How many guests does The Bayside Escape sleep?

Up to 24 guests across 6 bedrooms and 5 queen sleeper sofas. Sleeping breakdown: 1 King, 4 Queens, 4 Twins, and 5 Queen sofa sleepers (all in the main house).

Is The Bayside Escape pet-friendly?

Up to 2 dogs, $150 per stay. No cats.

What are the check-in and check-out times?

Check-in is at 4 PM and check-out is at 10 AM. Early check-in and late check-out are not available — back-to-back bookings require full turnaround time.

How do I book The Bayside Escape directly?

Book direct at thebaysideescape.com: there's no platform service fee, you earn 8% back in Bayside Rewards credit on every stay, and you deal with the owner directly.

What is the cancellation policy?

Full refund if you cancel 14 or more days before check-in. For a stay 14 or more days away, a 30% deposit is charged at booking and the remaining 70% balance is auto-charged 3 days before check-in; closer in, the stay is paid in full at booking. Inside the 14-day window, the booking is non-refundable.

Is parking available at The Bayside Escape?

Yes — the driveway accommodates 10 cars, including space for boat trailers.

What is the Flex Barn at The Bayside Escape?

The Flex Barn is a 1,600 sqft multi-use space included free with every booking. It features 16-ft ceilings, a 16-ft sliding barn door (drive-in capable), and rubber flooring. Perfect for yoga, corporate workshops, indoor games, movie nights, or gear storage. It is not a sleeping space — all sleeping is in the main house.

Blog/Labor Day Weekend on the Chesapeake Bay: The Last Great Weekend of Summer

Trip Ideas5 min read· June 2026

Labor Day Weekend on the Chesapeake Bay: The Last Great Weekend of Summer

Labor Day is summer's grand finale — and it's one of the best times of the whole year to be on the Chesapeake. The crabs are at their fattest, the water's still warm, and the three-day weekend is the perfect excuse to gather everyone for one last big stretch on the Bay before fall. Here's how to send summer off right on Hooper's Island.

The playset in the backyard at The Bayside Escape over Labor Day weekend

Peak crabs and warm water

Early September sits right in the peak of blue-crab season (which runs strongest July through September), and many regulars will tell you late-summer crabs are the heaviest and best of the year. The swimming beach a short drive away is still warm enough for it, the days are long, and a Labor Day crab feast on the deck is about as good as the Chesapeake gets. Pick up live crabs nearby, pile them on a paper-covered table, and let the weekend unfold.

The secret is the days right after

Here's the local tip: the stretch just after Labor Day may be the finest time to visit all year. The summer crowds vanish, the weather stays warm and clear, and rates ease into shoulder season — yet the crabs keep coming and the water stays swimmable well into September. The fall rockfish season reopens around the start of the month, and the first hints of fall migration begin. If your schedule allows, tack a few extra days onto the holiday weekend; you'll have the Bay almost to yourself.

Late-summer sunset over the Chesapeake Bay from The Bayside Escape

An all-weekend backyard

A house for the holiday means the celebration never has to leave home. Fire up the grill, set up lawn games, let the kids run between the water and the play area, and keep the cooler stocked all day. Paddle in the morning, crab in the afternoon, and gather at the fire pit in the evening as the lights glow warm and the stars come out. With six bedrooms and room for 24, everyone's together — and everyone has a comfortable place to land.

Book summer's last hurrah

The Bayside Escape sleeps 24 on the Chesapeake Bay in Fishing Creek, MD — peak crabs, warm water, and a big backyard. Create a free account and get $100 toward your first direct booking. Holiday weekends book early.

Create account and claim $100 Check your dates

Plan-ahead tips

Book early. Labor Day is a top summer weekend for a big house — reserve well ahead.
Consider extending. The post-Labor-Day days are quieter, cheaper, and just as beautiful.
Order crabs ahead; demand is high around the holiday.
Stock up in Cambridge (about 29 miles) on the way in.
Pack water gear and layers — warm days, cooler evenings.