Chessie Cottage-Chesapeake BayGreat views from easy single floor living!

Top rated by guests
Living Area 1
Gourmet Kitchen Island
Main Living Area
Tucked Away Second Living/Office Area with Sofa Bed
Swivel Chairs to Enjoy Living Area and Outdoor Views
review stars
10Outstanding
(10 Ratings)
"Words aren't enough....a picture is worth a thousand words. The adages are true, until Chessie Cottage. You have to BE there to believe it. We have been renting houses up and down the east coast fo..."
Becki H.
Don't miss out! Price and availability may change
10 / 10
Outstanding(10 Ratings)

Cottage in Kent Island, MD

8 guests · 2 bedrooms · 3 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
Top-tier experienceA high end property in this area

About this cottage rental

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.

Amenities at Chessie Cottage-Chesapeake BayGreat views from easy single floor living!

Non-smoking
Pets allowed
Family friendly

Map of Kent Island, MD


Ratings and reviews

10 / 10
Outstanding(10 Ratings)
10 / 10Outstanding·Nov 2025
Words aren't enough....a picture is worth a thousand words. The adages are true, until Chessie Cottage. You have to BE there to believe it. We have been renting houses up and down the east coast for over 30 years and not by any choice of our own, have sort of become vrbo snobs! Never has a place tickled all of our fancies until this one. There is quite honestly nothing the hosts haven't thought of for one's comfort and artistic pleasure, and neither is there a more peaceful spot on the coast to while away a day, a week, or whatever your heart desires. We have found our unicorn and struggled to pack up and leave. Thank you for making our stay picture perfect for us and the fur baby.
10 / 10Outstanding·Nov 2025
Words aren't enough....a picture is worth a thousand words. The adages are true, until Chessie Cottage. You have to BE there to believe it. We have been renting houses up and down the east coast for over 30 years and not by any choice of our own, have sort of become vrbo snobs! Never has a place tickled all of our fancies until this one. There is quite honestly nothing the hosts haven't thought of for one's comfort and artistic pleasure, and neither is there a more peaceful spot on the coast to while away a day, a week, or whatever your heart desires. We have found our unicorn and struggled to pack up and leave. Thank you for making our stay picture perfect for us and the fur baby.
10 / 10Outstanding·Nov 2025
We thoroughly enjoyed our stay at Chessie Cottage, from booking, through checking out. The owners greeted us and gave us a tour….we have rented homes on the Chesapeake for almost 20 years and this was the best greeting we have ever had; they were warm, welcoming and helpful. The home is stunning, completely stocked, and comfortable. The view…..amazing! The host, Janet, also went out of her way to make our stay wonderful. We highly recommend this home and the host. We will be back! Elizabeth, Kevin, and our dog Rocky.
10 / 10Outstanding·Oct 2025
Amazing cottage — beautiful views, very comfortable rooms with great attention to detail, amazing kitchen for those who like to cook. Bonus was that it’s pet-friendly. A great place to relax, retreat, feel cozy in the fall weather.

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FAQs

Is parking included with this cottage?

Parking is not specified as an available amenity at Chessie Cottage-Chesapeake BayGreat views from easy single floor living!. For more information, we encourage you to contact the property about where to park.

Is there a pool at this cottage?

We didn’t find pool listed as an amenity for this cottage. It may be worth double checking if a pool is important for your stay.

Is Chessie Cottage-Chesapeake BayGreat views from easy single floor living! pet friendly?

Yes! This cottage is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Chessie Cottage-Chesapeake BayGreat views from easy single floor living!?

We found 3 amenities for this rental. This includes non-smoking, pets allowed, and family friendly.