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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!

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 Included-Family Friendly-Screened Porch!

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!

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!

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.

Small Dream FantaSEA

Step out to your private paradise where you'll discover a world of outdoor entertainment. Unwind in the bubbling hot tub beneath the endless blue sky or catch your favorite movie under the stars at the outdoor theater. The deck and covered patio, complete with outdoor dining options, provide the perfect setting for al fresco meals and sunset cocktails. Gather around the fire pit to toast marshmallows and share stories under the moonlit sky. Golf Cart Included with your stay!

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.