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Indigo Loft - Nassawadox

Indigo loft is a 2nd story space that shares entry stair with a quiet Pilates & Yoga studio. Perfect for couples or singles wanting a quiet place to work, get away from the big city, or be in a central location for site-seeing on Virginia's Eastern Shore. Walking distance to Little Italy restaurant, and short distance to 2 convenience stores, post office, library & Brownsville Nature Preserve. Perfect for truck drivers and travelers with trailers and a large free parking lot across the street.

Harbor View- (Sun - Sun rental June- Aug.)

Harbor View is an early 1900's brick duplex with high ceilings, transom windows, and crown molding. Best of all, this home is located in a quiet neighborhood just one block from the beach and two blocks from Mason Ave. where you can find unique shops, restaurants and other amenities. It's an easy walk to the pier for a magnificent sunset, or to Brown Dog's for homemade ice cream. We invite you to enjoy our comfortable home, and explore the quiet ambience of a historic beach town vacation!

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.

Pet friendly comfy family home

Take TIME OUT at our comfortable home that has belonged in our family for years. Conveniently located next to Central Park and the old Cape Charles High School. Sit on the porch, sipping your favorite beverage while enjoying the weekly concerts during the summer. Location is key with this home. Just blocks from the entertainment and shopping district and also within walking distance to the beach. Relax in the historic small town atmosphere that is the newest vacation destination.

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.

Ultimate Cabin Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

The Shore House on Madison - Pet Friendly Unit!

The Shore House on Madison was fully renovated in 2019 and located in the Cape Charles Historic District within walking distance to the beach, park, the shops and restaurants. Our pet friendly unit can host up to 7 guests with 3 bedrooms, 2 full baths and 1 outdoor shower. Bedroom #1 includes 1 Queen bed, TV and work desk. Bedroom #2: 1 Queen bed. Bedroom #3: Bunk Bed (1 double / 1 twin). Fenced in backyard with patio.

Sea Salt Cottage: Tranquil Getaway 5 min to beach

Escape to the Eastern shore! Sea Salt Cottage is your quiet, off-the-beaten path getaway in charming Cape Charles. -Peaceful, rural feel with a 5 min drive to beach, quaint shops & restaurants. -Dog & kid friendly w/ large yard to park boats, RV's, etc. -Hammock, tree swing, outdoor dining, fire pit, romantic sunsets. -2 min to groceries, 10 min to Kiptopeake State Park, 70 min to Chincoteague Island

Waterfront Sunsets | Pet-Friendly Escape | No Fees

THE BANTRY BAYDREAM Get caught in a baydream on the Eastern Shore! Entire fenced-in cottage with endless views of the Chesapeake Bay on Silver Beach. Enjoy stunning sunsets from the private, fenced-in dock in the summer or the cozy, enclosed nook that overlooks the bay in the winter. Plus, NO FEES! Kids are free. Fur-babies are free. And we pay for the cleaning!