Vacation rentals with a kayak in Chincoteague

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Top-rated kayak rentals in Chincoteague

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Guest favorite

Home in Heathsville

4.93 out of 5 average rating, 120 reviews

The Hideaway at Mill Creek

We welcome 6 persons, however 4 adults max. Here you will find nestled in the woods atop a beautiful hill overlooking Mill Creek, a short distance from the Chesapeake Bay, an architect's home. With beautiful sunrises and sunsets, this hideaway gives you an escape from everyday life. Relax on the patio with a book, out on the water kayaking, fishing or crabbing off the dock or sitting watching the wildlife. You will never forget the views or the sight of the sailboats in for a rest from the bay.

Guest favorite

Home in Cambridge

4.99 out of 5 average rating, 161 reviews

Sunset Breezes - quiet waterfront retreat

Enjoy our waterfront home styled after historic bay lighthouses. Relax by the water in a hammock under the tall pines. Gather with family and friends around the fire pit. Take in the beautiful water sights while paddling in a kayak, canoe, or paddleboard. Laugh with family and friends while playing corn hole, croquet, or bocce ball waterside. Photograph abundant wildlife - bald eagles, blue herons, osprey, deer, turkey and numerous waterfowl. Dine on the deck while enjoying beautiful sunsets.

Guest favorite

Cottage in Hacksneck

4.94 out of 5 average rating, 108 reviews

Pretty Byrd Cottage, a Victorian Bayfront Getaway!

Imagine getting away from it all by crossing a footbridge to a private island with a Victorian cottage on your own private 3-acre lake! This property is a unique oasis that combines today's modern conveniences with the charm of elegant decor. Enter the front door and be taken in by the surrounding water views, and enjoy charming verandas and a balcony that overlook the lake and gardens surrounding the cottage. Guests can also enjoy the use of a private beach, fishing, kayaks and a paddleboat!

Superhost

Cottage in Deltaville

4.78 out of 5 average rating, 126 reviews

Stunning Beachfront Cottage on the Chesapeake

Take a break and unwind at this peaceful oasis. Near the end of a private road, enjoy direct beachfront access to the entrance of the Chesapeake Bay. Chill on your own sandy beach, wade in the water, and watch an endless display of boats at quiet Stingray Point. A private lighted pier, outdoor shower, and river room porch will make your stay worthwhile. With four bedrooms (one has bunk beds and a foosball table and is accessed through the third bedroom) you'll have all the room you need.

Guest favorite

Home in Cambridge

4.98 out of 5 average rating, 120 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Come relax at our casual, pristine waterfront home. We offer 4 bedrooms w/7 beds for 10 guests. We are nestled in a small neighborhood on the beautiful Choptank River. We provide bikes, kayaks, paddleboards & yard games. Just want to relax? Enjoy hanging in the hammock or kick back on the waterfront w/a private pier. Try fishing off the pier or simply chill on the back deck or patio. At night hang out by the firepit. Explore downtown Cambridge - it's a short walk/bike ride to town.

Guest favorite

Home in Chincoteague Island

4.97 out of 5 average rating, 200 reviews

Jay’s Retreat: EV Charger-Fire Pit-Kayaks-Bikes

Welcome to Jay's Retreat, your perfect escape just minutes from Assateague National Seashore and the iconic Chincoteague Ponies! This fully equipped 1,000 sq. ft. home features 3 cozy bedrooms, a fire pit for starry nights, kayaks, bikes, and a private dock for your water adventures. Enjoy swimming, fishing, hiking, and bird watching right at nature’s doorstep. With linens and towels included, plus an EV charger for your convenience, you’ll have everything you need for a memorable getaway.

Guest favorite

Cottage in Lewes

4.85 out of 5 average rating, 112 reviews

'Cottage by the bay', sleeps 8 near Rehoboth beach

This bayside getaway is a beautiful 'A' frame style cottage and is located along the Rehoboth bay with direct access to the water. The cottage is within the gated community of Angola by the Bay. About a block away from the front door is one of the three private crabbing/fishing docks, kayak launch and marina! Enjoy walking or biking along the water and trails throughout the community. The large pool is always a favorite too! Baywood greens golf is nearby also! Enjoy the beautiful sunsets!

Guest favorite

Rental unit in Selbyville

4.91 out of 5 average rating, 204 reviews

Dirickson Creek Waterfront Apartment

Spoil yourself in this 5 Star One bedroom ,great view of Dirckson’s Creek . Sunsets from a private waterfront deck or your private little beach & creek bar. 2nd floor over the garage with outside steps and private entrance. This apartment is very private u won’t be disappointed. No pets No Children three kayaks and stand up paddle boards to explore the Creek. We also have two beach chairs and umbrella for your use. Fresh ground coffee provided. Your own gas grill. Great for couples

Superhost

Houseboat in Snow Hill

4.76 out of 5 average rating, 120 reviews

"Serendipity"- Houseboat Getaway

Serendipity is docked at an active marina with watermen and pleasure cruisers, nestled off the Chincoteague Bay. Sleeps up to 4 adults craving coastal tranquility. From the boat, the Chincoteague Bay is in view and ready to be explored. Enjoy a full spectrum of awe-inspiring coastal wetlands, historic downtown areas, and beaches all within a few minutes' drive. Truly, the perfect setting for a much deserved recharge. 35 Minutes from Ocean City, Assateague Is, and Chincoteague Is.

Guest favorite

Home in Scotland

4.91 out of 5 average rating, 124 reviews

Spacious Gorgeous Waterfront Home with Sunset View

Dreamy weekends on the water, the perfect getaway for the entire family and friends in the southern tip of St Mary’s peninsula. This gorgeous newly remodeled house with 5 Bedroom 3.5 Bath sleeps 10 very comfortably. Wake up with amazing water views and access to the water with your own private pier. Spend your day crabbing, fishing, kayaking, or paddle boarding. Amazing beaches at Point Lookout State Park, just a few minutes away. High speed internet, WiFi, and cable.

Guest favorite

Cottage in Onancock

4.96 out of 5 average rating, 110 reviews

Little Cottage on the Creek

Experience Onancock....."a little slice of nowhere else". Whether you are looking for a romantic getaway for two, or just some rest and relaxation off the beaten path, Little Cottage on the Creek is the perfect place for your stay. Beautifully furnished and freshly renovated, this cozy waterfront cottage has all the comforts of home. Enjoy magnificent views of Onancock Creek along with the serenity for which the Eastern Shore is famous.

Guest favorite

Home in Cambridge

5 out of 5 average rating, 33 reviews

Serene getaway with great waterfront views!

Serene getaway with great waterfront views, private dock, and expansive deck. Located 10 minutes from Cambridge, MD, this home offers small groups and families a unique location with waterfront views throughout the house, updated spacious kitchen, kayaks, large back yard, grill for barbecue, and large dining and living rooms. Perfect for a quiet getaway to enjoy expansive views of the Choptank River at the mouth of Chesapeake Bay.