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/Mother's Day & Father's Day on the Chesapeake Bay

Trip Ideas5 min read· June 2026

Mother's Day & Father's Day on the Chesapeake Bay

The best gift for the parent who "doesn't need anything" isn't a thing at all — it's time together, somewhere beautiful. Mother's Day in May and Father's Day in June both land at a lovely moment on the Chesapeake, which makes a weekend by the Bay the kind of present everyone remembers. Here's how to make it happen.

The front deck at The Bayside Escape, looking across the road to the marsh and the bay

For Mom: a restful spring weekend

Mother's Day falls in mid-May, when the Eastern Shore is at its freshest — the marsh greening up, ospreys on the nests, songbirds passing through, and warm, gentle days. It's the ideal backdrop for the kind of weekend a mom actually wants: an unhurried pace, sunsets from the deck, a slow paddle or a walk, and a special meal cooked for her in the full kitchen for once. No brunch reservation, no rush — just the family together and the water doing the rest.

For Dad: crabs and a line in the water

Father's Day in June is peak Bay fun. It's prime soft-shell crab season, the hard crabs are coming on, and the fishing is good — so treat Dad to a crab feast on the deck, an afternoon crabbing from the shoreline across the road, or a fishing charter out on the water. Cap the day at the fire pit under the stars. For a lot of dads, a cooler, a rod, and the whole family around is the perfect holiday.

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

The whole family, together

Either holiday, the real gift is everyone under one roof. With six bedrooms and room for 24, the kids and grandkids can all come, the guest of honor gets surrounded by family without having to host a thing, and there's space for both the big celebration meal and the quiet morning coffee. It beats a crowded restaurant every time.

Give the gift of a weekend by the Bay

The Bayside Escape sleeps 24 on the Chesapeake Bay in Fishing Creek, MD — the whole family, a full kitchen, and the season at its best. Create a free account and get $100 toward your first direct booking.

Create account and claim $100 Check your dates

Planning tips

Book early — Mother's Day and Father's Day weekends are popular for a big house.
Plan the special meal and shop for it in Cambridge (about 29 miles) on the way in.
For Dad's weekend, order crabs ahead or line up a charter in advance.
Keep it low-key: the point is time together, not a packed schedule.