
Holiday rentals with a kayak in Gloucester County
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Gloucester County
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 Gloucester County
House rentals with a kayak

Beach Heron Retreat
This beautiful home is truly a gem! We mostly enjoyed the screened in porch with comfy furniture, ceiling fans, and a fantastic view. The quiet, peacefulness was a great escape. We didn't want to leave! Thank you Ashley for sharing your gorgeous home with us and for being so attentive to our needs. You put a lot of thought into creating a special experience for your guests and it shows. We hope to return soon.

Severnly Pointe Cottage Waterfront Retreat
This is the second time I've stayed at Tamara's place and I would absolutely stay again. The place is exactly what you expect and they have excellent instructions. Wonderful people, peaceful location, and you always know what to expect.

Charming Waterfront Cottage Small Beach
We thoroughly enjoyed our stay at the cottage. The location was peaceful and the river view was fantastic. We would definitely stay here again

East River/Mobjack Bay Mathews
We enjoyed our stay & really enjoyed being on the water. The dock was lovely to fish off of, there was plenty of yard space for our kids to run around & get energy out. Beds were comfortable. Was a really great stay & we will probably try to book again in the future!

Cozy Cottage on The North River
We had the most amazing weekend staying at this cozy cottage for my son’s birthday getaway. From the moment we arrived, everything was absolutely perfect. The space was clean, beautifully decorated, and had such a peaceful, welcoming vibe. It truly felt like peace from the moment we stepped out of the car. The cottage had everything we needed. It made settling in so easy and stress-free, especially with little one in tow. The hosts were beyond incredible. Their warmth, hospitality, and attention to detail made our stay unforgettable. They even went out of their way to help make my son’s birthday feel extra special by letting us do cake with family in their backyard, which meant the world to us. This trip was full of sweet memories, and a huge part of that was thanks to this beautiful cottage and its amazing hosts. If you’re looking for a relaxing, memorable stay, we 100% recommend booking here. We’ll definitely be back!

Sturgeon Creek Retreat
Chris was an excellent communicator. His place looked EXACTLY like the pictures. The setting is so serene and offered the right mix of Peace for working adults and fun activities for kids. The guest handbook was very helpful in identifying local good eats and things to do. Instructions were clear and easy to follow. Everything about the space was thoughtful—from the intentional setup to the little touches that made it feel so warm and inviting. We had everything we needed and more. The kids had a blast, and the adults got a much-needed break. It’s the kind of place you find yourself already planning to return to before you’ve even left. Definitely a 5-star stay. Highly recommend!

The Uncorked Cottage ~North River Retreat~North VA
We throughly enjoyed our stay at the Uncorked Cottage! Do yourself and family a favor and book here ! The amenities, the cleanliness, decor, and comfort will make you feel just like at home. Melany, our host, responded super fast so in case you have any questions, she will be right there. Cheers !

Updated Midcentury Waterfront Cottage
This is such a beautiful gem nestled down a quiet, private road and right off the water. The home is cozy, clean, and super comfortable. Hunter and Katie are wonderful and thoughtful hosts.
Cottage rentals with a kayak

The Crab Shack
My husband and I loved our stay at the Crab Shack! It was convenient for our weekend plans and we loved having direct water/dock access.

Hidden Heaven Lake house on private 1 acre.
Joyce has done a phenomenal job with this lake house. Everything has been thought through. The house actually looks even better than the pictures. You can tell a lot of thought went into the decor. And it is super clean. The kitchen is fully stacked with everything you would need ant home or away. Ample seasoned fire wood and starter sticks makes using their MASSIVE fire pit a breeze. The best part is she gives you access to both of their docks and you will not have to take your boat or kayak out of the water once. We kayak fished Johnson’s and Lacey’s with ease from her house. 100% coming back to stay again.

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.

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.

Modern 2 Bdrm Cottage in Historic River Community
Perfect getaway for rest, relaxation and fun! Kayaks were fun, too breezy and chilly waters for paddle boarding, maybe next time! Beautiful location! Clean and comfortable, felt like home!

Little Dipper -private beach,Kayaks & paddleboards
We loved our stay at the Little Dipper. The house is spacious and comfy - exactly as advertised. It is well-stocked yet neat and clean with no clutter. The screened-in porch is a real gem that connects to a boardwalk leading to a river-view deck. Whether home basing to travel, or tide-watching and kayaking, the Little Dipper's location and setting facilitates a relaxing stay with stunning view day and night. The general location is also super. Urbanna, VA is a quaint little town and you're not far from historic Yorktown or Williamsburg. If you are staying in this vicinity, the Little Dipper is a win. We would stay here again.

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.

TooFine Lakehouse, pet friendly waterfront cottage
We had a wonderful time! The atmosphere was incredibly peaceful and relaxing—perfect for unwinding, even on the rainy days we had. The space was beautiful, cozy and calm. Gina was a great host—very responsive and proactive in checking in to make sure everything was going well.
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.

Riverside R&R: Cabin, Dock, Kayak & Game Arcade
I am running a program out of this home all year long and we have 4 retreats at the property which I'll write a review for each time we stay. We got to experience the season of winter in January complete with a beautiful snowfall the last day of our trip. This time, we got to experience the spring...the season of rebirth. I am grateful for everything the home and land provided to us during this last experience. The home feels like our home while we are there and it has everything we need. Thank you so much!

Wickline Cabin on Moon Creek
We loved this cabin, and Caleb was such a gracious host! Arriving to a dozen farm fresh eggs was such a treat. We grabbed some bacon (Smithfield brand, of course) at the local Kroger and had eggs and bacon every day of our trip. The cabin is so quite and peaceful. It literally feels like you are in the middle of nowhere, but it's a 5 minute drive to all kinds of shops and activities. The povided kayaks were a major selling point for us. It was a very relaxing and beginner friendly paddle up the creek to the river. We saw all kinds of wildlife including otters playing in the creek! It is true that the hot tub is a little glitchy, but it was plenty warm and didn't impact our enjoyment of it at all. Caleb was kind enough to stack wood in the fire pit for us, making our evening campfire easy and streamline. The cabin is really close to great hiking, boutique and antique shops, the brewery, winery and restaurants. I wish we would have taken him up on the offer to bring our dogs. Next time!

Waterfront Lancaster Cabin ~ 10 Mi to Kilmarnock!
We piled 5 adults and a toddler into the house on Kelley Neck Drive, and it worked just fine! Bathrooms, AC, kitchen, appliances, etc, all worked perfectly, the furniture was comfortable and in good shape, and the house was spacious. The yard was perfect for us, but might have been small for older kids, and I wish there had been more than one kayak (but even one kayak was a bonus!) The heron was fishing at the mouth of the our private lagoon every morning, and an osprey and eagle visited as well. We barely heard any neighbors, and the nights were quiet and peaceful. Thank you!

Waterfront Cabin: beach, kayaks, hot tub & firepit
This is a wonderful place on a large creek off the Chesapeake Bay. This place oozes with charm and ambiance and feels so peaceful. We spent the first day just relaxing and doing nothing but looking at the water and chilling on the front porch. The house is updated on the inside and has a large lot with kayaks and a fishing pier. Great hiking at the natural preserves in the area too. We're grateful to the hosts for opening their home to us and we'll definitely come back.

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!

Stunning! River-Front Log Cabin Near Williamsburg
Thoroughly enjoyed our stay. The cabin and property are absolutely beautiful. Waking up to the birds and being surrounded by nature and wildlife is priceless. We spent our days outdoors fishing and finished our evening’s playing games inside. James is a great host who is very responsive. If you’re looking to make memories, this is where to do it!

6 acres of privacy - water access/firepit/kayaks
Cozy, quiet and clean little cabin. Dog had a blast running around. Fire pit was fun and they provide dry wood and fire starters. River was beautiful at sunset.
Destinations to explore
- Rentals with lake access Gloucester County
- Apartment rentals Gloucester County
- Serviced apartment rentals Gloucester County
- Rentals with a washing machine and dryer Gloucester County
- House rentals Gloucester County
- Rentals with a patio Gloucester County
- Resort rentals Gloucester County
- Rentals with pools Gloucester County
- Family-friendly rentals Gloucester County
- Pet-friendly rentals Gloucester County
- Family-friendly rentals Gloucester County
- Beachfront rentals Gloucester County
- Rentals with breakfast Gloucester County
- Waterfront rentals Gloucester County
- Rentals with beach access Gloucester County
- Hotel rentals Gloucester County
- Rentals with a fireplace Gloucester County
- Cottage rentals Gloucester County
- Rentals with outdoor seating Gloucester County
- Townhouse rentals Gloucester County
- Rentals with a sauna Gloucester County
- Rentals with a hot tub Gloucester County
- Flat rentals Gloucester County
- Bed and breakfasts Gloucester County
- Fitness-friendly rentals Gloucester County
- Rentals with a firepit Gloucester County
- 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
- Chesapeake Bay
- Virginia Beach Oceanfront
- Resort Beach
- Busch Gardens Williamsburg
- Bethel Beach
- Buckroe Beach
- First Landing State Park
- Kingsmill Resort
- Water Country USA
- Buckroe Beach and Park
- Grandview Beach
- Jamestown Settlement
- Sarah Constant Beach Park
- Wilkins Beach
- Haven Beach
- Norfolk Botanical Garden
- Grove Beach
- Golden Horseshoe Golf Club
- Royal New Kent Golf Club
- Outlook Beach
- Little Creek Beach
- Cape Charles Beachfront
- Chrysler Museum of Art
- Kiptopeke Beach