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/Planning a Small Wedding or Elopement on the Chesapeake Bay

Trip Ideas7 min read· June 2026

Planning a Small Wedding or Elopement on the Chesapeake Bay

Not every couple wants a 200-person ballroom. If your idea of the perfect wedding is close family, a sunset over the water, and a long, joyful dinner with the people who matter most, an intimate celebration on the Chesapeake Bay is hard to beat. Here's how a private water-view estate works as a small-wedding setting — and what to think about as you plan.

The lit pergola with swing chairs at night at The Bayside Escape, a romantic Chesapeake Bay setting

The whole celebration in one place

The magic of a small wedding at a private estate is that everything happens in one spot. The wedding party stays on-site — the house sleeps 24 across six bedrooms and five queen sofa-sleepers — so the people closest to you wake up together, get ready together, and don't scatter to hotels at the end of the night. There's no shuttle logistics, no venue clock-watching, no rushing off after the last dance. The celebration simply unfolds at its own pace, on the water.

A flexible barn for the ceremony or reception

The property's Flex Barn is a genuine asset for a small wedding: a flexible indoor space that can host a ceremony, a seated dinner, or a dance floor — and serve as your weather backup if the forecast turns. Pair it with an outdoor ceremony by the water and the lit pergola for evening — and the home's permanent programmable exterior lighting, which can be set to a soft, warm palette to wash the property in just the right glow after dark — and you have a setting that feels both natural and intentional, without the cost and rigidity of a traditional venue.

The Bayside Escape welcomes small events. Its rental terms have allowed for an intimate daytime ceremony with a limited guest count, plus up to 24 guests staying overnight. Event policies, guest caps, and any associated terms can change, so confirm the current event details with us when you inquire — it's the first thing to nail down before you set a date.

A setting that needs almost no decoration

The Eastern Shore does a lot of the work for you. Big skies, marsh grass catching the late light, and a sunset over the Bay are a backdrop money can't really buy. Photographers love the golden hour here, and a celebration that runs into the evening gets the lit pergola and a sky full of stars. Lean into the natural setting and you'll spend less on flowers and draping than you would fighting a blank ballroom.

A water-view wedding weekend, your way

The Bayside Escape sleeps 24 on the Chesapeake Bay in Fishing Creek, MD, with a flexible barn for your ceremony or reception. Create a free account and get $100 toward your first direct booking — and reach out to talk through event details and dates.

Create account and claim $100 Check your dates

Vendors, food, and the practical side

Cambridge (about 29 miles north) is your hub for caterers, florists, rentals, and supplies, and the Eastern Shore has a deep bench of seafood-forward catering — a raw bar of local oysters or a crab feast rehearsal dinner is a uniquely Chesapeake touch. Because the house has a full kitchen and real space, you have flexibility: bring in a caterer for the big day and cook casual meals for the rest of the weekend. Plan a multi-night stay so there's time to set up, host a welcome dinner, marry, and recover without rushing.

When to plan it

Late spring and early fall bring the most reliable weather and the best light, while the quieter shoulder seasons offer better value and availability. Whatever the season, book early — wedding weekends are claimed far in advance — and build a backup plan for weather into your day from the start (this is where the Flex Barn earns its keep). Start by confirming the date and the event terms; everything else follows from there.