
Holiday rentals with a kayak in Middlesex County
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Top-rated Accommodation with a Kayak in Middlesex County
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Holiday House Rentals with a Kayak

Secluded beach front cottage on the Chesapeake Bay
My absolute favorite airbnb ever ! This was the 3rd time I've stayed here, and if I could afford it, I'd go monthly. The location is perfect, right on the water, small private beach, lots of privacy and soooo incredibly relaxing. The house is very well laid out, super clean and comfortable. Keri provides more than most hosts, from the kitchen and bathrooms, to beach gear, movies, books, games, and the kayaks ! I love love love this house and location so very much. It feels like "my" home away from home and I'll continue to go back as much as possible. THANK YOU again Keri, for another amazing getaway !

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.

Waterfront~Private~Near Kilmarnock & Tides Inn
It is a wonderful, private and quiet location. Kayaking, fishing, crabbing, and all. Kristie was super responsive and helpful. I will be definitely returning.

Blue Pearl Cottage
Very cozy, comfortable cottage with charm and modern upgrades. Private and quiet; lovely view of the water. Comfortable beds and sofa. All amenities, just like home. Three TVs, large screens in LR and MSBR. Large screened porch overlooking water. Hosts were responsive and helpful.

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

The Perfect View Virginia Tiny Home
The Perfect view was a perfect place with a perfect host. We didn't know what to expect and can say our experience exceeded our expectations. The place feels very clean. The property is well thought out - with the landscaping/garden, the seats/firepit/jacuzzi overlooking the water, and the tranquil garden fountain. We enjoyed sitting on the porch, eating special meals prepared by Brenda and enjoying the company of her pets. Nellie Mae is the ideal sweet, soft, cuddly lap dog. (We normally are big dog people :) Brenda KNOWS hospitality and couldn't have been a better host. She makes the most delicious meals - we had her dinners and breakfasts several times and were never disappointed. Suprisingly, the fold-out King bed was extremely comfortable and the room had cool temperature with A/C and fan to help us sleep soundly every night. Delightful place with delightful host - one of our top Airbnb experiences! We will certainly be back. Thank you Ms. Brenda!!

Lancaster Waterfront Historic Home
Wonderful stay! I loved the home. Place was super clean and very comfy. Lots of nice touches in house. Went out for dinner one night. Options are limited unless you are willing to drive 30 minutes. Chitterchats second scoop ice cream is a great spot to hit up. It is helpful to have shoes that can stay in the water. There are bugs if wind isn’t blowing, so plan accordingly. No sand toys on property. I’d probably bring some next time for kids. The gas is not propane but charcoal, something I didn’t realize til I arrived. Saw turtles, snakes, bald eagle, deer, bunnies and even a shark sighting.

Waterfront Home - Dock, Kayaks, Fire Pit, Grill
Talk about being sad 😢to leave! Sometimes a location for an air BnB just hits it out of the park, and this is a great example. We LOVED our stay and took advantage of the yard and beautiful view daily! We fished off the dock and shore. Tip, since it is tidal water as long as you are on the shore or dock you don’t need a fishing license. Our pups loved the yard and going for a swim. There are a lot of great places to eat within a 30min drive. We were on a work trip, but would love to come back when we could take advantage of everything this place has to offer. It’s a gem! The surrounding area is fun to explore if you like antiques and boutiques. We loved the local vibe! You will have a great time.
Cottages with a kayak

Relaxing Waterfront Cottage w/ Private Dock/Kayaks
I’ve taken my son and nephew to the beach for a few days the last three summers. I decided on something different, and I’m glad that I did! The Pearly Oyster was everything you would want or need in a vacation home. We spent most of the days on the kayaks or fishing off the dock. The kitchen, in addition to the Blackstone, was wonderful for cooking quick meals including fresh seafood from Kellum Farms just a few miles down the road. We had a blast! The Pearly Oyster has been added to our list of places that we would return to.

Renovated, Waterfront Cottage on the Rappahannock!
We had a great long weekend stay. The house was spacious and well appointed. We loved sitting outside under the stars and playing with the kids in the sunroom. Was such a nice touch to have kids toys at the house and lots of space to gather. We had one issue with the HVAC but each space had a window AC unit and the host was super helpful and responsive. Would 100% recommend and stay again.

Locklies Innlet, A unique waterfront experience!
My husband and I had an absolutely wonderful time and the home played a big part in this. I was so impressed with all the extras that I just never see in other homes. The house is so cozy and such a beautiful location. Just perfect for relaxation. We will definitely want to come back. Thank you Cornelia for opening up your home to us.

The Cottage at Elm Bank
Our stay at The Cottage at Elm Bank exceeded our expectations. We traveled to Virginia from New Jersey. A single mom, her two big boys and her little pup. We were in town for a little getaway for Easter weekend. I was looking for some peace and tranquility. When we arrived, we were greeted by Susan and George. They were kind and welcoming. The property is absolutely breathtaking. Our accommodations were cozy and super clean. What stood out the most was all of the personal touches that Susan and George provided. We had a welcome basket waiting for us with many thoughtful things for us to snack on. It was as if they knew exactly what we liked. Susan was very responsive and George was very helpful, he even allowed the boys to use the kayaks and helped them set things up to get into the water. We were able to use the pickleball court and the basketball hoop. They set up wood for a wonderful fire and provided the marshmallows and sticks! It’s a beautiful property with wonderful hosts!

Cottage on Prentice Creek, PA
This Airbnb exceeded all expectations! From the moment we walked in, we were blown away by how beautiful and thoughtfully designed the space was - every detail with stylish, comfortable, and impeccably clean. What really stood out, though was how well stocked everything was. The kitchen had every tool and appliance we could possibly need, there were plenty of fresh towels, extra blankets, and even small touches like coffee, toiletries that made our stay so easy and enjoyable, and very dog friendly! It truly felt like a home away from home. Highly recommend this place, we can’t wait to come back. Thanks so much for sharing your home!

Restful river house with water & golf-course view
The cleanest place I haven’t rented in along time! Beautiful views, the family had a great time fishing! Host was very quick to respond! Beautiful home.

Creeks End Farmhouse
We had a great day wonderful views of the river. Love the screened in porch and the swing and the beds were super comfortable. The kitchen had everything we needed in my family loved fishing off the dock.

Tipsy Mermaid Rivah House - 5bed 3bath Waterfront
My group of 10 had a wonderful stay at the Rivah House! We could have fit several more people quite comfortably - we felt we had plenty of space in both common areas and rooms. Lots of fun, bright decor livens up the space and makes it feel homey. The house was clean, linens were nice, and beds were very comfy. We appreciated that there were different room configurations that could fit a variety of group types. The kitchen was extremely well-appointed, with plenty of dishes, utensils, and some pleasant surprises like a Crock-Pot! Our group had a great time cooking and eating together around the big table. Our stay was early March but if the weather had been warmer, we definitely would have spent more time sitting out by the dock watching the birds on the water, playing with all the outdoor toys (kayaks, etc.), and enjoying the spacious fire pit. Francesca was an excellent host, giving us clear check-in/out instructions, local advice, and responding promptly.
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
We are two families that met up for a relaxing getaway after celebrating a high school graduation. This was the perfect place. The downstairs had lots of games and a big screen for them to hook their switch up to. We watched movies upstairs. And use the well-equipped kitchen each night to make a big dinner. The kids took the kayaks and canoe out one afternoon as well. Although I would say they definitely wouldn’t swim there. Compass entertainment complex is very close and they enjoyed their time there. We also went to a movie there one night. It is a beautiful home in a peaceful setting. Especially down on the dock at night. It was very quiet. We would definitely recommend this home.

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!

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.

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
Ted and Jen couldn’t have been nicer and more accommodating. It’s a great spot and I’m hoping to return soon!

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!
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- Chesapeake Bay
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
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- Kingsmill Resort
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- Haven Beach
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- Golden Horseshoe Golf Club
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- Cape Charles Beachfront
- The Poe Museum
- James River Country Club
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- Langford Sand
- Lane Beach