
Hoopers Island, Maryland · on the Chesapeake Bay
Thanksgiving through March
Sleeps 24. Pick a stretch of the winter and we will show you what is free.
When are you thinking?
The cheapest stay open in each month of the winter, priced all in.
It is a real drive: Baltimore about 2 hours 30 minutes · Washington, DC about 2 hours 40 minutes · Philadelphia about 3 hours.
The named windows, each checked against the calendar and priced all in. The ones that have gone are shown too, rather than quietly left out.
Tap one and it loads into the booking card at the top of the page
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 photographWinter is the part of the year this house is best at: everybody indoors, the fire pit lit with the firewood provided, and an island quiet to the point of empty. Settle the drive before anybody commits — about 2 hours 40 minutes from Washington, about 2 hours from Annapolis and about 3 hours from Philadelphia. Hoopers Island is further out than most people picture, and it is better read here than found out on the road.
The same nightly rate as our Evolve listing, without the booking platform's service fee added at checkout.
Four ways in. Same house, same dates — pick whichever checkout you’d rather use.
Pick your dates and the total appears here, everything in, nothing added later.
Free cancellation 14+ days out. Card bookings are not charged until the owner approves.
$1,575
The whole house, 3 nights, Mon 7 Dec to Thu 10 Dec, with cleaning and Maryland tax. Split 20 ways, that's $79 each.
Those are the cheapest 3 nights still open. Your own dates will price differently; the calendar above quotes them from the same table.
Same nightly rate as our Evolve listing. Booking here removes the platform's service fee at checkout.
30% is due at booking and the balance 3 days before you arrive, so you are not asking anybody for their share months ahead.
Full refund if you cancel 14 or more days before check-in.
6 bedrooms, 14 beds, 24 people. Work out who goes where now rather than at midnight.
| Room | Beds | Sleeps | Floor | Bath |
|---|---|---|---|---|
| Master suite | 1 king | 2 | Main | Private en-suite, soaking tub and shower |
| Bedroom 2 | 1 queen | 2 | Main | Full bath off the small hall between bedrooms 2 and 3, with its own door |
| Bedroom 3 | 1 queen | 2 | Main | Full bath off the small hall between bedrooms 2 and 3, with its own door |
| Bedroom 4 | 1 queen + 1 queen sofa bed | 4 | Upstairs | Upstairs bath |
| Bedroom 5 | 1 queen + 1 twin | 3 | Upstairs | Jack and Jill, shared with bedroom 6 |
| Bedroom 6 | 3 twins | 3 | Upstairs | Jack and Jill, shared with bedroom 5 |
| Living rooms | 4 queen sofa-sleepers | 8 | Both | Hall baths |
Said plainly, because it decides who is happy on Saturday: 14 of those are real beds and the last ten sleep on queen sofa beds. Four of those sofa beds are in the living rooms and the fifth is inside bedroom 4, so sixteen sleep behind a bedroom door and eight do not. A group of 24 is not 24 people in bedrooms. Nobody sleeps in the barn.
For anyone who cannot manage stairs: the master is on the main floor with its own bath, and entry from the parking area is step-free. We do not claim ADA compliance — ask the chat for any measurement you need.
It is the first sum everybody does, so here is the honest version.
4 full baths and 1 half. The master has its own, and bedrooms 5 and 6 share a Jack and Jill upstairs. The half bath takes daytime traffic so nobody queues behind a shower.
The two main-floor queens share a full bath off the small hall between them. It has its own door onto that hall, so it is not a Jack and Jill — the Jack and Jill is upstairs, between bedrooms 5 and 6.
Spare towels are in the linen closet in that same small hall, beside the two main-floor queen bedrooms and just outside the downstairs full bath.
Two 50-gallon water heaters, so back-to-back showers hold up for a full house. With all 24 in, stagger the early birds and the night owls and nobody hits a cold one.
Two washers and two dryers, so a full house can run two loads at once.
Full refund if you cancel 14 or more days before check-in.
It is genuinely remote. That is most of why it is good, and all of why you shop on the way in.
The shop. The nearest full grocery is the Walmart Supercenter in Cambridge, 29 miles and about 40 minutes out, so stock up on the way in. Easton is bigger if the list is long, about an hour away. The General Store on the island is 5 miles and covers what you forgot, not the week's food.
Eating out. Old Salty's Restaurant is 3.6 miles up the road. Everything else worth the drive is in Cambridge.
If something goes wrong. Nearest emergency department: University of Maryland Shore Regional Health at Cambridge, 715 Cambridge Marketplace Blvd., open 24 hours. Call 911 first. Easton has a larger hospital about an hour away. A volunteer fire station on the island, about 10 minutes away.
Signal. High-speed Wi-Fi throughout the house and yard. It does not reach the Flex Barn — the metal walls block it, which makes the barn an accidental tech-free room. Coverage on the island is workable but not uniform across carriers. Ask the chat before you commit if the trip depends on it.
The full area guideCancelling. Cancel 14 or more days before check-in and you receive a full refund of everything you have paid, including the deposit, cleaning fee and taxes. Cancellations within 14 days of check-in are non-refundable.
The group shrinking or growing. The rate is for the house rather than per person, so losing two people does not change what you owe — it changes what each remaining share costs. Going over 24 overnight is the one thing that is not possible.
Minimum stay. 2 nights.
Dogs. Up to 2, no cats, $150 once for the stay rather than per dog.
Arriving and leaving. Check-in from 4 PM, check-out by 10 AM. Early check-in and late check-out are not offered, because the turnaround between groups needs the whole window.
The rear deck — smoker, golden retriever, and everyone at home
String lights, the bay, and no one else around
Sunset for two from the rocking chairs
Morning coffee in the rocking chairs, looking out over the marsh
Sunset from the front deck overlooking the Chesapeake Bay
Morning yoga on the front deckSee every room, photograph by photograph"We had such a fantastic stay! The house truly lived up to the listing—tons of space for our group of 20, and the layout made it easy for everyone to relax and enjoy. The host was amazing: super responsive, thoughtful, and proactive with details and local tips. The property itself is beautiful and private, with a great backyard and a huge flex barn. The kitchen had everything we needed, and all the linens were spotless. We'd absolutely come back for another stay!"
Smitha Ann
Group trip · July 2026
Verified review — see it on Airbnb"This is great property for folks looking for accessibility - there's a ramp and primary bedroom / bath are on the main floor. This was a must for us as we were traveling with elderly parents with limited mobility. The setting is scenic but the location is more remote than some — so good for those looking for a quiet and relaxing time. We enjoyed nearby restaurant called "Old Salty's." We appreciated how responsive the host was to our suggestions and questions. We appreciated small details, like laundry baskets in the rooms as well as Tupperware in the kitchen, puzzles and card games in the sitting area. I believe the host is continuing to add more amenities as guests send more suggestions!"
Anoka F.
Stayed 6 nights in Jul 2026 · Traveled with family and young children
Verified review — see it on Vrbo"We absolutely loved our stay. [The] house was beautiful, the amenities were excellent, and we loved the crabs!! We went for a family weekend (mix of 18 kids and adults) and it was very spacious and comfortable for everyone. The pergola in the back was an especially big hit! We highly recommend and would stay again."
Bridget C.
Stayed 2 nights in Aug 2026 · Traveled with family and young children
Verified review — see it on VrboWould rather book somewhere you have used before? The same house and the same dates are on Airbnb and VRBO. Each site shows its own total at its own checkout.
Nothing here is decorated for a holiday — no tree, no lights, no staging — and there is no catering and no staff. You cook, and the nearest full grocery is about 40 minutes away in Cambridge, so the shop happens on the way in. The 1,600 sq ft Flex Barn is not heated, which in January makes it a coats-on room rather than a second living room. The fireplaces indoors are decorative and do not burn; the fire that works is the fire pit outside. There is no hot tub and no pool. The property is water view — the shoreline is a short walk across a quiet road and the beach where people swim is a drive, and neither of them is on the lot.
Is it actually on the water?
It is water view, not waterfront. The house looks out over the bay and the marsh from the front deck, and the shoreline is a short walk across a quiet road — people crab from it. There is no dock, no private beach, and you cannot launch a boat from the yard. Hoopers Island is narrow enough that water is on both sides of you; it is just not on the lot.
Is the whole house ours?
Yes. Whole-house, every time. No shared rooms, no other party, nobody staying on site. Entry is a smart lock with your own code, so there is no key handover and no set arrival hour to hit beyond check-in from 4 PM.
Can we use the barn, and does it cost extra?
The 1,600 sq ft Flex Barn is included at no extra cost, with 16-ft ceilings, a rubber floor and a sliding door wide enough to drive through. It is deliberately empty: bring your own tables, chairs and games and make it whatever the weekend needs. Three things to know — nobody sleeps in it, it is not heated or cooled, and the Wi-Fi does not reach it, because the metal walls block the signal.
Can we have more people over for the day?
Up to 50 people on the property at once, and that number includes the 24 staying the night rather than sitting on top of them. So a full house of 24 may invite 26 more for the day. Ask before check-in — there is no fixed number of days — and the owner's approval must be in writing. Without that approval, a gathering beyond the people staying is not permitted. Events are only for stays booked on this site, never through a listing site.
Is there anything to do nearby?
Blackwater National Wildlife Refuge is 19 miles up the road — eagles year round, tundra swans and snow geese through the winter. Old Salty's is 3.6 miles away for crabs. The Harriet Tubman Underground Railroad park is 17.7 miles. Public boat ramps are minutes from the door, and collapsible crab traps live in the barn for anybody who wants to try from the shoreline.
How do we hold the dates?
Pick them on the calendar above and reserve. 30% is charged at booking and the balance 3 days before you arrive, so you are not chasing anybody for their share months in advance. The calendar is the live one — if a date shows as open, it is open.
Which winter dates can we actually have?
Whatever the picker at the top of this page is showing. It reads the same calendar the checkout does, scans the stretch you pick for windows where every single night is free, and prices each one all in. It shows the cheapest few rather than all of them, so a window it has not listed may still be open — change the length, change the month, or open the calendar and choose the dates yourself. What it will not do is show you a window it has not checked: when the calendar cannot be read at all, the page says so and gives you a number to call instead.
Is the house warm enough in the middle of winter?
It is heated throughout, which is the first thing anybody asks about a house on a narrow island in January, and the hot water is answered in its own section further down. The decks are cold — the wind comes straight off the water — so bring proper coats for the part that is outside. The barn is the exception indoors: it is not heated and the Wi-Fi does not reach it, so plan it as an afternoon room rather than the evening one.
What is there to do out here in January?
Blackwater National Wildlife Refuge is 19 miles up the road, and January is the best month of the year there — tundra swans, snow geese and bald eagles, with none of the warm-month crowds. The crabs run to mid-December, so early in the season the seafood is still worth the short drive. Restaurants nearby keep reduced winter hours, so check before you drive out. Back at the house it is the fire pit, the barn and a long meal, which for a winter weekend is most of the point.
Where does everybody sleep, and how many can eat at once?
14 of the twenty-four sleep in real beds; the house reaches 24 by adding five queen sofa beds, which is not the same thing as twenty-four people in bedrooms. Where those sofa beds are is what decides whether everybody gets privacy, so here it is plainly: all six bedrooms have their own door, and one of the five sofa beds is inside bedroom 4, so sixteen of the twenty-four sleep behind a door and eight sleep in the living rooms. Bedrooms 5 and 6 do not open into each other — they share a Jack-and-Jill bathroom with a door into each room — which makes those two a natural pair for children and a parent. Twenty eat at once: ten at the dining table, six at the breakfast table and four at the kitchen island. Ten is the most at any one table.
What if it snows, or somebody drops out?
Cancel 14 or more days before check-in and you receive a full refund of everything you have paid, including the deposit, cleaning fee and taxes. Cancellations within 14 days of check-in are non-refundable. There is no separate weather exception and none for somebody pulling out, so a group that is not yet certain is better off booking the window it is sure of. The rate is for the house rather than per person, so losing two people does not change what you owe — only what each remaining share costs.
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.
See every room24 sleep here. A wedding, anniversary party or milestone dinner can bring more for the day, approved in writing beforehand:
Without that approval, a gathering beyond the people staying is not permitted.
The full agreementNot ready to book yet?
Take the $100 first, and save the dates you are weighing up while you ask everyone.
No card needed, and nothing is held. The credit is good for twelve months.
Full refund if you cancel 14 or more days before check-in.