Vacation rentals with a kayak in Chincoteague

4.96 out of 5 average rating, 102 reviews

A back deck features a seating area composed of a sofa and ottoman with soft cushions, facing a calm canal. A wooden table is positioned nearby. A red umbrella is closed and stands beside the seating, while a sunset casts gentle hues across the water.

Home in Ocean City

3 BR Waterfront Home, Minutes to the Beach

Recently updated waterfront house located in the family-friendly Montego Bay community. Enjoy beautiful sunsets on the back deck or hop in one of the kayaks for a paddle around the wide-open canal. Try your hand at crabbing or fishing off the dock to catch your dinner. Within easy walking distance of the beach and Northside Park (about 10 minutes walk to both). Beach chairs, toys, boogie boards, and umbrellas are yours to use for fun in the sand and surf. The dock is available for boat tie-ups.

A covered deck area features a large black dining table surrounded by striped chairs. A ceiling fan is present above. Scenic views of the water and shoreline are framed by tall trees, creating a serene outdoor dining space.

4.99 out of 5 average rating, 171 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.

4.9 out of 5 average rating, 130 reviews

A serene waterfront view showcases the Chesapeake Bay, stretching towards the horizon under a clear sky. The shoreline features wooden docks and gentle waves, while quaint homes are seen along the sandy beach. Green trees provide shade in the foreground.

Home in Saint Leonard

Perfect Bay and Beach Getaway one hour from DC!

Our waterfront home with sweeping views of the Chesapeake Bay is close to beaches, the Flag Harbor Marina, Solomon's Island, Flag Pond Nature Preserve and Calvert Cliffs State Park. You’ll love the spectacular sunrises/sunsets over the Bay, diving ospreys and eagles, and exploring the bay by kayak, canoe, or paddle board. Our house is great for families (with kids), groups, and well-mannered dogs. New in 2023: we will be replaced the upstairs HVAC system, baby proofing, and fall 2023 paint

4.98 out of 5 average rating, 343 reviews

Two light blue Adirondack chairs are positioned on a wooden dock, facing a calm river. The sun sets over the water, casting a warm glow across the surface and creating a serene atmosphere. A weathered wooden table is placed nearby, enhancing the inviting scene.

Guest suite in Lusby

Riverfront Chalet Kayak/Canoe, pier, breakfast!

This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is Solomon’s island. This is a safe space for all🥰

4.81 out of 5 average rating, 53 reviews

An aerial view captures the beach house situated on a private peninsula, surrounded by water and sandy shores. The image highlights the expansive green lawn, rocky shoreline, and the tranquil bay. Nearby structures are visible, enhancing the coastal environment.

Home in White Stone

Beach House with Private Beach, Kayak, and Canoe

"A beautiful beach house with 580 feet of water frontage. Scenic views from every room. Tucked in a private peninsula and featuring a private beach, the 3-bedroom, 2-bath vacation rental boasts 2300 square feet of space designed for rest and relaxation. When you're not admiring the view from the floor-to-ceiling windows or large furnished deck, spend a relaxing day out in one of the provided kayaks and canoe of your coastal paradise, just 1.5 hours from Richmond and 2.5 hours from D.C.!"

Superhost

A comfortable blue futon is positioned against a large window, offering views of the marina and surrounding greenery. Two pillows, one with a floral design and another with a cheerful message, add a decorative touch. Natural light fills the space, accentuating the wooden walls.

Houseboat in Snow Hill

4.77 out of 5 average rating, 128 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.

4.91 out of 5 average rating, 129 reviews

Aerial view of a spacious house surrounded by lush greenery, with a private pier extending into the water. The house features a large, wrap-around porch and several trees dotting the landscape, creating a natural and serene setting by the water.

Home in Scotland

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.

Four white Adirondack chairs are arranged on a grassy area, facing the tranquil waterfront. A wooden pier extends into the calm river, surrounded by lush greenery and a single tree providing shade. The clear blue sky complements the serene setting.

4.98 out of 5 average rating, 127 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!

4.96 out of 5 average rating, 111 reviews

The exterior of a charming cottage is depicted, featuring a white wooden facade and a metal roof. A small stone patio with a bistro table and chairs sits at the entrance, surrounded by lush greenery and flowering plants. Two windows invite natural light into the space.

Cottage in Onancock

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.

Superhost

A scenic waterfront view is captured, featuring a spacious green yard with a double swing and a hammock situated under a tall tree. Calm waters reflect the sky, creating a serene atmosphere. Lush greenery lines the shore, enhancing the peaceful setting.

4.9 out of 5 average rating, 107 reviews

Waterfront Oasis! Hot tub! 2+ acres - Sleeps 8

HOT TUB!! WATERFRONT!! Relax with the entire family at this peaceful 3 bedroom fully remodeled private waterfront cottage on a quiet cove off the Choptank River/Chesapeake Bay. Enjoy the incredible views from your bed, from the large screened-in porch, from the oversized deck, from the hammock or double swinging chair out by the water! Launch a kayak right from the property and watch the gorgeous sunrises from the comfort of your bed!

A well-maintained green lawn extends toward the water, bordered by tall trees providing shade. The view includes the distant waterfront and a pier, with a clear blue sky above, creating a sense of openness and tranquility.

5 out of 5 average rating, 34 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.