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

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 🐾

Waterfront & Hot Tub! 4 BR/4 BA - Central Location
I enjoyed staying here for valentines weekend. House is large and very spacious. Only downside was there is limited basics in kitchen to cook with. I would recommend either bringing your own kitchen pans & baking sheets to cook with or just eat out. David was very communicative with questions I had.

Stunning Chesapeake waterfront home
This home was lovely to spend time in and out! I believe the best parts were the screened-in porch, the beautiful kitchen, the backyard by the private dock, the neighborhood kitties, the birds (including water fowl), the nearby walk to quaint Oxford, and much more! Lucas and Heather are fast at responding and enjoyable individuals. You will not be disappointed with this gem of a house! 5 star!

"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.

Spacious 4 bedroom waterfront home & boat access!
We only stayed a weekend but a great off the beach option for a group of 5-10 guests. Clean home, relaxing location, would book again.
Cottage rentals 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!

Waterfront w/Hot Tub & Beautiful Sunsets, Pier
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!
While we only stayed at this lovely cottage long enough to sleep each night while in town visiting family, I imagine it would be an idyllic spot for a getaway. The location is absolutely beautiful and the cottage was well stocked with anything you could need. We appreciated the dog bed and crate available for use as well! Would recommend!
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