
Holiday rentals with a kayak in Assateague Island
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Top-rated Accommodation with a Kayak in Assateague Island
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Holiday House Rentals with a Kayak

Dragonfli Bay House - Newly Renovated Home
Rachel's place was perfect for a peaceful weekend getaway trip with a group of friends. Despite the cold winter weather, we were able to enjoy our time inside the house with a well-stocked kitchen for cooking meals, living room/TV for movies and game night, and a beautiful sunroom for reading. It was clean and cozy for the six of us. The house is conveniently located for when we wanted to walk along the beach, and Rachel was a responsive and nice host.

The Quarter Deck/Spacious home with water views!
Our surprise 60th birthday celebration in Onancock was a great success! Plenty of space for longtime friends to reunite in a beautiful, comfortable home together. We all felt this was a special place for loved ones to share. Wonderful location and setting near the water with lots of great restaurants and cute town nearby. We visited in the winter and hopeful to check it out again in the Summer!

Luxury home by the bay
Great house and the community was very well maintained. My kids loved the amenities that came with the community, including the pool and the small, but kid friendly beach. Overall, this was the nicest Airbnb house we have stayed in. We’d love to come back.

Rumbley Retreat
Came down for a duck hunting trip! The place was perfect! Very clean and cozy! Hope the owner was very attentive and quick to respond with any questions! If in the area again I will definitely book again!

Georgo Family Beach House
We had a great vacation. The house was well-appointed and very comfortable. We walked to the beach everyday, which we basically had to ourselves. Our dog Willie Boy gives it 4 paws up and one waggly tail (highest rating possible). James is a great host - responsive and informative. Stay well, Don 🎺, Liz 🙏 and Willie Boy 🐾

3 bedroom/2.5 bath Smith Island bungalow with dock
Our stay exceeded all expectations! Duke is an excellent communicator, the village is welcoming, the home is comfortable, the decor is a reflection of life on Smith Island and we look forward to planning our next visit! Be sure to visit the local Market for delicious crab cakes and famous Smith Island cakes. We highly recommend this beautiful Smith Island Bungalow for a quaint getaway!!

Stunning Chesapeake waterfront home
Lucas was a fantastic host! From our first communication until our check out, Lucas made so many accommodations to help make our stay the best ever. Being the host of an Airbnb myself, I understand what makes guests stay memorable!! Lucas went the extra mile. My family was here from all over the country for my father’s funeral. Lucas offered a late check out after the funeral. This was so thoughtful and kind. The waterfront views and proximity to downtown Oxford was fantastic. The screened in porch was ideal for my family to congregate and talk around the outside fire. I cannot say enough about this home. We can’t wait to come back soon!

"Goose Landing" Waterfront Retreat
This was a great vacation. This place has it all from the pool to the kayaking, fishing, crabbing and the late night fires were we all just sat around the fire and enjoyed the time together. The house was awesome, plenty of room for all. The family had a great time. Definitely would rent this place again.
Cottages with a kayak

Sailor's Cottage - Private Waterfront
Jessica and Richard were very welcoming and friendly. Place was great right on water. Very private. Grandson and I fished off dock with good success. J&R lent us a crab pot and we had a blast.

Peaceful 5 bedroom cottage on the Eastern Shore...
We had an amazing time on our honeymoon here!

Coral Cottage-w/Guest House-Waterfront-Hot Tub
A fantastic weekend getaway! Natalie’s home is beautifully located, offers spectacular views, and is incredibly well appointed with thoughtful touches like extra plush towels and spices and coffee. We enjoyed everything and even though the weather did not cooperate we had days of exploring the natural beauty, history, and local towns.

A "True" Chesapeake Bay Waterfront Experience!
The Thicket Point Fish Camp was the perfect place for a peaceful private getaway! It’s like home away from home with a modern costal design. The views are absolutely amazing. The kitchen, bathrooms, and bedrooms have everything you need. Matt was a great host and easy to communicate with!

IDLEHOUR, 3 BEDROOMS 2 BATHS W/ DOCK
This was our 2nd stay on the island , but first time at Mary Kim's. Great hospitality including home cooked egg rolls that made the long journey even more worth it. The only downfall would be the dock and kayak spot is a couple doors down, but Mary Kim was very communicative. lastly, I highly recommend the golf cart service on the island, gives you more of an ability to explore the island.

Cottage on Cabin Creek
My husband and I traveled here for a night away from our children and work responsibilities. We were looking for some place that was private and on the water. This place was both and it did not disappoint! The loft was cozy and spacious and we loved looking out the windows at the water and rain. It was very clean and there were plenty of towels and blankets and other special touches. Janelle communicated with us ahead of time to make sure she was ready for our arrival and she was kind and responsive throughout the process. We also found it easy to get into Easton for dinner at The Stewart, which was a treat, and then return back to the cabin. I would stay here again in a heartbeat -- but hopefully for longer next time.

Pony Pines!Your Waterfront Getaway Cottage Awaits!
Eric's home was perfect for our portable family Thanksgiving. Everyone loved the stay. Even the 1-year old enjoyed running around outside and exploring a new home. We loved watching the ducks swim by in a drizzle and it was my first time seeing an oyster bed. Wow! I can see that it would be fantastic to visit during a warmer season and spend some time floating on the water. The house was clean and welcoming. My kids enjoyed the snacks and I appreciated the local recommendations. Thanks, Eric! We had a great time and would welcome visiting again.

Dog-Friendly Westover Cottage w/ River Access!
My husband, 2 daughters and our dogs absolutely loved the cottage. It was easily accessible, extremely clean, very cozy, and had everything we needed for the perfect quiet getaway we all needed. Kelly was very communicative, letting us know when the cottage was ready to check in (early!), and even suggested a star gazing event nearby. We loved waking up to the beautiful views. We didn’t need to leave the cottage for anything. Will definitely be back!
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