Chesapeake Paradise

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Chesapeake Paradise This two-acre, waterfront micro-resort offers more than just a place to stay. The space is also perfect for family gatherings and joyful reunions.

•Chesapeake Bay waterfront micro-resort 🌅
•5 unique stays south of Annapolis + near DC
•Slow down, reconnect, & breathe deeper💨
•Book Direct👇
https://www.chesapeakeparadise.com/ Chesapeake Paradise, set on the western shore of the Chesapeake Bay, offers a lovely get-away for individuals, couples, families, or small groups any time of the year! The sunrise and sunset water views are particularly dazzling in fall and winter months (when guests seem just as thrilled to be here as those who come during the warmer months). The shady lawn and bright open spaces, outdoor fire pit and hot tub, huge screened porch, tree swings, kayaks, and restorative pier afford a peaceful and inspirational setting while still being within close proximity to Annapolis, Baltimore, and DC. Many individuals or couples take a break from their business or sight-seeing for a restorative or romantic retreat; others come to Chesapeake Paradise to complete writing, art, or other projects that require sustained focus or a secluded work environment. Some guests even utilize the owner’s skilled support in writing, editing, and coaching to restore creativity or resolve stubborn life/health/work issues.

Sometimes you don’t need a big vacation. You need three nights, a comfortable king bed, water outside your window, and a...
10/19/2026

Sometimes you don’t need a big vacation. You need three nights, a comfortable king bed, water outside your window, and a place where there isn’t much you have to do.

The Sunrise Suite is our private 1-bedroom suite overlooking the water, with a huge en suite bath and its own balcony. Lisa spent time sitting outside watching the water, walked to Black Market Bakers for coffee and breakfast treats, and—always important—reported back that the bed was very comfortable.

It’s a lovely choice for a couple’s getaway, a few days on your own, or a peaceful home base when you want to explore the Chesapeake Bay area.

And we especially love hearing those six words: We can’t wait to come back.

— Guest Lisa, Sunrise Suite

10/05/2026

They go by way too fast to read. That’s kind of the point. 😊

These are real words from real Chesapeake Paradise guests—sharing everything from quiet mornings by the water and time out on the pier to kayaking, crabbing, family gatherings, and simply having a beautiful place to slow down together.

And these are just a handful.

We’re so grateful for the guests who take the time to tell us what they loved about their stay—and especially for the many who come back again. ❤️

Want to actually READ the reviews instead of trying to catch them as they fly by?

⭐ Tap the Reviews link in our bio. We regularly gather our latest reviews from Airbnb, Vrbo, Google, TripAdvisor, and our other booking sites, and load them up onto Chesapeakeparadise.com where you can also book direct!

And maybe next time, these will be your words flying across the screen. 😊
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MarylandVacationRental

⛵ Powerboat Show, Navy football, Sailboat Show, Navy Homecoming, and the Maryland Renaissance Festival—October is packed...
10/03/2026

⛵ Powerboat Show, Navy football, Sailboat Show, Navy Homecoming, and the Maryland Renaissance Festival—October is packed with reasons to come to the Annapolis area!

Need a last-minute stay for the Annapolis Powerboat Show—or planning ahead for one of the other big October weekends?

Make Chesapeake Paradise your waterfront home base. Just a short drive from Annapolis, our peaceful 2-acre waterfront property has five unique stays, from romantic spaces for two to larger homes for families and groups.

October highlights include:

⚓ Annapolis Powerboat Show — Oct. 8–11
🏈 Navy home game — Oct. 10
⛵ Annapolis Sailboat Show — Oct. 15–18
🏈 Navy Homecoming — Oct. 24
🏰 Maryland Renaissance Festival — weekends through Oct. 25

Availability varies by stay and date, so check what’s open for your weekend and book your Chesapeake getaway.

👉 Check availability & explore our five unique stays: https://www.chesapeakeparadise.com/accommodations

10/03/2026

Chesapeake Paradise doesn’t have a swimming pool—but we do have a hot tub with a waterfront view, a private pier, kayaks and a canoe, and two acres to slow down and enjoy being together.

Spend the afternoon paddling on Broadwater Creek, try crabbing from the pier, or settle into a chair and watch the sky change. Then enjoy a quiet soak in the hot tub.

Our five accommodation options in Churchton, near Deale, Maryland, offer stays for couples, families, and friends. The hot tub, pier, and watercraft may be shared with other parties staying on the property.

Trade your pool search for a little more horizon. 🌊 Explore our waterfront stays at ChesapeakeParadise.com and book direct for $100 off your first stay.
Click here:
https://www.chesapeakeparadise.com/
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Shawn here—owner and longtime host of Chesapeake Paradise. 🏄🤸I’ve been welcoming guests here since 2009, and somewhere a...
10/03/2026

Shawn here—owner and longtime host of Chesapeake Paradise. 🏄🤸

I’ve been welcoming guests here since 2009, and somewhere along the way, I realized that one of my favorite parts of hosting is thinking about the little things.

Yes, I care about the big things—the beautiful water views, comfortable beds, well-stocked kitchens, and making sure everything is ready when you arrive.

But I also think about the things you might suddenly wish you had once you’re here.

A warm blanket when you curl up with a book. Binoculars for watching the osprey or the watermen checking their crab pots. Games for the kids. A popcorn pan. Floats, life jackets, and kayaks. Crab pots, mallets, and even an outdoor cooker if you catch enough crabs for dinner. Books and magazines for a rainy afternoon. Firewood for a fire by the water.

And if you’re coming here to cook, I’m the kind of host who will take pictures of the kitchen equipment and send them to you ahead of time so you know what you don’t need to pack. 😊

I didn’t actually realize how much those things mattered until I started noticing how often guests mentioned them in their reviews.

One family wrote that I had “thoughtfully anticipated what her guests may want and need.” Another said I had “thought of everything.” Someone else described Chesapeake Paradise as feeling “curated with love.”

That means a lot to me because this has never felt like simply running vacation rentals.

Chesapeake Paradise has grown slowly, one space at a time, from the first upstairs Flat I renovated in 2009 into the little waterfront collection of stays it is today. And through all those years, I’ve wanted people to arrive and feel that somebody actually thought about them being here.

I’m also nearby much of the time, so if something comes up, ask. Need a restaurant recommendation? Wondering where to get a great almond croissant? Can’t figure something out? Forgot something? Want to know the best place to put in a kayak?

Ask me. We can usually figure it out.

Because for me, hospitality isn’t about making everything fancy.

It’s about making it easier for you to settle in, feel at home, and have what you need to enjoy this beautiful little corner of the Chesapeake Bay.

And maybe discover a few things you didn’t know you needed until you got here. ❤️
Come experience the little things for yourself.





Well, that might be one of our favorite measures of a successful family vacation. 😊One of the things families love about...
10/02/2026

Well, that might be one of our favorite measures of a successful family vacation. 😊

One of the things families love about staying at our 3-bedroom Waterfront Wonder Cottage is that there’s actually stuff to do here—without getting back in the car and going anywhere.

Walk over to the pier and try your hand at crabbing. Take out a kayak or canoe. Spread out on the two acres. Or just sit by the water while the kids discover that catching dinner can be considerably more interesting than a screen.

Julie’s family also loved something that surprises people about our location: Chesapeake Paradise feels tucked away, but you’re still within easy reach of Annapolis, DC, Baltimore, and everything else the DMV has to offer.

And apparently, two of her kids have already decided where the family should stay next time. We’ll take that endorsement. 🦀

— Guest Julie, Waterfront Wonder Cottage

Crabbing, kayaking, or doing absolutely nothing—which would you choose first?

SAVE this for the next time you’re craving a getaway with views like this. 🌅Sunrises and sunsets are kind of our thing a...
09/29/2026

SAVE this for the next time you’re craving a getaway with views like this. 🌅
Sunrises and sunsets are kind of our thing at Chesapeake Paradise.

With the nor’easter that just came through, we’ve been watching some pretty dramatic skies lately. Sunrises and sunsets often seem especially spectacular around a storm.

But this isn’t even from this week.

That’s the thing about Chesapeake Paradise. Sunrises and sunsets are kind of our thing here.

Some mornings the water is almost glass. Some evenings everything turns pink and gold. And sometimes the clouds put on a show like this.

You can catch it from a bedroom window, a balcony, the screened porch, the yard, or wander down to the pier with your coffee and watch the sky change over the water.

No driving to the scenic overlook. No planning an excursion.

The view is part of the stay.

SAVE this for the next time you’re craving a few days by the water—and come see what the sky decides to do while you’re here.

We’re starting to think the dogs are the ones booking the vacations. 🐾Big dogs. Little dogs. Serious swimmers. Sibling p...
09/29/2026

We’re starting to think the dogs are the ones booking the vacations. 🐾

Big dogs. Little dogs. Serious swimmers. Sibling packs. Pups who want to investigate every blade of grass…and pups whose idea of a perfect Chesapeake Bay getaway is simply finding a sunny spot and supervising everybody else.

Over the years, so many dogs have brought their families along for a stay at Chesapeake Paradise. 😉 And our little Ambassador Winnie is usually quite interested in who has arrived—ready to sniff hello and make sure the new guests know the important things: where the yard is, where the water is, and who might be willing to play.

Three of our waterfront accommodations welcome dogs, with plenty of outdoor space to explore, water just steps away, a private pier, dog swimming, and an outdoor rinse shower for those enthusiastic Bay swimmers.

So if you’ve been searching for a pet-friendly vacation rental in Maryland, a dog-friendly Chesapeake Bay getaway, or simply a place near Annapolis and DC where the dog can feel like part of the family vacation…this is pretty much what we mean. ❤️

Because nobody should have to stay home from vacation just because they have four legs.

Save this for your next pet-friendly Maryland waterfront getaway—or send it to the person who never travels without the dog.

🎉 25 RETREATS! 🎉Wait… did we really just reach 25 retreats?! 💦💜Twenty-five retreats.Twenty-five groups of incredible hum...
09/24/2026

🎉 25 RETREATS! 🎉

Wait… did we really just reach 25 retreats?! 💦💜

Twenty-five retreats.

Twenty-five groups of incredible humans.

Hundreds of stories.

Countless laughs, tears, breakthroughs, hugs, aha moments, deep conversations, and life-changing connections.

And every single retreat reminds me why I do what I do.

There is something incredibly powerful about stepping away from everyday life for a moment and giving yourself the space to breathe, reflect, connect, and see what might be possible when you stop doing everything the way you've always done it.

And now…

We’re celebrating our 25th retreat! 🥳

Our September retreat is going to be extra special as we celebrate this milestone together.

To everyone who has ever joined us:

THANK YOU. ❤️

Thank you for trusting the process.

Thank you for sharing your stories.

Thank you for showing up as you are.

Thank you for making each retreat what it becomes.

And to those of you who have been watching from the sidelines, wondering if one of these retreats might be for you…

Maybe this is your sign. ✨

25 retreats later, the magic is still happening.

And I’d love for you to be part of it.

💜 25th Retreat Celebration
💦 September Retreat
✨ A weekend of connection, laughter, breakthroughs & transformation

Here’s to 25 retreats—and to everything still ahead.

With love,

Shawn
~xoxo

You make the drive… and somewhere along the way, the rush starts to fade.By the time you arrive, it’s quiet, warm, and e...
08/15/2026

You make the drive… and somewhere along the way, the rush starts to fade.
By the time you arrive, it’s quiet, warm, and exactly what you needed.

“A cozy location worth the drive.”

It’s that feeling of landing somewhere that just fits—soft spaces, water nearby, and a kind of calm that settles in fast. Guests don’t mind the trip… because what’s waiting on the other side is worth it every time.

Follow to see more of what life looks like on the Chesapeake Bay.

Address

1087 Rodgers Road
Churchton, MD
20733

Telephone

+13017850545

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