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.
Guest favourite

Cottage in Woolford

5 out of 5 average rating, 60 reviews

Waterfront w/Hot Tub & Beautiful Sunsets, Pier

ChristopherRating, 5 stars2 months ago
Natalie’s place was very nice. Clean, well stocked inside and out, and and an excellent waterfront location. Would love to come back when the weather is warmer and we can get out on the water.
Guest favourite

Cottage in Smith Island

5 out of 5 average rating, 50 reviews

IDLEHOUR, 3 BEDROOMS 2 BATHS W/ DOCK

MelissaRating, 5 stars3 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.
Guest favourite

Cottage in East New Market

4.95 out of 5 average rating, 59 reviews

Cottage on Cabin Creek

KimberlyRating, 5 stars1 week ago
Beautiful cabin getaway. Janelle always responded in a timely manner and alerted us ahead of time of road conditions and activities going on in the area.
Guest favourite

Cottage in Lewes

4.92 out of 5 average rating, 39 reviews

Sunny Side Cottage🌞

MarkRating, 5 stars5 months ago
We stayed at Eileen’s several times this summer and always had a great stay. We felt as if it was our home away from home. Eileen is super responsive and her cottage was perfect for our beach getaways. Quiet, peaceful, yet close to all the attractions we enjoy. Thank you, Eileen!

Cottage in Chincoteague

4.89 out of 5 average rating, 137 reviews

Pony Pines!Your Waterfront Getaway Cottage Awaits!

KathleenRating, 5 stars1 month ago
Eric's home was perfect for our portable family Thanksgiving. Everyone loved the stay. Even the 1-year old enjoyed running around outside and exploring a new home. We loved watching the ducks swim by in a drizzle and it was my first time seeing an oyster bed. Wow! I can see that it would be fantastic to visit during a warmer season and spend some time floating on the water. The house was clean and welcoming. My kids enjoyed the snacks and I appreciated the local recommendations. Thanks, Eric! We had a great time and would welcome visiting again.

Cottage in Westover

4.8 out of 5 average rating, 25 reviews

Dog-Friendly Westover Cottage w/ River Access!

MeghanRating, 5 stars3 weeks ago
While we only stayed at this lovely cottage long enough to sleep each night while in town visiting family, I imagine it would be an idyllic spot for a getaway. The location is absolutely beautiful and the cottage was well stocked with anything you could need. We appreciated the dog bed and crate available for use as well! Would recommend!

Destinations to explore