Please wait..
Please wait..
25 Jul 2025 Plan Your Stay
There’s something special about packing for a place like Chesapeake Paradise. Whether you’re headed here for a solo reset, a family getaway, or a peaceful retreat, we want your arrival to feel as effortless as the stay itself. That’s why we created this guide—to give you a head start on what to expect, what to bring, and how to make the most of your visit.
Let’s take the guesswork out of your travel plans, so you can focus on what matters most: relaxing, reconnecting, and enjoying the magic of the Bay.
Getting here is simple—but knowing a few things ahead of time makes it even smoother.
After booking, you’ll receive a detailed arrival email with everything from parking instructions to door codes to Wi-Fi access. Each suite or house has its own unique setup, so be sure to check your specific instructions for The Cottage, The Flat-Plus, Sunrise Suite, or the full Chesapeake Paradise House.
Most guests drive in, and the final mile or so brings you through quiet waterfront neighborhoods—so slow down, roll down the windows, and let the peace of the place begin before you even park.
Pro Tip: Let your host know if you’ll be arriving after dark. While everything is clearly marked, it’s helpful to have your host on standby in case you need last-minute help.
You won’t need much—but here are a few things returning guests are always glad they brought:
Slippers or cozy socks for lounging indoors
Layers for breezy bayfront mornings and evenings
Your favorite journal, book, or creative tools
Swimsuits (yes, even in the off-season—for hot tub soaks or polar plunges!)
Groceries or specialty snacks—Deale has great local options, but many guests like to bring a few favorites
Of course, we provide plenty of soft towels, quality linens, basic toiletries, and a fully equipped kitchen. But if you have a specific creature comfort, feel free to bring it along. We want you to feel at home.
Each space at Chesapeake Paradise has its own rhythm and energy. Here’s how to think about it:
The Chesapeake Paradise House is perfect for groups, families, or retreats. With 6–7 bedrooms, a spacious kitchen, group-friendly rooms, and multiple decks and fire pits, it’s the heart of the property.
The Flat-Plus Suite is a private, second-story retreat with a solarium bedroom, deep tub, hot tub access, and a writing desk with treehouse views—perfect for romantic stays, solo sabbaticals, or work-from-anywhere getaways.
The Cottage is just next door and offers its own full kitchen, fireplace, new bay window lounge area, and water views—a cozy, family-friendly or midterm stay gem.
All homes share waterfront access and are steps from one another, allowing guests to rent one or combine multiple for larger gatherings.
You don’t have to venture far to find great food and essentials.
Downtown Deale is just a few minutes away and includes:
Local seafood spots like Skipper’s Pier and Dockside
Coffee shops, pizza, and casual eats
A well-stocked grocery store and liquor store
Farm stands in season, plus nearby vineyards and markets
Many guests choose to cook on-site and enjoy meals on the deck or around the firepit—but it’s also fun to explore local favorites.
Tip: If you’re coming for a special occasion, let us know. We can recommend local chefs, oyster shuckers, or wine tastings that elevate your stay.
Chesapeake Paradise is about more than just the physical space—it’s about what happens when you finally get to step away from the noise.
While we do have Wi-Fi and cell service, many guests say their best moments here happen when they unplug. Take a walk to the dock at sunset. Sit in the hot tub under the stars. Journal by the bay window. Watch herons glide through the creek.
Even just a weekend here can reset your nervous system and restore your sense of possibility. That’s the gift of this place.
It’s the little things. The soft lighting. The cozy throws. The handwritten chalkboard notes welcoming them by name. The kayak launches at dawn. The peace that sneaks up and stays with them long after checkout.
We’ve heard it again and again: “I didn’t realize how much I needed this.”
And that’s the magic we hope to create—every time.
Gorgeous August days are ahead—and we have some last-minute availability! [Check out our accommodations and book here.]