Thanksgiving in the Flex Barn
The Bayside Escape

Wednesday arrival, Sunday departure

One house. Nobody drives home in the dark.

4 nights, 25 November to 29 November 2026

$3,968$165 each

Your stay, ready to book. Nudge it if you need to.

ArriveWed 25 Nov
LeaveSun 29 Nov4 nights
Guests24 peopleThe house sleeps 24
$3,9684 nights, all in

$165 each, split 24 ways

$3,275 for the nights, $300 cleaning, $393 Maryland tax. No booking platform service fee.

One more night would add $871.

Free cancellation 14+ days out. Pay by card and nothing is charged until the owner confirms.

Guest favorite on Airbnb5.0 from 7 reviews · Airbnb and VRBO
4 people are looking at the property right now
A group booked their stay yesterday
Family playing games in the Flex Barn on a rainy afternoonRainy day? The Flex Barn has 1,600 sqft of reasons not to careLarge family reunion dinner for 20 in the Flex Barn under string lightsThe dining room set for a proper sit-down, under the lightsYoga class in the Flex Barn with natural light and open doorsSunrise yoga in 1,600 sqft — no studio requiredMultigenerational family on the sunny rear deck with bay marsh viewsThree generations, one deck, the whole Chesapeake BayFamily gathering in the backyard with the playset and pergola visibleThe backyard that keeps everyone outside from morning until midnightSee every room, photograph by photograph

The whole point of Thanksgiving is that everyone is in the same place at the same time, and the usual version has half the family leaving after dessert to beat the traffic. Four nights removes that. People arrive Wednesday, cook together Thursday, and still have two days left over.

4 nights works out to $3,968 all in for the house — $165 each with 24 of you, cleaning and Maryland tax included, and no booking platform service fee. That is the same nightly rate our Evolve listing shows.

What it actually costs

$3,968

The whole house, 4 nights, 25 November to 29 November 2026, with cleaning and Maryland tax. Split 24 ways, that's $165 each.

4 nights
$3,275
Cleaning
$300
Maryland tax (11%)
$393
Booking platform service fee
none
Total
$3,968
Split 24 ways
$165

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 queen2MainMain-floor full bath, shared with bedroom 3
Bedroom 31 queen2MainMain-floor full bath, shared with bedroom 2
Bedroom 41 queen2UpstairsUpstairs bath
Bedroom 51 queen + 1 twin3UpstairsJack and Jill, shared with bedroom 6
Bedroom 63 twins3UpstairsJack and Jill, shared with bedroom 5
Living rooms5 queen sofa-sleepers10BothHall 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-sleepers in the living rooms. 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; the two main-floor queens share the full bath beside them; bedrooms 5 and 6 share a Jack and Jill upstairs. The half bath takes daytime traffic so nobody queues behind a shower.

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 most groups 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 and is the one most groups walk into. Everything else worth the drive is in Cambridge.

If something goes wrong. UM Shore Medical Center at Dorchester, in Cambridge, about 40 minutes. 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.

Family around the fire pit at sunset — multigenerational gatheringEvery reunion ends hereFamily group under the lighted pergola at dusk — golden lightThe pergola moment that ends up in every family photo albumKids 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 in the kitchen that was built for itFamily 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 pergola — the Chesapeake Bay does this every nightSee 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. The nightly rate is the same either way — booking here simply means their service fee is not added on top.

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. Two things to know — nobody sleeps in it, 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. It needs approving in writing 30 days ahead, and 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 and is the reason a lot of people come at all — 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.

How many can sit down to eat at once?

Twenty, across three surfaces rather than one: ten at the formal dining table, six at the breakfast table and four at the kitchen island. Ten is the most at any single table, which is worth knowing before you picture the whole family at one. Most groups run the meal across all three and it works.

Is the kitchen up to cooking for that many?

It is built for it — a large oven, a gas stove and an island several people can work at without colliding. Two honest limits: there is one oven, not two, so the turkey and the sides need a running order; and there is no garbage disposal, because the house is on septic, so scraps go in the bin.

Can we arrive the night before?

Add the night on the calendar above and it prices straight in. What is not possible is arriving early on the day itself — check-in is 4 PM and early arrival is not offered, so the extra night is the way to have Wednesday morning.

Where do the children go?

The Flex Barn, 1,600 square feet of indoor floor, which is the whole reason it earns its place in November. There is also a play corner upstairs with giant Jenga and building blocks, and 75-inch televisions on both floors so the film happens somewhere the cooking is not.

Is four nights too long?

It is the difference between a meal and a holiday. Wednesday is arrival and unpacking, Thursday is the cook, and Friday and Saturday are the part people actually remember. Groups who book two nights over Thanksgiving spend most of it in the car.

Not ready to book yet?

Most groups this size need a week to agree on dates. Take the $100 first, and hold 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, you hear from us before it goes back on the listing sites.
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.