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
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Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
About the area
Chester
Located in Chester, this holiday home is on the waterfront. Chesapeake Bay Bridge and Maryland World War II Memorial are local landmarks, and travellers looking to shop may want to visit Queenstown Premium Outlets and Annapolis City Dock. Looking to enjoy an event or a game while in town? See what's happening at Alumni Hall or Tose Family Tennis Center.
Chesapeake Exploration Center - 8 min drive - 8.3 km
Paul Reed Smith Guitars - 8 min drive - 9.3 km
Matapeake State Park - 12 min drive - 13.1 km
Love Point State Park - 12 min drive - 14.7 km
Getting around
Easton, MD (ESN-Easton - Newnam) - 29 min drive
Restaurants
Chick-fil-A - 6 min drive
McDonald's - 7 min drive
Cracker Barrel - 10 min drive
Dunkin' - 8 min drive
Starbucks - 7 min drive
Frequently asked questions
Is Waterfront | Hot Tub, Fire Pit & Views pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Waterfront | Hot Tub, Fire Pit & Views?
As of 5 Apr, 2026, prices found for a 1-night stay for 2 adults at Waterfront | Hot Tub, Fire Pit & Views on 8 Jul, 2026 start from S$705, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Waterfront | Hot Tub, Fire Pit & Views?
On-site parking is available at the property.
What time is check-in at Waterfront | Hot Tub, Fire Pit & Views?
Check-in begins at 3:00 PM.
What time is check-out at Waterfront | Hot Tub, Fire Pit & Views?
Checkout is at 11:00 AM.
Where is Waterfront | Hot Tub, Fire Pit & Views located?
Situated on the waterfront, this holiday home is within 6 miles (10 km) of Island Dog Park, Chesapeake Exploration Center and Paul Reed Smith Guitars. Chesapeake Bay and Northern Chesapeake Bay are also within 9 miles (15 km).
Reviews
9.0
Wonderful
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
This was a great stay. The home was in a nice quiet neighborhood, but close to a lot of great restaurants. The home was very clean and well kept. Sheets and towels top quality. Very comfortable. And the grounds and dock were great too. Definitely recommend!
Stay was amazing. Neighborhood was perfect. The only thing that could have been better was privacy around the hot tub and shades or blinds on the front windows. Because of the lovely open floor plan it seemed that neighbors or passersby’s could look straight through the living areas even the evenings.
Anthony W.
Stayed 3 nights in Jul 2025
Verified
6/10 Okay
Theresa B.
3 Sept, 2025
Liked: Check-in, location
Disliked: Listing accuracy
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.