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

Waterfront Getaway with Dock
We loved the experience from booking to check-out. The setting exceeded our expectations. Peaceful and beautiful landscape. Easy to launch kayaks. Chickens were an added bonus. Appreciated the close proximity of Blackwater. Would love to return.

The Hideaway at Mill Creek
This little getaway exceeded my expectations and more. The pictures listed on Airbnb are beautiful, but it will never match the views in person. The house was clean and fully loaded with any and all things you may need. I will definitely be back! My dog LOVED playing with the neighbor dog, Bella. By the end of the weekend they were best of friends :)

Spacious waterfront family retreat. Dogs welcome!
What an amazing place! The photos did not do it justice. We had beautiful weather and the back patio/deck was the perfect hangout. We went kayaking, caught a lot of crabs, and enjoyed being by the water. We had the firepit going while one of us was grilling food and the vibes were perfect. The detached game room saw plenty of heated pool games with a great selection of music and sound system. Bedrooms were comfortable and the kitchen was a joy to cook in. Dawn provided very detailed instructions so that you know all that you need to do. All-in-all, great spot that is a perfect group getaway!

Newly Renovated Modern 3 bed 2 bath Water Front
The River House was phenomenal, a beautifully furnished place with large riverfront lawn and private boat launch. Exceptionally clean and well-stocked with everything you could think of for a comfy stay (fluffy towels, extra paper products, cleaning supplies, blankets, tons of pillows). Kitchen is as beautiful as the photos, and amply stocked with everything from ziplocs to pyrex to measuring cups and baking tools. The kayaks and canoe were easy to access and use. Easy place to paddle in a calm and quiet tributary. Highly recommend Lindy’s seafood a mile away. Host has compiled a guidebook with lots of local business recs and info. You will not be disappointed with a stay at this awesome retreat.

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!

Sunset Breezes - quiet waterfront retreat
Scott and Melinda's place was perfect for a peaceful getaway for our family of 5. The water was so nice to wake up to and fall asleep hearing the water move by! The thought of all the basic needs and had everything easily accessible from fresh eggs from their chickens, a great variety of coffee pods and creamer, and all the other small needs that come up while staying in an airbnb. This was great since it is off the beaten path. If you are looking for some peaceful family time or a secluded retreat with friends, this is a perfect place!

The Haven On The Chesapeake Bay
We love the Haven on the Bay! This was our third year staying here, and we can't rave enough about how perfect a space it is for us. The waterfront view is incredibly peaceful, the sunrise is gorgeous, and the physical space invites great quality time for the group. Ashley was a very gracious host, and was very quick to respond anytime we reached out with a question. We even had the joy of seeing dolphins while we were roasting s'mores around the fire pit!

The Rosé Retreat: Pool-Screened Porch-RELAX
We had a really nice stay at the Rose Retreat! The home is wonderfully appointed with nice furnishings. We especially appreciated the well stocked kitchen with upscale drink and dinnerware. The hand written welcome note, bottle of wine and snacks were so thoughtful - thank you! A perfect location from which to enjoy Irvington and the surrounding towns. We hope to come back in warmer weather to enjoy the pool!
Cottage rentals with a kayak

Peaceful 5 bedroom cottage on the Eastern Shore...
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.

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.

Cottage by the bay (private peaceful surroundings)
Very secluded but I don't mind that all. The home is beautiful and the host is very attentive.

IDLEHOUR, 3 BEDROOMS 2 BATHS W/ DOCK
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.

Cottage on Cabin Creek
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.

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.

Waterfront Bay Cottage w/ Your Own Private Beach
We had a fantastic stay at this charming cottage on a private beach! The peaceful setting and direct access to the water made for a truly relaxing getaway. We especially loved the Adirondack chairs and firepit overlooking the Chesapeake Bay—perfect for amazing views and cozy evenings. The master bedroom and living spaces offered beautiful water views that made every moment feel serene and special. The owner was incredibly accommodating with check-in and shared thoughtful, personal tips that made our stay even more enjoyable. Highly recommend this spot for anyone looking to unwind by the bay!

Little Cottage on the Creek
Karen’s place was a perfect weekend getaway for a couple. The place had everything we needed and the location was peaceful and beautiful. Karen was very helpful and responsive with recommendations. Would definitely stay here again!
Cabin rentals with a kayak

"Elderberries" Chesapeake Bayfront Cottage
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.

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!

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.

Waterfront Cabin: beach, kayaks, hot tub & firepit
We stayed for an annual ladies' trip. I loved the peaceful views from the porch and kayaking by herons. My friends got a kick out of catching and cooking crabs for the first time. When I asked about a crab pot for cooking their hoped-for haul, the hosts ordered one for delivery right away. Great place to hang with friends, but I'm sure my kids would also love the firepit, the dock, and the kayaks. Thank you!

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.

Beach Road Oasis, Tangier Island, VA
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!

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.
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.
Quick stats about vacation rentals with a kayak in Chincoteague
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ294 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
- Bayside Resort Golf Club
- Northside Park
- Jolly Roger at the Pier
- Assateague Beach
- 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
- Coin Beach
- Fenwick Island State Park Beach
- Assateague State Park
- Parramore Beach
- Gargathy Beach
- Guard Shore
- The Links at Lighthouse Sound
- Lost Treasure Golf