
Vacation rentals with a kayak in Chincoteague Bay
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Top-rated kayak rentals in Chincoteague Bay
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House rentals with a kayak

Peaceful and Cozy Waterfront Home (just renovated)
Had a great stay ! Would definitely stay again if the time comes for us to go back .

Peaceful bay retreat. Hot tub,water views,fire pit
A spacious home by the water. We celebrated Thanksgiving at this location and it was very special. The views are beautiful, had a fire right by the water and relaxed by the beach. A perfect getaway with family and friends. It has everything you need, the living room is super comfortable and great to relax with the family. The kitchen was spacious making it easy to cook and entertain the family. We loved the hot tub, playing pool and having family dinner. Overall a fabulous experience!! Great host- great communication. Highly recommend

The Hideaway at Mill Creek
Really cute and peaceful stay! Will stay again in the future if we need a quiet weekend! And Linda was super responsive and instructions were clear and simple for the area

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home
This air b&b is in a beautiful setting with plenty to do (kayaking, hot tub, fire pits, bird watching, etc). It's also very centrally located so we could easily get to more populated areas in no time. The most stunning part of the house is the master suite in my opinion which is on the upper level (the upper level is shared with another apartment, but you don't really hear the air b&b tenants of this suite and it's completely separate with a separate entrance). Stunning views from both the master bedroom and the bath tub in the master suite! The downstairs is also quite lovely with two regular bedrooms, one small bedroom, and a sun room that has a pull out couch (we didn't use it). It's a lovely house to entertain in. It has personal photographs to the owner downstairs that speak to the family's history. The owner is communicative. The overall experience was quite lovely. We'd be happy to return.

The River House
We had a relaxing weekend at the river. We had so much privacy and were super happy with the house

Spacious Gorgeous Waterfront Home with Sunset View
This house is perfect for large groups. It is very spacious, with plenty of room to spread out and get comfortable. We enjoyed sitting on the dock taking in the serene natural beauty of the Creek and observing the local birdlife, including Kingfishers, Great Blue Herons, and Bald Eagles. The house is situated very near to the entrance of Lookout Point State Park which we greatly enjoyed exploring on bicycles. Seeing a large wedge of Tundra Swans fly overhead was a special moment. If you want to spend some time relaxing in a beautiful setting in a beautiful and very interesting area with a large group, this house will serve you well.

Hutch's Bluff - Waterfront near Williamsburg
My wife and I along with our 9 and 10 yr old stayed here while visiting the Williamsburg attractions and it worked out perfectly. It was only a 20-30 min drive on scenic back roads and we never had issues with traffic. It was nice to escape the crowds at the end of the day and go back to the peace and quiet of Hutch’s Bluff.

Chesapeake Waterfront HotTub-Kayaks-Crabbing
Second time, we have stayed at this AIRBNB. The host, Natalie is very helpful and welcoming! Both stays were awesome! The home is cozy and comfortable for our family. Amazing water views with a fenced yard for our dog. We enjoyed making a bonfire and roasting marshmallows. Highly recommend this home, and will stay again when we are in the area.
Cottage rentals with a kayak

Chesapeake Bay Cottage
fantastic stay. clean and very quiet right on the bay. highly recommended. would definitely revisit again.

Octopus Cottage: Hot Tub | Kayaks | Fire Pit
Do not hesitate to stay here! It is spectacular. Right on the beach, immaculate and perfectly appointed. We can’t wait to come back!

Modern 2 Bdrm Cottage in Historic River Community
I enjoyed my stay at this location while I was working in the area. The house was very clean and had a great view of the river. I loved the area and all of the amenities that she had in the home. Would definitely return.

Levering Creek Cottage with Private Dock
We had a great stay at the cottage. Very peaceful getaway. We loved biking around the island and learning about the history. The cottage was very clean and Janet was very kind and helpful. Recommend for a cute unique getaway!

Weems Creek Cottage, Annapolis Waterfront
What a beautiful off the beaten path place to stay. You are within walking distance of restaurants, coffee, and grocery. But feel like you’re miles away. That’s the effect the cabin has on you. There is a beautiful waterfront that you can enjoy from just about every area of the home. Jim was more than helpful. He really went above and beyond over most host. We would definitely Stay again. It’s the perfect spot if you need to relax.

Ft. Smallwood Overlook. Waterfront with Kayaks!
The place is wonderful. We were down for Thanksgiving with my family and were travelling with our 2 dogs, Wally & Dolly. The location was perfect, close to Riviera Beach where our Family Thanksgiving Dinner was, very private, no noise or distractions for the dogs (that was great). The property was surrounded by water on three sides, great views! It is right next to Ft. Smallwood Park where we took the dogs for walks every day, they loved it. As for the house it was perfect for us, just about the size of our home, so that made it very comfortable for us. All one level, which made it great for us older people. It was furnished with very comfortable furniture. Lots of information about the local surroundings, things to do, and restaurants. Keith was wonderful to work with, very easy to communicate with which made the whole process very easy for us. We even had a conversation over the phone once we were in the house to make sure everything was to our liking, and we were happy !

Great little cottage with a "Rivah" view
The place was just like in the pictures—very quiet and peaceful. Directions were clear and access was super easy. We especially enjoyed the kayaking—it was very good! We weren’t lucky enough to catch anything this time, but we still had a great time out on the water. The owner was also super accommodating and let us check out late without asking for any extra money, which was really kind and appreciated. Overall, it’s a nice and cozy spot, perfect for a relaxing getaway.

Old World Cottage/Fabulous Sunsets/Polite Pets OK
A beautiful home with space for several people, close to the water and surrounded by beautiful pine trees. Clean and tidy with a coastal charm, pet friendly is an extra bonus! Owners were very supportive and communicative.
Cabin rentals with a kayak

True St. Michaels 6 Acre Waterfront w/heated pool
Marissa’s home was beautiful and had everything we needed - plus some. Plenty of clean/comfort space and restrooms for our party of 6. We had such a relaxing, warm stay during a snowy January weekend - even smores! Marissa was always responsive and provided suggestions for shopping and dining in St. Michael’s. It was lovely all the way around! Highly recommend this home and working with these owners. Top notch!

Riverside R&R: Cabin, Dock, Kayak & Game Arcade
Beautiful cabin in the woods. Remote but WiFi worked great. We were looking for cozy and relaxing and it delivered!

Warm and Cozy Historic Cabin on the Water
Such a cool cabin. Wish we could have stayed longer.

Awesome private off grid cabin with creek view.
Great place to stay for rest, relaxation, peace and quiet. In my short time there, I saw a wild turkey, a fox, an otter, red wing black birds, a woodpecker, and cardinals. And at night, I heard tree frogs and an owl was really close by. Terri is wonderful as a host!

Peaceful Waterfront Retreat on The Bay
A fair and open spaced home. Free of clutter. Many updated electronics I didn't expect. Only drawback was the microwave. It had a lagging door switch that locked when it was ready. If your impatience, it would test your nerves. A shower that was plenty hot and spacious. Loved the size of the home and location, I want to rent this again.

Hideaway on the Bay: Waterfront Vintage A Frame
We absolutely loved staying in this beautiful air b n b! The scenery was outstanding and was definitely one of the most peaceful stays we have experienced! We will 100% be booking again in the near future!

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade
This is a gem! The other 5* reviews and the description and photos are all accurate. My family had one of the best times we’ve had in a vacation rental…and we have done several all over the world. Wonderful place to relax, but also have things to do. Great for kids and adults alike.

Dinna Fash-3 BR Waterfront Log Cabin
Had a great one-night stay! The cabin was clean, comfortable, and just as described. Check-in was smooth, and the host was responsive. Perfect for a peaceful getaway—would book again!
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