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01-August-2026 Plan Your Stay
Some of the best days on the Chesapeake Bay begin without much of a plan.
Someone carries a cup of coffee toward the water. The kids wander down to see what is happening around the pier. A kayak gets pulled out. Someone else decides to bring a fishing rod. Before long, towels are drying in the sun, people are floating on rafts, and nobody seems especially concerned about what time it is.
That is part of what makes the waterfront experience at Chesapeake Paradise feel different.
Located in Deale and Churchton, Maryland, about 25 to 30 minutes from Annapolis, Chesapeake Paradise is a peaceful waterfront micro-resort where guests can spend much of their stay beside—or directly on—the water.
We provide kayaks and a canoe for guests to enjoy. Visitors may also bring their own stand-up paddleboards, giving families, couples, and friend groups several ways to explore the calmer waters near the property.
And you do not have to be an experienced paddler to enjoy being here. Some guests spend hours kayaking. Others are perfectly happy floating on a raft, fishing from the pier, watching the kids look for crabs, or sitting with their feet over the edge of the dock.
The point is not to fill every minute.
It is to let the water change the pace of the day.
Finding family-friendly places to paddleboard near Annapolis can be harder than it sounds.
Public launch areas may involve parking, carrying equipment a considerable distance, crowded waterfronts, or planning an entire outing around getting everyone and everything to the water.
At Chesapeake Paradise, the waterfront is part of your stay.
Guests who bring their own stand-up paddleboards can access the water from the property, subject to current water and weather conditions. Because depths, wind, and other conditions can change, we encourage guests to check with us before launching. We are happy to share what we are seeing that day and help you determine whether conditions are appropriate for your plans.
On a calm morning, paddleboarding can be one of the quietest ways to experience the Chesapeake.
The board glides over the water. Birds move through the grasses and shoreline trees. The houses behind you grow smaller. For a little while, there is only the sound of the paddle dipping into the creek and the occasional call of an osprey overhead.
For families with mixed interests, paddleboarding also works well alongside the other activities available here. One person can paddle while someone else kayaks, fishes from the pier, or relaxes nearby with younger children.
Families looking for a smaller, private waterfront home can also explore the Waterfront Wonder Cottage, a three-bedroom stay with easy access to the property’s pier and water activities.
Nobody has to choose the same activity to still feel like they are spending the day together.
Kayaking has become one of the most loved activities at Chesapeake Paradise.
Guests have described it as both peaceful and fun. Families have spent mornings kayaking and canoeing together, while couples and sisters’ groups have taken the kayaks out during the day before returning for a fire and s’mores beside the water in the evening.
Kayaks and paddles are available for guest use, along with life jackets stored in our Guest Fun & Supply Center. The kayaks and canoe are kept near the main house and can be launched from the pier.
For beginners, we recommend staying within the creek rather than heading into more open water. Wind can rise quickly on the Chesapeake Bay, and boat traffic may occasionally be present farther out. Water shoes or secure tennis shoes are also recommended when using the pier ladder because surfaces can be slippery and barnacles may be present.
Guests are welcome to text us before heading out. You do not need to request permission to use the kayaks or canoe, but we are glad to offer tips, help with setup, or talk through the conditions.
That small bit of local guidance can make the experience feel much easier, especially for families kayaking with children or people who have not paddled recently.
There is something wonderfully old-fashioned about taking a canoe out together.
Kayaks give each paddler a little independence. A canoe asks people to cooperate.
You have to settle into a rhythm. Someone steers. Someone notices a bird along the shoreline. Children may start out determined to paddle and eventually decide that sitting in the middle and watching the water is more enjoyable.
The canoe is available to Chesapeake Paradise guests and is especially popular with families and groups who want to experience the water together.
One family staying at Chesapeake Paradise House with several generations shared that younger family members enjoyed canoeing, kayaking, fishing, and crabbing, while relatives with mobility challenges could still feel connected to everything through the expansive waterfront views.
That is one of the quieter gifts of this property.
Not everyone has to climb into a kayak to be part of the waterfront day.
On warm days, guests may swim from the pier or relax on the large inflatable rafts available at the property.
Sometimes the greatest luxury is simply floating.
You can stretch out on a raft, feel the warmth of the sun, and drift gently between the sky and its reflection. Children may spend their time climbing in and out of the water while adults take turns swimming, watching from the pier, or settling into a chair nearby.
Swimming conditions naturally vary. Water depths change, and the bottom around the pier is muddy, so diving and jumping from the pier are not permitted. The swim ladder can also become slippery and should be used cautiously.
Sea nettles, commonly called jellyfish, occasionally appear during late summer. When they are present, guests may prefer to stay on the rafts or visit one of the nearby swimming beaches instead.
Floating does not have to mean being pulled behind a boat. In fact, the slower version may be more in keeping with the experience here.
A raft, a warm afternoon, and nowhere else you need to be can be plenty.
Fishing is another easy waterfront activity that does not require packing everyone into the car.
Guests are welcome to fish from the shared pier, and assorted fishing gear may be available in the Guest Fun & Supply Center. Families often enjoy fishing because people can participate at different levels. One person may be deeply invested in catching something, while another is mainly there to enjoy the view and conversation.
Children can watch the line, examine small fish, or simply learn the patience involved in waiting.
For fishing away from the pier—including fishing from a kayak—guests should review current Maryland licensing requirements before heading out.
Fishing at dusk can be especially peaceful. The light softens, reflections begin to stretch across the water, and the whole property seems to settle into evening.
For many visitors, crabbing is one of the activities that makes a Maryland waterfront stay feel distinctly connected to the Chesapeake Bay.
Crab pots and some crabbing supplies are available for guest use. Chesapeake Paradise also has a large outdoor crab cooker, along with tools that can help when it is time to sit down and enjoy the catch.
Guests have repeatedly mentioned crabbing as one of the highlights of their family stays. One intergenerational group described younger family members enjoying nonstop fishing and crabbing from the pier, along with kayaking and canoeing. Another family specifically recalled crabbing, canoeing, card games, and exploring the neighborhood together.
Crabbing tends to become more than an activity.
It becomes the thing everyone checks on throughout the day. Someone walks down to the pier to see whether anything has found the bait. Someone calls the children over. Someone starts looking up how to tell a male crab from a female.
It is simple, a little messy, and very Chesapeake.
Chesapeake Paradise is best suited to human-powered and close-to-shore water activities: kayaking, canoeing, paddleboarding, swimming, floating, fishing, and crabbing.
We do not advertise the property as a recreational boat launch or guarantee docking for guest boats.
Water depth and access conditions can vary, and any guest considering bringing a boat of any kind must receive owner approval in advance. Suitability may depend on the particular watercraft, changing depths, tides, weather, and conditions around the pier.
For most guests, there is already more than enough to enjoy without bringing a motorboat.
The kayaks and canoe are waiting. Paddleboards can be brought along. The pier is close. The rafts are ready for a warm afternoon.
It creates a waterfront vacation that is active without feeling scheduled—and playful without becoming loud or crowded.
One reason Chesapeake Paradise works well for family and multigenerational stays is that the waterfront can be enjoyed in so many different ways.
More adventurous guests may head out in the kayaks or bring their paddleboards. Younger children can look for crabs, play along the lawn, or watch the activity from a safe distance with an adult. Grandparents or family members who prefer a gentler pace can sit near the water, birdwatch, fish from the pier, or enjoy the view through the large windows.
A Chesapeake Paradise waterfront day might include:
~Kayaking in the creek
~Canoeing with family or friends
~Bringing your own stand-up paddleboard
~Swimming from the pier when conditions permit
~Floating on large inflatable rafts
~Fishing from the pier
~Crabbing with available gear
~Sitting on the pier with your feet over the water
~Birdwatching for osprey, herons, geese, ducks, and other Chesapeake wildlife
~Watching the sunset from the pier, yard, balcony, or waterfront fire pit
~Rinsing off after a swim in the outdoor shower
~Ending the day with s’mores or a quiet fire beside the water
The activities matter, but so do the spaces between them.
Wet towels draped over chairs. Cool drinks after kayaking. Children running across the lawn. Someone still in a bathing suit while dinner is being made. Everyone a little sun-tired and less interested in their phones.
Those are often the moments people remember.
All waterfront activities are undertaken at the guest’s own risk.
Life jackets should be worn while paddling, and children must be closely supervised around the water, pier, kayaks, canoe, paddleboards, rafts, and shoreline.
Conditions can change quickly. Wind may increase, water depths vary, and the creek and open Bay can feel very different from one another. Beginners should remain in the protected creek area and avoid going toward open water when it is windy.
Guests should also:
~Wear secure water shoes or tennis shoes when using the pier ladder
~Avoid diving or jumping from the pier
~Use care on slippery ladders and surfaces
~Check weather and wind before paddling
~Tell someone when heading out for an extended paddle
~Bring boats and equipment back from the pier after use
~Ask us whenever they are uncertain about conditions
We would always rather have someone check with us than feel unsure.
Chesapeake Paradise is close enough to Annapolis for a day of exploring, shopping, dining, or sightseeing—but peaceful enough that many guests decide they would rather stay by the water.
Some arrive with a list of things they plan to do nearby.
Then they see the kayaks.
They notice the pier.
The water is calm, the lawn is warm, and somebody suggests making dinner at home instead.
The schedule gets lighter.
People open up. Time together feels less rushed. And what began as a search for places near Annapolis to paddleboard or kayak becomes something a little more meaningful: a few days of remembering how good it feels to be outside, play together, and let the water hold your attention for a while.
At Chesapeake Paradise, you do not have to organize an elaborate waterfront vacation.
You can wake up beside it.
When you are ready to explore a quieter kind of Maryland waterfront getaway, come see which Chesapeake Paradise stay fits your family, couple, or group.
Shawn
Online