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Brownsville Cottage

This beautifully renovated home in the country is perfectly located next to a 1250 acre coastal reserve called the Brownsville Preserve maintained by The Nature Conservancy and only 15 min from beautiful, pristine Cape Charles Beach. Country living close to our historic downtown Cape Charles and less than an hour to Chincoteague Va! Visit both during easy day trips, this home is perfectly located to explore the Shore! Property is shared with a detached tiny home suited with a private entrance.

Golf Cart-Chef Kitchen-Screened Porch-Holiday Stay

Welcome to "Sage by the Sea", a charming, designer-renovated home in the historic district of Cape Charles. A quick stroll or golf cart ride in the complimentary cart to the beach, this property is perfect for an unforgettable family vacation. You'll enjoy a custom-built chef's kitchen, a private garden patio. Golf cart included for easy exploration of the town. This top-ranked listing combines tranquil living and convenient access to everything you need. Send us a message with any questions!

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).

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!

Sunshine Baydream Cape Charles

Sunshine Baydream is bay living at its finest! Vacation comfortably with 3 master suites, including one on the main floor. The kitchen has all you need for a comfortable stay. Have some fun playing head-to-head Ms Pac Man! The open floor plan is great for entertaining! Enjoy the grill on the rear deck or the large second floor deck. The home is in a quiet community with a pool on Stone Road just outside Historic Cape Charles. Owners' 6-person golf cart may also be rented in advance!

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.

The Laughing King Retreat Honeymoon Island Cottage

Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.