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Cozy Coastal Retreat Near Beach/ Bay & Trails

A contemporary home in a peaceful neighborhood on Virginia’s Eastern Shore. Enjoying lots of natural light, outdoor spaces for easy entertaining, a large rear yard with plenty of seating, gazebo and fire pit. 4 miles away from Kiptopeke State Park and 7.5 miles from Historic Cape Charles. * 4 bedroom 2.5 bath * Fully renovated/refinished and beautifully furnished * Spacious rear yard, perfect for a family / friend bbq * Fully stocked kitchen * Outdoor Fun - Fish and crabbing at state park

New Hot Tub~1st Floor King Bed~Fire Pit~Bunk Room!

Escape to where Bay Views Meet Coastal Comfort Welcome to your home away from home in one of America’s happiest seaside towns. Nestled within a peaceful, gated community, the Majestic Mermaid is more than just a house, it’s the backdrop for your family’s favorite memories. Whether you’re here to watch the legendary Cape Charles sunsets from your third-story deck, cruise the charming streets in a golf cart, or walk just a few steps to the sand, this is the coastal retreat you’ve been looking for.

The Strand: Free Golf Carts & Pool, 1 Blk to Beach

This Cape Charles family retreat is the perfect place for your family -- or even 2 or more families to vacation together! Renovated in 2021, this 4 bedroom, 3 bath home provides the perfect space for those who want to hang out together... or for those who need some quiet time. The Strand offers free access to two 6-passenger golf carts, beds that comfortably sleep 12 people, an extra pullout couch if needed, and rainy day activities like pool/billiards, ping pong, indoor shuffleboard, and more!

Family-Friendly Home Near Beach, Trails & Golf

Nestled near the shores of the Chesapeake Bay and historic downtown Cape Charles, Wave Haven offers a tranquil escape for up to 10 guests. The kid-friendly 3-bedroom, 2.5-bath home is a short walk to a private beach and nature preserve within Bay Creek. Contact host to add the resort package for access to 2 pools, 2 golf courses, and a fitness center ($75/day). The home has two separate workstations, ideal for remote work. The cleaning fee includes fresh linens ($100) and a deep clean ($200).

Historic Charm & Modern Comfort : Downtown Escape

Surrounded by an array of restaurants, bakeries and a variety of unique boutiques and experiences, this apartment offers the perfect blend of charm and convenience. Juliette balconies invite fresh air and natural light, creating a Parisian-inspired ambiance. Inside, a fireplace creates a cozy setting. The state-of-the-art kitchen, designed in a striking 1950s vintage style, features Smeg appliances and bold crimson red accents, seamlessly blending retro elegance with modern functionality.

Private Country Beach Retreat

Welcome to Mason Jar Retreats Beach Home. Our home is a private beachfront property with the best of both country and beach living. Located on 6 acres on a private road with only a few steps to take to your private oasis on the Chesapeake Bay. Enjoy sunsets from the beautiful porches while taking in the natural surroundings. Our home is only three miles from a vineyard and winery and 20 minutes to Cape Charles with lots of shopping and dining in a quaint beach town. *LGBTQ+Friendly Home

Bay Breeze on Tazewell (Sun-Sun rental June-Aug.)

Bay Breeze on Tazewell is a recently remodeled Cassatt cottage with historic charm and modern amenities. The home includes a fabulous, sunny kitchen stocked to meet your needs. We provide fresh linens and towels for your stay. In the shed, you will find lots of items for the beach, a wagon, and bikes which we are happy to share. Bay Breeze is just a short walk to the beach, various restaurants, boutiques, and marina. If our home is not available, try our new Airbnb home ...Harbor View!

Kings Creek Cottage | Waterfront Retreat

Bring your boat and unwind. Brand-new waterfront retreat, just a scenic 1.3-mile boat ride to the bay. This 4br 3.5ba set on 2.5 acres features a private dock for boating, fishing, or simply lounging by the water. Relax on the screened-in porch. Gather around the fire pit. Take in stunning sunsets. Thoughtfully designed for comfort and laid-back coastal living, a charming escape inviting families and friends to slow down, savor the beauty of the Shore, and create unforgettable memories.

Oysterman's Pearl Golf Cart Included

Luxury Home with Golf cart included! Spacious beach house with a luxury touches. Great place to escape and enjoy the private amenities of Bay Creek while being a short walk or golf cart ride to downtown Cape Charles. Relax on the screened in porch or enjoy the breeze from the crows nest on the 3rd floor. This home has everything you need to have a relaxing beach vacation with the comforts of feeling at home. Bay Creek HOA pool, tennis courts, and YMCA pool and gym passes included.

Dog friendly, large fenced yard! 1st Floor Bedroom

Welcome to Bayside Fun! Our 1880's home on Randolph Ave. is located in the Cape Charles Historic District. Enjoy our large fenced in backyard or sit on our wrap around front porch and watch the world go by. We are within walking distance to restaurants, shops, and the beach (5 blocks). This house comfortably sleeps 6 adults with 3 bedrooms, 2 bathrooms, outside shower, and bonus sleeping area. All sleeping areas have smart TV's and the 1st floor bedroom features an en suite bathroom.

Coastal Red Barn Retreat

Located on the coastal seaside of Cape Charles, this barn was originally built in 1893. It has been lovingly restored to reflect the area's rich history, while providing modern comforts for today's guests. The Red Barn is nestled in the midst of scenic farmland, yet is only a few miles from the charming downtown, with its eclectic restaurants and unique shops. Enjoy the fresh breezes of the Atlantic and watch the sunrise over the fields from the comfort of the barn's private deck.

Romantic Coastal Retreat w/ Private Balcony

This charming and unique one-bedroom apartment is the perfect retreat. Filled with natural light, it offers picturesque views of Cape Charles’ main street featuring a beautifully crafted, vintage-inspired kitchen. Nestled above Lemon Tree Gallery, experience an ideal blend of character and comfort in a prime location—steps from the best dining, shopping, and attractions. Plus, the beautiful Cape Charles Beach is only a few blocks away, perfect for a relaxing seaside escape.