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/Memorial Day Weekend on the Chesapeake Bay: Kick Off Summer on the Water

Trip Ideas5 min read· June 2026

Memorial Day Weekend on the Chesapeake Bay: Kick Off Summer on the Water

Memorial Day weekend is the unofficial start of summer — and there's no better way to ring it in than on the water with your whole group. Hooper's Island gives you the three-day weekend you're after: long days, warming water, the first crabs of the season, and zero boardwalk crowds. Here's how to plan it.

The backyard with play area at The Bayside Escape, ready for a Memorial Day weekend

The kickoff weekend

By late May, the Eastern Shore is waking all the way up. The days are long, the water is warming enough for the brave to swim, and the marsh is green and alive with ospreys and herons. A three-day weekend is the perfect length to gather the family or friend group, settle into a house with room for 24, and ease into summer without rushing anywhere.

Soft-shells and the first crabs

For seafood lovers, the timing is excellent. Late May falls right in the heart of soft-shell crab season, which peaks in May and June as the crabs molt in the warming water — a true seasonal delicacy lightly fried and eaten whole. The hard-crab season (open since April 1) is ramping up too, so the year's first proper crab feast on the deck is well within reach. It's the freshest, most local way to start the summer.

Sunset over the Chesapeake Bay from The Bayside Escape on a late-spring evening

An all-weekend backyard

The magic of a house for a holiday weekend is that the party stays home. Fire up the grill, set up lawn games, let the kids run between the play area and the Flex Barn, and keep a cooler stocked all day. Paddle the marsh in the morning, crab from the shoreline across the road in the afternoon, and gather around the fire pit in the evening as the permanent exterior lights glow warm and the sky fills with stars. With six bedrooms, everyone has a soft landing at the end of the day.

Book the summer kickoff

The Bayside Escape sleeps 24 on the Chesapeake Bay in Fishing Creek, MD — a big backyard, water access, and the season's first crabs. 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. Memorial Day is one of the most in-demand weekends of the year for a big house.
Stock up in Cambridge (about 29 miles) on the way in — groceries, drinks, and cookout supplies.
Order soft-shells or crabs ahead so the seasonal star is on your table.
Pack water gear and sun protection — the water's warming, but bring layers for cool evenings.
Leave a day unplanned for the simple pleasure of doing nothing by the water.