Hoopers Island, Maryland · on the Chesapeake Bay
About
The house, and who looks after it
A family house on Hoopers Island, run by its owner.
Sunrise yoga in 1,600 sqft — no studio required
Every reunion ends here
1.2 acres and a golden retriever — the kids won't ask to leave
Group cooking at the kitchen island
The pergola seats 20 — and that's before people pull up extra chairs
Golden hour on the pergolaSee every room, photograph by photographThe Bayside Escape is one house on 1.2 acres on Hoopers Island, in a working watermen's community about forty minutes from Cambridge.
It is owner-run, and the answers on this site are specific, and occasionally unflattering, on purpose. Call or text (223) 289-0934 and the person who answers is the person whose house it is.
1 King + 4 Queens + 4 Twins + 5 Queen sofa-sleepers, across 6 bedrooms and 4.5 baths — 14 in beds and 10 on queen sofa-sleepers. The main house is 3,842 sq ft on 1.2 acres, with parking for about 10 cars and a 1,600 sq ft Flex Barn.
Step-free entry from the parking area to the front door. The yard is open and not fenced.
2144 Hoopersville Road, Fishing Creek, MD 21634, in Dorchester County, MD. About miles to Cambridge, 19 miles to the Blackwater refuge. Baltimore is about 2 hours 30 minutes away, Washington DC about 2 hours 40 minutes, and Philadelphia about 3 hours.
$1,161
The whole house for 2 nights, cleaning and Maryland tax included. The cheapest 2 nights still open are Mon 7 Dec to Wed 9 Dec. Pick your own dates above to see yours.
That total is the nights, one $300 cleaning fee however long you stay, and 11% Maryland tax. A dog adds $150 for the stay. 30% is due when you book and the rest 3 days before you arrive.
Same nightly rate as our Evolve listing. Booking here removes the platform's service fee, not the rate.
Full refund if you cancel 14 or more days before check-in.
Up to 50 people on the property, including the 24 staying the night during an approved event.
- Events are only for stays booked on this site, never through a listing site.
- Ask before check-in — no fixed number of days — and the approval must be in writing
- $500 deposit, refunded after the stay
- Acoustic only — guitarist, string quartet, small unplugged ensemble. No amplified outdoor sound, no DJ.
- Day guests leave by 10 PM; only the 24 overnight guests stay past that
- You clear up afterwards — there is no event staff
Without that approval it is a whole-house stay for the 24 people staying, and a gathering beyond them is not permitted.
The full agreement