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Family Reunion on the Bay

2020 prices through 2025! Unpretentious, clean & family-friendly. Bright open-plan home for easy living. Generous seating throughout. Loads of games, toys. Ideal for extended families. Side-door ramp, 1st-floor ADA bedroom, step-in shower w/seat & grab bar nearby. Backyard fire pit, picnic tables, grill, corn hole. Free firewood, propane, stand-up paddleboard, beach chairs & toys. IMPORTANT NOTES: 1. Absolutely NO PETS ALLOWED! ($750 fine) 2. Only weekly, Sat.-to-Sat. rentals June thru Aug. 30.

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The Cheriton Loft

Located in the heart of Cheriton, The Loft is a bright and sunny apartment. It is perfect for a couple and one child, three friends or one person. Cheriton is an up and coming village which is home to several galleries and an art center. It is less than 4 miles to the charming town and beach of Cape Charles, 3 miles to Oyster Boat Landing and 8 miles to Kiptopeke State Park. The apartment is owned and decorated by"The Sheep Lady", a local painter, illustrator and writer of children's books.

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Steps to the Sea at Salt Box

Relax & recharge at The Salt Box, a charming historic getaway one block from the beach. This Airbnb is one side of a duplex on a quiet, leafy street in the Historic District - a short walk to the beach, shops, restaurants, the pier, the harbor and central park. Refer to our Guidebooks for our very favorite things to eat, see and do! We're always just a text away if you'd like additional recommendations before or during your stay. You can also Airbnb the other side of our duplex, Salt Box II!

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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!

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Private Guesthouse on Secluded Waterfront Farm

Just 5 miles from Cape Charles and 30 minutes from Virginia Beach, our contemporary Guesthouse gives you the peace and solitude characteristic of the Eastern Shore along with the convenience of being close to urban centers. Our twenty acre waterfront farm, which has plenty of nearby walking or biking, and a dock onto a secluded arm of Plantation Creek, an inlet of the Chesapeake Bay, is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

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Peach Haven II: Sunny spot 3 blocks to beach

Welcome to Peach Haven II, a newly renovated duplex in the Cape Charles historic district. Just 1 block from the park and 3 blocks from the beach, it's perfectly situated for your Cape Charles escape. This pet-friendly rental sleeps 5 guests comfortably with a master bedroom (queen bed) and a second bedroom with a custom full-over-full bunkbed. The house has been thoughtfully stocked with everything you'll need for a comfortable stay. Need more space? Ask about renting the other side, too!

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Wander Cape Charles

A sanctuary, an oasis, a one of a kind experience communing with nature while lounging in civilized splendor—all are apt descriptions of this New York architect designed beach house on the shores of the Chesapeake Bay. Guests enjoy stunning waterfront views from a finished floor height of 36 feet. The Eastern Shore of Virginia is famous for its flat tidewaters, but this property is perched amongst unusual relic Sandhills, complete with pines, gum trees and vast sea and sunset vistas.

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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.

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Fully Renovated! 1 Block to Historic DT & Bakery

This centrally located, century old brick duplex is newly renovated and ready for guests. It's a short walk next door to the Coastal Baking Company to get your morning coffee and freshly baked cinnamon roll. Sit on the front porch and enjoy the calm, quaint, historic town of Cape Charles. Take a swim in the bay or cast your poles from the dock just blocks down Main Street. Central Park, is a short stroll, and a great place for a picnic while the kids enjoy the playground.

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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.

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Sunshine Rays: Historic district backyard bliss!

Situated on a peaceful block of Cape Charles' charming historic district, Sunshine Rays was designed as a retreat for families visiting the Eastern Shore. With space for up to eight guests, an incredible backyard, and thoughtful amenities throughout, it's the perfect base for your Cape Charles getaway. We are just six blocks from the beach and even closer to our Central Park and the town's main street with all of its restaurants, bakeries, and shops.

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Summer Camp Tiny Cottage Walk to the beach & shops

At less than 470 sq feet, this 1920s house is super fun & ready to be enjoyed for a couples, friends, and small families! • King sized bed with smart tv on the first floor • Two twin beds in a cozy sleeping loft • Small kitchen with propane stove, Nespresso maker & living space with a smart tv • Patio w/ charcoal grill, solo stove, & dining table • Paddle board & floats Please read through our totally honest disclaimer below!

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Slowtide Cottage

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Historic, Pet Friendly Cottage-Three Little Birds

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Hot Tub/Fire Pit/Yard Games! Lots of space!

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"Awenasa" Luxury Beach Retreat

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Cape Charles cottage, family friendly, in town

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Fully Renovated in 2023

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The BeeHouse

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JC's Retreat; boat parking on site

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Ybalon where sun meets the sea and sea gulls soar.

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Cozy Cape Charles Apartment: Walk to Beaches!

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The Portal

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Cozy Mermaid Hideaway

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Thelma's Dawn Getaway. No Drama Zone

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Juliet: Romantic Getaway with Balcony

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Bayside Getaways - Crab Crib

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"Seahorse Retreat" Condo 1 block from Beach in his

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Crabba-Dabba-Doo

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Above it All - Chesapeake Properties

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