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Chesapeake Paradise is a peaceful, two-acre waterfront micro-resort near Deale, Maryland, with two houses and several ways to enjoy them—whether you're traveling as a couple, a family, or a larger group.
Our five accommodation options are:
Chesapeake Paradise House: The entire main house, with 6–7 bedrooms and 4 bathrooms.
Chesapeake Paradise LITE: Most of the main house, with 4–5 bedrooms and 3 bathrooms, excluding the upstairs Flat + Solarium apartment.
Sky-Lit Flat + Solarium: A private upstairs apartment within the main house, with its own separate entrance, two sleeping areas, a luxury bathroom, and waterfront balcony.
Sunrise Suite: A spacious upstairs king suite within the main house, with an ensuite bathroom, wet bar, and private waterfront balcony.
Waterfront Wonder Cottage: A separate, fully equipped 3-bedroom, 2-bathroom house next door.
All five options are part of the same Chesapeake Paradise property, but they are not five separate houses.
Explore Your Options:
Chesapeake Paradise House is the entire main house, including the upstairs Sky-Lit Flat + Solarium apartment and Sunrise Suite. You'll have 6–7 bedrooms, 4 bathrooms, a full kitchen, spacious gathering areas, screened porch, decks, and balconies.
Chesapeake Paradise LITE is a smaller configuration of that same house, with 4–5 bedrooms and 3 bathrooms. It includes the main floor, the upstairs Sunrise Suite with its ensuite bathroom and balcony, an additional upstairs bathroom, the screened porch, and deck.
The key difference: LITE does not include the Sky-Lit Flat + Solarium apartment. That upstairs apartment has its own secure entrance and may be occupied by another party during your stay.
Both options enjoy the waterfront grounds and outdoor amenities, which may be shared with guests staying in the separate Cottage.
Explore & Compare:
Chesapeake Paradise House | Chesapeake Paradise LITE | 3D Tours & Floor Plans
No. The Flat + Solarium is a private apartment occupying part of the upstairs of Chesapeake Paradise House.
It has its own secure entrance, so you won't need to walk through anyone else's living space. Inside, you'll find a sky-lit studio with a queen bed, sitting area, wet-bar kitchen, spacious marble bathroom with soaking tub and shower, plus a beautiful Solarium bedroom with a full bed, walls of windows, and a balcony overlooking the water.
When you book the Flat + Solarium, the rest of the main house may be occupied by another party or the owner. Your apartment remains private, while some outdoor amenities are shared.
Explore the Flat:
The Sunrise Suite is located upstairs within Chesapeake Paradise House. It features a king bed, spacious ensuite bathroom with soaking tub, a wet bar, and its own waterfront balcony.
Unlike the Flat + Solarium, the Sunrise Suite is accessed through the main house foyer and staircase. Your suite has lockable double doors, so your bedroom, bathroom, and balcony are private.
The downstairs portion of the house may be occupied by the owner or another party, and the Flat + Solarium may also be separately occupied.
Explore the Sunrise Suite:
Sunrise Suite Accommodation | Videos & Tours | Photo Gallery
Possibly! Chesapeake Paradise is a small waterfront micro-resort rather than a single vacation rental. Depending on which accommodation you book, other guests or the owner may be staying in a separate part of the main house or in the Cottage next door.
Your reserved bedrooms, bathrooms, and designated indoor living areas are private. You won't be sharing your accommodation's kitchen or bathroom with strangers.
Outdoor amenities that may be shared include:
The waterfront pier
Kayaks, canoe, and water equipment
Hot tub
Certain waterfront lawn areas, swings, and fire pits
Guest Fun & Supply Center
Some outdoor spaces are designated for particular accommodations. For example, the screened porch and main deck are included with House and LITE bookings, not with separate Flat + Solarium reservations.
Most guests simply enjoy the property at their own pace. You may see others enjoying the pier or hot tub—or you may hardly see anyone at all.
See How It Works:
Compare Accommodations | 3D Tours & Floor Plans | Guest Manuals
Yes, depending on availability!
Booking Chesapeake Paradise House gives your group the entire main house, including the Flat + Solarium and Sunrise Suite.
For even more space, you can inquire about booking the separate Waterfront Wonder Cottage as well.
It's a lovely setup for extended families or friends who want time together while still having comfortable places to spread out.
The outdoor amenities may still be subject to shared-use arrangements, so please ask if exclusive use of the grounds is important to your plans.
Explore Larger Stays:
Chesapeake Paradise House | Waterfront Wonder Cottage | Contact Us
Absolutely—and we encourage it!
Our video and interactive 3D tours help you see how the spaces connect and what each accommodation includes.
On our Videos page, you'll find interactive tours of Chesapeake Paradise House and the Waterfront Wonder Cottage. Within each tour, you can select 3D TOUR, PHOTOS, or FLOOR PLAN to explore different views and see the room layouts.
This is especially helpful when deciding between the entire Chesapeake Paradise House, Chesapeake Paradise LITE, or one of the private upstairs suites.
We also have photo galleries and videos highlighting the rooms, grounds, and waterfront amenities.
Take a Look Around:
Videos, 3D Tours & Floor Plans | Photo Gallery | All Accommodations
There are some wonderful places to eat around Deale, Churchton, and nearby Chesapeake Bay communities, from casual breakfast spots and local pubs to waterfront seafood restaurants and traditional Maryland crab houses.
Whether you're hoping for a relaxed lunch overlooking the water, steamed blue crabs, live music, or a special dinner, you'll find plenty of options.
We've collected local restaurant recommendations on our Attractions page, and Shawn is always happy to share her current favorites or help you choose a place that fits your plans.
Explore Local Dining:
You can spend an entire vacation enjoying Chesapeake Paradise without getting in your car! Our guests love kayaking, canoeing, fishing, crabbing, swimming, birdwatching, relaxing in the hot tub, and watching spectacular sunrises, sunsets, and stars over the Bay.
When you're ready to explore, you'll find:
Historic Annapolis, with its beautiful waterfront, shops, restaurants, and Naval Academy
Local marinas, sailing, boating, and fishing excursions
Waterfront restaurants and traditional Maryland crab houses
Parks, nature trails, and nearby beaches
Seasonal festivals, boat shows, and Naval Academy events
Day-trip possibilities in Washington, DC, and Baltimore
Check our Attractions page for plenty of ideas, or ask Shawn for suggestions based on your interests.
Plan Your Adventures:
Nearby Attractions & Sightseeing | All Attractions | Chesapeake Paradise Blog
Yes! Christopher's Fine Foods, our convenient local grocery store, is just a short drive away.
You'll also find Giant and Safeway farther north, along with Whole Foods, Trader Joe's, Aldi, and plenty of additional shopping options in the Annapolis area.
If you enjoy cooking, Chesapeake Paradise House, LITE, and the Waterfront Wonder Cottage all have fully equipped kitchens. The Sunrise Suite and Flat + Solarium have smaller kitchenettes for preparing lighter meals and snacks.
Explore Nearby Shopping:
Groceries, Wellness & Local Shopping | Explore Accommodations
Yes! Our waterfront pier is one of the most popular spots at Chesapeake Paradise.
Guests enjoy swimming, floating, fishing, crabbing, watching boats and wildlife, or simply relaxing with their feet dangling above the water.
You may swim from the pier using the ladder, but please use caution. Water depths vary, the bottom can be muddy, and the ladder may be slippery. No diving or jumping from the pier.
Sea nettles (jellyfish) sometimes appear in late summer, so swimming conditions vary with the season.
Fishing and crabbing are welcome. Please follow applicable Maryland regulations, including any licensing requirements.
Because the pier is a shared amenity, we ask guests to be considerate when others would also like to enjoy it.
See More:
Yes! We provide kayaks and a canoe for our overnight guests to enjoy, with no additional rental charge.
Life jackets and paddles are also available in our Guest Fun & Supply Center.
You can explore our beautiful protected creek, which is especially enjoyable for beginners, or paddle farther toward the Chesapeake Bay when conditions are appropriate for your experience level.
Please wear life jackets, supervise children carefully, and watch for changing winds and boat traffic. All water activities are at your own risk.
We love helping first-time paddlers get comfortable, so feel free to ask us for tips before heading out.
Explore Waterfront Fun:
Yes! We have crab traps, basic fishing and crabbing supplies, large cooking pots, an outdoor crab cooker, and tools for preparing and enjoying your catch.
One of the fun things about staying here is the possibility of catching your own Maryland blue crabs right from the pier and then enjoying a fresh crab feast overlooking the water.
Equipment is shared among accommodations and subject to availability.
Please follow current Maryland crabbing rules, and let us know if you'd like pointers on getting started.
Explore More:
Absolutely! Our waterfront hot tub accommodates approximately 4–5 people and is available for quiet relaxation.
Depending on who is staying at Chesapeake Paradise, the hot tub may be shared with guests in other accommodations or with the owner.
Many guests don't use it, so you may find that you have it entirely to yourself at times. When others are interested, a little friendly communication usually makes sharing easy.
The hot tub is intended for peaceful enjoyment, not parties. It's a lovely place to relax under the stars or enjoy a quiet conversation.
Hot tub hours are generally 6 AM–10 PM, with use subject to weather, maintenance, and operating conditions.
Please let us know if you plan to use it so we can prepare appropriately, and review the hot tub guidelines in your Guest Manual.
Learn More:
Yes! We welcome approved dogs in our pet-friendly accommodations.
Chesapeake Paradise offers two acres of lovely waterfront grounds, grassy areas, and a spacious meadow for enjoying walks and outdoor time with your four-legged family members.
Because this is a peaceful micro-resort with other guests and neighboring homes, we do have some important expectations:
Advance approval: Please include your dog in your reservation and confirm any applicable pet fees or restrictions before arriving.
Supervision: Dogs must be supervised and kept under control throughout their stay.
Outdoor safety: Dogs must be appropriately leashed or under approved collar control when outside.
Respect for others: Excessive barking or other disturbances to guests and neighbors are not permitted.
Cleanliness: Please clean up after your dog and protect furniture, bedding, and the property.
Shared spaces: Please be considerate of other guests who may be using the lawns, pier, and outdoor amenities.
We want both our two-legged and four-legged guests to have a wonderful visit!
If you're traveling with more than one dog, or have questions about your pet's needs, please contact us before booking.
Explore Pet-Friendly Stays:
All Accommodations | Guest Manuals & Property Guidelines | Contact Us About Your Dog
Dogs may enjoy the waterfront with appropriate supervision, but please be especially careful around the pier.
The ladder can be slippery, barnacles may have sharp edges, water depths change, and occasional jellyfish can make swimming hazardous. Not every dog can safely enter or exit the water from a pier.
Please check with us before allowing your dog to swim so we can discuss the safest options.
We also have an outdoor shower that's useful for rinsing off pets after water activities.
More Information:
It's one of our favorite little extras!
Located behind the maroon garage door near the Cottage, our shared Guest Fun & Supply Center is stocked with useful equipment and supplies to help make your stay more convenient and enjoyable.
Depending on availability, you'll find things like:
Life jackets, paddles, and inflatable floats
Crabbing and fishing supplies
Large cooking pots and crab-cooking equipment
Lawn games, toys, and outdoor recreation supplies
Extra toiletries, cleaning supplies, and coffee supplies
Some baby equipment and other practical extras
We love having things on hand that save our guests from having to pack or purchase everything themselves.
If you're looking for something particular, just ask!
Learn More:
Chesapeake Paradise is now focused primarily on peaceful waterfront vacations, family stays, and time together with friends and loved ones.
We no longer advertise or operate as a wedding or large-event venue. Large parties, loud gatherings, and events involving substantial numbers of outside visitors are not permitted.
Small, quiet get-togethers among registered overnight guests are generally welcome as part of a normal stay, provided they respect the property, our neighbors, and other guests.
Certain special arrangements, such as intimate retreats or small group activities, may be considered with advance owner approval.
If you have something particular in mind, please contact us before booking so we can determine whether it would be a good fit.
Explore Your Options:
Possibly, but all visitors who are not included in your reservation must be approved in advance by the owner, even if they won't be staying overnight.
A small number of additional visitors may be possible depending on the accommodation, parking availability, timing, and purpose of the visit.
Please contact us ahead of time with the number of visitors, additional vehicles, expected arrival and departure times, and the nature of your plans.
Only registered guests and specifically approved visitors are permitted on the property.
We love helping families and friends spend meaningful time together while also preserving the peaceful setting that everyone comes here to enjoy.
Questions About Visitors?
Yes. One of the special things about Chesapeake Paradise is its peaceful waterfront setting, where you can enjoy birdsong, beautiful skies, and the sounds of nature.
Although the property feels spacious and country-like, sound carries easily across the water and neighboring lawns.
We ask guests to reduce outdoor noise significantly after 8 PM or dusk, whichever comes first, and remain considerate of others throughout their stay.
The hot tub is also a quiet-enjoyment area, with additional guidelines regarding conversation and jets.
Of course, laughter, conversation, and enjoying time together are all part of a wonderful visit. We simply ask everyone to be mindful of sound levels and respect our neighbors and fellow guests.
Review House Guidelines:
Yes! All our accommodations have heating and air conditioning, although systems and controls differ by space.
The main house has separate heating and cooling zones, and the Sky-Lit Flat has its own ductless system. The Waterfront Wonder Cottage also has independent climate controls.
Some spaces have fireplaces for additional warmth and atmosphere.
Your Guest Manual includes instructions for your specific accommodation. Just reach out if you have any questions or need help adjusting temperatures.
Explore Amenities:
All Accommodations | Guest Manuals
Yes! We have high-speed internet, and many of our guests work remotely, attend online meetings, stream movies, or simply stay connected during their visits.
Download speeds are generally very good, although upload speeds can be slower and internet performance may occasionally vary.
Several accommodations offer particularly lovely spots for working with a waterfront view—including the sunny Solarium and Sunrise Suite.
If you have important video conferences or unusual technical requirements, feel free to check with us before booking.
Find Your Waterfront Workspace:
Flat + Solarium | Sunrise Suite | All Accommodations
Sometimes!
Shawn, the owner and longtime caretaker of Chesapeake Paradise, often stays or works on the property or nearby, although she also travels frequently.
Depending on which accommodation you've reserved, she may be staying in another private part of the main house or elsewhere on the property.
Your reserved private rooms and living areas remain yours, and we respect your privacy throughout your stay.
Shawn and her team are always happy to help with questions, local recommendations, or anything you need to make your visit comfortable.
Get to Know Chesapeake Paradise:
Please don't hesitate to reach out! We want you to be comfortable and have everything you need. Most questions or small problems can be resolved quickly, and we're always happy to help.
The best way to reach us during your stay is to call or text Shawn directly or our property manager, Carly. You should have their phone numbers in your reservation confirmation, arrival instructions, or previous texts and emails from us.
You're also welcome to message us through your booking platform, but for anything time-sensitive, calling or texting directly is usually best.
Whether you need help operating an appliance, finding something in the house, getting ready to kayak, or choosing a good restaurant, we're here to help!
We're Here for You:
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