Holiday rentals with a kayak in Chincoteague

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.

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

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.!"

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.

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!

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.

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.

Waterfront, SUPs, Yaks, & Bikes! Walk 2 the Beach

Beautiful Bayfront Home w/Private Pier & deep water for SUP & Kayak excursions, boating, Fishing & Crabbing! Plus, short walk to the ocean... Discounts Available! Complimentary! 2 SUPs 2 Kayaks 2 Bikes 6 Beach Chairs 1 Beach Cart 1 Beach Umbrella 2 Boogie Boards 3 Beach Parking Passes Free Parking on Property Private Garage to store your belongings Private Patio Bar w/music & frig This will save you big bucks on rental equipment!

Beachfront Escape with Horizon Views of the Bay

Modern beachfront Panabode log cabin with sweeping Chesapeake Bay views. Relax on the deck, in the hot tub, swing, beach, or by the fire pit. Enjoy kayaks, paddleboards, shallow water, landscaping, and wildlife sightings. Main bedroom has king bed and ensuite bath. No pets, visitors, or street parking. Guests must bring linens, towels, and remove trash. Peaceful beachfront escape with modern, rustic charm, and unforgettable views.