Entire home
Chessie Cottage-Chesapeake Bay Great views from easy single floor living!
Waterfront cottage with kitchen and patio
Photo gallery for Chessie Cottage-Chesapeake Bay Great views from easy single floor living!





Reviews
10 out of 10
Exceptional
2 bedrooms 3 bathrooms Sleeps 8
Popular amenities
Explore the area

- Place, Matapeake State Park
- Place, Chesapeake Bay Bridge
- Place, U.S. Naval Academy
- Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
Rooms & beds
2 bedrooms (sleeps 8)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Living Room 1
2 Double Sofa Beds
3 bathrooms
Bathroom 1
Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer
Bathroom 2
Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer
Bathroom 3
Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer
Spaces
Deck or patio
Kitchen
Outdoor play area
Garden
Dining area
About this property
Chessie Cottage-Chesapeake Bay Great views from easy single floor living!
Welcome to Chessie Cottage on The Bay! There is an intangible quality to a cottage coming from a unique combination of architectural details, use of historic materials, enchanting setting. These are but a few of the elements creating this charming storybook cottage. Exit Bay Bridge, a short 4-mile drive delivers you to our little neighborhood, and at the final bend in the road, we have private parking. Accessing the house immediately via the brick/limestone walkway leads to a true cottage entrance; a steeply gabled roof over mahogany arched Dutch door, a true storybook welcome home! Bay views greet you before ever entering the cottage, visible from the Dutch door straight through the west facing wall of windows overlooking the bay. Three windows, each 5ft. tall x 8ft. long plus double glass French doors provide over 30ft of uninterrupted open shoreline views. The morning sunrise filtering through the trees lights the east Dutch door window starting a day of relaxation in this cozy cottage, ending with the sunsets and long-lasting afterglows on the water. The Chesapeake Bay is the largest estuary in the U.S., 3rd largest in the world, and one of the most productive bodies of water in the world.
We offer you endless views from our 150+ feet of private shoreline.
This custom home was created and built by artists so when NOT watching the never-ending array of eagles, herons, ducks, nesting ospreys, songbirds, dragonflies, and everything that floats, go by; from jet skis, crab boats, sailboats, to giant freighters and cruise ships traveling the deep-water channel…there’s endless interest & beauty all around. Open floorplan provides amazing views from every room, every seat. Large, well appointed, open, airy kitchen is ready to make all your meals memorable. Dine stylishly at the mid-century-modern Danish table or sit high and comfy at the custom designed butcherblock peninsula, originally from the Old Faithful Inn kitchen, Yellowstone National Park. Kitchen sink is, itself, a treat; a Ruvati 45” long, stainless steel Wonder Station of prep, serve, buffet, clean-up cheffing fun. Soft natural light pours in from 3 enchanting rooftop eyebrow windows, sunset reflects thousands of brilliant sparkles against the hand-laid ironstone wall in the living area. Main living area has 2 Queen sleeper sofas, one in a cozy alcove easily doubles as a dedicated office space with tilt-top coffee table for laptop, and office supplies. (If you must work, you can leave things set up to take a ‘bay break’.) Two private bedrooms each with king beds, smart TV’s, private en suite bathrooms, and inviting bay window seats for private moments reading or just watching the water. There is a 3rd full bath which services the main house located just past the well-stocked library nook where you’ll find games, puzzles, cards, and books for kids to adults.
We hope you find our home to be as enchanting, relaxing, and restorative as we do. Someday it will become our everyday home, but until then we look forward to sharing it with you.
We offer you endless views from our 150+ feet of private shoreline.
This custom home was created and built by artists so when NOT watching the never-ending array of eagles, herons, ducks, nesting ospreys, songbirds, dragonflies, and everything that floats, go by; from jet skis, crab boats, sailboats, to giant freighters and cruise ships traveling the deep-water channel…there’s endless interest & beauty all around. Open floorplan provides amazing views from every room, every seat. Large, well appointed, open, airy kitchen is ready to make all your meals memorable. Dine stylishly at the mid-century-modern Danish table or sit high and comfy at the custom designed butcherblock peninsula, originally from the Old Faithful Inn kitchen, Yellowstone National Park. Kitchen sink is, itself, a treat; a Ruvati 45” long, stainless steel Wonder Station of prep, serve, buffet, clean-up cheffing fun. Soft natural light pours in from 3 enchanting rooftop eyebrow windows, sunset reflects thousands of brilliant sparkles against the hand-laid ironstone wall in the living area. Main living area has 2 Queen sleeper sofas, one in a cozy alcove easily doubles as a dedicated office space with tilt-top coffee table for laptop, and office supplies. (If you must work, you can leave things set up to take a ‘bay break’.) Two private bedrooms each with king beds, smart TV’s, private en suite bathrooms, and inviting bay window seats for private moments reading or just watching the water. There is a 3rd full bath which services the main house located just past the well-stocked library nook where you’ll find games, puzzles, cards, and books for kids to adults.
We hope you find our home to be as enchanting, relaxing, and restorative as we do. Someday it will become our everyday home, but until then we look forward to sharing it with you.
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning
Have a question?
Get instant answers with AI powered search of property information and reviews.
Similar properties

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
- Kitchen
- Washer
- Dryer
- Free WiFi
10.0 out of 10, (41 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 23
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed: dogs (limit 2 total)
Keep Pets on leash but NOT tied up left alone.
Smoking
Smoking is not permitted
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
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
We should mention
This property does not have any lifts
About the area
Stevensville
Located in Stevensville, this cottage is on the waterfront. Hammond-Harwood House and ARTFX Gallery of Fine Crafts and Arts are cultural highlights, and some of the area's activities can be experienced at Queenstown Harbor Golf Links and Queenstown Harbor Golf Club. Looking to enjoy an event or a game while in town? See what's happening at Alumni Hall or Navy-Marine Corps Memorial Stadium.

Stevensville, MD
What's nearby
- Matapeake State Park - 6 min drive - 3.4 km
- Sandy Point State Park - 19 min drive - 16.8 km
- Chesapeake Bay Bridge - 19 min drive - 17.5 km
- Annapolis City Dock - 33 min drive - 34.5 km
- U.S. Naval Academy - 35 min drive - 35.2 km
Getting around
Restaurants
- McDonald's - 9 min drive
- Cracker Barrel - 9 min drive
- Dunkin' - 11 min drive
- Friendly Food Store - 11 min drive
- Starbucks - 9 min drive
Frequently asked questions
About the host
Hosted by Janet Craig

I host this lovely, newly built/renovated waterfront cottage for my Sister and Brother-in-law. I love being a host and helping people to enjoy their much deserved Get-A-Ways.
The area is wonderful for any water activities, relaxing on the water, visiting with family and friends. Lots of waterfront dining and breweries and wineries and distilleries to visit. There are Environmental Centers, Beaches, Waterfront Parks, and Bike Paths and Trails.
I have lived on the Island 20 years and would love to answer any questions that you might have.
Kindly, Janet
The area is wonderful for any water activities, relaxing on the water, visiting with family and friends. Lots of waterfront dining and breweries and wineries and distilleries to visit. There are Environmental Centers, Beaches, Waterfront Parks, and Bike Paths and Trails.
I have lived on the Island 20 years and would love to answer any questions that you might have.
Kindly, Janet
What makes this property unique
One level living makes this a great property for family gatherings with several seating areas and of course the wonderful views of the Chesapeake Bay.
Walk just a few steps next door to a nice Community Playground.
Walk just a few steps next door to a nice Community Playground.
Languages:
English
Tell us how we can improve our siteShare feedback