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The Port - Large condo on Mason Avenue!

Welcome to The Portal - a newly remodeled escape in a historic building on Mason Ave. Enjoy modern luxury in the heart of downtown, complete with high ceilings, two spacious bedrooms, two bathrooms, and a gourmet kitchen. Relax on your private balcony with views of the charming Main street below. Property offers 2 coveted off-street parking spaces, 1 golf cart space with charging, and an outdoor shower for beach days. Each room and the living room feature flat-screen TVs for your entertainment.

Pretty Byrd Cottage, a Victorian Bayfront Getaway!

Imagine getting away from it all by crossing a footbridge to a private island with a Victorian cottage on your own private 3-acre lake! This property is a unique oasis that combines today's modern conveniences with the charm of elegant decor. Enter the front door and be taken in by the surrounding water views, and enjoy charming verandas and a balcony that overlook the lake and gardens surrounding the cottage. Guests can also enjoy the use of a private beach, fishing, kayaks and a paddleboat!

Bay Breeze Home on private waterfront

On Virginia's beautiful Eastern Shore, the Bay Breeze Home on Occohannock Creek is the ultimate getaway for two or a large family desiring outside adventures. This 1970's spacious home has plenty of room. Experience the water with our three kayaks or family canoe and watch the abundant wildlife. Right outside your door, you may see Ospreys, Great Blue Herons, Eagles, wild ducks, porpoises, deer, geese, otters, & more. Be our guest and forget your worries in this spacious and serene spot.

Stylishly Renovated | Golf Cart Avail. | Bakery!

Nectarine 15 is centrally located. Next door, you’ll find the Coastal Bakery. A great place for breakfast or Treat. Relax on the charming front porch and soak in the calm, historic vibe of Cape Charles. A Quick walk to historic Downtown, Take a swim in the bay or cast a line off the dock. Central Park is also nearby, offering a great spot for a family picnic while the kids enjoy the playground. Golf carts are available to rent(Cart Rentals are only available during the House rental period)

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

Parkside South, Cape Charles

Parkside offers the perfect getaway for families and/or friends! Conveniently located next to Central Park, 2 blocks from the beach and the main street (Mason Ave). In peak summer we have full weeks available (Sun-Sun) or partial (Sun-Thurs). We open corresponding weekends once the Sun-Thurs books. Check our calendar or social media for weekend openings! We recommend a max of 4 adults or 2 adults and 3 (possibly 4) children, depending on their ages. Our family of 5 stays comfortably!

1891 Coastal Charmer: fully renovated farmhouse

Built in 1891, this farmhouse has been totally renovated by a professional designer. The Cottage is filled with coastal colors and accessories so it feels fun and updated but still retains the feeling of walking into a well loved family beach cottage. We are pet friendly as any beach cottage should be and love seeing our guests and their pets enjoying the cottage. Follow the cottage on social media @ BlueOysterCottage for more pictures, design ideas and local places to visit.

Egret’s Point on the Creek

Egrets Point on the Creek, is a beautiful and peaceful place to relax and plan your Eastern Shore exploration. Whether you are enjoying the fire pit by the creek, or taking a nap in the hammocks, canoeing, walking or exploring historic Onancock, life by the creek is sweet. Chincoteague to the north, Cape Charles to the south. Excitement abounds. Coastal exploration, boating, fishing, fine dining, artisan shops, art galleries, farmers markets and sandy beaches. Come and enjoy!

"Dragonfly" Waterfront Cottage on Chesapeake Bay

Bayfront beach vacation? Kayak out to dolphins? Breathtaking sunrises & sunsets? Yes, please! Relaxation and fun await at 'Dragonfly', a gorgeous cottage right on the Chesapeake Bay with spectacular views from every room. Nestled on acres and acres of waterfront, this magical property has its own cove for all the swimming, kayaking, SUP boarding and fishing you can manage. If you love nature, bring your water shoes and sense of adventure and we will take care of the rest!

Summer Camp Tiny Cottage Walk to the beach & shops

OPEN SUMMER!: 8/16-20, 8/31-9/4 (2 night min!) At less than 470 sq feet, this 1920s house is super fun & ready to be enjoyed for couples, friends, & small families! • King bed w/ smart tv on the first floor • Two twins in cozy sleeping loft • Small kitchen w/ propane stove, Nespresso • Patio w/ charcoal grill & solo stove • Paddle board & floats Please read through our totally honest disclaimer below! *We have a security camera on the front exterior of the home.

Oyster Cottage In Historic Fishing Village

Discover the quiet beauty of Virginia’s Eastern Shore at Oyster Cottage, a cozy seaside retreat tucked away in the quaint village of Oyster. Located just minutes from Cape Charles, this charming cottage offers the perfect balance of relaxation, nature, and heritage in one of the Eastern Shore's best-kept secrets. Step inside to a bright and welcoming space with coastal touches, comfortable furnishings, and all the essentials you need for a stress-free stay.