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

The Puskar’s Landing
Such a beautiful home! It also was very cozy and peaceful. The beach and pier is a nice walk away and the hot tub was perfect for relaxing. Host was very friendly and responsive if we needed anything. I will most definitely be staying here again!

Waterfront Retreat| Kayak+Beaches+Pool | Gameroom
Connie’s place was great! Looked just like the photos. The house was clean and in a great area. Nice and friendly neighbors. We enjoyed the community beaches that are super close, clean and dog friendly. It was a prefect weekend trip. We would book here again!

Private pool, waterfront, kayaks, bikes, firepits!
We can't wait to return to Golden Quarter Farm! Charming and expansive, the property has everything we were looking for in a place to spend a relaxing weekend with extended family. The historic house is bright and roomy with a well-appointed kitchen; the bedrooms are unique, comfortable, and private; and the living space homey and inviting -- perfect for spending time together. The beautiful views of the riverfront drew everyone outside for walks down the pier, through the fields, and down the sun-dappled forest trails. It was a bit too chilly during our April stay, but the possibilities for enjoying the river (canoe, kayay, SUP) and lovely pool were nonetheless enticing. Finally, I must mention that Evie and Mary were extraordinarily welcoming and accomodating, from communicating proactively to preparing the home for our stay and checking in to make sure everything was perfect. Highly recommend!

Private Country Beach Retreat
Kristy’s place was so peaceful! If you are looking for a quiet space then this is the place for you! Everything from the location to the details in the home curated a calm environment. And if you need to hear a little noise Cape Charles is just a drive away! Also check out the lovely Chatham vineyard just down the road!

1891 Coastal Charmer: fully renovated farmhouse
We loved the ocean decor, beautiful place! Highlights for us were hanging out and having meals on the screened porch and kayaking in the bay. Mary Lou was super responsive and helpful, provided a full list of places to eat, see, and do. Wed’d love to go back in the fall!

The Haven On The Chesapeake Bay
The Haven was truly a gem. It was so private and secluded- just what we needed to relax and reset. Ashley was so friendly and provided so many helpful accommodations that you’d typically not find elsewhere, such as complimentary coffee and a stocked s'mores station. Collectively, I think my family most enjoyed using the kayaks and paddle boards to explore the bay everyday. The kids absolutely loved hunting for wildlife around the house and pond. I’ll never forget this trip!

Beach Please! River cottage w/private beach & dock
Our family had beautiful weather on our vacation! Everything was as described, Mary & Shelly thought of everything. We would highly recommend.

Living on Island Time
Had a great week fishing and crabbing from the doc, kayaking, game playing, eating and visiting local attractions! Can’t say enough about how friendly Melissa was. Would definitely return!
Cottage rentals with a kayak

The Crab Shack
This was our 1st visit to The Crab Shack. All I can say is Wow, just Wow! This was the cleanest, nicest and cutest Airbnb that we have ever stayed at over the years! It was amazing! My husband and I traveled from Sarver, PA with our 2 Golden Retrievers to celebrate our 10 year Wedding Anniversary! We all had the best time ever! We spent most of the time here at the Shack just cooking on the grill and listening to music and the girls did a lot of swimming fetching for balls! Thank you Carlisle and Mary for making our 10 year Anniversary simply perfect! ❤️☀️😎🥂🍾🦀 We can’t wait to come back! ☺️

Cottage with a view!
Beautiful place to stay. Quite peaceful area with friendly neighbors. Home was cozy and welcoming. Kitchen had everything you could need. Amenities were amazing. Had a spectacular time would definitely come back to stay again.

Chesapeake Bay Cottage
Lovely stay on the water! Mini beach is an added bonus. Great restaurants nearby!

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.

A "True" Chesapeake Bay Waterfront Experience!
Awesome house and location. Very nicely furnished and stocked with more items that I am accustomed to for an air bnb.

Levering Creek Cottage with Private Dock
Janet has a unique property considering the destination is on an island... it has it's own dock which affords guests the ultimate in flexibility. It was the main reason we elected to overnight there. My son and I only had one night for the fishing trip in our own boat over father's day weekend so it was not a deal-breaker we had to book 2 nights. The simplicity of motoring up after a day on the water with all of our gear and the convenience for being up early to catch the right tide was a perfect fit. Wish we had 2 nights to stay and have better luck with the weather... and the fish, but we will be back. Thanks Janet!

Bayfront home on Sunset Lake.
Pauls place was truly a home away from home. The house and property are absolutely beautiful. We loved sitting out on both the porch and dock every single day. It was so peaceful and the sunset view is SPECTACULAR. Paul was a great host and checked in on us to ensure we had everything we needed throughout our stay. He is also very quick to respond- love that! (Thank you, Paul!!) This will definitely be our new vacation spot when we come down to the beach! Its perfect!

TooFine Lakehouse, pet friendly waterfront cottage
Beautiful surroundings, with the lake just steps from the door. The cabin had everything we needed for a 4 night stay. Great mix of indoor and outdoor spaces to enjoy. We absolutely loved it!
Cabin rentals with a kayak

True St. Michaels 6 Acre Waterfront w/heated pool
WOW. This was one of the most wonderful homes we’ve ever stayed in. Everything was clean, comfortable and accessible. Marissa was so helpful with recommendations, flexible check-in times so we could get my little one down for a nap, my three-year-old love the pool, dedicated playroom, toys, swing set and s’mores that were such a perfect gift from Marissa. My son asked if we could move there! My husband and I loved the kayaks and pond. We saw bunnies in the morning - it’s truly magical. It’s so private and just 2 mins away from town. We made so many memories and I can’t recommend staying at this property enough.

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.

Pizza Friday
Pizza Friday was an amazing find! We spent a family reunion on the porch making pizza's in the oven. We obtained crusts from an Italian restaurant in California on our way and it proved to the perfect choice for us. We also enjoyed the dock and even caught a few crabs to show the kids. In addition we sat around the fire pit in the evenings. The beds were comfortable and everything was clean inside although we spent most of our time outside on the porch.

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.

Peaceful Waterfront Retreat on The Bay
Incredible space! Devin’s place on the water has everything you need. It would be tight with more than two adults but it worked great for us and our small dog.

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade
We stayed at Julie’s home with a group of friends and our families and had a wonderful time. The lakefront setting was incredibly relaxing—we found ourselves rarely leaving the property because it had everything we needed. From soaking in the hot tub to enjoying the game room, there was something for everyone. The kids loved having space to run around in the basement, while the adults enjoyed peaceful mornings and evenings on the screened-in porch. Julie was very responsive and answered all of our questions quickly, which made the entire experience seamless. We would absolutely stay here again!

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!
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