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

Oyster Creek Retreat: Waterfront | Dock | 2 Kings
We liked Charlie’s spot so much we came back again this year! Family loves the space, outdoor water sports, and crabbing off the dock (which has been nicely upgraded). I recommend paddling out to the recommended sandbars. Great views, peaceful, and a nice mix of outdoor activity without having to drive anywhere. Highly recommended and we’ll likely be back.

Waterfront, Private Beach, Dock, HotTub, GameRoom
5 stars! We have stayed at a number of Airbnbs in the US and Canada over the years. While we have never had a negative experience, this home exceeded ALL our expectations - a tall order indeed when traveling with 3 generations! The property struck a rare balance of serenity and fun. This was our first trip to the Chesapeake Bay and the home was a perfect example of hospitality and beauty we enjoyed around every turn of our adventure.

Oyster Haven- private beach front home 3 bedrooms
Oyster Haven was exactly what I hoped for! The home was clean and beautiful. The location is private and peaceful. This was the perfect spot to enjoy the beach, but avoid the crowds. My kids spent hours at the private beach everyday we stayed! The screened in porch was a life saver against the bugs, and my in-laws spent hours bird watching. It was such a peaceful and relaxing location, and the house was fully stocked. Could not be happier!

Exclusive Beachfront Home w/ 180° Views & Hot Tub!
I could not wait to write a review about our stay. So much so that we are not even home yet. We had a glorious week at Bay Bliss! Bliss is the perfect description. Anywhere in this beautiful home you can hear the waves of the ocean. There was nothing better than listening to that while falling asleep on the comfiest bed in the master bedroom. Hosts were extremely responsive, helpful with local recommendations and extremely friendly. I have stayed at lot of AirBnb’s and hotels. Honestly, I have never felt so at home and I felt that way from the second I walked in the door. We will definitely be back.

Coastal Farmhouse Getaway
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.

Piper’s Landing: Relaxing beach house near the Bay
This was was a great spot for us to relax on our way home from OBX. The house is big and comfortable and we felt right at home. We managed to get to the Bethel Beach Nature Preserve (nearby and on the bay), Haven Beach (recommended for swimming), and we went to the farmer's market. We met a number of locals who were all friendly. We wish we had more time to try out the kayaks.

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!
Cottages 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.

Locklies Innlet, A unique waterfront experience!
What a perfect cottage! Beautifully (but comfortably) furnished, right on the water, incredibly well-stocked. Arranged so families can spread out, or gather together. Everything you could possibly require or desire for a vacation or getaway was there. And the area is full of things to do--walks, birdwatching, antiquing, or, if you're an architecture geek like me, historic sites and buildings. You're also a 3-minute walk from the best restaurant on the Northern Neck, Merroir Tasting Room. Can't wait to come back.

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.

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!

3 BR Bay Home w Private Dock & all the Amenities
Our trip to The Half Shell Haven was great! The place was clean, extremely well stocked, and included many extras! We had crazy weather the first two days, but we had plenty to do at the house. My boys loved being on the water and the game room and my daughter loved the hot tub and bicycling. My daughters service dog enjoyed a nice reprieve and seemed so happy. We had a great time, and were honestly sad to go! If we find ourselves back up in Virginia we will definitely stay here! Thank you for the care and attention to detail to ensure a great trip!

The Nook; Peaceful 2 bedroom cottage by the bay
My family and I have stayed in Jason's place before multiple times. This was the first time we have rented it ourselves. His place is always amazing to stay at. We love the view from the table, the bikes to ride, grill and fire pit. Jason responds very quickly if you need anything. The place is very relaxing and an amazing home away from home.
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.

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!

Waterfront Cabin: beach, kayaks, hot tub & firepit
Great place! We really enjoyed all of the outdoor amenities. The kayaks, paddle boards, fishing, hot tub, hammocks were all great. Have two teens who very much enjoyed. Was relaxing but a lot to do there also. Lots of jellyfish so we did not swim at all. Definitely a lot of fish and crabs that can be caught right at the dock. If more serious and knowledgeable about fishing then us, may want to bring extra hooks and tackle box. Definitely some size-able fish. Bait shop in town has a lot of supplies but very limited hours. The house had tons of towels, washcloths, etc. which was nice. Kitchen had oil, spices, plenty of cooking utensils, pots / pans, dinnerware etc. Blackstone was nice. Made it very easy to cook. Very few restaurants open M-F. Of those that were, most closed by about 3. Newsome’s was a great local place for lunch. Crab cakes were outstanding. Definitely would stay again. Had a great time!

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 holiday rentals with a kayak in Cape Charles
Total rentals
20 properties
Nightly prices starting at
$216 NZD before taxes and fees
Total number of reviews
520 reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wi-Fi availability
20 properties include access to Wi-Fi
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