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

Waterfront Retreat
We had a wonderful stay at Abubakar’s place. It was relaxing but had the right amount of opportunities for entertainment. The natural setting was beautiful - we walked to the beach and viewed migrating horseshoe crabs and the accompanying shorebirds. (The insects were in full force this time of year, so we did cover up well. )The screened in porch was a perfect place for enjoying the sights and sounds. We took advantage of the ping pong tables,bicycles and big screen tv. The local pickleball courts are within biking distance and we enjoyed a few games. Great host and property. We hope to return!

Waterfront | Kayaks+Beach+Pool | Gameroom+Firepit
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!

Charming Waterfront Cottage w/2 King Suites + Dock
This is our fourth stay at the beach shack and as always, it was a true 5-star affair. Jennifer’s sense of design is impeccable—you will feel at home and in a constant state of chill staying here. Super serene with the bay just outside the sunroom, ultra quiet neighborhood and super comfortable furniture. Jennifer is the best communicator, reminding you pre trip, during trip and even post trip how much she values her role as a host, and YOU as her guest. Can’t wait to return this winter for a pre new years getaway, and another fun summer stay in 2026!

2 houses from Bay with hot tub, fully fenced in!
We had a lovely time at this bayfront home! The views from the balconies were amazing. The house was very very clean and had everything we needed. Host answered our questions and had helpful communications. We hope to visit again soon!

Peace Point - Waterfront, Secluded, Home w/hot tub
We visited Southern Maryland for a family wedding. The property is beautiful and peaceful. Beds are comfy, house comfy, and they thought of the little things like : a full sized ironing board & Iron, beach towels, good soaps, and all you need for s’mores!Their welcome handbook was very detailed. Our only regret was that we could not spend more time on the property itself (because of family events). Would have loved to use the kayaks and the fire pit. My brother did use hot tub. Great stay! Highly recommend

Steps to Beach. Peaceful. Pet-Friendly. + Linens
The house was perfect and we had a wonderful stay.

Beautiful Waterfront Home on LBI!
This spot is worth every penny!! The amazing views, the roof deck, all the bedrooms/bathrooms. We had amazing communication with Michael leading up to the stay. We felt very informed prior to check in. If you’re a first time visitor he really knows his stuff. We have been coming down for decades and this was the best stay we’ve ever had! Can’t wait to go back again :)

Bowers Beach - pets ok - low cleaning fee
Wonderful little get away to an adorable bayside "village". Enjoyed our visit, brought back memories of living in Delaware years ago. Thanks for having us!
Cottage rentals with a kayak

Chesapeake Bay Cottage
We absolutely loved this place and would love to make it our yearly girls trip destination! Highly recommend. Beautiful setting, private, and the house was super cute and very clean!!

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!

Weems Creek Cottage, Annapolis Waterfront
Cottage is very cute and the perfect size for a couple. Beautiful view and has all the necessary amenities. Jim was very responsive and communicative!

Waterfront Chesapeake Bay Sunrises w/Private PIER!
I had an amazing stay for my wedding weekend. The view of the water was unbeatable and the brand new outdoor furniture was great! Heather was very responsive and it was overall a great place to stay!

Four houses from the Sand! Welcome to Arbor Road
Our entire family had an absolutely wonderful stay at Teresa’s place! It’s a cozy, quiet, and charming home. It’s conveniently located near the bay, making it an easy walk to the beach. The house’s size is perfect for a small family, and everything looks exactly as depicted in the pictures. Teresa is an excellent host, incredibly friendly and welcoming. We thoroughly enjoyed our stay and will definitely be returning!

Potomac River cheerful cottage
Linda’s beach house is a real gem. The house is beautiful and clean. Has great views of the river and a large sand beach. I can’t wait to visit again

Newly Renovated 2BR Waterfront Cottage with Dock
What an absolutely beautiful space! Once we arrived, we didn’t want to leave. The house was super clean and well laid out. This is a perfect spot to unwind or recharge. Bring all your food and drink and just enjoy the beautiful views. We saw lots of wildlife, including herons, bald eagles, osprey, little lizards, deer, turtle, and some jumping fishies. We checked out Fossil Beach at Westmoreland State Park. Lots of walking trails and a lot of eagles. We enjoyed some bbq from Fishers at the Barn. The rest of the time we lounged on one of the decks or the dock and just took in the sights and sounds. Thanks for sharing the beautiful space!! We hope to visit again this fall! 10/10.

"Wittman Cottage"
Wonderful location. Excellent accommodations. Been there a few times and each visit has been most pleasant.
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.

Conewago Cabin #1 (No Cleaning Fee!)
Great responsive hosts. Really neat cabin and property. Like the short hiking trail and sitting on the screened in porch to enjoy the creek. Clean and cozy cabin. We had some rainy weather so wasn’t able to enjoy the firepit. Small brewery nearby. A dollar store for any forgotten items. Would stay here again.

Cozy Historic Cabin on the Water
Staying at Shawna and Keith's cabin was a wonderful experience. Peaceful and serene, it was relaxing just to wake up in this private oasis. Shawna and Keith were very friendly and easy to get in touch with if we had any questions. They even provided items for some of the activities we decided to try while staying there. The cabin was clean, quaint, quiet, well-equipped; and looked exactly as described. We would definitely return for another weekend getaway! Thanks again!

Large Cabin w/ RiverView&Hot Tub
We had a great stay at this cabin—very clean, well-stocked, and comfortable. The kitchen, bathrooms, and laundry were all in excellent shape and stocked well, and the washer/dryer was high quality. Beds and linens were comfortable, and the hot tub was a relaxing bonus. Appreciated the availability of streaming TV. Beautiful, peaceful setting. Only wish the patio furniture had been a bit more usable. Overall, highly recommend!

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.

Unique Stay Fantasy Book Themed Cabin Kayaks +more
We had an amazing night sleep! The bed in the "tub room" was like a warm hug! Soooo comfortable we didn't want to get up the next morning to check out.... we appreciated the option of a 1 night stay since we were just passing thru not alot of Airbnbs offer that option! The hosts were quick to reply and in helping us find a spot to park our Dually and trailer.

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.

Cabin on the Creek ~ Kayaks and Fire Pit
This is may be my favorite airbnb that I've ever stayed at. The house was so well stocked--not just with the essentials but with all kinds of wonderful extras (soap, shampoo, tea, coffee, etc.) and the kitchen was not only well stocked but the knives were actually sharp and the pans were great quality etc. The area was beautiful, and we thoroughly enjoyed the fire pit (fire wood was well stocked). The dock was lovely and the kayaks in great condition. We enjoyed several kayaking ventures on the creek, which was beautiful and quiet. It felt like we had the creek all to ourselves!
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