
Holiday rentals with a kayak in Chincoteague
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Top-rated Accommodation with a Kayak in Chincoteague
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Holiday House Rentals with a Kayak

Serene Waterfront Metompkin Retreat - Entire Home
We really enjoyed our 3 night stay! Great house on a quiet marsh. The morning sunrises were beautiful, loved being able to use the kayaks to paddle to the ocean, and great bird watching. Would love to come back.

Beachfront Chesapeake Bay Retreat
I loved it, very comfortable, nice beach and organized, I recommend it

Leave your paw prints by the bay
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.

Blue Heron WaterSide
Of my many Airbnb stays, Laura’s comes up with the very best. Her home is lovely, inside and out, with a lot of fun activities to choose from. Located on a beautiful creek opening to wide water gave us a chance to explore in her kayaks and paddle board. Rainy weather meant indoor board games, reading etc on the beautiful protected porch. The kitchen had all sorts of amenities for cooking. Plenty of bedrooms for sleeping in the peaceful atmosphere. I can’t wait to return there!

The Haven On The Chesapeake Bay
The Haven was truly a gem. It was so private and secluded- just what we needed to relax and reset. Ashley was so friendly and provided so many helpful accommodations that you’d typically not find elsewhere, such as complimentary coffee and a stocked s'mores station. Collectively, I think my family most enjoyed using the kayaks and paddle boards to explore the bay everyday. The kids absolutely loved hunting for wildlife around the house and pond. I’ll never forget this trip!

"No Bad Days" in this Fabulous Beachhouse w/ Dock!
this was our second time visiting after 2 years it looked fresh and clean and beautiful as our first stay the house is beautifully appointed with furnishings and all the comforts of home right down to drink shaker and hand mixer needed for me to make goodies to take to my families home nearby they also filled fridge with all sorts of goodies like eggs butter bagels juice pancake mix and strawberries just all sorts of things it really made us feel just like home can’t wait to go back again next year

Living on Island Time
Had a great week fishing and crabbing from the doc, kayaking, game playing, eating and visiting local attractions! Can’t say enough about how friendly Melissa was. Would definitely return!

Cove Point Cottage with Chesapeake Bay views
Very nice house in a great walkable neighborhood. Host were very helpful and responsive.
Cottages with a kayak

The Crab Shack
This was our 1st visit to The Crab Shack. All I can say is Wow, just Wow! This was the cleanest, nicest and cutest Airbnb that we have ever stayed at over the years! It was amazing! My husband and I traveled from Sarver, PA with our 2 Golden Retrievers to celebrate our 10 year Wedding Anniversary! We all had the best time ever! We spent most of the time here at the Shack just cooking on the grill and listening to music and the girls did a lot of swimming fetching for balls! Thank you Carlisle and Mary for making our 10 year Anniversary simply perfect! ❤️☀️😎🥂🍾🦀 We can’t wait to come back! ☺️

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

Locklies Innlet, A unique waterfront experience!
My husband and I had an absolutely wonderful time and the home played a big part in this. I was so impressed with all the extras that I just never see in other homes. The house is so cozy and such a beautiful location. Just perfect for relaxation. We will definitely want to come back. Thank you Cornelia for opening up your home to us.

Cottage with a view!
Beautiful place to stay. Quite peaceful area with friendly neighbors. Home was cozy and welcoming. Kitchen had everything you could need. Amenities were amazing. Had a spectacular time would definitely come back to stay again.

Private point on the Bay🌤hammock, hot tub, kayaks❤️
We loved out time at this Bayside home. My boys spent outside upon hours at the little private beach, where the water doesn't really get deep for quite a ways and the waves were never very rough. it was perfect for them. we all enjoyed the hot tub, kayaks, comfortable beds. My personal favorite was the hammock right by the water, listening to nothing but the waves and the calls of the ospreys that made the area their home. Forget the overly built up touristy areas and give this place a try. You will not regret it.

Levering Creek Cottage with Private Dock
Janet has a unique property considering the destination is on an island... it has it's own dock which affords guests the ultimate in flexibility. It was the main reason we elected to overnight there. My son and I only had one night for the fishing trip in our own boat over father's day weekend so it was not a deal-breaker we had to book 2 nights. The simplicity of motoring up after a day on the water with all of our gear and the convenience for being up early to catch the right tide was a perfect fit. Wish we had 2 nights to stay and have better luck with the weather... and the fish, but we will be back. Thanks Janet!

Mystic Seahorse Cottage & game room
Mystic Is a quaint, clean and welcoming houae. All details from pictures to knick knacks create a complete theme. Instructions were easy and thoughtful. Communications were prompt and thorough. This home and its owners create a perfect sanctuary.

Little Cottage on the Creek
My wife and I stayed at the cottage while in town for a wedding. The location is very central and walking distance to many of the towns attractions. The neighborhood is quiet and beautiful. Lots of cool nature and kind people. Karen was very friendly and helpful. Would recommend!
Cabin rentals with a kayak

Riverside R&R: Cabin, Dock, Kayak & Game Arcade
We are two families that met up for a relaxing getaway after celebrating a high school graduation. This was the perfect place. The downstairs had lots of games and a big screen for them to hook their switch up to. We watched movies upstairs. And use the well-equipped kitchen each night to make a big dinner. The kids took the kayaks and canoe out one afternoon as well. Although I would say they definitely wouldn’t swim there. Compass entertainment complex is very close and they enjoyed their time there. We also went to a movie there one night. It is a beautiful home in a peaceful setting. Especially down on the dock at night. It was very quiet. We would definitely recommend this home.

Pizza Friday
Pizza Friday was an amazing find! We spent a family reunion on the porch making pizza's in the oven. We obtained crusts from an Italian restaurant in California on our way and it proved to the perfect choice for us. We also enjoyed the dock and even caught a few crabs to show the kids. In addition we sat around the fire pit in the evenings. The beds were comfortable and everything was clean inside although we spent most of our time outside on the porch.

Awesome private off grid cabin with creek view.
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.

Peaceful Waterfront Retreat on The Bay
Incredible space! Devin’s place on the water has everything you need. It would be tight with more than two adults but it worked great for us and our small dog.

The Boathouse on the Creek
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!

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade
We stayed at Julie’s home with a group of friends and our families and had a wonderful time. The lakefront setting was incredibly relaxing—we found ourselves rarely leaving the property because it had everything we needed. From soaking in the hot tub to enjoying the game room, there was something for everyone. The kids loved having space to run around in the basement, while the adults enjoyed peaceful mornings and evenings on the screened-in porch. Julie was very responsive and answered all of our questions quickly, which made the entire experience seamless. We would absolutely stay here again!

Dinna Fash-3 BR Waterfront Log Cabin
Said it last time and I’ll say it again; 11/10 stars. This place is undisputed best bang for your buck.l! It’s beautiful, comfortable, and private. This is my favorite place in the area and I try to snag it anytime it’s open! Close enough to do all the exploring; far enough out to do some good relaxing!

Covenant Cove (Cove Point Beach)
We absolutely loved this place. It was a short drive to the bay and certainly worth it. The cottage was secluded enough from the neighbors and we could hear the waves with the windows open. The beach was a very short walk from the cottage and was also very private. We spent a good chunk of our time finding sharks teeth and relaxing on the porch. Grocery stores and gas stations are also fairly close. We even booked our stay for next year already.
Quick stats about holiday rentals with a kayak in Chincoteague
Total rentals
20 properties
Nightly prices starting at
$124 AUD 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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- Chesapeake Bay
- Ocean City Beach
- Assateague Island National Seashore
- Ocean City Boardwalk
- Jolly Roger Amusement Park
- Northside Park
- Assateague Beach
- Bayside Resort Golf Club
- Jolly Roger at the Pier
- Delaware Seashore State Park
- Snead Beach
- Peninsula Golf & Country Club
- Plantation Lakes Golf and Country Club
- Bear Trap Dunes
- Wallops Beach
- Trimper Rides of Ocean City
- Fenwick Island State Park Beach
- Coin Beach
- Bow Beach
- Assateague State Park
- Parramore Beach
- Gargathy Beach
- Guard Shore
- Langford Sand