House in Kent Island, MD
8 guests · 2 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
High-end valueWell priced for this area
About this house rental
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
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
Amenities at Waterfront | Hot Tub, Fire Pit & Views
Non-smoking
Pets allowed
Family friendly
Map of Kent Island, MD
Ratings and reviews
10 / 10Outstanding·Oct 2025
Very easy hosts to work with and a lovely property. We will definitely stay again!
10 / 10Outstanding·Oct 2025
Great time at this home. Beautiful location on the water. Great size for a family. Close to fun activities and restaurants. We enjoyed our stay!
10 / 10Outstanding·Aug 2025
Our stay was great! The convenience to nearby restaurants and stores worked really well for oir quick weekend trip!
6 / 10Average·Sep 2025
The home in Chester Md is in a quiet location, and the back yard was private with great crabbing from the pier this time of year. Kitchen was fully stocked and there's a nice big TV in the living Room and master bedroom. The beds and linens were comfortable; the master could use a dresser. The host, Jarrod, a nice young man sent us a hair dryer that was delivered the next day; however, I don't think the host has ever been to this house, otherwise I don't think he would host it. We had to change the dates once that was well within the timeframe and it took a week, VRBO and the Host really need to fix this communication problem. Towels were left in the dryer packed in so tight they were still wet and by the time we noticed they smelled of mold, clearly the cleaning folks don't know what they're doing. Slider doors would barely open to the back yard. There are huge windows in the front of the house without any curtains which made it impossible for privacy, especially in the kitchen. The outdoor grill was disgusting and in an area that was hazardous to get to. Master bath shower drain was clogged. The owner and host did not prepare this home properly to host guests besides having someone come in and do a quick basic cleaning. I don't think this is acceptable considering how much money we were charged.
$$$$
Top rated by guests
9Outstanding
(7 Ratings)
"Very easy hosts to work with and a lovely property. We will definitely stay again!"
Caleb A.Don't miss out! Price and availability may change
