
Holiday rentals with a kayak in Chincoteague
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Top-rated rentals with kayak in Chincoteague
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House rentals with a kayak

Waterfront Getaway with Dock
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.

Charming Waterfront Cottage w/2 King Suites + Dock
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.

The Hideaway at Mill Creek
We had a wonderful long weekend away. The views were amazing. The home is well equipped. We had a lot of fun exploring the area, hiking on trails, banks of the Chesapeake and taking out the kayaks. It was a very relaxing and much needed getaway!

Rumbley Retreat
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!

Jackson Creek Home w/ optional Guest Cottage
I stayed at Meg's beautiful home with my bridesmaids for my wedding weekend in Deltaville, and it was absolutely perfect! The house is spacious, clean, and well-organized, which made it a comfortable and relaxing place to stay during such a special time. Meg was so kind and responsive, providing helpful local recommendations and detailed instructions for the house. She truly went above and beyond to make our stay enjoyable, and her hospitality made my wedding weekend even better. I couldn’t have asked for a better experience—thank you, Meg!

Piper’s Landing: Relaxing beach house near the Bay
We love this house! Our dogs love to sit in outside porch and they have lots of room to play outside.

Bay Breeze Home on private waterfront
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.

Fiddler On The Creek-Kayaks, Canoe & Shared Pier!
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!
Cottage rentals with a kayak

The Crab Shack
There is nothing more serene than waking up in the ‘crab shack’ with the sunrise. What a comfortable and scenic spot. Even our dog, Juno, loved it! Took a sunset sail to celebrate a birthday and got front pier service! Our host, Carlisle, was extremely attentive and kind with any needs we had or hadn’t thought of. Wish we had booked longer. We hope to return very soon!!

'Cottage by the bay', sleeps 8 near Rehoboth beach
Wonderful little A frame beach cabin feel. Timothy is very helpful and responsive. We did the dogfish dash and was the perfect little place to stay the night before our run. There is only 1 bathroom which wasn’t ideal in the morning for 4 people, but everything else is amazing!! Highly recommend :)

Cottage with a view!
We had a wonderful stay at the Rivah house. it's a beautiful location and kayaks are provided. there's also a full kitchen, lots of sleeping space, and a big tv. A great place to enjoy time in the water and see a beautiful and lesser known part of Virginia.

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

A "True" Chesapeake Bay Waterfront Experience!
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!

Mystic Seahorse Cottage & game room
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!

Heaven on the Bay - A Peaceful Waterfront Retreat
The views of the Bay, dock, and kayaks were incredible. The kitchen and family room had a great vibe, it felt like we were at the Bay!

Pretty Byrd Cottage, a Victorian Bayfront Getaway!
This property is magical. Everything I have imagined and more since I discovered it more than 10 years ago. So thankful I finally got to experience it.
Cabin rentals with a kayak

"Elderberries" Chesapeake Bayfront Cottage
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.

Dinna Fash-3 BR Waterfront Log Cabin
This house is very clean and well maintained. The seclusion is nice to just hang out with friends and relax

Covenant Cove (Cove Point Beach)
Log cabin meets beach cottage, cute and cozy. Both beds were comfy with sufficient linen and towels provided. Electric fireplace was nice touch in evenings. Easy walk to the beach for shell seekers and curve around point to see lighthouse. Enjoyed screened porch and watching birds and bunnies. Would definitely return for another couple’s relaxing weekend.

Pizza Friday
The weather blessed us with warmth upon arrival to Pizza Friday. Although making pizza was a new skill we gained in the moment, the fun we had while doing it was everything we wanted. We had a chance to use the fire pit, kayaks and games in the house. The kids enjoyed sleeping in tents on the ground and the Easter egg hunt scattered along the lovely property. The host was super responsive and allowed us to check in early at no additional cost. I think I may have messaged him a few times about AC and fire wood and there was no hesitation on getting back to me. The family loved this Airbnb and we have already planned an additional trip in the future.

Waterfront Cabin: beach, kayaks, hot tub & firepit
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.

Two Bedroom + Loft Cabin on the Bay
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!

Awesome private off grid cabin with creek view.
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!
Quick stats about holiday rentals with a kayak in Chincoteague
Total rentals
20 properties
Nightly prices starting at
£60 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Ocean City Beach
- Assateague Island National Seashore
- Ocean City Boardwalk
- Jolly Roger Amusement Park
- Northside Park
- Jolly Roger at the Pier
- Peninsula Golf & Country Club
- Bayside Resort Golf Club
- Delaware Seashore State Park
- Bow Beach
- Guard Shore
- Plantation Lakes Golf and Country Club
- Langford Sand
- Wallops Beach
- Trimper Rides of Ocean City
- Coin Beach
- Lost Treasure Golf
- Assateague State Park
- Parramore Beach
- Snead Beach
- Assateague Beach
- The Links at Lighthouse Sound
- Bear Trap Dunes
- York Beach Crossing