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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2
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Bathrooms
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2
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House Rules
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Pets allowed;Charge may apply
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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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8
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Property Id
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4651500
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Summary:
Sink into the hot tub and watch the sun set over the Chesapeake Bay. This waterfront home in Chester has everything you need to unplug — a 270-degree sunroom with stunning water views, a fire pit for evening hangouts, a cozy indoor fireplace, and two comfortable bedrooms that sleep up to 8. The full kitchen is ready for group meals, and the sofa bed adds extra space. Minutes from Kent Island restaurants and the Bay Bridge. Annapolis and the Eastern Shore's best spots are an easy drive.
The Space:
BEDROOMS
Two bedrooms. Bedroom 1 has a queen bed. Bedroom 2 has a queen plus a double — great for families. The living room sofa bed provides extra sleeping space. Sleeps up to 8.
BATHROOMS
Two full bathrooms stocked with towels, soap, and essentials.
KITCHEN
Fully equipped with stove, oven, microwave, dishwasher, coffee maker, cookware, dishes, and utensils. Everything for cooking meals at home.
LIVING AREAS
The living room has a large Smart TV and comfortable seating. But the sunroom steals the show — 270 degrees of windows with panoramic waterfront views. This is where you'll spend most of your time.
OUTDOOR LIVING
Hot tub with water views — the best way to end any day. Fire pit for evening s'mores and conversation. BBQ grill and patio seating overlooking the Chesapeake Bay. Indoor fireplace for colder nights.
PARKING
Free parking on the property.
LOCATION
Waterfront in Chester, Maryland on the Eastern Shore. Minutes from Kent Island restaurants and shops. Just across the Bay Bridge — about 25 minutes to Annapolis. Easy access to the Eastern Shore's best attractions, wineries, and waterfront dining.
GOOD TO KNOW
Check-in: 3:00 PM / Checkout: 11:00 AM
Self check-in with smart lock
No smoking
Guest Access:
Front door with code. Guests will not have access to the hallway storage closet and garage.
The Neighborhood:
Located in a quiet neighborhood just 3 miles from a large shopping center.
Interaction with Guests:
Available via text, call, or message in the app whenever needed
Located in Chester, this vacation home is on the waterfront. Shoppers can check out Annapolis City Dock, while everyone can enjoy the natural beauty of Sandy Point State Park and Chesapeake Bay. Looking to enjoy an event or a game while in town? See what's happening at Alumni Hall or Tose Family Tennis Center.
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