Holiday rentals with a kayak in Chesapeake

Find and book unique kayak rentals on Airbnb

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Popular amenities for kayak rentals in Chesapeake

House rentals with a kayak

Top guest favourite
Home in Buckroe Beach
5 out of 5 average rating, 64 reviews

The Canary Island … Keep Calm and Fish On

MichaelRating, 5 stars6 days ago
The property is spectacular. Everything about the accommodations was excellent. Not one complaint. Just praise. The host was very friendly and helpful. So were the neighbors!
Guest favourite
Home in Newport News
4.93 out of 5 average rating, 81 reviews

1-Bedroom Home Near Christopher Newport University

MikeRating, 5 stars2 weeks ago
We absolutely loved the house and all of the decor! There was no need to leave the house if we didn't want to due to the movies, records, stereo system, arcade machine and hot tub! But, my personal favorite was the kitchen! We will definitely be going back and staying at Adam's!! Side Note: The Legos are AMAZING!
Superhost
Home in Norfolk
5 out of 5 average rating, 4 reviews

Beachfront Getaway, pet friendly

JasonRating, 5 stars6 months ago
Our family enjoyed our weekend at Big Blue. It was special because it was my wife's birthday and there was plenty of family with us. We really liked how the 2nd and 3rd floor are duplicates of each other. It's like 2 different apartments , but we had access to both. The kids on the 2nd floor and the adults on the 3rd. Very clean open spaces. The host were responsive and proactive. We hope to make the Willoughby Spit area a regular vacation spot, very lovely.
Guest favourite
Home in Sandbridge
5 out of 5 average rating, 5 reviews

Captain's Corner

ZachariahRating, 5 stars1 month ago
Very close walk to the beach, had a great weekend with friends
Top guest favourite
Home in Gloucester County
4.95 out of 5 average rating, 57 reviews

York River | Chesapeake Bay Bliss: Fishing Retreat

AmyRating, 5 stars5 days ago
We had a two night stay at this beautiful house. Everything was nice and clean. We loved sitting on the deck, overlooking the river. It was a perfect place to drink our morning coffee!
Guest favourite
Home in Portsmouth
5 out of 5 average rating, 6 reviews

Escape to the water!

ChristinaRating, 5 stars2 weeks ago
Sabrina was extremely nice, helpful , and responsive. The house is as described, very clean, and had everything we needed. I'm sure if there was something we needed Sabrina would have taken care of it. We felt very safe in the neighborhood. We took our dog on walks by the water. It was a dead end street & so peaceful. We even met a few neighbors that made us feel extremely welcomed. We will definitely stay again! I would like to caution you to only visit the nearby Walmart, 7 Eleven & other stores during the day.
Guest favourite
Home in Cape Charles
4.95 out of 5 average rating, 144 reviews

Harbor View- (Sun - Sun rental June- Aug.)

TheresaRating, 5 stars1 month ago
We absolutely loved the stay at Janie’s place! It was great and such a short walk to the beach. The beach wagon, chairs, and umbrellas were a nice touch and saved us from having to bring our own! There is also a propane and charcoal grill available for use, which is amazing. We look forward to booking our next trip to Cape Charles here, hopefully sooner rather than later! We have heard Christmas time is beautiful!
Guest favourite
Home in Sandbridge
5 out of 5 average rating, 25 reviews

Pool, hot tub, beach house. Msg for shorter stays

KristineRating, 5 stars1 month ago
We had a wonderful stay at the Great Escape. The home was very clean and comfortable with plenty of space. The amenities were perfect and the beach is just a short walk with easy access. Cody was a wonderful host with quick responses. Thank you for sharing your home. We made wondrful memories in Virgina Beach.

Cottage rentals with a kayak

Top guest favourite
Cottage in Surry
4.96 out of 5 average rating, 50 reviews

Riverfront Oasis | Kayaks, Private Beach, & More

PaulRating, 5 stars1 month ago
This place was just amazing. The views of James River, and even the Jamestown settlement across the river (using binoculars) was just mind-blowing! Kevin and Jamie left a wide variety of amenities that were extremely thoughtful and useful, to include hygiene products, charging cords (which was a life saver because for literally the first time ever, I forgot my phone and iPad cords), coffee, and even a margarita kit! The cottage is so cozy, and was very clean. I’m definitely going to book here again.
Cottage in Surry
5 out of 5 average rating, 3 reviews

James River Beach Cottage - Private Beach & Pier!

MicheleRating, 5 stars21 months ago
Deena was extremely helpful from the start. I was looking between 2 properties however since Deena was the first person to email me information of the area the history on the home and ideas for things to do for the kids I booked with her. When we got to the cottage we easily checked in had a ton of amenities and the cottage was clean spotless clean. We really enjoyed our stay with Deena and we look forward to another a stay at her cottage.
Cottage in Surry
4.78 out of 5 average rating, 9 reviews

James River Beach Retreat - Private Beach & Pier

JanineRating, 5 stars21 months ago
Deena’s place was actually better than pictured. Such great decor—we loved the colors and the owls. Everything was set up perfectly, very comfortable and relaxing. Terrific to be right next to the ferry, as we spent most of our time exploring Jamestown, Yorktown. TV, wifi worked well. Having kayaks especially nice. Deena was extremely communicative and informative and a all around great host!
Cottage in Norfolk
4.79 out of 5 average rating, 146 reviews

Beach Cottage - On Beach with Wrap Around Porch

BomaniRating, 5 stars1 week ago
good location and a nice place for a getaway from the city
Cottage in Norfolk
4.79 out of 5 average rating, 121 reviews

Beach Cottage-Bay Views Loft on Beach & Veranda

ShannonRating, 5 stars2 days ago
This was our second year staying in one of John's places in Oceanview Norfolk. Last year was great but we enjoyed this year even more. This place had more room for our family of 5! It was beautiful inside and out. Very quite and too yourself. But John is usually right there if ya need him or have any questions. We will definitely be back next year. And I'd recommend this place to Any and Everyone looking for a wonderful place too stay! Thanks for sharing your property with us as Always!
Guest favourite
Cottage in Sandbridge
5 out of 5 average rating, 23 reviews

Epic Sunsets | Waterfront Cottage | Pet Friendly

CateRating, 5 stars1 week ago
This place was the most charming airbnb I have ever stayed in. Badria and Jay made every detail of our stay perfect with all of their extra touches, including saltwater taffy and a box of croissants, slippers and a lavender mask, and a fully stocked coffee station with syrups. We instantly felt at home and in vacation mode at their place and literally laid out on the dock the entire time. A perfect spot for kayaking, laying out in the sun, and I even brought out my mat and did some yoga on the dock. The views were unreal. The couch was so comfortable I accidentally fell asleep there the whole night and woke up to the gorgeous window views. Amazing hosts and location!
Guest favourite
Cottage in Coinjock
4.89 out of 5 average rating, 38 reviews

WaterView | Private Dock | Kayaks | Chef's Kitchen

CarlyRating, 5 stars5 days ago
My family and I had a great time while staying in the cottage. The house was very clean and cozy. The views from the house were beautiful and it was very peaceful. I would definitely recommend this place for anyone wanting a peaceful getaway.
Guest favourite
Cottage in Norfolk
4.92 out of 5 average rating, 173 reviews

Poseidon - Beach Carriage House - 120 Years Old

JesseRating, 5 stars6 days ago
everything was awesome hope to be back soon.

Quick stats about holiday rentals with a kayak in Chesapeake

  • Total rentals

    10 properties

  • Nightly prices starting at

    $77 SGD before taxes and fees

  • Total number of reviews

    640 reviews

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi and Pool

  • Local attractions

    Chrysler Museum of Art, Nauticus and Cinemark Chesapeake Square

Destinations to explore