Updated on Jul 20, 2026
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Type
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Private vacation home
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Bedrooms
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4
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Bathrooms
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3
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House Rules
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No pets allowed
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Children allowed: ages 0-17
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Smoking is not permitted
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No events allowed
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Max Occupancy
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10
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Host Language
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English
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Property Id
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2431835
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LOCATION. LOCATION. LOCATION! Chesapeake Dream is just 4 houses from the beach and 2 blocks from the main street with shopping, dining, and entertainment. A stately 3200 square foot restored Victorian built in 1912 comfortably sleeps up to 10, making for a perfect getaway for the multi-generational family and friends.
Sitting on a double, corner lot the fenced back yard provides family fun with a charcoal grill, fire pit and plenty of grassy lawn for family games. Cornhole is provided, as well as a beach cart for your convenience. Or simply sit at the table in the backyard under the solar party lights and gaze at the large gardens with flowers pretty much all times of the year. Bring some firewood and make samores over the backyard fire pit or enjoy some drinks at the outdoor bar. There is also a fresh herb garden provided for the gourmet chefs to spice up their homecooked meals. The large columned wrap-around front porch provides plenty of space to host those special dinner parties, or simply just sit in the rockers and sip your coffee (or wine).
And don't forget the enclosed outdoor shower located right out the back door so you can wash off all the sand and go right into the house from there.
Come in off the porch through the vestibule. After entering the grand first-floor foyer, complete with a sitting area, gather the family for TV viewing or enjoy an adult beverage and conversation in the spacious living room after the children are safely snuggled in bed. Families will have more than enough room to enjoy meals together, whether it is a quick breakfast in the sunroom with a table seating 6 and a sitting area, or in the formal dining room seating 8, complete with a beautiful marble fireplace and a 100 plus-year-old pump organ (both for aesthetics only).
The bright white kitchen has modern appliances and is thoroughly stocked with anything you could possibly need to cook family meals at home if you are seeking a break from dining out at the fabulous local restaurants. Coffee lovers delight as it has a regular brewing coffee pot, Nespresso, and Keurig. Set off the kitchen is a lovely wood-paneled office with an oversized leather chair and oak desk for those who need a workstation. Through the office is a half bath, leading to the laundry room which provides a washer, dryer, a sink, a wine refrigerator, and a stand-alone freezer for additional storage for extras such as bait for the fishermen or perhaps a large ice cream cake for those special celebrations.
Up the original carved banister staircase, the second floor provides a queen master with an ensuite bath with bay windows looking down onto the tops of the crepe myrtles surrounding the house, a coastal beachy children’s room with 4 twin beds (one a fun trundle!), and a beautiful Victorian bedroom with a double bed. There is a spacious second-floor bathroom for these two bedrooms to share.
Take the next flight of stairs to the third-floor retreat, consisting of a king master ensuite with an extra twin bed. There are two window seats to curl up and read a book or catch a peek of the bay with exquisite sunsets. A table and chairs provide an additional workstation or extra space for games and puzzles.
Amenities include broadband internet with secured WiFi, 3 televisions (one on each floor) with satellite TV, a DVD player with a collection of movies to enjoy. Card decks and games are provided for some extra family fun in the evenings or on rainy days. The home is climate controlled with split-level HVAC units and for the winter months still uses snuggly radiant heat to warm those extra chilly nights. No matter what time of year you want to take a vacation or even a quick getaway from urban life, the owners of Chesapeake Dream welcome you and your family with a nice gift of gratitude for your visit to their home.
For those curious about the surrounding area, Cape Charles is a historic Victorian railroad town hugging the shores of the Chesapeake Bay. This area offers everything for all personality types. For the adventurous, there are plenty of water and land activities, like kayaking, paddleboarding, and bicycle rentals. Like hiking? There are plenty of nature trails and beach dunes nearby. Is golfing your thing? There are two golf courses at nearby Bay Creek (one is a Nicklaus and one is a Palmer). If you bring your own boat, there is a public boat launch in the harbor. The public pier provides fishing and crabbing opportunities without the need for a fishing license. The calm waters of the Bay provide plenty of family fun and swimming along the public beach. Don’t forget to stop at the LOVE sign on the corner of Bay Avenue and Mason Street for your photo op. Also, Cape Charles is a golf cart-friendly town, but don’t worry, if you don’t have your own, there are two rental places in town. For the history buff, don’t miss the Cape Charles Museum in town and the Barrier Island Center just north on Route 13.
After all the daily activities, feeling a little hungry and desiring some entertainment? Chesapeake Dream sits just 2 blocks to Mason Street where you will find plenty of shopping, dining, and entertainment. On summer Friday nights, you can even catch live music on Strawberry Street at the Lemon Tree Gallery, Cape Charles Brewing Company or at the C-Pier at the Oyster Farm on Friday and Saturday nights, just a quick bike or golf cart ride away. Both offer drinks to enjoy while listening. There are also free summer concerts in the park on Saturday nights where they bring in diverse bands and exemplify the town’s warm and friendly spirit. Festive Fridays in late November and early December are a great way to kick off the holidays.
Day trips to Chincoteague Island, Tangier Island, Colonial Williamsburg, or Virginia Beach open up new opportunities for adventure.
During peak season a week minimum rental required. Check in is 4:00 pm on Sundays. Check out is 10:00 am on Sundays. We are more flexible in the shoulder seasons.
Located in Historic Downtown Cape Charles, a neighborhood in Cape Charles, this vacation home is near theme parks and near the beach. The area's natural beauty can be seen at Chesapeake Bay and Cape Charles Beach. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with hiking/biking trails and ecotours.
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