
Holiday rentals with a kayak in Chesapeake
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Chesapeake
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for kayak rentals in Chesapeake
House rentals with a kayak

The Canary Island … Keep Calm and Fish On
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!

1-Bedroom Home Near Christopher Newport University
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!

Beachfront Getaway, pet friendly
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.

Captain's Corner
Very close walk to the beach, had a great weekend with friends

York River | Chesapeake Bay Bliss: Fishing Retreat
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!

Escape to the water!
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.

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

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

Riverfront Oasis | Kayaks, Private Beach, & More
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.

James River Beach Cottage - Private Beach & Pier!
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.

James River Beach Retreat - Private Beach & Pier
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!

Beach Cottage - On Beach with Wrap Around Porch
good location and a nice place for a getaway from the city

Beach Cottage-Bay Views Loft on Beach & Veranda
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!

Epic Sunsets | Waterfront Cottage | Pet Friendly
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!

WaterView | Private Dock | Kayaks | Chef's Kitchen
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.

Poseidon - Beach Carriage House - 120 Years Old
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
- Virginia Beach Holiday rentals
- Williamsburg Holiday rentals
- Richmond Holiday rentals
- Shanghai Holiday rentals
- Myrtle Beach Holiday rentals
- Charlotte Holiday rentals
- Outer Banks Holiday rentals
- Washington Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Jersey Shore Holiday rentals
- New York Holiday rentals
- Family-friendly rentals Chesapeake
- House rentals Chesapeake
- Townhouse rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Rentals with breakfast Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Waterfront rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Cottage rentals Chesapeake
- Beach house rentals Chesapeake
- Rentals with beach access Chesapeake
- Beachfront rentals Chesapeake
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- Rentals with lake access Chesapeake
- Rentals with pools Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a firepit Chesapeake
- Rentals with a hot tub Chesapeake
- Flat rentals Chesapeake
- Apartment rentals Chesapeake
- Rentals with a kayak Virginia
- Rentals with a kayak United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- First Landing State Park
- Water Country USA
- Buckroe Beach and Park
- Kingsmill Resort
- Grandview Beach
- Currituck Beach Lighthouse
- Outlook Beach
- Jamestown Settlement
- Haven Beach
- Ocean Breeze Waterpark
- Sarah Constant Beach Park
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
- Wilkins Beach
- Bonito St. Public Beach Access
- Little Creek Beach
- Kiptopeke Beach
- Golden Horseshoe Golf Club