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/Keeping Teens Happy on a Hooper's Island Vacation

Family Travel5 min read· June 2026

Keeping Teens Happy on a Hooper's Island Vacation

Every parent planning a quiet-island trip has the same worry: "Won't the teenagers be bored?" Here's the good news — a Hooper's Island stay has more for teens than it looks, from on-the-water adventure to genuinely cool downtime. Here's how to plan a trip the whole family, even the hard-to-impress members, will enjoy.

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

Adventure on the water

Teens want to do things, and the water delivers. Kayaking and paddleboarding the calm marsh, and turning crabbing and fishing into a friendly competition ("who lands the biggest?") all hit different when there's a leaderboard involved. Give them a challenge — most keepers, first fish of the day, farthest paddle — and the quiet island becomes a playground.

Day trips with a cool factor

Build in an outing or two with real wow. The wild ponies of Assateague are a genuine bucket-list sight, St. Michaels makes a fun day out with shops and the harbor, and a fishing charter is an adventure even reluctant teens get into once a rod bends. These are the days that end up on their feeds — in a good way.

Open water for kayaking and fishing near The Bayside Escape

The surprisingly cool quiet stuff

Don't underestimate the slow magic. A bonfire at the fire pit, sunsets worth photographing, and some of the darkest night skies on the Eastern Shore for stargazing (and astrophotography with nothing more than a phone and a little patience) land surprisingly well with teens. It's the kind of "unplugged but actually cool" that a packed resort never offers.

Room to be themselves

Maybe the biggest win: space. With six bedrooms, teens can have their own room to retreat to, and the big common areas are made for late-night games, movies, and hanging out. Everyone gets together for meals and the fire, then peels off to their own corners — exactly the balance a multi-age family needs.

A trip the whole family will love

The Bayside Escape sleeps 24 across six bedrooms and five queen sofa-sleepers on the Chesapeake Bay in Fishing Creek, MD — water sports, adventure day trips, and room for everyone. Create a free account and get $100 toward your first direct booking.

Create account and claim $100 Check your dates

Tips for parents

Let each teen pick one activity — buy-in beats a forced itinerary.
Bring the gear: games, a speaker, a paddleboard, a real camera if they're into photos.
Lean into a little competition — crabbing and fishing scoreboards work wonders.
Embrace some downtime; a slower trip is a feature, not a bug, once they settle in.