Team offsite
The Bayside Escape

Hoopers Island, Maryland · on the Chesapeake Bay

A house, not a hotel block

The conversation carries on after the session ends.

Everyone under one roof, three hours from the office.

When are you thinking?

The cheapest stay open in each of the next few months, 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.

Guest favorite on Airbnb5.0 from 8 reviews · Airbnb and VRBO
The barn, 1,600 sq ft and empty on purposeThe barn, 1,600 sq ft and empty on purposeThe dining table, which seats tenThe dining table, which seats tenThe main living room, French doors to the deckThe main living room, French doors to the deckAn island several people can work atAn island several people can work atThe sitting room, looking through to the dining tableThe sitting room, looking through to the dining tableThe front deck, and the reason nobody nips back to the officeThe front deck, and the reason nobody nips back to the officeSee every room, photograph by photograph

An offsite in a hotel ends when people go back to their rooms. In one house it does not: the useful part usually happens in the kitchen at ten at night, which is the entire reason for leaving the office.

The same nightly rate as our Evolve listing, without the booking platform's service fee added at checkout.

Book it whichever way suits you

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.

Or book it where you already have an account:

Same house, same dates. Each site shows its own total at its own checkout.

What it actually costs

$1,575

The whole house, 3 nights, Mon 7 Dec to Thu 10 Dec, with cleaning and Maryland tax. Split 14 ways, that's $113 each.

3 nights
$1,119
Cleaning
$300
Maryland tax (11%)
$156
Booking platform service fee
none
Total
$1,575
Split 14 ways
$113

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.

Who sleeps where

6 bedrooms, 14 beds, 24 people. Work out who goes where now rather than at midnight.

RoomBedsSleepsFloorBath
Master suite1 king2MainPrivate en-suite, soaking tub and shower
Bedroom 21 queen2MainFull bath off the small hall between bedrooms 2 and 3, with its own door
Bedroom 31 queen2MainFull bath off the small hall between bedrooms 2 and 3, with its own door
Bedroom 41 queen + 1 queen sofa bed4UpstairsUpstairs bath
Bedroom 51 queen + 1 twin3UpstairsJack and Jill, shared with bedroom 6
Bedroom 63 twins3UpstairsJack and Jill, shared with bedroom 5
Living rooms4 queen sofa-sleepers8BothHall baths
Master suite.
Reachable without steps from the parking area, like bedrooms 2 and 3.
Bedroom 2.
Just past the big downstairs living room — the one with the 75-inch television.
Bedroom 3.
Just past the big downstairs living room — the one with the 75-inch television.
Bedroom 4.
The giant windows and the best Bay views in the house — the biggest window anywhere in it. The queen sofa bed is the fifth of the five, moved in here to leave the upstairs living room open.
Bedroom 5.
The mother-and-child room: a queen and a twin, with its own door like every bedroom here. The Jack and Jill it shares with bedroom 6 puts the adult next door to the children.
Bedroom 6.
Its own door onto the landing — the two rooms are joined by the Jack and Jill between them, not by a doorway. Three twins, so it is the room most groups give the children, with an adult next door in bedroom 5. Or however your group wants to use it.
Living rooms.
Two downstairs and two upstairs. Not bedrooms: these eight sleep in shared living space, and that is the real limit on privacy here.

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.

4.5 baths for 24 people

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.

Getting here, and getting fed

It is genuinely remote. That is most of why it is good, and all of why you shop on the way in.

  • Baltimore — about 2 hours 30 minutes
  • Washington, DC — about 2 hours 40 minutes
  • Philadelphia — about 3 hours
  • Annapolis — about 2 hours
  • Salisbury — about 1 hour 20 minutes

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 guide

If the plan changes

Cancelling. 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.

Yoga class in the Flex Barn with natural light and open doorsSunrise yoga in 1,600 sqft — no studio requiredFamily around the fire pit at sunset — multigenerational gatheringEvery reunion ends hereKids and a dog playing frisbee on the front lawn with the house in the background1.2 acres and a golden retriever — the kids won't ask to leaveThree generations gathered around the kitchen island during meal prepGroup cooking at the kitchen islandFamily gathered at the pergola during a daytime cookoutThe pergola seats 20 — and that's before people pull up extra chairsFamily with a dog on the pergola swings at golden hourGolden hour on the pergolaSee every room, photograph by photograph

What guests said

"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 Vrbo

Would 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.

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.

Where does a working session actually happen?

The Flex Barn: 1,600 square feet, sixteen-foot ceilings, a rubber floor and a sliding door wide enough to drive through. It comfortably holds a team of twenty-four in a circle or in rows. It is deliberately empty, so bring chairs, a folding table and anything you want to write on. Included at no extra cost.

Is the Wi-Fi good enough for video calls?

High-speed Wi-Fi covers the house and the yard and the credentials are on the fridge. It does not reach the barn — the metal walls block the signal, which makes the barn an accidental no-laptop room and a problem if you were planning to dial someone in from it. Run remote sessions indoors. If a particular speed is make-or-break, ask the chat before you book.

Can we set up a projector or a screen?

Bring your own and there is power and wall space in the barn for it. There is no AV, no screen and no whiteboard here. Both living rooms have 75-inch televisions if a smaller group would rather use one of those.

How many if nobody shares a bed?

Nine, in six bedrooms — one king, four queens and four twins, with bedroom 5 taking a queen plus a twin. The house reaches twenty-four by adding five queen sofa beds — two downstairs, two in the upstairs living room and one inside bedroom 4 — which is not single occupancy. Worth agreeing before you book rather than in the driveway.

Can we get an invoice or a receipt for expenses?

Yes. Ask the chat and the owner will issue one made out to the company, with the dates and the total itemised. It is a normal request.

How far is it from a city?

About 2.5 hours from Baltimore, 2 hours 40 minutes from Washington and 3 hours from Philadelphia, and roughly forty minutes past the nearest real town. Far enough that nobody nips back to the office for the afternoon.

Not ready to book yet?

Take the $100 first, and save the dates you are weighing up while you ask everyone.

  • $100 toward your first stay. Yours once you set up an account — it comes off the total at checkout whenever you book.
  • Save the dates you are considering. If a window you are watching opens up, we email you.
Claim $100 and save my dates

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.

Check datesSee the total before you pay
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